diff --git a/surfsense_backend/app/agents/new_chat/chat_deepagent.py b/surfsense_backend/app/agents/new_chat/chat_deepagent.py
index d3cf456d6..4e831265f 100644
--- a/surfsense_backend/app/agents/new_chat/chat_deepagent.py
+++ b/surfsense_backend/app/agents/new_chat/chat_deepagent.py
@@ -305,6 +305,32 @@ async def create_surfsense_deep_agent(
         ]
         modified_disabled_tools.extend(google_drive_tools)
 
+    # Disable Google Calendar action tools if no Google Calendar connector is configured
+    has_google_calendar_connector = (
+        available_connectors is not None
+        and "GOOGLE_CALENDAR_CONNECTOR" in available_connectors
+    )
+    if not has_google_calendar_connector:
+        calendar_tools = [
+            "create_calendar_event",
+            "update_calendar_event",
+            "delete_calendar_event",
+        ]
+        modified_disabled_tools.extend(calendar_tools)
+
+    # Disable Gmail action tools if no Gmail connector is configured
+    has_gmail_connector = (
+        available_connectors is not None
+        and "GOOGLE_GMAIL_CONNECTOR" in available_connectors
+    )
+    if not has_gmail_connector:
+        gmail_tools = [
+            "create_gmail_draft",
+            "send_gmail_email",
+            "trash_gmail_email",
+        ]
+        modified_disabled_tools.extend(gmail_tools)
+
     # Build tools using the async registry (includes MCP tools)
     _t0 = time.perf_counter()
     tools = await build_tools_async(
diff --git a/surfsense_backend/app/agents/new_chat/tools/gmail/__init__.py b/surfsense_backend/app/agents/new_chat/tools/gmail/__init__.py
new file mode 100644
index 000000000..3b6325ae6
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/gmail/__init__.py
@@ -0,0 +1,15 @@
+from app.agents.new_chat.tools.gmail.create_draft import (
+    create_create_gmail_draft_tool,
+)
+from app.agents.new_chat.tools.gmail.send_email import (
+    create_send_gmail_email_tool,
+)
+from app.agents.new_chat.tools.gmail.trash_email import (
+    create_trash_gmail_email_tool,
+)
+
+__all__ = [
+    "create_create_gmail_draft_tool",
+    "create_send_gmail_email_tool",
+    "create_trash_gmail_email_tool",
+]
diff --git a/surfsense_backend/app/agents/new_chat/tools/gmail/create_draft.py b/surfsense_backend/app/agents/new_chat/tools/gmail/create_draft.py
new file mode 100644
index 000000000..246c7d16f
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/gmail/create_draft.py
@@ -0,0 +1,320 @@
+import asyncio
+import base64
+import logging
+from datetime import datetime
+from email.mime.text import MIMEText
+from typing import Any
+
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.gmail import GmailToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_create_gmail_draft_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def create_gmail_draft(
+        to: str,
+        subject: str,
+        body: str,
+        cc: str | None = None,
+        bcc: str | None = None,
+    ) -> dict[str, Any]:
+        """Create a draft email in Gmail.
+
+        Use when the user asks to draft, compose, or prepare an email without
+        sending it.
+
+        Args:
+            to: Recipient email address.
+            subject: Email subject line.
+            body: Email body content.
+            cc: Optional CC recipient(s), comma-separated.
+            bcc: Optional BCC recipient(s), comma-separated.
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", or "error"
+            - draft_id: Gmail draft ID (if success)
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined the action.
+              Respond with a brief acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "insufficient_permissions", the connector lacks the required OAuth scope.
+              Inform the user they need to re-authenticate and do NOT retry the action.
+
+        Examples:
+            - "Draft an email to alice@example.com about the meeting"
+            - "Compose a reply to Bob about the project update"
+        """
+        logger.info(
+            f"create_gmail_draft called: to='{to}', subject='{subject}'"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Gmail tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GmailToolMetadataService(db_session)
+            context = await metadata_service.get_creation_context(
+                search_space_id, user_id
+            )
+
+            if "error" in context:
+                logger.error(f"Failed to fetch creation context: {context['error']}")
+                return {"status": "error", "message": context["error"]}
+
+            accounts = context.get("accounts", [])
+            if accounts and all(a.get("auth_expired") for a in accounts):
+                logger.warning("All Gmail accounts have expired authentication")
+                return {
+                    "status": "auth_error",
+                    "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "gmail",
+                }
+
+            logger.info(
+                f"Requesting approval for creating Gmail draft: to='{to}', subject='{subject}'"
+            )
+            approval = interrupt(
+                {
+                    "type": "gmail_draft_creation",
+                    "action": {
+                        "tool": "create_gmail_draft",
+                        "params": {
+                            "to": to,
+                            "subject": subject,
+                            "body": body,
+                            "cc": cc,
+                            "bcc": bcc,
+                            "connector_id": None,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The draft was not created. Do not ask again or suggest alternatives.",
+                }
+
+            final_params: dict[str, Any] = {}
+            edited_action = decision.get("edited_action")
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_to = final_params.get("to", to)
+            final_subject = final_params.get("subject", subject)
+            final_body = final_params.get("body", body)
+            final_cc = final_params.get("cc", cc)
+            final_bcc = final_params.get("bcc", bcc)
+            final_connector_id = final_params.get("connector_id")
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _GMAIL_TYPES = [
+                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+            ]
+
+            if final_connector_id is not None:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                    }
+                actual_connector_id = connector.id
+            else:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                    }
+                actual_connector_id = connector.id
+
+            logger.info(
+                f"Creating Gmail draft: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this Gmail connector.",
+                    }
+            else:
+                from google.oauth2.credentials import Credentials
+
+                from app.config import config
+                from app.utils.oauth_security import TokenEncryption
+
+                config_data = dict(connector.config)
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and config.SECRET_KEY:
+                    token_encryption = TokenEncryption(config.SECRET_KEY)
+                    if config_data.get("token"):
+                        config_data["token"] = token_encryption.decrypt_token(
+                            config_data["token"]
+                        )
+                    if config_data.get("refresh_token"):
+                        config_data["refresh_token"] = token_encryption.decrypt_token(
+                            config_data["refresh_token"]
+                        )
+                    if config_data.get("client_secret"):
+                        config_data["client_secret"] = token_encryption.decrypt_token(
+                            config_data["client_secret"]
+                        )
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            from googleapiclient.discovery import build
+
+            gmail_service = build("gmail", "v1", credentials=creds)
+
+            message = MIMEText(final_body)
+            message["to"] = final_to
+            message["subject"] = final_subject
+            if final_cc:
+                message["cc"] = final_cc
+            if final_bcc:
+                message["bcc"] = final_bcc
+            raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
+
+            try:
+                created = await asyncio.get_event_loop().run_in_executor(
+                    None,
+                    lambda: gmail_service.users()
+                    .drafts()
+                    .create(userId="me", body={"message": {"raw": raw}})
+                    .execute(),
+                )
+            except Exception as api_err:
+                from googleapiclient.errors import HttpError
+
+                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                    logger.warning(
+                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
+                    )
+                    return {
+                        "status": "insufficient_permissions",
+                        "connector_id": actual_connector_id,
+                        "message": "This Gmail account needs additional permissions. Please re-authenticate.",
+                    }
+                raise
+
+            logger.info(
+                f"Gmail draft created: id={created.get('id')}"
+            )
+
+            kb_message_suffix = ""
+            try:
+                from app.services.gmail import GmailKBSyncService
+
+                kb_service = GmailKBSyncService(db_session)
+                draft_message = created.get("message", {})
+                kb_result = await kb_service.sync_after_create(
+                    message_id=draft_message.get("id", ""),
+                    thread_id=draft_message.get("threadId", ""),
+                    subject=final_subject,
+                    sender="me",
+                    date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
+                    body_text=final_body,
+                    connector_id=actual_connector_id,
+                    search_space_id=search_space_id,
+                    user_id=user_id,
+                )
+                if kb_result["status"] == "success":
+                    kb_message_suffix = " Your knowledge base has also been updated."
+                else:
+                    kb_message_suffix = " This draft will be added to your knowledge base in the next scheduled sync."
+            except Exception as kb_err:
+                logger.warning(f"KB sync after create failed: {kb_err}")
+                kb_message_suffix = " This draft will be added to your knowledge base in the next scheduled sync."
+
+            return {
+                "status": "success",
+                "draft_id": created.get("id"),
+                "message": f"Successfully created Gmail draft with subject '{final_subject}'.{kb_message_suffix}",
+            }
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error creating Gmail draft: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while creating the draft. Please try again.",
+            }
+
+    return create_gmail_draft
diff --git a/surfsense_backend/app/agents/new_chat/tools/gmail/send_email.py b/surfsense_backend/app/agents/new_chat/tools/gmail/send_email.py
new file mode 100644
index 000000000..93c7933a5
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/gmail/send_email.py
@@ -0,0 +1,321 @@
+import asyncio
+import base64
+import logging
+from datetime import datetime
+from email.mime.text import MIMEText
+from typing import Any
+
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.gmail import GmailToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_send_gmail_email_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def send_gmail_email(
+        to: str,
+        subject: str,
+        body: str,
+        cc: str | None = None,
+        bcc: str | None = None,
+    ) -> dict[str, Any]:
+        """Send an email via Gmail.
+
+        Use when the user explicitly asks to send an email. This sends the
+        email immediately - it cannot be unsent.
+
+        Args:
+            to: Recipient email address.
+            subject: Email subject line.
+            body: Email body content.
+            cc: Optional CC recipient(s), comma-separated.
+            bcc: Optional BCC recipient(s), comma-separated.
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", or "error"
+            - message_id: Gmail message ID (if success)
+            - thread_id: Gmail thread ID (if success)
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined the action.
+              Respond with a brief acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "insufficient_permissions", the connector lacks the required OAuth scope.
+              Inform the user they need to re-authenticate and do NOT retry the action.
+
+        Examples:
+            - "Send an email to alice@example.com about the meeting"
+            - "Email Bob the project update"
+        """
+        logger.info(
+            f"send_gmail_email called: to='{to}', subject='{subject}'"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Gmail tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GmailToolMetadataService(db_session)
+            context = await metadata_service.get_creation_context(
+                search_space_id, user_id
+            )
+
+            if "error" in context:
+                logger.error(f"Failed to fetch creation context: {context['error']}")
+                return {"status": "error", "message": context["error"]}
+
+            accounts = context.get("accounts", [])
+            if accounts and all(a.get("auth_expired") for a in accounts):
+                logger.warning("All Gmail accounts have expired authentication")
+                return {
+                    "status": "auth_error",
+                    "message": "All connected Gmail accounts need re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "gmail",
+                }
+
+            logger.info(
+                f"Requesting approval for sending Gmail email: to='{to}', subject='{subject}'"
+            )
+            approval = interrupt(
+                {
+                    "type": "gmail_email_send",
+                    "action": {
+                        "tool": "send_gmail_email",
+                        "params": {
+                            "to": to,
+                            "subject": subject,
+                            "body": body,
+                            "cc": cc,
+                            "bcc": bcc,
+                            "connector_id": None,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The email was not sent. Do not ask again or suggest alternatives.",
+                }
+
+            final_params: dict[str, Any] = {}
+            edited_action = decision.get("edited_action")
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_to = final_params.get("to", to)
+            final_subject = final_params.get("subject", subject)
+            final_body = final_params.get("body", body)
+            final_cc = final_params.get("cc", cc)
+            final_bcc = final_params.get("bcc", bcc)
+            final_connector_id = final_params.get("connector_id")
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _GMAIL_TYPES = [
+                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+            ]
+
+            if final_connector_id is not None:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Gmail connector is invalid or has been disconnected.",
+                    }
+                actual_connector_id = connector.id
+            else:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "No Gmail connector found. Please connect Gmail in your workspace settings.",
+                    }
+                actual_connector_id = connector.id
+
+            logger.info(
+                f"Sending Gmail email: to='{final_to}', subject='{final_subject}', connector={actual_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this Gmail connector.",
+                    }
+            else:
+                from google.oauth2.credentials import Credentials
+
+                from app.config import config
+                from app.utils.oauth_security import TokenEncryption
+
+                config_data = dict(connector.config)
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and config.SECRET_KEY:
+                    token_encryption = TokenEncryption(config.SECRET_KEY)
+                    if config_data.get("token"):
+                        config_data["token"] = token_encryption.decrypt_token(
+                            config_data["token"]
+                        )
+                    if config_data.get("refresh_token"):
+                        config_data["refresh_token"] = token_encryption.decrypt_token(
+                            config_data["refresh_token"]
+                        )
+                    if config_data.get("client_secret"):
+                        config_data["client_secret"] = token_encryption.decrypt_token(
+                            config_data["client_secret"]
+                        )
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            from googleapiclient.discovery import build
+
+            gmail_service = build("gmail", "v1", credentials=creds)
+
+            message = MIMEText(final_body)
+            message["to"] = final_to
+            message["subject"] = final_subject
+            if final_cc:
+                message["cc"] = final_cc
+            if final_bcc:
+                message["bcc"] = final_bcc
+            raw = base64.urlsafe_b64encode(message.as_bytes()).decode()
+
+            try:
+                sent = await asyncio.get_event_loop().run_in_executor(
+                    None,
+                    lambda: gmail_service.users()
+                    .messages()
+                    .send(userId="me", body={"raw": raw})
+                    .execute(),
+                )
+            except Exception as api_err:
+                from googleapiclient.errors import HttpError
+
+                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                    logger.warning(
+                        f"Insufficient permissions for connector {actual_connector_id}: {api_err}"
+                    )
+                    return {
+                        "status": "insufficient_permissions",
+                        "connector_id": actual_connector_id,
+                        "message": "This Gmail account needs additional permissions. Please re-authenticate.",
+                    }
+                raise
+
+            logger.info(
+                f"Gmail email sent: id={sent.get('id')}, threadId={sent.get('threadId')}"
+            )
+
+            kb_message_suffix = ""
+            try:
+                from app.services.gmail import GmailKBSyncService
+
+                kb_service = GmailKBSyncService(db_session)
+                kb_result = await kb_service.sync_after_create(
+                    message_id=sent.get("id", ""),
+                    thread_id=sent.get("threadId", ""),
+                    subject=final_subject,
+                    sender="me",
+                    date_str=datetime.now().strftime("%Y-%m-%d %H:%M:%S"),
+                    body_text=final_body,
+                    connector_id=actual_connector_id,
+                    search_space_id=search_space_id,
+                    user_id=user_id,
+                )
+                if kb_result["status"] == "success":
+                    kb_message_suffix = " Your knowledge base has also been updated."
+                else:
+                    kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
+            except Exception as kb_err:
+                logger.warning(f"KB sync after send failed: {kb_err}")
+                kb_message_suffix = " This email will be added to your knowledge base in the next scheduled sync."
+
+            return {
+                "status": "success",
+                "message_id": sent.get("id"),
+                "thread_id": sent.get("threadId"),
+                "message": f"Successfully sent email to '{final_to}' with subject '{final_subject}'.{kb_message_suffix}",
+            }
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error sending Gmail email: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while sending the email. Please try again.",
+            }
+
+    return send_gmail_email
diff --git a/surfsense_backend/app/agents/new_chat/tools/gmail/trash_email.py b/surfsense_backend/app/agents/new_chat/tools/gmail/trash_email.py
new file mode 100644
index 000000000..417839bb1
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/gmail/trash_email.py
@@ -0,0 +1,319 @@
+import asyncio
+import logging
+from datetime import datetime
+from typing import Any
+
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.gmail import GmailToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_trash_gmail_email_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def trash_gmail_email(
+        email_subject_or_id: str,
+        delete_from_kb: bool = False,
+    ) -> dict[str, Any]:
+        """Move an email to trash in Gmail.
+
+        Use when the user asks to delete, remove, or trash an email.
+
+        Args:
+            email_subject_or_id: The exact subject line or message ID of the
+                email to trash (as it appears in the inbox).
+            delete_from_kb: Whether to also remove the email from the knowledge base.
+                           Default is False.
+                           Set to True to remove from both Gmail and knowledge base.
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", "not_found", or "error"
+            - message_id: Gmail message ID (if success)
+            - deleted_from_kb: whether the document was removed from the knowledge base
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined. Respond with a brief
+              acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "not_found", relay the exact message to the user and ask them
+              to verify the email subject or check if it has been indexed.
+            - If status is "insufficient_permissions", the connector lacks the required OAuth scope.
+              Inform the user they need to re-authenticate and do NOT retry this tool.
