feat: implement Jira OAuth integration and connector routes

- Added support for Jira OAuth with new environment variables for client ID, client secret, and redirect URI.
- Implemented Jira connector routes for OAuth flow, including authorization and callback handling.
- Enhanced Jira connector to support both OAuth 2.0 and legacy API token authentication methods.
- Updated Jira indexing logic to utilize OAuth credentials with auto-refresh capabilities.
- Removed outdated Jira UI components and adjusted frontend logic to reflect the new integration.

surfsense_backend/.env.example

@@ -50,6 +50,11 @@ DISCORD_CLIENT_SECRET=your_discord_client_secret_here
 DISCORD_REDIRECT_URI=http://localhost:8000/api/v1/auth/discord/connector/callback
 DISCORD_BOT_TOKEN=your_bot_token_from_developer_portal
 
+# Jira OAuth Configuration
+JIRA_CLIENT_ID=our_jira_client_id
+JIRA_CLIENT_SECRET=your_jira_client_secret
+JIRA_REDIRECT_URI=http://localhost:8000/api/v1/auth/jira/connector/callback
+
 # OAuth for Linear Connector
 LINEAR_CLIENT_ID=your_linear_client_id
 LINEAR_CLIENT_SECRET=your_linear_client_secret

surfsense_backend/app/connectors/jira_connector.py

@@ -3,6 +3,7 @@ Jira Connector Module
 
 A module for retrieving data from Jira.
 Allows fetching issue lists and their comments, projects and more.
+Supports both OAuth 2.0 (preferred) and legacy API token authentication.
 """
 
 import base64
@@ -18,6 +19,8 @@ class JiraConnector:
     def __init__(
         self,
         base_url: str | None = None,
+        access_token: str | None = None,
+        cloud_id: str | None = None,
         email: str | None = None,
         api_token: str | None = None,
     ):
@@ -25,18 +28,39 @@ class JiraConnector:
         Initialize the JiraConnector class.
 
         Args:
-            base_url: Jira instance base URL (e.g., 'https://yourcompany.atlassian.net') (optional)
-            email: Jira account email address (optional)
-            api_token: Jira API token (optional)
+            base_url: Jira instance base URL (e.g., 'https://yourcompany.atlassian.net')
+            access_token: OAuth 2.0 access token (preferred method)
+            cloud_id: Atlassian cloud ID (used with OAuth for API URL construction)
+            email: Jira account email address (legacy method, used with api_token)
+            api_token: Jira API token (legacy method, used with email)
         """
         self.base_url = base_url.rstrip("/") if base_url else None
+        self.access_token = access_token
+        self.cloud_id = cloud_id
         self.email = email
         self.api_token = api_token
         self.api_version = "3"  # Jira Cloud API version
+        self._use_oauth = access_token is not None
+
+    def set_oauth_credentials(
+        self, base_url: str, access_token: str, cloud_id: str | None = None
+    ) -> None:
+        """
+        Set OAuth 2.0 credentials (preferred method).
+
+        Args:
+            base_url: Jira instance base URL
+            access_token: OAuth 2.0 access token
+            cloud_id: Atlassian cloud ID (optional, used for API URL construction)
+        """
+        self.base_url = base_url.rstrip("/")
+        self.access_token = access_token
+        self.cloud_id = cloud_id
+        self._use_oauth = True
 
     def set_credentials(self, base_url: str, email: str, api_token: str) -> None:
         """
-        Set the Jira credentials.
+        Set the Jira credentials (legacy method using API token).
 
         Args:
             base_url: Jira instance base URL
@@ -46,50 +70,69 @@ class JiraConnector:
         self.base_url = base_url.rstrip("/")
         self.email = email
         self.api_token = api_token
+        self._use_oauth = False
 
     def set_email(self, email: str) -> None:
         """
-        Set the Jira account email.
+        Set the Jira account email (legacy method).
 
         Args:
             email: Jira account email address
         """
         self.email = email
+        self._use_oauth = False
 
     def set_api_token(self, api_token: str) -> None:
         """
-        Set the Jira API token.
+        Set the Jira API token (legacy method).
 
         Args:
             api_token: Jira API token
         """
         self.api_token = api_token
+        self._use_oauth = False
 
     def get_headers(self) -> dict[str, str]:
         """
-        Get headers for Jira API requests using Basic Authentication.
+        Get headers for Jira API requests.
+
+        Uses OAuth Bearer token if available, otherwise falls back to Basic Auth.
 
         Returns:
             Dictionary of headers
 
         Raises:
-            ValueError: If email, api_token, or base_url have not been set
+            ValueError: If credentials have not been set
         """
-        if not all([self.base_url, self.email, self.api_token]):
-            raise ValueError(
-                "Jira credentials not initialized. Call set_credentials() first."
-            )
+        if self._use_oauth:
+            # OAuth 2.0 authentication
+            if not self.base_url or not self.access_token:
+                raise ValueError(
+                    "Jira OAuth credentials not initialized. Call set_oauth_credentials() first."
+                )
 
-        # Create Basic Auth header using email:api_token
-        auth_str = f"{self.email}:{self.api_token}"
-        auth_bytes = auth_str.encode("utf-8")
-        auth_header = "Basic " + base64.b64encode(auth_bytes).decode("ascii")
+            return {
+                "Content-Type": "application/json",
+                "Authorization": f"Bearer {self.access_token}",
+                "Accept": "application/json",
+            }
+        else:
+            # Legacy Basic Auth
+            if not all([self.base_url, self.email, self.api_token]):
+                raise ValueError(
+                    "Jira credentials not initialized. Call set_credentials() first."
+                )
 
-        return {
-            "Content-Type": "application/json",
-            "Authorization": auth_header,
-            "Accept": "application/json",
-        }
+            # Create Basic Auth header using email:api_token
+            auth_str = f"{self.email}:{self.api_token}"
+            auth_bytes = auth_str.encode("utf-8")
+            auth_header = "Basic " + base64.b64encode(auth_bytes).decode("ascii")
+
+            return {
+                "Content-Type": "application/json",
+                "Authorization": auth_header,
+                "Accept": "application/json",
+            }
 
     def make_api_request(
         self,
@@ -104,22 +147,26 @@ class JiraConnector:
         Args:
             endpoint: API endpoint (without base URL)
             params: Query parameters for the request (optional)
+            method: HTTP method (GET or POST)
+            json_payload: JSON payload for POST requests (optional)
 
         Returns:
             Response data from the API
 
         Raises:
-            ValueError: If email, api_token, or base_url have not been set
+            ValueError: If credentials have not been set
             Exception: If the API request fails
         """
-        if not all([self.base_url, self.email, self.api_token]):
-            raise ValueError(
-                "Jira credentials not initialized. Call set_credentials() first."
-            )
-
-        url = f"{self.base_url}/rest/api/{self.api_version}/{endpoint}"
         headers = self.get_headers()
 
+        # Construct API URL based on authentication method
+        if self