+
+        Examples:
+            - "Delete the email about 'Meeting Cancelled'"
+            - "Trash the email from Bob about the project"
+        """
+        logger.info(
+            f"trash_gmail_email called: email_subject_or_id='{email_subject_or_id}', delete_from_kb={delete_from_kb}"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Gmail tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GmailToolMetadataService(db_session)
+            context = await metadata_service.get_trash_context(
+                search_space_id, user_id, email_subject_or_id
+            )
+
+            if "error" in context:
+                error_msg = context["error"]
+                if "not found" in error_msg.lower():
+                    logger.warning(f"Email not found: {error_msg}")
+                    return {"status": "not_found", "message": error_msg}
+                logger.error(f"Failed to fetch trash context: {error_msg}")
+                return {"status": "error", "message": error_msg}
+
+            account = context.get("account", {})
+            if account.get("auth_expired"):
+                logger.warning(
+                    "Gmail account %s has expired authentication",
+                    account.get("id"),
+                )
+                return {
+                    "status": "auth_error",
+                    "message": "The Gmail account for this email needs re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "gmail",
+                }
+
+            email = context["email"]
+            message_id = email["message_id"]
+            document_id = email.get("document_id")
+            connector_id_from_context = context["account"]["id"]
+
+            if not message_id:
+                return {
+                    "status": "error",
+                    "message": "Message ID is missing from the indexed document. Please re-index the email and try again.",
+                }
+
+            logger.info(
+                f"Requesting approval for trashing Gmail email: '{email_subject_or_id}' (message_id={message_id}, delete_from_kb={delete_from_kb})"
+            )
+            approval = interrupt(
+                {
+                    "type": "gmail_email_trash",
+                    "action": {
+                        "tool": "trash_gmail_email",
+                        "params": {
+                            "message_id": message_id,
+                            "connector_id": connector_id_from_context,
+                            "delete_from_kb": delete_from_kb,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The email was not trashed. Do not ask again or suggest alternatives.",
+                }
+
+            edited_action = decision.get("edited_action")
+            final_params: dict[str, Any] = {}
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_message_id = final_params.get("message_id", message_id)
+            final_connector_id = final_params.get(
+                "connector_id", connector_id_from_context
+            )
+            final_delete_from_kb = final_params.get("delete_from_kb", delete_from_kb)
+
+            if not final_connector_id:
+                return {
+                    "status": "error",
+                    "message": "No connector found for this email.",
+                }
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _GMAIL_TYPES = [
+                SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+            ]
+
+            result = await db_session.execute(
+                select(SearchSourceConnector).filter(
+                    SearchSourceConnector.id == final_connector_id,
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type.in_(_GMAIL_TYPES),
+                )
+            )
+            connector = result.scalars().first()
+            if not connector:
+                return {
+                    "status": "error",
+                    "message": "Selected Gmail connector is invalid or has been disconnected.",
+                }
+
+            logger.info(
+                f"Trashing Gmail email: message_id='{final_message_id}', connector={final_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this Gmail connector.",
+                    }
+            else:
+                from google.oauth2.credentials import Credentials
+
+                from app.config import config
+                from app.utils.oauth_security import TokenEncryption
+
+                config_data = dict(connector.config)
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and config.SECRET_KEY:
+                    token_encryption = TokenEncryption(config.SECRET_KEY)
+                    if config_data.get("token"):
+                        config_data["token"] = token_encryption.decrypt_token(
+                            config_data["token"]
+                        )
+                    if config_data.get("refresh_token"):
+                        config_data["refresh_token"] = token_encryption.decrypt_token(
+                            config_data["refresh_token"]
+                        )
+                    if config_data.get("client_secret"):
+                        config_data["client_secret"] = token_encryption.decrypt_token(
+                            config_data["client_secret"]
+                        )
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            from googleapiclient.discovery import build
+
+            gmail_service = build("gmail", "v1", credentials=creds)
+
+            try:
+                await asyncio.get_event_loop().run_in_executor(
+                    None,
+                    lambda: gmail_service.users()
+                    .messages()
+                    .trash(userId="me", id=final_message_id)
+                    .execute(),
+                )
+            except Exception as api_err:
+                from googleapiclient.errors import HttpError
+
+                if isinstance(api_err, HttpError) and api_err.resp.status == 403:
+                    logger.warning(
+                        f"Insufficient permissions for connector {connector.id}: {api_err}"
+                    )
+                    return {
+                        "status": "insufficient_permissions",
+                        "connector_id": connector.id,
+                        "message": "This Gmail account needs additional permissions. Please re-authenticate.",
+                    }
+                raise
+
+            logger.info(
+                f"Gmail email trashed: message_id={final_message_id}"
+            )
+
+            trash_result: dict[str, Any] = {
+                "status": "success",
+                "message_id": final_message_id,
+                "message": f"Successfully moved email '{email.get('subject', email_subject_or_id)}' to trash.",
+            }
+
+            deleted_from_kb = False
+            if final_delete_from_kb and document_id:
+                try:
+                    from app.db import Document
+
+                    doc_result = await db_session.execute(
+                        select(Document).filter(Document.id == document_id)
+                    )
+                    document = doc_result.scalars().first()
+                    if document:
+                        await db_session.delete(document)
+                        await db_session.commit()
+                        deleted_from_kb = True
+                        logger.info(
+                            f"Deleted document {document_id} from knowledge base"
+                        )
+                    else:
+                        logger.warning(f"Document {document_id} not found in KB")
+                except Exception as e:
+                    logger.error(f"Failed to delete document from KB: {e}")
+                    await db_session.rollback()
+                    trash_result["warning"] = (
+                        f"Email trashed, but failed to remove from knowledge base: {e!s}"
+                    )
+
+            trash_result["deleted_from_kb"] = deleted_from_kb
+            if deleted_from_kb:
+                trash_result["message"] = (
+                    f"{trash_result.get('message', '')} (also removed from knowledge base)"
+                )
+
+            return trash_result
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error trashing Gmail email: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while trashing the email. Please try again.",
+            }
+
+    return trash_gmail_email
diff --git a/surfsense_backend/app/agents/new_chat/tools/google_calendar/__init__.py b/surfsense_backend/app/agents/new_chat/tools/google_calendar/__init__.py
new file mode 100644
index 000000000..4fea648f0
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/google_calendar/__init__.py
@@ -0,0 +1,15 @@
+from app.agents.new_chat.tools.google_calendar.create_event import (
+    create_create_calendar_event_tool,
+)
+from app.agents.new_chat.tools.google_calendar.update_event import (
+    create_update_calendar_event_tool,
+)
+from app.agents.new_chat.tools.google_calendar.delete_event import (
+    create_delete_calendar_event_tool,
+)
+
+__all__ = [
+    "create_create_calendar_event_tool",
+    "create_update_calendar_event_tool",
+    "create_delete_calendar_event_tool",
+]
diff --git a/surfsense_backend/app/agents/new_chat/tools/google_calendar/create_event.py b/surfsense_backend/app/agents/new_chat/tools/google_calendar/create_event.py
new file mode 100644
index 000000000..cf96870df
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/google_calendar/create_event.py
@@ -0,0 +1,310 @@
+import asyncio
+import logging
+from datetime import datetime
+from typing import Any
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.google_calendar import GoogleCalendarToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_create_calendar_event_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def create_calendar_event(
+        summary: str,
+        start_datetime: str,
+        end_datetime: str,
+        description: str | None = None,
+        location: str | None = None,
+        attendees: list[str] | None = None,
+    ) -> dict[str, Any]:
+        """Create a new event on Google Calendar.
+
+        Use when the user asks to schedule, create, or add a calendar event.
+        Ask for event details if not provided.
+
+        Args:
+            summary: The event title.
+            start_datetime: Start time in ISO 8601 format (e.g. "2026-03-20T10:00:00").
+            end_datetime: End time in ISO 8601 format (e.g. "2026-03-20T11:00:00").
+            description: Optional event description.
+            location: Optional event location.
+            attendees: Optional list of attendee email addresses.
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", "auth_error", or "error"
+            - event_id: Google Calendar event ID (if success)
+            - html_link: URL to open the event (if success)
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined the action.
+              Respond with a brief acknowledgment and do NOT retry or suggest alternatives.
+
+        Examples:
+            - "Schedule a meeting with John tomorrow at 10am"
+            - "Create a calendar event for the team standup"
+        """
+        logger.info(
+            f"create_calendar_event called: summary='{summary}', start='{start_datetime}', end='{end_datetime}'"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Google Calendar tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GoogleCalendarToolMetadataService(db_session)
+            context = await metadata_service.get_creation_context(
+                search_space_id, user_id
+            )
+
+            if "error" in context:
+                logger.error(f"Failed to fetch creation context: {context['error']}")
+                return {"status": "error", "message": context["error"]}
+
+            accounts = context.get("accounts", [])
+            if accounts and all(a.get("auth_expired") for a in accounts):
+                logger.warning("All Google Calendar accounts have expired authentication")
+                return {
+                    "status": "auth_error",
+                    "message": "All connected Google Calendar accounts need re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "google_calendar",
+                }
+
+            logger.info(
+                f"Requesting approval for creating calendar event: summary='{summary}'"
+            )
+            approval = interrupt(
+                {
+                    "type": "google_calendar_event_creation",
+                    "action": {
+                        "tool": "create_calendar_event",
+                        "params": {
+                            "summary": summary,
+                            "start_datetime": start_datetime,
+                            "end_datetime": end_datetime,
+                            "description": description,
+                            "location": location,
+                            "attendees": attendees,
+                            "timezone": context.get("timezone"),
+                            "connector_id": None,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The event was not created. Do not ask again or suggest alternatives.",
+                }
+
+            final_params: dict[str, Any] = {}
+            edited_action = decision.get("edited_action")
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_summary = final_params.get("summary", summary)
+            final_start_datetime = final_params.get("start_datetime", start_datetime)
+            final_end_datetime = final_params.get("end_datetime", end_datetime)
+            final_description = final_params.get("description", description)
+            final_location = final_params.get("location", location)
+            final_attendees = final_params.get("attendees", attendees)
+            final_connector_id = final_params.get("connector_id")
+
+            if not final_summary or not final_summary.strip():
+                return {"status": "error", "message": "Event summary cannot be empty."}
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _CALENDAR_TYPES = [
+                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+            ]
+
+            if final_connector_id is not None:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.id == final_connector_id,
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "Selected Google Calendar connector is invalid or has been disconnected.",
+                    }
+                actual_connector_id = connector.id
+            else:
+                result = await db_session.execute(
+                    select(SearchSourceConnector).filter(
+                        SearchSourceConnector.search_space_id == search_space_id,
+                        SearchSourceConnector.user_id == user_id,
+                        SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+                    )
+                )
+                connector = result.scalars().first()
+                if not connector:
+                    return {
+                        "status": "error",
+                        "message": "No Google Calendar connector found. Please connect Google Calendar in your workspace settings.",
+                    }
+                actual_connector_id = connector.id
+
+            logger.info(
+                f"Creating calendar event: summary='{final_summary}', connector={actual_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this connector.",
+                    }
+            else:
+                config_data = dict(connector.config)
+
+                from app.config import config as app_config
+                from app.utils.oauth_security import TokenEncryption
+
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and app_config.SECRET_KEY:
+                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                    for key in ("token", "refresh_token", "client_secret"):
+                        if config_data.get(key):
+                            config_data[key] = token_encryption.decrypt_token(config_data[key])
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            service = await asyncio.get_event_loop().run_in_executor(
+                None, lambda: build("calendar", "v3", credentials=creds)
+            )
+
+            tz = context.get("timezone", "UTC")
+            event_body: dict[str, Any] = {
+                "summary": final_summary,
+                "start": {"dateTime": final_start_datetime, "timeZone": tz},
+                "end": {"dateTime": final_end_datetime, "timeZone": tz},
+            }
+            if final_description:
+                event_body["description"] = final_description
+            if final_location:
+                event_body["location"] = final_location
+            if final_attendees:
+                event_body["attendees"] = [
+                    {"email": e.strip()} for e in final_attendees if e.strip()
+                ]
+
+            created = await asyncio.get_event_loop().run_in_executor(
+                None,
+                lambda: service.events()
+                .insert(calendarId="primary", body=event_body)
+                .execute(),
+            )
+
+            logger.info(
+                f"Calendar event created: id={created.get('id')}, summary={created.get('summary')}"
+            )
+
+            kb_message_suffix = ""
+            try:
+                from app.services.google_calendar import GoogleCalendarKBSyncService
+
+                kb_service = GoogleCalendarKBSyncService(db_session)
+                kb_result = await kb_service.sync_after_create(
+                    event_id=created.get("id"),
+                    event_summary=final_summary,
+                    calendar_id="primary",
+                    start_time=final_start_datetime,
+                    end_time=final_end_datetime,
+                    location=final_location,
+                    html_link=created.get("htmlLink"),
+                    description=final_description,
+                    connector_id=actual_connector_id,
+                    search_space_id=search_space_id,
+                    user_id=user_id,
+                )
+                if kb_result["status"] == "success":
+                    kb_message_suffix = " Your knowledge base has also been updated."
+                else:
+                    kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
+            except Exception as kb_err:
+                logger.warning(f"KB sync after create failed: {kb_err}")
+                kb_message_suffix = " This event will be added to your knowledge base in the next scheduled sync."
+
+            return {
+                "status": "success",
+                "event_id": created.get("id"),
+                "html_link": created.get("htmlLink"),
+                "message": f"Successfully created '{final_summary}' on Google Calendar.{kb_message_suffix}",
+            }
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error creating calendar event: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while creating the event. Please try again.",
+            }
+
+    return create_calendar_event
diff --git a/surfsense_backend/app/agents/new_chat/tools/google_calendar/delete_event.py b/surfsense_backend/app/agents/new_chat/tools/google_calendar/delete_event.py
new file mode 100644
index 000000000..3a4570737
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/google_calendar/delete_event.py
@@ -0,0 +1,295 @@
+import asyncio
+import logging
+from datetime import datetime
+from typing import Any
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.google_calendar import GoogleCalendarToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_delete_calendar_event_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def delete_calendar_event(
+        event_title_or_id: str,
+        delete_from_kb: bool = False,
+    ) -> dict[str, Any]:
+        """Delete a Google Calendar event.
+
+        Use when the user asks to delete, remove, or cancel a calendar event.
+
+        Args:
+            event_title_or_id: The exact title or event ID of the event to delete.
+            delete_from_kb: Whether to also remove the event from the knowledge base.
+                          Default is False.
+                          Set to True to remove from both Google Calendar and knowledge base.
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", "not_found", "auth_error", or "error"
+            - event_id: Google Calendar event ID (if success)
+            - deleted_from_kb: whether the document was removed from the knowledge base
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined. Respond with a brief
+              acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "not_found", relay the exact message to the user and ask them
+              to verify the event name or check if it has been indexed.
+
+        Examples:
+            - "Delete the team standup event"
+            - "Cancel my dentist appointment on Friday"
+        """
+        logger.info(
+            f"delete_calendar_event called: event_ref='{event_title_or_id}', delete_from_kb={delete_from_kb}"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Google Calendar tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GoogleCalendarToolMetadataService(db_session)
+            context = await metadata_service.get_deletion_context(
+                search_space_id, user_id, event_title_or_id
+            )
+
+            if "error" in context:
+                error_msg = context["error"]
+                if "not found" in error_msg.lower():
+                    logger.warning(f"Event not found: {error_msg}")
+                    return {"status": "not_found", "message": error_msg}
+                logger.error(f"Failed to fetch deletion context: {error_msg}")
+                return {"status": "error", "message": error_msg}
+
+            account = context.get("account", {})
+            if account.get("auth_expired"):
+                logger.warning(
+                    "Google Calendar account %s has expired authentication",
+                    account.get("id"),
+                )
+                return {
+                    "status": "auth_error",
+                    "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "google_calendar",
+                }
+
+            event = context["event"]
+            event_id = event["event_id"]
+            document_id = event.get("document_id")
+            connector_id_from_context = context["account"]["id"]
+
+            if not event_id:
+                return {
+                    "status": "error",
+                    "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
+                }
+
+            logger.info(
+                f"Requesting approval for deleting calendar event: '{event_title_or_id}' (event_id={event_id}, delete_from_kb={delete_from_kb})"
+            )
+            approval = interrupt(
+                {
+                    "type": "google_calendar_event_deletion",
+                    "action": {
+                        "tool": "delete_calendar_event",
+                        "params": {
+                            "event_id": event_id,
+                            "connector_id": connector_id_from_context,
+                            "delete_from_kb": delete_from_kb,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The event was not deleted. Do not ask again or suggest alternatives.",
+                }
+
+            edited_action = decision.get("edited_action")
+            final_params: dict[str, Any] = {}
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_event_id = final_params.get("event_id", event_id)
+            final_connector_id = final_params.get(
+                "connector_id", connector_id_from_context
+            )
+            final_delete_from_kb = final_params.get("delete_from_kb", delete_from_kb)
+
+            if not final_connector_id:
+                return {
+                    "status": "error",
+                    "message": "No connector found for this event.",
+                }
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _CALENDAR_TYPES = [
+                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+            ]
+
+            result = await db_session.execute(
+                select(SearchSourceConnector).filter(
+                    SearchSourceConnector.id == final_connector_id,
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+                )
+            )
+            connector = result.scalars().first()
+            if not connector:
+                return {
+                    "status": "error",
+                    "message": "Selected Google Calendar connector is invalid or has been disconnected.",
+                }
+
+            actual_connector_id = connector.id
+
+            logger.info(
+                f"Deleting calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this connector.",
+                    }
+            else:
+                config_data = dict(connector.config)
+
+                from app.config import config as app_config
+                from app.utils.oauth_security import TokenEncryption
+
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and app_config.SECRET_KEY:
+                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                    for key in ("token", "refresh_token", "client_secret"):
+                        if config_data.get(key):
+                            config_data[key] = token_encryption.decrypt_token(config_data[key])
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            service = await asyncio.get_event_loop().run_in_executor(
+                None, lambda: build("calendar", "v3", credentials=creds)
+            )
+
+            await asyncio.get_event_loop().run_in_executor(
+                None,
+                lambda: service.events()
+                .delete(calendarId="primary", eventId=final_event_id)
+                .execute(),
+            )
+
+            logger.info(
+                f"Calendar event deleted: event_id={final_event_id}"
+            )
+
+            delete_result: dict[str, Any] = {
+                "status": "success",
+                "event_id": final_event_id,
+                "message": f"Successfully deleted the calendar event '{event.get('summary', event_title_or_id)}'.",
+            }
+
+            deleted_from_kb = False
+            if final_delete_from_kb and document_id:
+                try:
+                    from app.db import Document
+
+                    doc_result = await db_session.execute(
+                        select(Document).filter(Document.id == document_id)
+                    )
+                    document = doc_result.scalars().first()
+                    if document:
+                        await db_session.delete(document)
+                        await db_session.commit()
+                        deleted_from_kb = True
+                        logger.info(
+                            f"Deleted document {document_id} from knowledge base"
+                        )
+                    else:
+                        logger.warning(f"Document {document_id} not found in KB")
+                except Exception as e:
+                    logger.error(f"Failed to delete document from KB: {e}")
+                    await db_session.rollback()
+                    delete_result["warning"] = (
+                        f"Event deleted, but failed to remove from knowledge base: {e!s}"
+                    )
+
+            delete_result["deleted_from_kb"] = deleted_from_kb
+            if deleted_from_kb:
+                delete_result["message"] = (
+                    f"{delete_result.get('message', '')} (also removed from knowledge base)"
+                )
+
+            return delete_result
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error deleting calendar event: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while deleting the event. Please try again.",
+            }
+
+    return delete_calendar_event
diff --git a/surfsense_backend/app/agents/new_chat/tools/google_calendar/update_event.py b/surfsense_backend/app/agents/new_chat/tools/google_calendar/update_event.py
new file mode 100644
index 000000000..98f20a3c7
--- /dev/null
+++ b/surfsense_backend/app/agents/new_chat/tools/google_calendar/update_event.py
@@ -0,0 +1,325 @@
+import asyncio
+import logging
+from datetime import datetime
+from typing import Any
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.services.google_calendar import GoogleCalendarToolMetadataService
+
+logger = logging.getLogger(__name__)
+
+
+def create_update_calendar_event_tool(
+    db_session: AsyncSession | None = None,
+    search_space_id: int | None = None,
+    user_id: str | None = None,
+):
+    @tool
+    async def update_calendar_event(
+        event_title_or_id: str,
+        new_summary: str | None = None,
+        new_start_datetime: str | None = None,
+        new_end_datetime: str | None = None,
+        new_description: str | None = None,
+        new_location: str | None = None,
+        new_attendees: list[str] | None = None,
+    ) -> dict[str, Any]:
+        """Update an existing Google Calendar event.
+
+        Use when the user asks to modify, reschedule, or change a calendar event.
+
+        Args:
+            event_title_or_id: The exact title or event ID of the event to update.
+            new_summary: New event title (if changing).
+            new_start_datetime: New start time in ISO 8601 format (if rescheduling).
+            new_end_datetime: New end time in ISO 8601 format (if rescheduling).
+            new_description: New event description (if changing).
+            new_location: New event location (if changing).
+            new_attendees: New list of attendee email addresses (if changing).
+
+        Returns:
+            Dictionary with:
+            - status: "success", "rejected", "not_found", "auth_error", or "error"
+            - event_id: Google Calendar event ID (if success)
+            - html_link: URL to open the event (if success)
+            - message: Result message
+
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined. Respond with a brief
+              acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "not_found", relay the exact message to the user and ask them
+              to verify the event name or check if it has been indexed.
+
+        Examples:
+            - "Reschedule the team standup to 3pm"
+            - "Change the location of my dentist appointment"
+        """
+        logger.info(
+            f"update_calendar_event called: event_ref='{event_title_or_id}'"
+        )
+
+        if db_session is None or search_space_id is None or user_id is None:
+            return {
+                "status": "error",
+                "message": "Google Calendar tool not properly configured. Please contact support.",
+            }
+
+        try:
+            metadata_service = GoogleCalendarToolMetadataService(db_session)
+            context = await metadata_service.get_update_context(
+                search_space_id, user_id, event_title_or_id
+            )
+
+            if "error" in context:
+                error_msg = context["error"]
+                if "not found" in error_msg.lower():
+                    logger.warning(f"Event not found: {error_msg}")
+                    return {"status": "not_found", "message": error_msg}
+                logger.error(f"Failed to fetch update context: {error_msg}")
+                return {"status": "error", "message": error_msg}
+
+            if context.get("auth_expired"):
+                logger.warning(
+                    "Google Calendar account has expired authentication"
+                )
+                return {
+                    "status": "auth_error",
+                    "message": "The Google Calendar account for this event needs re-authentication. Please re-authenticate in your connector settings.",
+                    "connector_type": "google_calendar",
+                }
+
+            event = context["event"]
+            event_id = event["event_id"]
+            document_id = event.get("document_id")
+            connector_id_from_context = context["account"]["id"]
+
+            if not event_id:
+                return {
+                    "status": "error",
+                    "message": "Event ID is missing from the indexed document. Please re-index the event and try again.",
+                }
+
+            logger.info(
+                f"Requesting approval for updating calendar event: '{event_title_or_id}' (event_id={event_id})"
+            )
+            approval = interrupt(
+                {
+                    "type": "google_calendar_event_update",
+                    "action": {
+                        "tool": "update_calendar_event",
+                        "params": {
+                            "event_id": event_id,
+                            "document_id": document_id,
+                            "connector_id": connector_id_from_context,
+                            "new_summary": new_summary,
+                            "new_start_datetime": new_start_datetime,
+                            "new_end_datetime": new_end_datetime,
+                            "new_description": new_description,
+                            "new_location": new_location,
+                            "new_attendees": new_attendees,
+                        },
+                    },
+                    "context": context,
+                }
+            )
+
+            decisions_raw = (
+                approval.get("decisions", []) if isinstance(approval, dict) else []
+            )
+            decisions = (
+                decisions_raw if isinstance(decisions_raw, list) else [decisions_raw]
+            )
+            decisions = [d for d in decisions if isinstance(d, dict)]
+            if not decisions:
+                logger.warning("No approval decision received")
+                return {"status": "error", "message": "No approval decision received"}
+
+            decision = decisions[0]
+            decision_type = decision.get("type") or decision.get("decision_type")
+            logger.info(f"User decision: {decision_type}")
+
+            if decision_type == "reject":
+                return {
+                    "status": "rejected",
+                    "message": "User declined. The event was not updated. Do not ask again or suggest alternatives.",
+                }
+
+            edited_action = decision.get("edited_action")
+            final_params: dict[str, Any] = {}
+            if isinstance(edited_action, dict):
+                edited_args = edited_action.get("args")
+                if isinstance(edited_args, dict):
+                    final_params = edited_args
+            elif isinstance(decision.get("args"), dict):
+                final_params = decision["args"]
+
+            final_event_id = final_params.get("event_id", event_id)
+            final_connector_id = final_params.get(
+                "connector_id", connector_id_from_context
+            )
+            final_new_summary = final_params.get("new_summary", new_summary)
+            final_new_start_datetime = final_params.get("new_start_datetime", new_start_datetime)
+            final_new_end_datetime = final_params.get("new_end_datetime", new_end_datetime)
+            final_new_description = final_params.get("new_description", new_description)
+            final_new_location = final_params.get("new_location", new_location)
+            final_new_attendees = final_params.get("new_attendees", new_attendees)
+
+            if not final_connector_id:
+                return {
+                    "status": "error",
+                    "message": "No connector found for this event.",
+                }
+
+            from sqlalchemy.future import select
+
+            from app.db import SearchSourceConnector, SearchSourceConnectorType
+
+            _CALENDAR_TYPES = [
+                SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+                SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+            ]
+
+            result = await db_session.execute(
+                select(SearchSourceConnector).filter(
+                    SearchSourceConnector.id == final_connector_id,
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type.in_(_CALENDAR_TYPES),
+                )
+            )
+            connector = result.scalars().first()
+            if not connector:
+                return {
+                    "status": "error",
+                    "message": "Selected Google Calendar connector is invalid or has been disconnected.",
+                }
+
+            actual_connector_id = connector.id
+
+            logger.info(
+                f"Updating calendar event: event_id='{final_event_id}', connector={actual_connector_id}"
+            )
+
+            if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR:
+                from app.utils.google_credentials import build_composio_credentials
+
+                cca_id = connector.config.get("composio_connected_account_id")
+                if cca_id:
+                    creds = build_composio_credentials(cca_id)
+                else:
+                    return {
+                        "status": "error",
+                        "message": "Composio connected account ID not found for this connector.",
+                    }
+            else:
+                config_data = dict(connector.config)
+
+                from app.config import config as app_config
+                from app.utils.oauth_security import TokenEncryption
+
+                token_encrypted = config_data.get("_token_encrypted", False)
+                if token_encrypted and app_config.SECRET_KEY:
+                    token_encryption = TokenEncryption(app_config.SECRET_KEY)
+                    for key in ("token", "refresh_token", "client_secret"):
+                        if config_data.get(key):
+                            config_data[key] = token_encryption.decrypt_token(config_data[key])
+
+                exp = config_data.get("expiry", "")
+                if exp:
+                    exp = exp.replace("Z", "")
+
+                creds = Credentials(
+                    token=config_data.get("token"),
+                    refresh_token=config_data.get("refresh_token"),
+                    token_uri=config_data.get("token_uri"),
+                    client_id=config_data.get("client_id"),
+                    client_secret=config_data.get("client_secret"),
+                    scopes=config_data.get("scopes", []),
+                    expiry=datetime.fromisoformat(exp) if exp else None,
+                )
+
+            service = await asyncio.get_event_loop().run_in_executor(
+                None, lambda: build("calendar", "v3", credentials=creds)
+            )
+
+            update_body: dict[str, Any] = {}
+            if final_new_summary is not None:
+                update_body["summary"] = final_new_summary
+            if final_new_start_datetime is not None:
+                tz = context.get("timezone", "UTC") if isinstance(context, dict) else "UTC"
+                update_body["start"] = {"dateTime": final_new_start_datetime, "timeZone": tz}
+            if final_new_end_datetime is not None:
+                tz = context.get("timezone", "UTC") if isinstance(context, dict) else "UTC"
+                update_body["end"] = {"dateTime": final_new_end_datetime, "timeZone": tz}
+            if final_new_description is not None:
+                update_body["description"] = final_new_description
+            if final_new_location is not None:
+                update_body["location"] = final_new_location
+            if final_new_attendees is not None:
+                update_body["attendees"] = [
+                    {"email": e.strip()} for e in final_new_attendees if e.strip()
+                ]
+
+            if not update_body:
+                return {
+                    "status": "error",
+                    "message": "No changes specified. Please provide at least one field to update.",
+                }
+
+            updated = await asyncio.get_event_loop().run_in_executor(
+                None,
+                lambda: service.events()
+                .patch(calendarId="primary", eventId=final_event_id, body=update_body)
+                .execute(),
+            )
+
+            logger.info(
+                f"Calendar event updated: event_id={final_event_id}"
+            )
+
+            kb_message_suffix = ""
+            if document_id is not None:
+                try:
+                    from app.services.google_calendar import GoogleCalendarKBSyncService
+
+                    kb_service = GoogleCalendarKBSyncService(db_session)
+                    kb_result = await kb_service.sync_after_update(
+                        document_id=document_id,
+                        event_id=final_event_id,
+                        connector_id=actual_connector_id,
+                        search_space_id=search_space_id,
+                        user_id=user_id,
+                    )
+                    if kb_result["status"] == "success":
+                        kb_message_suffix = " Your knowledge base has also been updated."
+                    else:
+                        kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
+                except Exception as kb_err:
+                    logger.warning(f"KB sync after update failed: {kb_err}")
+                    kb_message_suffix = " The knowledge base will be updated in the next scheduled sync."
+
+            return {
+                "status": "success",
+                "event_id": final_event_id,
+                "html_link": updated.get("htmlLink"),
+                "message": f"Successfully updated the calendar event.{kb_message_suffix}",
+            }
+
+        except Exception as e:
+            from langgraph.errors import GraphInterrupt
+
+            if isinstance(e, GraphInterrupt):
+                raise
+
+            logger.error(f"Error updating calendar event: {e}", exc_info=True)
+            return {
+                "status": "error",
+                "message": "Something went wrong while updating the event. Please try again.",
+            }
+
+    return update_calendar_event
diff --git a/surfsense_backend/app/agents/new_chat/tools/registry.py b/surfsense_backend/app/agents/new_chat/tools/registry.py
index c2592207a..6fa3a1586 100644
--- a/surfsense_backend/app/agents/new_chat/tools/registry.py
+++ b/surfsense_backend/app/agents/new_chat/tools/registry.py
@@ -47,6 +47,16 @@ from app.db import ChatVisibility
 
 from .display_image import create_display_image_tool
 from .generate_image import create_generate_image_tool
+from .gmail import (
+    create_create_gmail_draft_tool,
+    create_send_gmail_email_tool,
+    create_trash_gmail_email_tool,
+)
+from .google_calendar import (
+    create_create_calendar_event_tool,
+    create_delete_calendar_event_tool,
+    create_update_calendar_event_tool,
+)
 from .google_drive import (
     create_create_google_drive_file_tool,
     create_delete_google_drive_file_tool,
@@ -336,6 +346,74 @@ BUILTIN_TOOLS: list[ToolDefinition] = [
         ),
         requires=["db_session", "search_space_id", "user_id"],
     ),
+    # =========================================================================
+    # GOOGLE CALENDAR TOOLS - create, update, delete events
+    # Auto-disabled when no Google Calendar connector is configured
+    # =========================================================================
+    ToolDefinition(
+        name="create_calendar_event",
+        description="Create a new event on Google Calendar",
+        factory=lambda deps: create_create_calendar_event_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
+    ToolDefinition(
+        name="update_calendar_event",
+        description="Update an existing indexed Google Calendar event",
+        factory=lambda deps: create_update_calendar_event_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
+    ToolDefinition(
+        name="delete_calendar_event",
+        description="Delete an existing indexed Google Calendar event",
+        factory=lambda deps: create_delete_calendar_event_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
+    # =========================================================================
+    # GMAIL TOOLS - create drafts, send emails, trash emails
+    # Auto-disabled when no Gmail connector is configured
+    # =========================================================================
+    ToolDefinition(
+        name="create_gmail_draft",
+        description="Create a draft email in Gmail",
+        factory=lambda deps: create_create_gmail_draft_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
+    ToolDefinition(
+        name="send_gmail_email",
+        description="Send an email via Gmail",
+        factory=lambda deps: create_send_gmail_email_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
+    ToolDefinition(
+        name="trash_gmail_email",
+        description="Move an indexed email to trash in Gmail",
+        factory=lambda deps: create_trash_gmail_email_tool(
+            db_session=deps["db_session"],
+            search_space_id=deps["search_space_id"],
+            user_id=deps["user_id"],
+        ),
+        requires=["db_session", "search_space_id", "user_id"],
+    ),
 ]
 
 
diff --git a/surfsense_backend/app/services/gmail/__init__.py b/surfsense_backend/app/services/gmail/__init__.py
new file mode 100644
index 000000000..4de115171
--- /dev/null
+++ b/surfsense_backend/app/services/gmail/__init__.py
@@ -0,0 +1,13 @@
+from app.services.gmail.kb_sync_service import GmailKBSyncService
+from app.services.gmail.tool_metadata_service import (
+    GmailAccount,
+    GmailMessage,
+    GmailToolMetadataService,
+)
+
+__all__ = [
+    "GmailAccount",
+    "GmailKBSyncService",
+    "GmailMessage",
+    "GmailToolMetadataService",
+]
diff --git a/surfsense_backend/app/services/gmail/kb_sync_service.py b/surfsense_backend/app/services/gmail/kb_sync_service.py
new file mode 100644
index 000000000..279a6d78e
--- /dev/null
+++ b/surfsense_backend/app/services/gmail/kb_sync_service.py
@@ -0,0 +1,163 @@
+import logging
+from datetime import datetime
+
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from app.db import Document, DocumentType
+from app.services.llm_service import get_user_long_context_llm
+from app.utils.document_converters import (
+    create_document_chunks,
+    embed_text,
+    generate_content_hash,
+    generate_document_summary,
+    generate_unique_identifier_hash,
+)
+
+logger = logging.getLogger(__name__)
+
+
+class GmailKBSyncService:
+    def __init__(self, db_session: AsyncSession):
+        self.db_session = db_session
+
+    async def sync_after_create(
+        self,
+        message_id: str,
+        thread_id: str,
+        subject: str,
+        sender: str,
+        date_str: str,
+        body_text: str | None,
+        connector_id: int,
+        search_space_id: int,
+        user_id: str,
+    ) -> dict:
+        from app.tasks.connector_indexers.base import (
+            check_document_by_unique_identifier,
+            check_duplicate_document_by_hash,
+            get_current_timestamp,
+            safe_set_chunks,
+        )
+
+        try:
+            unique_hash = generate_unique_identifier_hash(
+                DocumentType.GOOGLE_GMAIL_CONNECTOR, message_id, search_space_id
+            )
+
+            existing = await check_document_by_unique_identifier(
+                self.db_session, unique_hash
+            )
+            if existing:
+                logger.info(
+                    "Document for Gmail message %s already exists (doc_id=%s), skipping",
+                    message_id,
+                    existing.id,
+                )
+                return {"status": "success"}
+
+            indexable_content = (
+                f"Gmail Message: {subject}\n\nFrom: {sender}\nDate: {date_str}\n\n"
+                f"{body_text or ''}"
+            ).strip()
+            if not indexable_content:
+                indexable_content = f"Gmail message: {subject}"
+
+            content_hash = generate_content_hash(indexable_content, search_space_id)
+
+            with self.db_session.no_autoflush:
+                dup = await check_duplicate_document_by_hash(
+                    self.db_session, content_hash
+                )
+            if dup:
+                logger.info(
+                    "Content-hash collision for Gmail message %s -- identical content "
+                    "exists in doc %s. Using unique_identifier_hash as content_hash.",
+                    message_id,
+                    dup.id,
+                )
+                content_hash = unique_hash
+
+            user_llm = await get_user_long_context_llm(
+                self.db_session,
+                user_id,
+                search_space_id,
+                disable_streaming=True,
+            )
+
+            doc_metadata_for_summary = {
+                "subject": subject,
+                "sender": sender,
+                "document_type": "Gmail Message",
+                "connector_type": "Gmail",
+            }
+
+            if user_llm:
+                summary_content, summary_embedding = await generate_document_summary(
+                    indexable_content, user_llm, doc_metadata_for_summary
+                )
+            else:
+                logger.warning("No LLM configured -- using fallback summary")
+                summary_content = f"Gmail Message: {subject}\n\n{indexable_content}"
+                summary_embedding = embed_text(summary_content)
+
+            chunks = await create_document_chunks(indexable_content)
+            now_str = datetime.now().strftime("%Y-%m-%d %H:%M:%S")
+
+            document = Document(
+                title=subject,
+                document_type=DocumentType.GOOGLE_GMAIL_CONNECTOR,
+                document_metadata={
+                    "message_id": message_id,
+                    "thread_id": thread_id,
+                    "subject": subject,
+                    "sender": sender,
+                    "date": date_str,
+                    "connector_id": connector_id,
+                    "indexed_at": now_str,
+                },
+                content=summary_content,
+                content_hash=content_hash,
+                unique_identifier_hash=unique_hash,
+                embedding=summary_embedding,
+                search_space_id=search_space_id,
+                connector_id=connector_id,
+                source_markdown=body_text,
+                updated_at=get_current_timestamp(),
+            )
+
+            self.db_session.add(document)
+            await self.db_session.flush()
+            await safe_set_chunks(self.db_session, document, chunks)
+            await self.db_session.commit()
+
+            logger.info(
+                "KB sync after create succeeded: doc_id=%s, subject=%s, chunks=%d",
+                document.id,
+                subject,
+                len(chunks),
+            )
+            return {"status": "success"}
+
+        except Exception as e:
+            error_str = str(e).lower()
+            if (
+                "duplicate key value violates unique constraint" in error_str
+                or "uniqueviolationerror" in error_str
+            ):
+                logger.warning(
+                    "Duplicate constraint hit during KB sync for message %s. "
+                    "Rolling back -- periodic indexer will handle it. Error: %s",
+                    message_id,
+                    e,
+                )
+                await self.db_session.rollback()
+                return {"status": "error", "message": "Duplicate document detected"}
+
+            logger.error(
+                "KB sync after create failed for message %s: %s",
+                message_id,
+                e,
+                exc_info=True,
+            )
+            await self.db_session.rollback()
+            return {"status": "error", "message": str(e)}
diff --git a/surfsense_backend/app/services/gmail/tool_metadata_service.py b/surfsense_backend/app/services/gmail/tool_metadata_service.py
new file mode 100644
index 000000000..bc3685ac6
--- /dev/null
+++ b/surfsense_backend/app/services/gmail/tool_metadata_service.py
@@ -0,0 +1,298 @@
+import asyncio
+import logging
+from dataclasses import dataclass
+from datetime import datetime
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from sqlalchemy import and_, func, or_
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy.future import select
+from sqlalchemy.orm.attributes import flag_modified
+
+from app.db import (
+    Document,
+    DocumentType,
+    SearchSourceConnector,
+    SearchSourceConnectorType,
+)
+from app.utils.google_credentials import build_composio_credentials
+
+logger = logging.getLogger(__name__)
+
+
+@dataclass
+class GmailAccount:
+    id: int
+    name: str
+    email: str
+
+    @classmethod
+    def from_connector(cls, connector: SearchSourceConnector) -> "GmailAccount":
+        return cls(id=connector.id, name=connector.name, email="")
+
+    def to_dict(self) -> dict:
+        return {"id": self.id, "name": self.name, "email": self.email}
+
+
+@dataclass
+class GmailMessage:
+    message_id: str
+    thread_id: str
+    subject: str
+    sender: str
+    date: str
+    connector_id: int
+    document_id: int
+
+    @classmethod
+    def from_document(cls, document: Document) -> "GmailMessage":
+        meta = document.document_metadata or {}
+        return cls(
+            message_id=meta.get("message_id", ""),
+            thread_id=meta.get("thread_id", ""),
+            subject=meta.get("subject", document.title),
+            sender=meta.get("sender", ""),
+            date=meta.get("date", ""),
+            connector_id=document.connector_id,
+            document_id=document.id,
+        )
+
+    def to_dict(self) -> dict:
+        return {
+            "message_id": self.message_id,
+            "thread_id": self.thread_id,
+            "subject": self.subject,
+            "sender": self.sender,
+            "date": self.date,
+            "connector_id": self.connector_id,
+            "document_id": self.document_id,
+        }
+
+
+class GmailToolMetadataService:
+    def __init__(self, db_session: AsyncSession):
+        self._db_session = db_session
+
+    async def _build_credentials(self, connector: SearchSourceConnector) -> Credentials:
+        if (
+            connector.connector_type
+            == SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR
+        ):
+            cca_id = connector.config.get("composio_connected_account_id")
+            if cca_id:
+                return build_composio_credentials(cca_id)
+
+        config_data = dict(connector.config)
+
+        from app.config import config
+        from app.utils.oauth_security import TokenEncryption
+
+        token_encrypted = config_data.get("_token_encrypted", False)
+        if token_encrypted and config.SECRET_KEY:
+            token_encryption = TokenEncryption(config.SECRET_KEY)
+            if config_data.get("token"):
+                config_data["token"] = token_encryption.decrypt_token(
+                    config_data["token"]
+                )
+            if config_data.get("refresh_token"):
+                config_data["refresh_token"] = token_encryption.decrypt_token(
+                    config_data["refresh_token"]
+                )
+            if config_data.get("client_secret"):
+                config_data["client_secret"] = token_encryption.decrypt_token(
+                    config_data["client_secret"]
+                )
+
+        exp = config_data.get("expiry", "")
+        if exp:
+            exp = exp.replace("Z", "")
+
+        return Credentials(
+            token=config_data.get("token"),
+            refresh_token=config_data.get("refresh_token"),
+            token_uri=config_data.get("token_uri"),
+            client_id=config_data.get("client_id"),
+            client_secret=config_data.get("client_secret"),
+            scopes=config_data.get("scopes", []),
+            expiry=datetime.fromisoformat(exp) if exp else None,
+        )
+
+    async def _check_account_health(self, connector_id: int) -> bool:
+        """Check if a Gmail connector's credentials are still valid.
+
+        Uses a lightweight ``users().getProfile(userId='me')`` call.
+
+        Returns True if the credentials are expired/invalid, False if healthy.
+        """
+        try:
+            result = await self._db_session.execute(
+                select(SearchSourceConnector).where(
+                    SearchSourceConnector.id == connector_id
+                )
+            )
+            connector = result.scalar_one_or_none()
+            if not connector:
+                return True
+
+            creds = await self._build_credentials(connector)
+            service = build("gmail", "v1", credentials=creds)
+            await asyncio.get_event_loop().run_in_executor(
+                None, lambda: service.users().getProfile(userId="me").execute()
+            )
+            return False
+        except Exception as e:
+            logger.warning(
+                "Gmail connector %s health check failed: %s",
+                connector_id,
+                e,
+            )
+            return True
+
+    async def _persist_auth_expired(self, connector_id: int) -> None:
+        """Persist ``auth_expired: True`` to the connector config if not already set."""
+        try:
+            result = await self._db_session.execute(
+                select(SearchSourceConnector).where(
+                    SearchSourceConnector.id == connector_id
+                )
+            )
+            db_connector = result.scalar_one_or_none()
+            if db_connector and not db_connector.config.get("auth_expired"):
+                db_connector.config = {**db_connector.config, "auth_expired": True}
+                flag_modified(db_connector, "config")
+                await self._db_session.commit()
+                await self._db_session.refresh(db_connector)
+        except Exception:
+            logger.warning(
+                "Failed to persist auth_expired for connector %s",
+                connector_id,
+                exc_info=True,
+            )
+
+    async def _get_accounts(
+        self, search_space_id: int, user_id: str
+    ) -> list[GmailAccount]:
+        result = await self._db_session.execute(
+            select(SearchSourceConnector)
+            .filter(
+                and_(
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type.in_([
+                        SearchSourceConnectorType.GOOGLE_GMAIL_CONNECTOR,
+                        SearchSourceConnectorType.COMPOSIO_GMAIL_CONNECTOR,
+                    ]),
+                )
+            )
+            .order_by(SearchSourceConnector.last_indexed_at.desc())
+        )
+        connectors = result.scalars().all()
+        return [GmailAccount.from_connector(c) for c in connectors]
+
+    async def get_creation_context(self, search_space_id: int, user_id: str) -> dict:
+        accounts = await self._get_accounts(search_space_id, user_id)
+
+        if not accounts:
+            return {
+                "accounts": [],
+                "error": "No Gmail account connected",
+            }
+
+        accounts_with_status = []
+        for acc in accounts:
+            acc_dict = acc.to_dict()
+            auth_expired = await self._check_account_health(acc.id)
+            acc_dict["auth_expired"] = auth_expired
+            if auth_expired:
+                await self._persist_auth_expired(acc.id)
+            else:
+                try:
+                    result = await self._db_session.execute(
+                        select(SearchSourceConnector).where(
+                            SearchSourceConnector.id == acc.id
+                        )
+                    )
+                    connector = result.scalar_one_or_none()
+                    if connector:
+                        creds = await self._build_credentials(connector)
+                        service = build("gmail", "v1", credentials=creds)
+                        profile = await asyncio.get_event_loop().run_in_executor(
+                            None,
+                            lambda: service.users()
+                            .getProfile(userId="me")
+                            .execute(),
+                        )
+                        acc_dict["email"] = profile.get("emailAddress", "")
+                except Exception:
+                    logger.warning(
+                        "Failed to fetch email for Gmail connector %s",
+                        acc.id,
+                        exc_info=True,
+                    )
+            accounts_with_status.append(acc_dict)
+
+        return {"accounts": accounts_with_status}
+
+    async def get_trash_context(
+        self, search_space_id: int, user_id: str, email_ref: str
+    ) -> dict:
+        document, connector = await self._resolve_email(
+            search_space_id, user_id, email_ref
+        )
+
+        if not document or not connector:
+            return {
+                "error": (
+                    f"Email '{email_ref}' not found in your indexed Gmail messages. "
+                    "This could mean: (1) the email doesn't exist, "
+                    "(2) it hasn't been indexed yet, "
+                    "or (3) the subject is different."
+                )
+            }
+
+        account = GmailAccount.from_connector(connector)
+        message = GmailMessage.from_document(document)
+
+        acc_dict = account.to_dict()
+        auth_expired = await self._check_account_health(connector.id)
+        acc_dict["auth_expired"] = auth_expired
+        if auth_expired:
+            await self._persist_auth_expired(connector.id)
+
+        return {
+            "account": acc_dict,
+            "email": message.to_dict(),
+        }
+
+    async def _resolve_email(
+        self, search_space_id: int, user_id: str, email_ref: str
+    ) -> tuple[Document | None, SearchSourceConnector | None]:
+        result = await self._db_session.execute(
+            select(Document, SearchSourceConnector)
+            .join(
+                SearchSourceConnector,
+                Document.connector_id == SearchSourceConnector.id,
+            )
+            .filter(
+                and_(
+                    Document.search_space_id == search_space_id,
+                    Document.document_type.in_([
+                        DocumentType.GOOGLE_GMAIL_CONNECTOR,
+                        DocumentType.COMPOSIO_GMAIL_CONNECTOR,
+                    ]),
+                    SearchSourceConnector.user_id == user_id,
+                    or_(
+                        func.lower(
+                            Document.document_metadata["subject"].astext
+                        )
+                        == func.lower(email_ref),
+                        func.lower(Document.title) == func.lower(email_ref),
+                    ),
+                )
+            )
+        )
+        row = result.first()
+        if row:
+            return row[0], row[1]
+        return None, None
diff --git a/surfsense_backend/app/services/google_calendar/__init__.py b/surfsense_backend/app/services/google_calendar/__init__.py
new file mode 100644
index 000000000..38368b0a0
--- /dev/null
+++ b/surfsense_backend/app/services/google_calendar/__init__.py
@@ -0,0 +1,13 @@
+from app.services.google_calendar.kb_sync_service import GoogleCalendarKBSyncService
+from app.services.google_calendar.tool_metadata_service import (
+    GoogleCalendarAccount,
+    GoogleCalendarEvent,
+    GoogleCalendarToolMetadataService,
+)
+
+__all__ = [
+    "GoogleCalendarAccount",
+    "GoogleCalendarEvent",
+    "GoogleCalendarKBSyncService",
+    "GoogleCalendarToolMetadataService",
+]
diff --git a/surfsense_backend/app/services/google_calendar/kb_sync_service.py b/surfsense_backend/app/services/google_calendar/kb_sync_service.py
new file mode 100644
index 000000000..b26433bb9
--- /dev/null
+++ b/surfsense_backend/app/services/google_calendar/kb_sync_service.py
@@ -0,0 +1,348 @@
+import asyncio
+import logging
+from datetime import datetime
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy.future import select
+from sqlalchemy.orm.attributes import flag_modified
+
+from app.db import Document, DocumentType, SearchSourceConnector, SearchSourceConnectorType
+from app.services.llm_service import get_user_long_context_llm
+from app.utils.document_converters import (
+    create_document_chunks,
+    embed_text,
+    generate_content_hash,
+    generate_document_summary,
+    generate_unique_identifier_hash,
+)
+from app.utils.google_credentials import build_composio_credentials
+
+logger = logging.getLogger(__name__)
+
+
+class GoogleCalendarKBSyncService:
+    def __init__(self, db_session: AsyncSession):
+        self.db_session = db_session
+
+    async def sync_after_create(
+        self,
+        event_id: str,
+        event_summary: str,
+        calendar_id: str,
+        start_time: str,
+        end_time: str,
+        location: str | None,
+        html_link: str | None,
+        description: str | None,
+        connector_id: int,
+        search_space_id: int,
+        user_id: str,
+    ) -> dict:
+        from app.tasks.connector_indexers.base import (
+            check_document_by_unique_identifier,
+            check_duplicate_document_by_hash,
+            get_current_timestamp,
+            safe_set_chunks,
+        )
+
+        try:
+            unique_hash = generate_unique_identifier_hash(
+                DocumentType.GOOGLE_CALENDAR_CONNECTOR, event_id, search_space_id
+            )
+
+            existing = await check_document_by_unique_identifier(
+                self.db_session, unique_hash
+            )
+            if existing:
+                logger.info(
+                    "Document for Calendar event %s already exists (doc_id=%s), skipping",
+                    event_id,
+                    existing.id,
+                )
+                return {"status": "success"}
+
+            indexable_content = (
+                f"Google Calendar Event: {event_summary}\n\n"
+                f"Start: {start_time}\n"
+                f"End: {end_time}\n"
+                f"Location: {location or 'N/A'}\n\n"
+                f"{description or ''}"
+            ).strip()
+
+            content_hash = generate_content_hash(indexable_content, search_space_id)
+
+            with self.db_session.no_autoflush:
+                dup = await check_duplicate_document_by_hash(
+                    self.db_session, content_hash
+                )
+            if dup:
+                logger.info(
+                    "Content-hash collision for Calendar event %s -- identical content "
+                    "exists in doc %s. Using unique_identifier_hash as content_hash.",
+                    event_id,
+                    dup.id,
+                )
+                content_hash = unique_hash
+
+            user_llm = await get_user_long_context_llm(
+                self.db_session,
+                user_id,
+                search_space_id,
+                disable_streaming=True,
+            )
+
+            doc_metadata_for_summary = {
+                "event_summary": event_summary,
+                "start_time": start_time,
+                "end_time": end_time,
+                "document_type": "Google Calendar Event",
+                "connector_type": "Google Calendar",
+            }
+
+            if user_llm:
+                summary_content, summary_embedding = await generate_document_summary(
+                    indexable_content, user_llm, doc_metadata_for_summary
+                )
+            else:
+                logger.warning("No LLM configured -- using fallback summary")
+                summary_content = f"Google Calendar Event: {event_summary}\n\n{indexable_content}"
+                summary_embedding = embed_text(summary_content)
+
+            chunks = await create_document_chunks(indexable_content)
+            now_str = datetime.now().strftime("%Y-%m-%d %H:%M:%S")
+
+            document = Document(
+                title=event_summary,
+                document_type=DocumentType.GOOGLE_CALENDAR_CONNECTOR,
+                document_metadata={
+                    "event_id": event_id,
+                    "event_summary": event_summary,
+                    "calendar_id": calendar_id,
+                    "start_time": start_time,
+                    "end_time": end_time,
+                    "location": location,
+                    "html_link": html_link,
+                    "source_connector": "google_calendar",
+                    "indexed_at": now_str,
+                    "connector_id": connector_id,
+                },
+                content=summary_content,
+                content_hash=content_hash,
+                unique_identifier_hash=unique_hash,
+                embedding=summary_embedding,
+                search_space_id=search_space_id,
+                connector_id=connector_id,
+                source_markdown=indexable_content,
+                updated_at=get_current_timestamp(),
+            )
+
+            self.db_session.add(document)
+            await self.db_session.flush()
+            await safe_set_chunks(self.db_session, document, chunks)
+            await self.db_session.commit()
+
+            logger.info(
+                "KB sync after create succeeded: doc_id=%s, event=%s, chunks=%d",
+                document.id,
+                event_summary,
+                len(chunks),
+            )
+            return {"status": "success"}
+
+        except Exception as e:
+            error_str = str(e).lower()
+            if (
+                "duplicate key value violates unique constraint" in error_str
+                or "uniqueviolationerror" in error_str
+            ):
+                logger.warning(
+                    "Duplicate constraint hit during KB sync for event %s. "
+                    "Rolling back -- periodic indexer will handle it. Error: %s",
+                    event_id,
+                    e,
+                )
+                await self.db_session.rollback()
+                return {"status": "error", "message": "Duplicate document detected"}
+
+            logger.error(
+                "KB sync after create failed for event %s: %s",
+                event_id,
+                e,
+                exc_info=True,
+            )
+            await self.db_session.rollback()
+            return {"status": "error", "message": str(e)}
+
+    async def sync_after_update(
+        self,
+        document_id: int,
+        event_id: str,
+        connector_id: int,
+        search_space_id: int,
+        user_id: str,
+    ) -> dict:
+        from app.tasks.connector_indexers.base import (
+            get_current_timestamp,
+            safe_set_chunks,
+        )
+
+        try:
+            document = await self.db_session.get(Document, document_id)
+            if not document:
+                logger.warning("Document %s not found in KB", document_id)
+                return {"status": "not_indexed"}
+
+            creds = await self._build_credentials_for_connector(connector_id)
+            loop = asyncio.get_event_loop()
+            service = await loop.run_in_executor(
+                None, lambda: build("calendar", "v3", credentials=creds)
+            )
+
+            calendar_id = (document.document_metadata or {}).get("calendar_id", "primary")
+            live_event = await loop.run_in_executor(
+                None,
+                lambda: service.events()
+                .get(calendarId=calendar_id, eventId=event_id)
+                .execute(),
+            )
+
+            event_summary = live_event.get("summary", "")
+            description = live_event.get("description", "")
+            location = live_event.get("location", "")
+
+            start_data = live_event.get("start", {})
+            start_time = start_data.get("dateTime", start_data.get("date", ""))
+
+            end_data = live_event.get("end", {})
+            end_time = end_data.get("dateTime", end_data.get("date", ""))
+
+            attendees = [
+                {"email": a.get("email", ""), "responseStatus": a.get("responseStatus", "")}
+                for a in live_event.get("attendees", [])
+            ]
+
+            indexable_content = (
+                f"Google Calendar Event: {event_summary}\n\n"
+                f"Start: {start_time}\n"
+                f"End: {end_time}\n"
+                f"Location: {location or 'N/A'}\n\n"
+                f"{description or ''}"
+            ).strip()
+
+            if not indexable_content:
+                return {"status": "error", "message": "Event produced empty content"}
+
+            user_llm = await get_user_long_context_llm(
+                self.db_session, user_id, search_space_id, disable_streaming=True
+            )
+
+            doc_metadata_for_summary = {
+                "event_summary": event_summary,
+                "start_time": start_time,
+                "end_time": end_time,
+                "document_type": "Google Calendar Event",
+                "connector_type": "Google Calendar",
+            }
+
+            if user_llm:
+                summary_content, summary_embedding = await generate_document_summary(
+                    indexable_content, user_llm, doc_metadata_for_summary
+                )
+            else:
+                summary_content = f"Google Calendar Event: {event_summary}\n\n{indexable_content}"
+                summary_embedding = embed_text(summary_content)
+
+            chunks = await create_document_chunks(indexable_content)
+            now_str = datetime.now().strftime("%Y-%m-%d %H:%M:%S")
+
+            document.title = event_summary
+            document.content = summary_content
+            document.content_hash = generate_content_hash(
+                indexable_content, search_space_id
+            )
+            document.embedding = summary_embedding
+
+            document.document_metadata = {
+                **(document.document_metadata or {}),
+                "event_id": event_id,
+                "event_summary": event_summary,
+                "calendar_id": calendar_id,
+                "start_time": start_time,
+                "end_time": end_time,
+                "location": location,
+                "description": description,
+                "attendees": attendees,
+                "html_link": live_event.get("htmlLink", ""),
+                "indexed_at": now_str,
+                "connector_id": connector_id,
+            }
+            flag_modified(document, "document_metadata")
+
+            await safe_set_chunks(self.db_session, document, chunks)
+            document.updated_at = get_current_timestamp()
+
+            await self.db_session.commit()
+
+            logger.info(
+                "KB sync after update succeeded for document %s (event: %s)",
+                document_id,
+                event_summary,
+            )
+            return {"status": "success"}
+
+        except Exception as e:
+            logger.error(
+                "KB sync after update failed for document %s: %s",
+                document_id,
+                e,
+                exc_info=True,
+            )
+            await self.db_session.rollback()
+            return {"status": "error", "message": str(e)}
+
+    async def _build_credentials_for_connector(self, connector_id: int) -> Credentials:
+        result = await self.db_session.execute(
+            select(SearchSourceConnector).where(
+                SearchSourceConnector.id == connector_id
+            )
+        )
+        connector = result.scalar_one_or_none()
+        if not connector:
+            raise ValueError(f"Connector {connector_id} not found")
+
+        if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR:
+            cca_id = connector.config.get("composio_connected_account_id")
+            if cca_id:
+                return build_composio_credentials(cca_id)
+            raise ValueError("Composio connected_account_id not found")
+
+        config_data = dict(connector.config)
+
+        from app.config import config as app_config
+        from app.utils.oauth_security import TokenEncryption
+
+        token_encrypted = config_data.get("_token_encrypted", False)
+        if token_encrypted and app_config.SECRET_KEY:
+            token_encryption = TokenEncryption(app_config.SECRET_KEY)
+            if config_data.get("token"):
+                config_data["token"] = token_encryption.decrypt_token(config_data["token"])
+            if config_data.get("refresh_token"):
+                config_data["refresh_token"] = token_encryption.decrypt_token(config_data["refresh_token"])
+            if config_data.get("client_secret"):
+                config_data["client_secret"] = token_encryption.decrypt_token(config_data["client_secret"])
+
+        exp = config_data.get("expiry", "")
+        if exp:
+            exp = exp.replace("Z", "")
+
+        return Credentials(
+            token=config_data.get("token"),
+            refresh_token=config_data.get("refresh_token"),
+            token_uri=config_data.get("token_uri"),
+            client_id=config_data.get("client_id"),
+            client_secret=config_data.get("client_secret"),
+            scopes=config_data.get("scopes", []),
+            expiry=datetime.fromisoformat(exp) if exp else None,
+        )
diff --git a/surfsense_backend/app/services/google_calendar/tool_metadata_service.py b/surfsense_backend/app/services/google_calendar/tool_metadata_service.py
new file mode 100644
index 000000000..f2a8b08c3
--- /dev/null
+++ b/surfsense_backend/app/services/google_calendar/tool_metadata_service.py
@@ -0,0 +1,403 @@
+import asyncio
+import logging
+from dataclasses import dataclass
+from datetime import datetime
+
+from google.oauth2.credentials import Credentials
+from googleapiclient.discovery import build
+from sqlalchemy import and_, func, or_
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy.future import select
+from sqlalchemy.orm.attributes import flag_modified
+
+from app.db import (
+    Document,
+    DocumentType,
+    SearchSourceConnector,
+    SearchSourceConnectorType,
+)
+from app.utils.google_credentials import build_composio_credentials
+
+logger = logging.getLogger(__name__)
+
+CALENDAR_CONNECTOR_TYPES = [
+    SearchSourceConnectorType.GOOGLE_CALENDAR_CONNECTOR,
+    SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+]
+
+CALENDAR_DOCUMENT_TYPES = [
+    DocumentType.GOOGLE_CALENDAR_CONNECTOR,
+    DocumentType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR,
+]
+
+
+@dataclass
+class GoogleCalendarAccount:
+    id: int
+    name: str
+
+    @classmethod
+    def from_connector(cls, connector: SearchSourceConnector) -> "GoogleCalendarAccount":
+        return cls(id=connector.id, name=connector.name)
+
+    def to_dict(self) -> dict:
+        return {"id": self.id, "name": self.name}
+
+
+@dataclass
+class GoogleCalendarEvent:
+    event_id: str
+    summary: str
+    start: str
+    end: str
+    description: str
+    location: str
+    attendees: list
+    calendar_id: str
+    document_id: int
+    indexed_at: str | None
+
+    @classmethod
+    def from_document(cls, document: Document) -> "GoogleCalendarEvent":
+        meta = document.document_metadata or {}
+        return cls(
+            event_id=meta.get("event_id", ""),
+            summary=meta.get("event_summary", document.title),
+            start=meta.get("start_time", ""),
+            end=meta.get("end_time", ""),
+            description=meta.get("description", ""),
+            location=meta.get("location", ""),
+            attendees=meta.get("attendees", []),
+            calendar_id=meta.get("calendar_id", "primary"),
+            document_id=document.id,
+            indexed_at=meta.get("indexed_at"),
+        )
+
+    def to_dict(self) -> dict:
+        return {
+            "event_id": self.event_id,
+            "summary": self.summary,
+            "start": self.start,
+            "end": self.end,
+            "description": self.description,
+            "location": self.location,
+            "attendees": self.attendees,
+            "calendar_id": self.calendar_id,
+            "document_id": self.document_id,
+            "indexed_at": self.indexed_at,
+        }
+
+
+class GoogleCalendarToolMetadataService:
+    def __init__(self, db_session: AsyncSession):
+        self._db_session = db_session
+
+    async def _build_credentials(self, connector: SearchSourceConnector) -> Credentials:
+        if connector.connector_type == SearchSourceConnectorType.COMPOSIO_GOOGLE_CALENDAR_CONNECTOR:
+            cca_id = connector.config.get("composio_connected_account_id")
+            if cca_id:
+                return build_composio_credentials(cca_id)
+            raise ValueError("Composio connected_account_id not found")
+
+        config_data = dict(connector.config)
+
+        from app.config import config as app_config
+        from app.utils.oauth_security import TokenEncryption
+
+        token_encrypted = config_data.get("_token_encrypted", False)
+        if token_encrypted and app_config.SECRET_KEY:
+            token_encryption = TokenEncryption(app_config.SECRET_KEY)
+            if config_data.get("token"):
+                config_data["token"] = token_encryption.decrypt_token(config_data["token"])
+            if config_data.get("refresh_token"):
+                config_data["refresh_token"] = token_encryption.decrypt_token(config_data["refresh_token"])
+            if config_data.get("client_secret"):
+                config_data["client_secret"] = token_encryption.decrypt_token(config_data["client_secret"])
+
+        exp = config_data.get("expiry", "")
+        if exp:
+            exp = exp.replace("Z", "")
+
+        return Credentials(
+            token=config_data.get("token"),
+            refresh_token=config_data.get("refresh_token"),
+            token_uri=config_data.get("token_uri"),
+            client_id=config_data.get("client_id"),
+            client_secret=config_data.get("client_secret"),
+            scopes=config_data.get("scopes", []),
+            expiry=datetime.fromisoformat(exp) if exp else None,
+        )
+
+    async def _check_account_health(self, connector_id: int) -> bool:
+        """Check if a Google Calendar connector's credentials are still valid.
+
+        Uses a lightweight calendarList.list(maxResults=1) call to verify access.
+
+        Returns True if the credentials are expired/invalid, False if healthy.
+        """
+        try:
+            result = await self._db_session.execute(
+                select(SearchSourceConnector).where(
+                    SearchSourceConnector.id == connector_id
+                )
+            )
+            connector = result.scalar_one_or_none()
+            if not connector:
+                return True
+
+            creds = await self._build_credentials(connector)
+            loop = asyncio.get_event_loop()
+            await loop.run_in_executor(
+                None,
+                lambda: build("calendar", "v3", credentials=creds)
+                .calendarList()
+                .list(maxResults=1)
+                .execute(),
+            )
+            return False
+        except Exception as e:
+            logger.warning(
+                "Google Calendar connector %s health check failed: %s",
+                connector_id,
+                e,
+            )
+            return True
+
+    async def _persist_auth_expired(self, connector_id: int) -> None:
+        """Persist ``auth_expired: True`` to the connector config if not already set."""
+        try:
+            result = await self._db_session.execute(
+                select(SearchSourceConnector).where(
+                    SearchSourceConnector.id == connector_id
+                )
+            )
+            db_connector = result.scalar_one_or_none()
+            if db_connector and not db_connector.config.get("auth_expired"):
+                db_connector.config = {**db_connector.config, "auth_expired": True}
+                flag_modified(db_connector, "config")
+                await self._db_session.commit()
+                await self._db_session.refresh(db_connector)
+        except Exception:
+            logger.warning(
+                "Failed to persist auth_expired for connector %s",
+                connector_id,
+                exc_info=True,
+            )
+
+    async def _get_accounts(
+        self, search_space_id: int, user_id: str
+    ) -> list[GoogleCalendarAccount]:
+        result = await self._db_session.execute(
+            select(SearchSourceConnector)
+            .filter(
+                and_(
+                    SearchSourceConnector.search_space_id == search_space_id,
+                    SearchSourceConnector.user_id == user_id,
+                    SearchSourceConnector.connector_type.in_(CALENDAR_CONNECTOR_TYPES),
+                )
+            )
+            .order_by(SearchSourceConnector.last_indexed_at.desc())
+        )
+        connectors = result.scalars().all()
+        return [GoogleCalendarAccount.from_connector(c) for c in connectors]
+
+    async def get_creation_context(self, search_space_id: int, user_id: str) -> dict:
+        accounts = await self._get_accounts(search_space_id, user_id)
+
+        if not accounts:
+            return {
+                "accounts": [],
+                "error": "No Google Calendar account connected",
+            }
+
+        accounts_with_status = []
+        for acc in accounts:
+            acc_dict = acc.to_dict()
+            auth_expired = await self._check_account_health(acc.id)
+            acc_dict["auth_expired"] = auth_expired
+            if auth_expired:
+                await self._persist_auth_expired(acc.id)
+            accounts_with_status.append(acc_dict)
+
+        healthy_account = next(
+            (a for a in accounts_with_status if not a.get("auth_expired")), None
+        )
+        if not healthy_account:
+            return {
+                "accounts": accounts_with_status,
+                "calendars": [],
+                "timezone": "",
+                "error": "All connected Google Calendar accounts have expired credentials",
+            }
+
+        connector_id = healthy_account["id"]
+        result = await self._db_session.execute(
+            select(SearchSourceConnector).where(
+                SearchSourceConnector.id == connector_id
+            )
+        )
+        connector = result.scalar_one_or_none()
+
+        calendars = []
+        timezone_str = ""
+        if connector:
+            try:
+                creds = await self._build_credentials(connector)
+                loop = asyncio.get_event_loop()
+                service = await loop.run_in_executor(
+                    None, lambda: build("calendar", "v3", credentials=creds)
+                )
+
+                cal_list = await loop.run_in_executor(
+                    None, lambda: service.calendarList().list().execute()
+                )
+                for cal in cal_list.get("items", []):
+                    calendars.append({
+                        "id": cal.get("id", ""),
+                        "summary": cal.get("summary", ""),
+                        "primary": cal.get("primary", False),
+                    })
+
+                tz_setting = await loop.run_in_executor(
+                    None,
+                    lambda: service.settings().get(setting="timezone").execute(),
+                )
+                timezone_str = tz_setting.get("value", "")
+            except Exception:
+                logger.warning(
+                    "Failed to fetch calendars/timezone for connector %s",
+                    connector_id,
+                    exc_info=True,
+                )
+
+        return {
+            "accounts": accounts_with_status,
+            "calendars": calendars,
+            "timezone": timezone_str,
+        }
+
+    async def get_update_context(
+        self, search_space_id: int, user_id: str, event_ref: str
+    ) -> dict:
+        resolved = await self._resolve_event(search_space_id, user_id, event_ref)
+        if not resolved:
+            return {
+                "error": (
+                    f"Event '{event_ref}' not found in your indexed Google Calendar events. "
+                    "This could mean: (1) the event doesn't exist, (2) it hasn't been indexed yet, "
+                    "or (3) the event name is different."
+                )
+            }
+
+        document, connector = resolved
+        account = GoogleCalendarAccount.from_connector(connector)
+        event = GoogleCalendarEvent.from_document(document)
+
+        acc_dict = account.to_dict()
+        auth_expired = await self._check_account_health(connector.id)
+        acc_dict["auth_expired"] = auth_expired
+        if auth_expired:
+            await self._persist_auth_expired(connector.id)
+            return {
+                "error": "Google Calendar credentials have expired. Please re-authenticate.",
+                "auth_expired": True,
+                "connector_id": connector.id,
+            }
+
+        event_dict = event.to_dict()
+        try:
+            creds = await self._build_credentials(connector)
+            loop = asyncio.get_event_loop()
+            service = await loop.run_in_executor(
+                None, lambda: build("calendar", "v3", credentials=creds)
+            )
+            calendar_id = event.calendar_id or "primary"
+            live_event = await loop.run_in_executor(
+                None,
+                lambda: service.events()
+                .get(calendarId=calendar_id, eventId=event.event_id)
+                .execute(),
+            )
+
+            event_dict["summary"] = live_event.get("summary", event_dict["summary"])
+            event_dict["description"] = live_event.get("description", event_dict["description"])
+            event_dict["location"] = live_event.get("location", event_dict["location"])
+
+            start_data = live_event.get("start", {})
+            event_dict["start"] = start_data.get("dateTime", start_data.get("date", event_dict["start"]))
+
+            end_data = live_event.get("end", {})
+            event_dict["end"] = end_data.get("dateTime", end_data.get("date", event_dict["end"]))
+
+            event_dict["attendees"] = [
+                {"email": a.get("email", ""), "responseStatus": a.get("responseStatus", "")}
+                for a in live_event.get("attendees", [])
+            ]
+        except Exception:
+            logger.warning(
+                "Failed to fetch live event data for event %s, using KB metadata",
+                event.event_id,
+                exc_info=True,
+            )
+
+        return {
+            "account": acc_dict,
+            "event": event_dict,
+        }
+
+    async def get_deletion_context(
+        self, search_space_id: int, user_id: str, event_ref: str
+    ) -> dict:
+        resolved = await self._resolve_event(search_space_id, user_id, event_ref)
+        if not resolved:
+            return {
+                "error": (
+                    f"Event '{event_ref}' not found in your indexed Google Calendar events. "
+                    "This could mean: (1) the event doesn't exist, (2) it hasn't been indexed yet, "
+                    "or (3) the event name is different."
+                )
+            }
+
+        document, connector = resolved
+        account = GoogleCalendarAccount.from_connector(connector)
+        event = GoogleCalendarEvent.from_document(document)
+
+        acc_dict = account.to_dict()
+        auth_expired = await self._check_account_health(connector.id)
+        acc_dict["auth_expired"] = auth_expired
+        if auth_expired:
+            await self._persist_auth_expired(connector.id)
+
+        return {
+            "account": acc_dict,
+            "event": event.to_dict(),
+        }
+
+    async def _resolve_event(
+        self, search_space_id: int, user_id: str, event_ref: str
+    ) -> tuple[Document, SearchSourceConnector] | None:
+        result = await self._db_session.execute(
+            select(Document, SearchSourceConnector)
+            .join(
+                SearchSourceConnector,
+                Document.connector_id == SearchSourceConnector.id,
+            )
+            .filter(
+                and_(
+                    Document.search_space_id == search_space_id,
+                    Document.document_type.in_(CALENDAR_DOCUMENT_TYPES),
+                    SearchSourceConnector.user_id == user_id,
+                    or_(
+                        func.lower(
+                            Document.document_metadata["event_summary"].astext
+                        )
+                        == func.lower(event_ref),
+                        func.lower(Document.title) == func.lower(event_ref),
+                    ),
+                )
+            )
+        )
+        row = result.first()
+        if row:
+            return row[0], row[1]
+        return None
diff --git a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
index a17d7362b..3a7c71caa 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/new-chat/[[...chat_id]]/page.tsx
@@ -41,6 +41,16 @@ import type { ThinkingStep } from "@/components/tool-ui/deepagent-thinking";
 import { DisplayImageToolUI } from "@/components/tool-ui/display-image";
 import { GeneratePodcastToolUI } from "@/components/tool-ui/generate-podcast";
 import { GenerateReportToolUI } from "@/components/tool-ui/generate-report";
+import {
+	CreateCalendarEventToolUI,
+	UpdateCalendarEventToolUI,
+	DeleteCalendarEventToolUI,
+} from "@/components/tool-ui/google-calendar";
+import {
+	CreateGmailDraftToolUI,
+	SendGmailEmailToolUI,
+	TrashGmailEmailToolUI,
+} from "@/components/tool-ui/gmail";
 import {
 	CreateGoogleDriveFileToolUI,
 	DeleteGoogleDriveFileToolUI,
@@ -160,6 +170,12 @@ const TOOLS_WITH_UI = new Set([
 	"delete_linear_issue",
 	"create_google_drive_file",
 	"delete_google_drive_file",
+	"create_calendar_event",
+	"update_calendar_event",
+	"delete_calendar_event",
+	"create_gmail_draft",
+	"send_gmail_email",
+	"trash_gmail_email",
 	"execute",
 	// "write_todos", // Disabled for now
 ]);
@@ -1676,6 +1692,12 @@ export default function NewChatPage() {
 			<DeleteLinearIssueToolUI />
 			<CreateGoogleDriveFileToolUI />
 			<DeleteGoogleDriveFileToolUI />
+			<CreateCalendarEventToolUI />
+			<UpdateCalendarEventToolUI />
+			<DeleteCalendarEventToolUI />
+			<CreateGmailDraftToolUI />
+			<SendGmailEmailToolUI />
+			<TrashGmailEmailToolUI />
 			<SandboxExecuteToolUI />
 			{/* <WriteTodosToolUI /> Disabled for now */}
 			<div key={searchSpaceId} className="flex h-[calc(100dvh-64px)] overflow-hidden">
diff --git a/surfsense_web/atoms/chat/hitl-edit-panel.atom.ts b/surfsense_web/atoms/chat/hitl-edit-panel.atom.ts
index eec3879ab..a1c748266 100644
--- a/surfsense_web/atoms/chat/hitl-edit-panel.atom.ts
+++ b/surfsense_web/atoms/chat/hitl-edit-panel.atom.ts
@@ -1,12 +1,20 @@
 import { atom } from "jotai";
 import { rightPanelCollapsedAtom, rightPanelTabAtom } from "@/atoms/layout/right-panel.atom";
 
+export interface ExtraField {
+	label: string;
+	key: string;
+	value: string;
+	type: "text" | "email" | "datetime-local" | "textarea";
+}
+
 interface HitlEditPanelState {
 	isOpen: boolean;
 	title: string;
 	content: string;
 	toolName: string;
-	onSave: ((title: string, content: string) => void) | null;
+	extraFields?: ExtraField[];
+	onSave: ((title: string, content: string, extraFieldValues?: Record<string, string>) => void) | null;
 }
 
 const initialState: HitlEditPanelState = {
@@ -14,6 +22,7 @@ const initialState: HitlEditPanelState = {
 	title: "",
 	content: "",
 	toolName: "",
+	extraFields: undefined,
 	onSave: null,
 };
 
@@ -30,7 +39,8 @@ export const openHitlEditPanelAtom = atom(
 			title: string;
 			content: string;
 			toolName: string;
-			onSave: (title: string, content: string) => void;
+			extraFields?: ExtraField[];
+			onSave: (title: string, content: string, extraFieldValues?: Record<string, string>) => void;
 		}
 	) => {
 		if (!get(hitlEditPanelAtom).isOpen) {
@@ -41,6 +51,7 @@ export const openHitlEditPanelAtom = atom(
 			title: payload.title,
 			content: payload.content,
 			toolName: payload.toolName,
+			extraFields: payload.extraFields,
 			onSave: payload.onSave,
 		});
 		set(rightPanelTabAtom, "hitl-edit");
diff --git a/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx b/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
index 8618d68e9..8851d7821 100644
--- a/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
+++ b/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
@@ -7,14 +7,19 @@ import {
 	closeHitlEditPanelAtom,
 	hitlEditPanelAtom,
 } from "@/atoms/chat/hitl-edit-panel.atom";
+import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
 import { PlateEditor } from "@/components/editor/plate-editor";
 import { Button } from "@/components/ui/button";
 import { Drawer, DrawerContent, DrawerHandle, DrawerTitle } from "@/components/ui/drawer";
+import { Input } from "@/components/ui/input";
+import { Label } from "@/components/ui/label";
+import { Textarea } from "@/components/ui/textarea";
 import { useMediaQuery } from "@/hooks/use-media-query";
 
 export function HitlEditPanelContent({
 	title: initialTitle,
 	content: initialContent,
+	extraFields,
 	onSave,
 	onClose,
 	showCloseButton = true,
@@ -22,24 +27,38 @@ export function HitlEditPanelContent({
 	title: string;
 	content: string;
 	toolName: string;
-	onSave: (title: string, content: string) => void;
+	extraFields?: ExtraField[];
+	onSave: (title: string, content: string, extraFieldValues?: Record<string, string>) => void;
 	onClose?: () => void;
 	showCloseButton?: boolean;
 }) {
 	const [editedTitle, setEditedTitle] = useState(initialTitle);
 	const markdownRef = useRef(initialContent);
 	const [isSaving, setIsSaving] = useState(false);
+	const [extraFieldValues, setExtraFieldValues] = useState<Record<string, string>>(() => {
+		if (!extraFields) return {};
+		const initial: Record<string, string> = {};
+		for (const field of extraFields) {
+			initial[field.key] = field.value;
+		}
+		return initial;
+	});
 
 	const handleMarkdownChange = useCallback((md: string) => {
 		markdownRef.current = md;
 	}, []);
 
+	const handleExtraFieldChange = useCallback((key: string, value: string) => {
+		setExtraFieldValues((prev) => ({ ...prev, [key]: value }));
+	}, []);
+
 	const handleSave = useCallback(() => {
 		if (!editedTitle.trim()) return;
 		setIsSaving(true);
-		onSave(editedTitle, markdownRef.current);
+		const extras = extraFields && extraFields.length > 0 ? extraFieldValues : undefined;
+		onSave(editedTitle, markdownRef.current, extras);
 		onClose?.();
-	}, [editedTitle, onSave, onClose]);
+	}, [editedTitle, onSave, onClose, extraFields, extraFieldValues]);
 
 	return (
 		<>
@@ -59,6 +78,34 @@ export function HitlEditPanelContent({
 				)}
 			</div>
 
+			{extraFields && extraFields.length > 0 && (
+				<div className="flex flex-col gap-3 px-4 py-3 border-b">
+					{extraFields.map((field) => (
+						<div key={field.key} className="flex flex-col gap-1.5">
+							<Label htmlFor={`extra-field-${field.key}`} className="text-xs font-medium text-muted-foreground">
+								{field.label}
+							</Label>
+							{field.type === "textarea" ? (
+								<Textarea
+									id={`extra-field-${field.key}`}
+									value={extraFieldValues[field.key] ?? ""}
+									onChange={(e) => handleExtraFieldChange(field.key, e.target.value)}
+									className="text-sm min-h-[60px]"
+								/>
+							) : (
+								<Input
+									id={`extra-field-${field.key}`}
+									type={field.type}
+									value={extraFieldValues[field.key] ?? ""}
+									onChange={(e) => handleExtraFieldChange(field.key, e.target.value)}
+									className="text-sm"
+								/>
+							)}
+						</div>
+					))}
+				</div>
+			)}
+
 			<div className="flex-1 overflow-hidden">
 				<PlateEditor
 					markdown={initialContent}
@@ -90,6 +137,7 @@ function DesktopHitlEditPanel() {
 				title={panelState.title}
 				content={panelState.content}
 				toolName={panelState.toolName}
+				extraFields={panelState.extraFields}
 				onSave={panelState.onSave}
 				onClose={closePanel}
 			/>
@@ -124,6 +172,7 @@ function MobileHitlEditDrawer() {
 						title={panelState.title}
 						content={panelState.content}
 						toolName={panelState.toolName}
+						extraFields={panelState.extraFields}
 						onSave={panelState.onSave}
 						onClose={closePanel}
 						showCloseButton={false}
diff --git a/surfsense_web/components/tool-ui/gmail/create-draft.tsx b/surfsense_web/components/tool-ui/gmail/create-draft.tsx
new file mode 100644
index 000000000..c42901a4e
--- /dev/null
+++ b/surfsense_web/components/tool-ui/gmail/create-draft.tsx
@@ -0,0 +1,450 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CornerDownLeftIcon,
+	FileEditIcon,
+	MailIcon,
+	Pen,
+	UserIcon,
+	UsersIcon,
+} from "lucide-react";
+import { useCallback, useEffect, useMemo, useState } from "react";
+import { Button } from "@/components/ui/button";
+import {
+	Select,
+	SelectContent,
+	SelectItem,
+	SelectTrigger,
+	SelectValue,
+} from "@/components/ui/select";
+import { PlateEditor } from "@/components/editor/plate-editor";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+import { useSetAtom } from "jotai";
+import { openHitlEditPanelAtom } from "@/atoms/chat/hitl-edit-panel.atom";
+import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
+
+interface GmailAccount {
+	id: number;
+	name: string;
+	email: string;
+	auth_expired?: boolean;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject" | "edit";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "edit" | "reject">;
+	}>;
+	context?: {
+		accounts?: GmailAccount[];
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	draft_id?: string;
+	message_id?: string;
+	message?: string;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type CreateGmailDraftResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function ApprovalCard({
+	args,
+	interruptData,
+	onDecision,
+}: {
+	args: { to: string; subject: string; body: string; cc?: string; bcc?: string };
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject" | "edit";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const [decided, setDecided] = useState<"approve" | "reject" | "edit" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [isPanelOpen, setIsPanelOpen] = useState(false);
+	const openHitlEditPanel = useSetAtom(openHitlEditPanelAtom);
+
+	const accounts = interruptData.context?.accounts ?? [];
+	const validAccounts = accounts.filter((a) => !a.auth_expired);
+	const expiredAccounts = accounts.filter((a) => a.auth_expired);
+
+	const defaultAccountId = useMemo(() => {
+		if (validAccounts.length === 1) return String(validAccounts[0].id);
+		return "";
+	}, [validAccounts]);
+
+	const [selectedAccountId, setSelectedAccountId] = useState<string>(defaultAccountId);
+
+	const canApprove = !!selectedAccountId;
+
+	const reviewConfig = interruptData.review_configs[0];
+	const allowedDecisions = reviewConfig?.allowed_decisions ?? ["approve", "reject"];
+	const canEdit = allowedDecisions.includes("edit");
+
+	const handleApprove = useCallback(() => {
+		if (decided || isPanelOpen || !canApprove) return;
+		if (!allowedDecisions.includes("approve")) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: {
+					...args,
+					connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+				},
+			},
+		});
+	}, [decided, isPanelOpen, canApprove, allowedDecisions, onDecision, interruptData, args, selectedAccountId]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<FileEditIcon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Gmail Draft Rejected"
+								: decided === "approve" || decided === "edit"
+									? "Gmail Draft Approved"
+									: "Create Gmail Draft"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Draft creation was cancelled"
+								: decided === "edit"
+									? "Draft creation is in progress with your changes"
+									: decided === "approve"
+										? "Draft creation is in progress"
+										: "Requires your approval to proceed"}
+						</p>
+					</div>
+				</div>
+				{!decided && canEdit && (
+					<Button
+						size="sm"
+						variant="ghost"
+						className="rounded-lg text-muted-foreground -mt-1 -mr-2"
+						onClick={() => {
+							setIsPanelOpen(true);
+							const extraFields: ExtraField[] = [
+								{ key: "to", label: "To", type: "email", value: args.to || "" },
+								{ key: "cc", label: "CC", type: "email", value: args.cc || "" },
+								{ key: "bcc", label: "BCC", type: "email", value: args.bcc || "" },
+							];
+							openHitlEditPanel({
+								title: args.subject ?? "",
+								content: args.body ?? "",
+								toolName: "Gmail Draft",
+								extraFields,
+								onSave: (newTitle, newContent, extraFieldValues) => {
+									setIsPanelOpen(false);
+									setDecided("edit");
+									const extras = extraFieldValues ?? {};
+									onDecision({
+										type: "edit",
+										edited_action: {
+											name: interruptData.action_requests[0].name,
+											args: {
+												...args,
+												subject: newTitle,
+												body: newContent,
+												to: extras.to ?? args.to,
+												cc: extras.cc ?? args.cc,
+												bcc: extras.bcc ?? args.bcc,
+												connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+											},
+										},
+									});
+								},
+							});
+						}}
+					>
+						<Pen className="size-3.5" />
+						Edit
+					</Button>
+				)}
+			</div>
+
+			{/* Account selector */}
+			{!decided && interruptData.context && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{interruptData.context.error ? (
+							<p className="text-sm text-destructive">{interruptData.context.error}</p>
+						) : (
+							<>
+								{accounts.length > 0 && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">
+											Gmail Account <span className="text-destructive">*</span>
+										</p>
+										<Select value={selectedAccountId} onValueChange={setSelectedAccountId}>
+											<SelectTrigger className="w-full">
+												<SelectValue placeholder="Select an account" />
+											</SelectTrigger>
+											<SelectContent>
+												{validAccounts.map((account) => (
+													<SelectItem key={account.id} value={String(account.id)}>
+														{account.email}
+													</SelectItem>
+												))}
+												{expiredAccounts.map((a) => (
+													<div
+														key={a.id}
+														className="relative flex w-full cursor-default items-center gap-2 rounded-sm py-1.5 px-2 text-sm select-none opacity-50 pointer-events-none"
+													>
+														{a.email} (expired, retry after re-auth)
+													</div>
+												))}
+											</SelectContent>
+										</Select>
+									</div>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* Email headers + body preview */}
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 pt-3 pb-2 space-y-1.5 select-none">
+				{args.to && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UserIcon className="size-3 shrink-0" />
+						<span>To: {args.to}</span>
+					</div>
+				)}
+				{args.cc && args.cc.trim() !== "" && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UsersIcon className="size-3 shrink-0" />
+						<span>CC: {args.cc}</span>
+					</div>
+				)}
+				{args.bcc && args.bcc.trim() !== "" && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UsersIcon className="size-3 shrink-0" />
+						<span>BCC: {args.bcc}</span>
+					</div>
+				)}
+			</div>
+
+			<div className="px-5 pt-1">
+				{args.subject != null && (
+					<p className="text-sm font-medium text-foreground">{args.subject}</p>
+				)}
+				{args.body != null && (
+					<div
+						className="mt-2 max-h-[7rem] overflow-hidden text-sm"
+						style={{
+							maskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+							WebkitMaskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+						}}
+					>
+						<PlateEditor
+							markdown={String(args.body)}
+							readOnly
+							preset="readonly"
+							editorVariant="none"
+							className="h-auto [&_[data-slate-editor]]:!min-h-0 [&_[data-slate-editor]>*:first-child]:!mt-0"
+						/>
+					</div>
+				)}
+			</div>
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						{allowedDecisions.includes("approve") && (
+							<Button
+								size="sm"
+								className="rounded-lg gap-1.5"
+								onClick={handleApprove}
+								disabled={!canApprove}
+							>
+								Approve
+								<CornerDownLeftIcon className="size-3 opacity-60" />
+							</Button>
+						)}
+						{allowedDecisions.includes("reject") && (
+							<Button
+								size="sm"
+								variant="ghost"
+								className="rounded-lg text-muted-foreground"
+								onClick={() => {
+									setDecided("reject");
+									onDecision({ type: "reject", message: "User rejected the action." });
+								}}
+							>
+								Reject
+							</Button>
+						)}
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to create Gmail draft</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Gmail authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<div className="flex items-center gap-2">
+					<MailIcon className="size-4 text-muted-foreground shrink-0" />
+					<p className="text-sm font-semibold text-foreground">
+						{result.message || "Gmail draft created successfully"}
+					</p>
+				</div>
+			</div>
+		</div>
+	);
+}
+
+export const CreateGmailDraftToolUI = makeAssistantToolUI<
+	{ to: string; subject: string; body: string; cc?: string; bcc?: string },
+	CreateGmailDraftResult
+>({
+	toolName: "create_gmail_draft",
+	render: function CreateGmailDraftUI({ args, result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Creating Gmail draft..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					args={args}
+					interruptData={result}
+					onDecision={(decision) => {
+						window.dispatchEvent(
+							new CustomEvent("hitl-decision", { detail: { decisions: [decision] } })
+						);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});
diff --git a/surfsense_web/components/tool-ui/gmail/index.ts b/surfsense_web/components/tool-ui/gmail/index.ts
new file mode 100644
index 000000000..27c1f4dd0
--- /dev/null
+++ b/surfsense_web/components/tool-ui/gmail/index.ts
@@ -0,0 +1,3 @@
+export { CreateGmailDraftToolUI } from "./create-draft";
+export { SendGmailEmailToolUI } from "./send-email";
+export { TrashGmailEmailToolUI } from "./trash-email";
diff --git a/surfsense_web/components/tool-ui/gmail/send-email.tsx b/surfsense_web/components/tool-ui/gmail/send-email.tsx
new file mode 100644
index 000000000..79697157d
--- /dev/null
+++ b/surfsense_web/components/tool-ui/gmail/send-email.tsx
@@ -0,0 +1,449 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CornerDownLeftIcon,
+	MailIcon,
+	Pen,
+	SendIcon,
+	UserIcon,
+	UsersIcon,
+} from "lucide-react";
+import { useCallback, useEffect, useMemo, useState } from "react";
+import { Button } from "@/components/ui/button";
+import {
+	Select,
+	SelectContent,
+	SelectItem,
+	SelectTrigger,
+	SelectValue,
+} from "@/components/ui/select";
+import { PlateEditor } from "@/components/editor/plate-editor";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+import { useSetAtom } from "jotai";
+import { openHitlEditPanelAtom } from "@/atoms/chat/hitl-edit-panel.atom";
+import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
+
+interface GmailAccount {
+	id: number;
+	name: string;
+	email: string;
+	auth_expired?: boolean;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject" | "edit";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "edit" | "reject">;
+	}>;
+	context?: {
+		accounts?: GmailAccount[];
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	message_id?: string;
+	message?: string;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type SendGmailEmailResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function ApprovalCard({
+	args,
+	interruptData,
+	onDecision,
+}: {
+	args: { to: string; subject: string; body: string; cc?: string; bcc?: string };
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject" | "edit";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const [decided, setDecided] = useState<"approve" | "reject" | "edit" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [isPanelOpen, setIsPanelOpen] = useState(false);
+	const openHitlEditPanel = useSetAtom(openHitlEditPanelAtom);
+
+	const accounts = interruptData.context?.accounts ?? [];
+	const validAccounts = accounts.filter((a) => !a.auth_expired);
+	const expiredAccounts = accounts.filter((a) => a.auth_expired);
+
+	const defaultAccountId = useMemo(() => {
+		if (validAccounts.length === 1) return String(validAccounts[0].id);
+		return "";
+	}, [validAccounts]);
+
+	const [selectedAccountId, setSelectedAccountId] = useState<string>(defaultAccountId);
+
+	const canApprove = !!selectedAccountId;
+
+	const reviewConfig = interruptData.review_configs[0];
+	const allowedDecisions = reviewConfig?.allowed_decisions ?? ["approve", "reject"];
+	const canEdit = allowedDecisions.includes("edit");
+
+	const handleApprove = useCallback(() => {
+		if (decided || isPanelOpen || !canApprove) return;
+		if (!allowedDecisions.includes("approve")) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: {
+					...args,
+					connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+				},
+			},
+		});
+	}, [decided, isPanelOpen, canApprove, allowedDecisions, onDecision, interruptData, args, selectedAccountId]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<SendIcon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Email Sending Rejected"
+								: decided === "approve" || decided === "edit"
+									? "Email Sending Approved"
+									: "Send Email"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Email sending was cancelled"
+								: decided === "edit"
+									? "Email is being sent with your changes"
+									: decided === "approve"
+										? "Email is being sent"
+										: "This will send the email immediately"}
+						</p>
+					</div>
+				</div>
+				{!decided && canEdit && (
+					<Button
+						size="sm"
+						variant="ghost"
+						className="rounded-lg text-muted-foreground -mt-1 -mr-2"
+						onClick={() => {
+							setIsPanelOpen(true);
+							const extraFields: ExtraField[] = [
+								{ key: "to", label: "To", type: "email", value: args.to || "" },
+								{ key: "cc", label: "CC", type: "email", value: args.cc || "" },
+								{ key: "bcc", label: "BCC", type: "email", value: args.bcc || "" },
+							];
+							openHitlEditPanel({
+								title: args.subject ?? "",
+								content: args.body ?? "",
+								toolName: "Send Email",
+								extraFields,
+								onSave: (newTitle, newContent, extraFieldValues) => {
+									setIsPanelOpen(false);
+									setDecided("edit");
+									const extras = extraFieldValues ?? {};
+									onDecision({
+										type: "edit",
+										edited_action: {
+											name: interruptData.action_requests[0].name,
+											args: {
+												...args,
+												subject: newTitle,
+												body: newContent,
+												to: extras.to ?? args.to,
+												cc: extras.cc ?? args.cc,
+												bcc: extras.bcc ?? args.bcc,
+												connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+											},
+										},
+									});
+								},
+							});
+						}}
+					>
+						<Pen className="size-3.5" />
+						Edit
+					</Button>
+				)}
+			</div>
+
+			{/* Account selector */}
+			{!decided && interruptData.context && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{interruptData.context.error ? (
+							<p className="text-sm text-destructive">{interruptData.context.error}</p>
+						) : (
+							<>
+								{accounts.length > 0 && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">
+											Gmail Account <span className="text-destructive">*</span>
+										</p>
+										<Select value={selectedAccountId} onValueChange={setSelectedAccountId}>
+											<SelectTrigger className="w-full">
+												<SelectValue placeholder="Select an account" />
+											</SelectTrigger>
+											<SelectContent>
+												{validAccounts.map((account) => (
+													<SelectItem key={account.id} value={String(account.id)}>
+														{account.email}
+													</SelectItem>
+												))}
+												{expiredAccounts.map((a) => (
+													<div
+														key={a.id}
+														className="relative flex w-full cursor-default items-center gap-2 rounded-sm py-1.5 px-2 text-sm select-none opacity-50 pointer-events-none"
+													>
+														{a.email} (expired, retry after re-auth)
+													</div>
+												))}
+											</SelectContent>
+										</Select>
+									</div>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* Email headers + body preview */}
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 pt-3 pb-2 space-y-1.5 select-none">
+				{args.to && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UserIcon className="size-3 shrink-0" />
+						<span>To: {args.to}</span>
+					</div>
+				)}
+				{args.cc && args.cc.trim() !== "" && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UsersIcon className="size-3 shrink-0" />
+						<span>CC: {args.cc}</span>
+					</div>
+				)}
+				{args.bcc && args.bcc.trim() !== "" && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UsersIcon className="size-3 shrink-0" />
+						<span>BCC: {args.bcc}</span>
+					</div>
+				)}
+			</div>
+
+			<div className="px-5 pt-1">
+				{args.subject != null && (
+					<p className="text-sm font-medium text-foreground">{args.subject}</p>
+				)}
+				{args.body != null && (
+					<div
+						className="mt-2 max-h-[7rem] overflow-hidden text-sm"
+						style={{
+							maskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+							WebkitMaskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+						}}
+					>
+						<PlateEditor
+							markdown={String(args.body)}
+							readOnly
+							preset="readonly"
+							editorVariant="none"
+							className="h-auto [&_[data-slate-editor]]:!min-h-0 [&_[data-slate-editor]>*:first-child]:!mt-0"
+						/>
+					</div>
+				)}
+			</div>
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						{allowedDecisions.includes("approve") && (
+							<Button
+								size="sm"
+								className="rounded-lg gap-1.5"
+								onClick={handleApprove}
+								disabled={!canApprove}
+							>
+								Send
+								<CornerDownLeftIcon className="size-3 opacity-60" />
+							</Button>
+						)}
+						{allowedDecisions.includes("reject") && (
+							<Button
+								size="sm"
+								variant="ghost"
+								className="rounded-lg text-muted-foreground"
+								onClick={() => {
+									setDecided("reject");
+									onDecision({ type: "reject", message: "User rejected the action." });
+								}}
+							>
+								Reject
+							</Button>
+						)}
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to send email</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Gmail authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<div className="flex items-center gap-2">
+					<MailIcon className="size-4 text-muted-foreground shrink-0" />
+					<p className="text-sm font-semibold text-foreground">
+						{result.message || "Email sent successfully"}
+					</p>
+				</div>
+			</div>
+		</div>
+	);
+}
+
+export const SendGmailEmailToolUI = makeAssistantToolUI<
+	{ to: string; subject: string; body: string; cc?: string; bcc?: string },
+	SendGmailEmailResult
+>({
+	toolName: "send_gmail_email",
+	render: function SendGmailEmailUI({ args, result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Sending email..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					args={args}
+					interruptData={result}
+					onDecision={(decision) => {
+						window.dispatchEvent(
+							new CustomEvent("hitl-decision", { detail: { decisions: [decision] } })
+						);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});
diff --git a/surfsense_web/components/tool-ui/gmail/trash-email.tsx b/surfsense_web/components/tool-ui/gmail/trash-email.tsx
new file mode 100644
index 000000000..bffed373c
--- /dev/null
+++ b/surfsense_web/components/tool-ui/gmail/trash-email.tsx
@@ -0,0 +1,406 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CalendarIcon,
+	CornerDownLeftIcon,
+	MailIcon,
+	Trash2Icon,
+	TriangleAlertIcon,
+	UserIcon,
+} from "lucide-react";
+import { useCallback, useEffect, useState } from "react";
+import { Button } from "@/components/ui/button";
+import { Checkbox } from "@/components/ui/checkbox";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+
+interface GmailAccount {
+	id: number;
+	name: string;
+	email: string;
+	auth_expired?: boolean;
+}
+
+interface GmailMessage {
+	message_id: string;
+	thread_id?: string;
+	subject: string;
+	sender: string;
+	date: string;
+	connector_id: number;
+	document_id: number;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "reject">;
+	}>;
+	context?: {
+		account?: GmailAccount;
+		email?: GmailMessage;
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	message_id?: string;
+	message?: string;
+	deleted_from_kb?: boolean;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface NotFoundResult {
+	status: "not_found";
+	message: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type TrashGmailEmailResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| NotFoundResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isNotFoundResult(result: unknown): result is NotFoundResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as NotFoundResult).status === "not_found"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function formatDate(dateStr: string): string {
+	return new Date(dateStr).toLocaleDateString(undefined, { dateStyle: "medium" });
+}
+
+function ApprovalCard({
+	interruptData,
+	onDecision,
+}: {
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const [decided, setDecided] = useState<"approve" | "reject" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [deleteFromKb, setDeleteFromKb] = useState(false);
+
+	const account = interruptData.context?.account;
+	const email = interruptData.context?.email;
+
+	const handleApprove = useCallback(() => {
+		if (decided) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: {
+					message_id: email?.message_id,
+					connector_id: email?.connector_id ?? account?.id,
+					delete_from_kb: deleteFromKb,
+				},
+			},
+		});
+	}, [decided, onDecision, interruptData, email, account?.id, deleteFromKb]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<Trash2Icon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Email Trash Rejected"
+								: decided === "approve"
+									? "Email Trash Approved"
+									: "Trash Email"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Email trash was cancelled"
+								: decided === "approve"
+									? "Email is being trashed"
+									: "Requires your approval to proceed"}
+						</p>
+					</div>
+				</div>
+			</div>
+
+			{/* Context — read-only account and email info */}
+			{!decided && interruptData.context && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{interruptData.context.error ? (
+							<p className="text-sm text-destructive">{interruptData.context.error}</p>
+						) : (
+							<>
+								{account && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Gmail Account</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm">
+											{account.email}
+										</div>
+									</div>
+								)}
+
+								{email && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Email to Trash</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm space-y-1.5">
+											<div className="flex items-center gap-1.5">
+												<MailIcon className="size-3 shrink-0 text-muted-foreground" />
+												<span className="font-medium">{email.subject}</span>
+											</div>
+											<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+												<UserIcon className="size-3 shrink-0" />
+												<span>From: {email.sender}</span>
+											</div>
+											<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+												<CalendarIcon className="size-3 shrink-0" />
+												<span>Date: {formatDate(email.date)}</span>
+											</div>
+										</div>
+									</div>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* delete_from_kb toggle */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 select-none">
+						<div className="flex items-center gap-2.5">
+							<Checkbox
+								id="gmail-delete-from-kb"
+								checked={deleteFromKb}
+								onCheckedChange={(v) => setDeleteFromKb(v === true)}
+								className="shrink-0"
+							/>
+							<label htmlFor="gmail-delete-from-kb" className="flex-1 cursor-pointer">
+								<span className="text-sm text-foreground">Also remove from knowledge base</span>
+								<p className="text-xs text-muted-foreground mt-0.5">
+									This will permanently delete the email from your knowledge base (cannot be undone)
+								</p>
+							</label>
+						</div>
+					</div>
+				</>
+			)}
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						<Button
+							size="sm"
+							className="rounded-lg gap-1.5"
+							onClick={handleApprove}
+						>
+							Approve
+							<CornerDownLeftIcon className="size-3 opacity-60" />
+						</Button>
+						<Button
+							size="sm"
+							variant="ghost"
+							className="rounded-lg text-muted-foreground"
+							onClick={() => {
+								setDecided("reject");
+								onDecision({ type: "reject", message: "User rejected the action." });
+							}}
+						>
+							Reject
+						</Button>
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to trash email</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Gmail authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function NotFoundCard({ result }: { result: NotFoundResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border border-amber-500/50 bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<div className="flex items-center gap-2">
+					<TriangleAlertIcon className="size-4 text-amber-500 shrink-0" />
+					<p className="text-sm font-semibold text-amber-600 dark:text-amber-400">
+						Email not found
+					</p>
+				</div>
+			</div>
+			<div className="mx-5 h-px bg-amber-500/30" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-foreground">
+					{result.message || "Email moved to trash successfully"}
+				</p>
+			</div>
+			{result.deleted_from_kb && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 text-xs">
+						<span className="text-green-600 dark:text-green-500">
+							Also removed from knowledge base
+						</span>
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+export const TrashGmailEmailToolUI = makeAssistantToolUI<
+	{ email_subject_or_id: string; delete_from_kb?: boolean },
+	TrashGmailEmailResult
+>({
+	toolName: "trash_gmail_email",
+	render: function TrashGmailEmailUI({ result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Trashing email..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					interruptData={result}
+					onDecision={(decision) => {
+						window.dispatchEvent(
+							new CustomEvent("hitl-decision", { detail: { decisions: [decision] } })
+						);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isNotFoundResult(result)) return <NotFoundCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});
diff --git a/surfsense_web/components/tool-ui/google-calendar/create-event.tsx b/surfsense_web/components/tool-ui/google-calendar/create-event.tsx
new file mode 100644
index 000000000..08c098e99
--- /dev/null
+++ b/surfsense_web/components/tool-ui/google-calendar/create-event.tsx
@@ -0,0 +1,559 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CalendarPlusIcon,
+	ClockIcon,
+	MapPinIcon,
+	UsersIcon,
+	GlobeIcon,
+	CornerDownLeftIcon,
+	Pen,
+} from "lucide-react";
+import { useCallback, useEffect, useMemo, useState } from "react";
+import { useSetAtom } from "jotai";
+import { Button } from "@/components/ui/button";
+import {
+	Select,
+	SelectContent,
+	SelectItem,
+	SelectTrigger,
+	SelectValue,
+} from "@/components/ui/select";
+import { PlateEditor } from "@/components/editor/plate-editor";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+import { openHitlEditPanelAtom } from "@/atoms/chat/hitl-edit-panel.atom";
+import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
+
+interface GoogleCalendarAccount {
+	id: number;
+	name: string;
+	auth_expired?: boolean;
+}
+
+interface CalendarEntry {
+	id: string;
+	summary: string;
+	primary?: boolean;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject" | "edit";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "edit" | "reject">;
+	}>;
+	context?: {
+		accounts?: GoogleCalendarAccount[];
+		calendars?: CalendarEntry[];
+		timezone?: string;
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	event_id: string;
+	html_link?: string;
+	message?: string;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type CreateCalendarEventResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function formatDateTime(iso: string): string {
+	try {
+		return new Date(iso).toLocaleString(undefined, {
+			dateStyle: "medium",
+			timeStyle: "short",
+		});
+	} catch {
+		return iso;
+	}
+}
+
+function ApprovalCard({
+	args,
+	interruptData,
+	onDecision,
+}: {
+	args: {
+		summary: string;
+		start_datetime: string;
+		end_datetime: string;
+		description?: string;
+		location?: string;
+		attendees?: string[];
+	};
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject" | "edit";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const [decided, setDecided] = useState<"approve" | "reject" | "edit" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [isPanelOpen, setIsPanelOpen] = useState(false);
+	const openHitlEditPanel = useSetAtom(openHitlEditPanelAtom);
+
+	const accounts = interruptData.context?.accounts ?? [];
+	const validAccounts = accounts.filter((a) => !a.auth_expired);
+	const expiredAccounts = accounts.filter((a) => a.auth_expired);
+	const calendars = interruptData.context?.calendars ?? [];
+	const timezone = interruptData.context?.timezone ?? "";
+
+	const defaultAccountId = useMemo(() => {
+		if (validAccounts.length === 1) return String(validAccounts[0].id);
+		return "";
+	}, [validAccounts]);
+
+	const defaultCalendarId = useMemo(() => {
+		const primary = calendars.find((c) => c.primary);
+		if (primary) return primary.id;
+		if (calendars.length === 1) return calendars[0].id;
+		return "";
+	}, [calendars]);
+
+	const [selectedAccountId, setSelectedAccountId] = useState<string>(defaultAccountId);
+	const [selectedCalendarId, setSelectedCalendarId] = useState<string>(defaultCalendarId);
+
+	const reviewConfig = interruptData.review_configs[0];
+	const allowedDecisions = reviewConfig?.allowed_decisions ?? ["approve", "reject"];
+	const canEdit = allowedDecisions.includes("edit");
+
+	const canApprove =
+		!!selectedAccountId &&
+		!!selectedCalendarId &&
+		!!args.summary?.trim();
+
+	const handleApprove = useCallback(() => {
+		if (decided || isPanelOpen || !canApprove) return;
+		if (!allowedDecisions.includes("approve")) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: {
+					...args,
+					connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+					calendar_id: selectedCalendarId || null,
+				},
+			},
+		});
+	}, [decided, isPanelOpen, canApprove, allowedDecisions, onDecision, interruptData, args, selectedAccountId, selectedCalendarId]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	const attendeesList = (args.attendees as string[]) ?? [];
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<CalendarPlusIcon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Calendar Event Rejected"
+								: decided === "approve" || decided === "edit"
+									? "Calendar Event Approved"
+									: "Create Calendar Event"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Event creation was cancelled"
+								: decided === "edit"
+									? "Event creation is in progress with your changes"
+									: decided === "approve"
+										? "Event creation is in progress"
+										: "Requires your approval to proceed"}
+						</p>
+					</div>
+				</div>
+				{!decided && canEdit && (
+					<Button
+						size="sm"
+						variant="ghost"
+						className="rounded-lg text-muted-foreground -mt-1 -mr-2"
+						onClick={() => {
+							setIsPanelOpen(true);
+							const extraFields: ExtraField[] = [
+								{ key: "start_datetime", label: "Start", type: "datetime-local", value: args.start_datetime || "" },
+								{ key: "end_datetime", label: "End", type: "datetime-local", value: args.end_datetime || "" },
+								{ key: "location", label: "Location", type: "text", value: args.location || "" },
+								{ key: "attendees", label: "Attendees (comma-separated emails)", type: "text", value: attendeesList.join(", ") },
+							];
+							openHitlEditPanel({
+								title: args.summary ?? "",
+								content: args.description ?? "",
+								toolName: "Calendar Event",
+								extraFields,
+								onSave: (newTitle, newContent, extraFieldValues) => {
+									setIsPanelOpen(false);
+									setDecided("edit");
+
+									const editedArgs: Record<string, unknown> = {
+										...args,
+										summary: newTitle,
+										description: newContent,
+										connector_id: selectedAccountId ? Number(selectedAccountId) : null,
+										calendar_id: selectedCalendarId || null,
+									};
+
+									if (extraFieldValues) {
+										if (extraFieldValues.start_datetime) editedArgs.start_datetime = extraFieldValues.start_datetime;
+										if (extraFieldValues.end_datetime) editedArgs.end_datetime = extraFieldValues.end_datetime;
+										if (extraFieldValues.location !== undefined) editedArgs.location = extraFieldValues.location;
+										if (extraFieldValues.attendees !== undefined) {
+											editedArgs.attendees = extraFieldValues.attendees
+												.split(",")
+												.map((e) => e.trim())
+												.filter(Boolean);
+										}
+									}
+
+									onDecision({
+										type: "edit",
+										edited_action: {
+											name: interruptData.action_requests[0].name,
+											args: editedArgs,
+										},
+									});
+								},
+							});
+						}}
+					>
+						<Pen className="size-3.5" />
+						Edit
+					</Button>
+				)}
+			</div>
+
+			{/* Context section */}
+			{!decided && interruptData.context && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{interruptData.context.error ? (
+							<p className="text-sm text-destructive">{interruptData.context.error}</p>
+						) : (
+							<>
+								{accounts.length > 0 && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">
+											Google Calendar Account <span className="text-destructive">*</span>
+										</p>
+										<Select value={selectedAccountId} onValueChange={setSelectedAccountId}>
+											<SelectTrigger className="w-full">
+												<SelectValue placeholder="Select an account" />
+											</SelectTrigger>
+											<SelectContent>
+												{validAccounts.map((account) => (
+													<SelectItem key={account.id} value={String(account.id)}>
+														{account.name}
+													</SelectItem>
+												))}
+												{expiredAccounts.map((a) => (
+													<div
+														key={a.id}
+														className="relative flex w-full cursor-default items-center gap-2 rounded-sm py-1.5 px-2 text-sm select-none opacity-50 pointer-events-none"
+													>
+														{a.name} (expired, retry after re-auth)
+													</div>
+												))}
+											</SelectContent>
+										</Select>
+									</div>
+								)}
+
+								{calendars.length > 0 && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">
+											Calendar <span className="text-destructive">*</span>
+										</p>
+										<Select value={selectedCalendarId} onValueChange={setSelectedCalendarId}>
+											<SelectTrigger className="w-full">
+												<SelectValue placeholder="Select a calendar" />
+											</SelectTrigger>
+											<SelectContent>
+												{calendars.map((cal) => (
+													<SelectItem key={cal.id} value={cal.id}>
+														{cal.summary}{cal.primary ? " (primary)" : ""}
+													</SelectItem>
+												))}
+											</SelectContent>
+										</Select>
+									</div>
+								)}
+
+								{timezone && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Timezone</p>
+										<div className="flex items-center gap-2 w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm">
+											<GlobeIcon className="size-3.5 text-muted-foreground shrink-0" />
+											{timezone}
+										</div>
+									</div>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* Content preview */}
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 pt-3 pb-3 space-y-2">
+				{args.summary && (
+					<p className="text-sm font-medium text-foreground">{args.summary}</p>
+				)}
+
+				{(args.start_datetime || args.end_datetime) && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<ClockIcon className="size-3.5 shrink-0" />
+						<span>
+							{args.start_datetime ? formatDateTime(args.start_datetime) : ""}
+							{args.start_datetime && args.end_datetime ? " — " : ""}
+							{args.end_datetime ? formatDateTime(args.end_datetime) : ""}
+						</span>
+					</div>
+				)}
+
+				{args.location && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<MapPinIcon className="size-3.5 shrink-0" />
+						<span>{args.location}</span>
+					</div>
+				)}
+
+				{attendeesList.length > 0 && (
+					<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+						<UsersIcon className="size-3.5 shrink-0" />
+						<span>{attendeesList.join(", ")}</span>
+					</div>
+				)}
+
+				{args.description && (
+					<div
+						className="mt-2 max-h-[7rem] overflow-hidden text-sm"
+						style={{
+							maskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+							WebkitMaskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+						}}
+					>
+						<PlateEditor
+							markdown={String(args.description)}
+							readOnly
+							preset="readonly"
+							editorVariant="none"
+							className="h-auto [&_[data-slate-editor]]:!min-h-0 [&_[data-slate-editor]>*:first-child]:!mt-0"
+						/>
+					</div>
+				)}
+			</div>
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						{allowedDecisions.includes("approve") && (
+							<Button
+								size="sm"
+								className="rounded-lg gap-1.5"
+								onClick={handleApprove}
+								disabled={!canApprove}
+							>
+								Approve
+								<CornerDownLeftIcon className="size-3 opacity-60" />
+							</Button>
+						)}
+						{allowedDecisions.includes("reject") && (
+							<Button
+								size="sm"
+								variant="ghost"
+								className="rounded-lg text-muted-foreground"
+								onClick={() => {
+									setDecided("reject");
+									onDecision({ type: "reject", message: "User rejected the action." });
+								}}
+							>
+								Reject
+							</Button>
+						)}
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to create calendar event</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Google Calendar authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-foreground">
+					{result.message || "Calendar event created successfully"}
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4 space-y-2 text-xs">
+				{result.html_link && (
+					<div>
+						<a
+							href={result.html_link}
+							target="_blank"
+							rel="noopener noreferrer"
+							className="text-primary hover:underline"
+						>
+							Open in Google Calendar
+						</a>
+					</div>
+				)}
+			</div>
+		</div>
+	);
+}
+
+export const CreateCalendarEventToolUI = makeAssistantToolUI<
+	{
+		summary: string;
+		start_datetime: string;
+		end_datetime: string;
+		description?: string;
+		location?: string;
+		attendees?: string[];
+	},
+	CreateCalendarEventResult
+>({
+	toolName: "create_calendar_event",
+	render: function CreateCalendarEventUI({ args, result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Preparing calendar event..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					args={args}
+					interruptData={result}
+					onDecision={(decision) => {
+						window.dispatchEvent(
+							new CustomEvent("hitl-decision", { detail: { decisions: [decision] } })
+						);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});
diff --git a/surfsense_web/components/tool-ui/google-calendar/delete-event.tsx b/surfsense_web/components/tool-ui/google-calendar/delete-event.tsx
new file mode 100644
index 000000000..590e2d99e
--- /dev/null
+++ b/surfsense_web/components/tool-ui/google-calendar/delete-event.tsx
@@ -0,0 +1,459 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CalendarX2Icon,
+	CalendarIcon,
+	ClockIcon,
+	MapPinIcon,
+	CornerDownLeftIcon,
+	TriangleAlertIcon,
+} from "lucide-react";
+import { useCallback, useEffect, useState } from "react";
+import { Button } from "@/components/ui/button";
+import { Checkbox } from "@/components/ui/checkbox";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+
+interface GoogleCalendarAccount {
+	id: number;
+	name: string;
+	auth_expired?: boolean;
+}
+
+interface CalendarEvent {
+	event_id: string;
+	summary: string;
+	start: string;
+	end: string;
+	description?: string;
+	location?: string;
+	attendees?: Array<{ email: string }>;
+	calendar_id: string;
+	document_id: number;
+	indexed_at?: string;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "reject">;
+	}>;
+	context?: {
+		account?: GoogleCalendarAccount;
+		event?: CalendarEvent;
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	event_id: string;
+	message?: string;
+	deleted_from_kb?: boolean;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface NotFoundResult {
+	status: "not_found";
+	message: string;
+}
+
+interface WarningResult {
+	status: "success";
+	warning: string;
+	event_id?: string;
+	message?: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type DeleteCalendarEventResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| NotFoundResult
+	| WarningResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isNotFoundResult(result: unknown): result is NotFoundResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as NotFoundResult).status === "not_found"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function isWarningResult(result: unknown): result is WarningResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as WarningResult).status === "success" &&
+		"warning" in result &&
+		typeof (result as WarningResult).warning === "string"
+	);
+}
+
+function formatDateTime(iso: string): string {
+	try {
+		return new Date(iso).toLocaleString(undefined, {
+			dateStyle: "medium",
+			timeStyle: "short",
+		});
+	} catch {
+		return iso;
+	}
+}
+
+function ApprovalCard({
+	interruptData,
+	onDecision,
+}: {
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const [decided, setDecided] = useState<"approve" | "reject" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [deleteFromKb, setDeleteFromKb] = useState(false);
+
+	const context = interruptData.context;
+	const account = context?.account;
+	const event = context?.event;
+
+	const handleApprove = useCallback(() => {
+		if (decided) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: {
+					event_id: event?.event_id,
+					connector_id: account?.id,
+					delete_from_kb: deleteFromKb,
+				},
+			},
+		});
+	}, [decided, onDecision, interruptData, event?.event_id, account?.id, deleteFromKb]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<CalendarX2Icon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Calendar Event Deletion Rejected"
+								: decided === "approve"
+									? "Calendar Event Deletion Approved"
+									: "Delete Calendar Event"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Event deletion was cancelled"
+								: decided === "approve"
+									? "Event deletion is in progress"
+									: "Requires your approval to proceed"}
+						</p>
+					</div>
+				</div>
+			</div>
+
+			{/* Context section */}
+			{!decided && context && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{context.error ? (
+							<p className="text-sm text-destructive">{context.error}</p>
+						) : (
+							<>
+								{account && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Google Calendar Account</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm">
+											{account.name}
+										</div>
+									</div>
+								)}
+
+								{event && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Event to Delete</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm space-y-1.5">
+											<div className="flex items-center gap-1.5">
+												<CalendarIcon className="size-3 shrink-0 text-muted-foreground" />
+												<span className="font-medium">{event.summary}</span>
+											</div>
+											{(event.start || event.end) && (
+												<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+													<ClockIcon className="size-3 shrink-0" />
+													<span>
+														{event.start ? formatDateTime(event.start) : ""}
+														{event.start && event.end ? " — " : ""}
+														{event.end ? formatDateTime(event.end) : ""}
+													</span>
+												</div>
+											)}
+											{event.location && (
+												<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+													<MapPinIcon className="size-3 shrink-0" />
+													<span>{event.location}</span>
+												</div>
+											)}
+										</div>
+									</div>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* delete_from_kb toggle */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 select-none">
+						<div className="flex items-center gap-2.5">
+							<Checkbox
+								id="calendar-delete-from-kb"
+								checked={deleteFromKb}
+								onCheckedChange={(v) => setDeleteFromKb(v === true)}
+								className="shrink-0"
+							/>
+							<label htmlFor="calendar-delete-from-kb" className="flex-1 cursor-pointer">
+								<span className="text-sm text-foreground">Also remove from knowledge base</span>
+								<p className="text-xs text-muted-foreground mt-0.5">
+									This will permanently delete the event from your knowledge base (cannot be undone)
+								</p>
+							</label>
+						</div>
+					</div>
+				</>
+			)}
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						<Button
+							size="sm"
+							className="rounded-lg gap-1.5"
+							onClick={handleApprove}
+						>
+							Approve
+							<CornerDownLeftIcon className="size-3 opacity-60" />
+						</Button>
+						<Button
+							size="sm"
+							variant="ghost"
+							className="rounded-lg text-muted-foreground"
+							onClick={() => {
+								setDecided("reject");
+								onDecision({ type: "reject", message: "User rejected the action." });
+							}}
+						>
+							Reject
+						</Button>
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to delete calendar event</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Google Calendar authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function NotFoundCard({ result }: { result: NotFoundResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border border-amber-500/50 bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<div className="flex items-center gap-2">
+					<TriangleAlertIcon className="size-4 text-amber-500 shrink-0" />
+					<p className="text-sm font-semibold text-amber-600 dark:text-amber-400">
+						Event not found
+					</p>
+				</div>
+			</div>
+			<div className="mx-5 h-px bg-amber-500/30" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function WarningCard({ result }: { result: WarningResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="flex items-start gap-3 border-b px-5 py-4">
+				<TriangleAlertIcon className="size-4 mt-0.5 shrink-0 text-amber-500" />
+				<p className="text-sm font-medium text-amber-600 dark:text-amber-500">Partial success</p>
+			</div>
+			<div className="px-5 py-4 space-y-2 text-xs">
+				<p className="text-sm text-muted-foreground">{result.warning}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-foreground">
+					{result.message || "Calendar event deleted successfully"}
+				</p>
+			</div>
+			{result.deleted_from_kb && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 text-xs">
+						<span className="text-green-600 dark:text-green-500">
+							Also removed from knowledge base
+						</span>
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+export const DeleteCalendarEventToolUI = makeAssistantToolUI<
+	{ event_ref: string; delete_from_kb?: boolean },
+	DeleteCalendarEventResult
+>({
+	toolName: "delete_calendar_event",
+	render: function DeleteCalendarEventUI({ result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Deleting calendar event..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					interruptData={result}
+					onDecision={(decision) => {
+						const event = new CustomEvent("hitl-decision", {
+							detail: { decisions: [decision] },
+						});
+						window.dispatchEvent(event);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isNotFoundResult(result)) return <NotFoundCard result={result} />;
+		if (isWarningResult(result)) return <WarningCard result={result} />;
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});
diff --git a/surfsense_web/components/tool-ui/google-calendar/index.ts b/surfsense_web/components/tool-ui/google-calendar/index.ts
new file mode 100644
index 000000000..f4d432ae8
--- /dev/null
+++ b/surfsense_web/components/tool-ui/google-calendar/index.ts
@@ -0,0 +1,3 @@
+export { CreateCalendarEventToolUI } from "./create-event";
+export { UpdateCalendarEventToolUI } from "./update-event";
+export { DeleteCalendarEventToolUI } from "./delete-event";
diff --git a/surfsense_web/components/tool-ui/google-calendar/update-event.tsx b/surfsense_web/components/tool-ui/google-calendar/update-event.tsx
new file mode 100644
index 000000000..7629b9821
--- /dev/null
+++ b/surfsense_web/components/tool-ui/google-calendar/update-event.tsx
@@ -0,0 +1,602 @@
+"use client";
+
+import { makeAssistantToolUI } from "@assistant-ui/react";
+import {
+	CalendarIcon,
+	ClockIcon,
+	MapPinIcon,
+	UsersIcon,
+	ArrowRightIcon,
+	CornerDownLeftIcon,
+	Pen,
+	TriangleAlertIcon,
+} from "lucide-react";
+import { useCallback, useEffect, useState } from "react";
+import { useSetAtom } from "jotai";
+import { Button } from "@/components/ui/button";
+import { PlateEditor } from "@/components/editor/plate-editor";
+import { TextShimmerLoader } from "@/components/prompt-kit/loader";
+import { openHitlEditPanelAtom } from "@/atoms/chat/hitl-edit-panel.atom";
+import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
+
+interface GoogleCalendarAccount {
+	id: number;
+	name: string;
+	auth_expired?: boolean;
+}
+
+interface CalendarEvent {
+	event_id: string;
+	summary: string;
+	start: string;
+	end: string;
+	description?: string;
+	location?: string;
+	attendees?: Array<{ email: string }>;
+	calendar_id: string;
+	document_id: number;
+	indexed_at?: string;
+}
+
+interface InterruptResult {
+	__interrupt__: true;
+	__decided__?: "approve" | "reject" | "edit";
+	action_requests: Array<{
+		name: string;
+		args: Record<string, unknown>;
+	}>;
+	review_configs: Array<{
+		action_name: string;
+		allowed_decisions: Array<"approve" | "edit" | "reject">;
+	}>;
+	context?: {
+		account?: GoogleCalendarAccount;
+		event?: CalendarEvent;
+		error?: string;
+	};
+}
+
+interface SuccessResult {
+	status: "success";
+	event_id: string;
+	html_link?: string;
+	message?: string;
+}
+
+interface ErrorResult {
+	status: "error";
+	message: string;
+}
+
+interface NotFoundResult {
+	status: "not_found";
+	message: string;
+}
+
+interface AuthErrorResult {
+	status: "auth_error";
+	message: string;
+	connector_type?: string;
+}
+
+type UpdateCalendarEventResult =
+	| InterruptResult
+	| SuccessResult
+	| ErrorResult
+	| NotFoundResult
+	| AuthErrorResult;
+
+function isInterruptResult(result: unknown): result is InterruptResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"__interrupt__" in result &&
+		(result as InterruptResult).__interrupt__ === true
+	);
+}
+
+function isErrorResult(result: unknown): result is ErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as ErrorResult).status === "error"
+	);
+}
+
+function isNotFoundResult(result: unknown): result is NotFoundResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as NotFoundResult).status === "not_found"
+	);
+}
+
+function isAuthErrorResult(result: unknown): result is AuthErrorResult {
+	return (
+		typeof result === "object" &&
+		result !== null &&
+		"status" in result &&
+		(result as AuthErrorResult).status === "auth_error"
+	);
+}
+
+function formatDateTime(iso: string): string {
+	try {
+		return new Date(iso).toLocaleString(undefined, {
+			dateStyle: "medium",
+			timeStyle: "short",
+		});
+	} catch {
+		return iso;
+	}
+}
+
+function ApprovalCard({
+	interruptData,
+	onDecision,
+}: {
+	interruptData: InterruptResult;
+	onDecision: (decision: {
+		type: "approve" | "reject" | "edit";
+		message?: string;
+		edited_action?: { name: string; args: Record<string, unknown> };
+	}) => void;
+}) {
+	const actionArgs = interruptData.action_requests[0]?.args ?? {};
+	const context = interruptData.context;
+	const account = context?.account;
+	const event = context?.event;
+
+	const [decided, setDecided] = useState<"approve" | "reject" | "edit" | null>(
+		interruptData.__decided__ ?? null
+	);
+	const [isPanelOpen, setIsPanelOpen] = useState(false);
+	const openHitlEditPanel = useSetAtom(openHitlEditPanelAtom);
+
+	const reviewConfig = interruptData.review_configs[0];
+	const allowedDecisions = reviewConfig?.allowed_decisions ?? ["approve", "reject"];
+	const canEdit = allowedDecisions.includes("edit");
+
+	const currentAttendees = event?.attendees?.map((a) => a.email) ?? [];
+	const proposedAttendees = Array.isArray(actionArgs.new_attendees)
+		? (actionArgs.new_attendees as string[])
+		: null;
+
+	const changes: Array<{ label: string; oldVal: string; newVal: string }> = [];
+
+	if (actionArgs.new_summary && String(actionArgs.new_summary) !== event?.summary) {
+		changes.push({ label: "Summary", oldVal: event?.summary ?? "", newVal: String(actionArgs.new_summary) });
+	}
+	if (actionArgs.new_start_datetime && String(actionArgs.new_start_datetime) !== event?.start) {
+		changes.push({
+			label: "Start",
+			oldVal: event?.start ? formatDateTime(event.start) : "",
+			newVal: formatDateTime(String(actionArgs.new_start_datetime)),
+		});
+	}
+	if (actionArgs.new_end_datetime && String(actionArgs.new_end_datetime) !== event?.end) {
+		changes.push({
+			label: "End",
+			oldVal: event?.end ? formatDateTime(event.end) : "",
+			newVal: formatDateTime(String(actionArgs.new_end_datetime)),
+		});
+	}
+	if (actionArgs.new_location !== undefined && String(actionArgs.new_location ?? "") !== (event?.location ?? "")) {
+		changes.push({ label: "Location", oldVal: event?.location ?? "", newVal: String(actionArgs.new_location ?? "") });
+	}
+	if (proposedAttendees) {
+		const oldStr = currentAttendees.join(", ");
+		const newStr = proposedAttendees.join(", ");
+		if (oldStr !== newStr) {
+			changes.push({ label: "Attendees", oldVal: oldStr, newVal: newStr });
+		}
+	}
+
+	const hasDescriptionChange =
+		actionArgs.new_description !== undefined &&
+		String(actionArgs.new_description ?? "") !== (event?.description ?? "");
+
+	const buildFinalArgs = useCallback(() => {
+		return {
+			event_id: event?.event_id,
+			document_id: event?.document_id,
+			connector_id: account?.id,
+			new_summary: actionArgs.new_summary ?? null,
+			new_description: actionArgs.new_description ?? null,
+			new_start_datetime: actionArgs.new_start_datetime ?? null,
+			new_end_datetime: actionArgs.new_end_datetime ?? null,
+			new_location: actionArgs.new_location ?? null,
+			new_attendees: proposedAttendees ?? null,
+		};
+	}, [event, account, actionArgs, proposedAttendees]);
+
+	const handleApprove = useCallback(() => {
+		if (decided || isPanelOpen) return;
+		if (!allowedDecisions.includes("approve")) return;
+		setDecided("approve");
+		onDecision({
+			type: "approve",
+			edited_action: {
+				name: interruptData.action_requests[0].name,
+				args: buildFinalArgs(),
+			},
+		});
+	}, [decided, isPanelOpen, allowedDecisions, onDecision, interruptData, buildFinalArgs]);
+
+	useEffect(() => {
+		const handler = (e: KeyboardEvent) => {
+			if (e.key === "Enter" && !e.shiftKey && !e.ctrlKey && !e.metaKey) {
+				handleApprove();
+			}
+		};
+		window.addEventListener("keydown", handler);
+		return () => window.removeEventListener("keydown", handler);
+	}, [handleApprove]);
+
+	if (decided && decided !== "reject") return null;
+
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 transition-all duration-300">
+			{/* Header */}
+			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
+				<div className="flex items-center gap-2">
+					<CalendarIcon className="size-4 text-muted-foreground shrink-0" />
+					<div>
+						<p className="text-sm font-semibold text-foreground">
+							{decided === "reject"
+								? "Calendar Event Update Rejected"
+								: decided === "approve" || decided === "edit"
+									? "Calendar Event Update Approved"
+									: "Update Calendar Event"}
+						</p>
+						<p className="text-xs text-muted-foreground mt-0.5">
+							{decided === "reject"
+								? "Event update was cancelled"
+								: decided === "edit"
+									? "Event update is in progress with your changes"
+									: decided === "approve"
+										? "Event update is in progress"
+										: "Requires your approval to proceed"}
+						</p>
+					</div>
+				</div>
+				{!decided && canEdit && (
+					<Button
+						size="sm"
+						variant="ghost"
+						className="rounded-lg text-muted-foreground -mt-1 -mr-2"
+						onClick={() => {
+							setIsPanelOpen(true);
+							const proposedSummary = actionArgs.new_summary
+								? String(actionArgs.new_summary)
+								: (event?.summary ?? "");
+							const proposedDescription = actionArgs.new_description
+								? String(actionArgs.new_description)
+								: (event?.description ?? "");
+							const proposedStart = actionArgs.new_start_datetime
+								? String(actionArgs.new_start_datetime)
+								: (event?.start ?? "");
+							const proposedEnd = actionArgs.new_end_datetime
+								? String(actionArgs.new_end_datetime)
+								: (event?.end ?? "");
+							const proposedLocation = actionArgs.new_location !== undefined
+								? String(actionArgs.new_location ?? "")
+								: (event?.location ?? "");
+							const proposedAttendeesStr = proposedAttendees
+								? proposedAttendees.join(", ")
+								: currentAttendees.join(", ");
+
+							const extraFields: ExtraField[] = [
+								{ key: "start_datetime", label: "Start", type: "datetime-local", value: proposedStart },
+								{ key: "end_datetime", label: "End", type: "datetime-local", value: proposedEnd },
+								{ key: "location", label: "Location", type: "text", value: proposedLocation },
+								{ key: "attendees", label: "Attendees (comma-separated emails)", type: "text", value: proposedAttendeesStr },
+							];
+							openHitlEditPanel({
+								title: proposedSummary,
+								content: proposedDescription,
+								toolName: "Calendar Event",
+								extraFields,
+								onSave: (newTitle, newContent, extraFieldValues) => {
+									setIsPanelOpen(false);
+									setDecided("edit");
+
+									const editedArgs: Record<string, unknown> = {
+										event_id: event?.event_id,
+										document_id: event?.document_id,
+										connector_id: account?.id,
+										new_summary: newTitle || null,
+										new_description: newContent || null,
+									};
+
+									if (extraFieldValues) {
+										editedArgs.new_start_datetime = extraFieldValues.start_datetime || null;
+										editedArgs.new_end_datetime = extraFieldValues.end_datetime || null;
+										editedArgs.new_location = extraFieldValues.location || null;
+										if (extraFieldValues.attendees !== undefined) {
+											editedArgs.new_attendees = extraFieldValues.attendees
+												.split(",")
+												.map((e) => e.trim())
+												.filter(Boolean);
+										}
+									}
+
+									onDecision({
+										type: "edit",
+										edited_action: {
+											name: interruptData.action_requests[0].name,
+											args: editedArgs,
+										},
+									});
+								},
+							});
+						}}
+					>
+						<Pen className="size-3.5" />
+						Edit
+					</Button>
+				)}
+			</div>
+
+			{/* Context section */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 space-y-4 select-none">
+						{context?.error ? (
+							<p className="text-sm text-destructive">{context.error}</p>
+						) : (
+							<>
+								{account && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Google Calendar Account</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm">
+											{account.name}
+										</div>
+									</div>
+								)}
+
+								{event && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Current Event</p>
+										<div className="w-full rounded-md border border-input bg-muted/50 px-3 py-2 text-sm space-y-1.5">
+											<div className="font-medium">{event.summary}</div>
+											{(event.start || event.end) && (
+												<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+													<ClockIcon className="size-3 shrink-0" />
+													<span>
+														{event.start ? formatDateTime(event.start) : ""}
+														{event.start && event.end ? " — " : ""}
+														{event.end ? formatDateTime(event.end) : ""}
+													</span>
+												</div>
+											)}
+											{event.location && (
+												<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+													<MapPinIcon className="size-3 shrink-0" />
+													<span>{event.location}</span>
+												</div>
+											)}
+											{currentAttendees.length > 0 && (
+												<div className="flex items-center gap-1.5 text-xs text-muted-foreground">
+													<UsersIcon className="size-3 shrink-0" />
+													<span>{currentAttendees.join(", ")}</span>
+												</div>
+											)}
+										</div>
+									</div>
+								)}
+
+								{(changes.length > 0 || hasDescriptionChange) && (
+									<div className="space-y-2">
+										<p className="text-xs font-medium text-muted-foreground">Proposed Changes</p>
+										<div className="space-y-2">
+											{changes.map((change) => (
+												<div key={change.label} className="text-xs space-y-0.5">
+													<span className="text-muted-foreground">{change.label}</span>
+													<div className="flex items-center gap-1.5 flex-wrap">
+														<span className="text-muted-foreground line-through">{change.oldVal || "(empty)"}</span>
+														<ArrowRightIcon className="size-3 text-muted-foreground shrink-0" />
+														<span className="font-medium text-foreground">{change.newVal || "(empty)"}</span>
+													</div>
+												</div>
+											))}
+											{hasDescriptionChange && (
+												<div className="text-xs space-y-0.5">
+													<span className="text-muted-foreground">Description</span>
+													<div
+														className="mt-1 max-h-[5rem] overflow-hidden"
+														style={{
+															maskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+															WebkitMaskImage: "linear-gradient(to bottom, black 50%, transparent 100%)",
+														}}
+													>
+														<PlateEditor
+															markdown={String(actionArgs.new_description ?? "")}
+															readOnly
+															preset="readonly"
+															editorVariant="none"
+															className="h-auto [&_[data-slate-editor]]:!min-h-0 [&_[data-slate-editor]>*:first-child]:!mt-0"
+														/>
+													</div>
+												</div>
+											)}
+										</div>
+									</div>
+								)}
+
+								{changes.length === 0 && !hasDescriptionChange && (
+									<p className="text-sm text-muted-foreground italic">No changes proposed</p>
+								)}
+							</>
+						)}
+					</div>
+				</>
+			)}
+
+			{/* Action buttons */}
+			{!decided && (
+				<>
+					<div className="mx-5 h-px bg-border/50" />
+					<div className="px-5 py-4 flex items-center gap-2 select-none">
+						{allowedDecisions.includes("approve") && (
+							<Button
+								size="sm"
+								className="rounded-lg gap-1.5"
+								onClick={handleApprove}
+							>
+								Approve
+								<CornerDownLeftIcon className="size-3 opacity-60" />
+							</Button>
+						)}
+						{allowedDecisions.includes("reject") && (
+							<Button
+								size="sm"
+								variant="ghost"
+								className="rounded-lg text-muted-foreground"
+								onClick={() => {
+									setDecided("reject");
+									onDecision({ type: "reject", message: "User rejected the action." });
+								}}
+							>
+								Reject
+							</Button>
+						)}
+					</div>
+				</>
+			)}
+		</div>
+	);
+}
+
+function ErrorCard({ result }: { result: ErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">Failed to update calendar event</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function AuthErrorCard({ result }: { result: AuthErrorResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-destructive">
+					Google Calendar authentication expired
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function NotFoundCard({ result }: { result: NotFoundResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border border-amber-500/50 bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<div className="flex items-center gap-2">
+					<TriangleAlertIcon className="size-4 text-amber-500 shrink-0" />
+					<p className="text-sm font-semibold text-amber-600 dark:text-amber-400">
+						Event not found
+					</p>
+				</div>
+			</div>
+			<div className="mx-5 h-px bg-amber-500/30" />
+			<div className="px-5 py-4">
+				<p className="text-sm text-muted-foreground">{result.message}</p>
+			</div>
+		</div>
+	);
+}
+
+function SuccessCard({ result }: { result: SuccessResult }) {
+	return (
+		<div className="my-4 max-w-lg overflow-hidden rounded-2xl border bg-muted/30 select-none">
+			<div className="px-5 pt-5 pb-4">
+				<p className="text-sm font-semibold text-foreground">
+					{result.message || "Calendar event updated successfully"}
+				</p>
+			</div>
+			<div className="mx-5 h-px bg-border/50" />
+			<div className="px-5 py-4 space-y-2 text-xs">
+				{result.html_link && (
+					<div>
+						<a
+							href={result.html_link}
+							target="_blank"
+							rel="noopener noreferrer"
+							className="text-primary hover:underline"
+						>
+							Open in Google Calendar
+						</a>
+					</div>
+				)}
+			</div>
+		</div>
+	);
+}
+
+export const UpdateCalendarEventToolUI = makeAssistantToolUI<
+	{
+		event_ref: string;
+		new_summary?: string;
+		new_description?: string;
+		new_start_datetime?: string;
+		new_end_datetime?: string;
+		new_location?: string;
+		new_attendees?: string[];
+	},
+	UpdateCalendarEventResult
+>({
+	toolName: "update_calendar_event",
+	render: function UpdateCalendarEventUI({ result, status }) {
+		if (status.type === "running") {
+			return (
+				<div className="my-4 max-w-lg rounded-2xl border bg-muted/30 px-5 py-4 select-none">
+					<TextShimmerLoader text="Looking up calendar event..." size="sm" />
+				</div>
+			);
+		}
+
+		if (!result) return null;
+
+		if (isInterruptResult(result)) {
+			return (
+				<ApprovalCard
+					interruptData={result}
+					onDecision={(decision) => {
+						window.dispatchEvent(
+							new CustomEvent("hitl-decision", { detail: { decisions: [decision] } })
+						);
+					}}
+				/>
+			);
+		}
+
+		if (
+			typeof result === "object" &&
+			result !== null &&
+			"status" in result &&
+			(result as { status: string }).status === "rejected"
+		) {
+			return null;
+		}
+
+		if (isNotFoundResult(result)) return <NotFoundCard result={result} />;
+		if (isAuthErrorResult(result)) return <AuthErrorCard result={result} />;
+		if (isErrorResult(result)) return <ErrorCard result={result} />;
+
+		return <SuccessCard result={result as SuccessResult} />;
+	},
+});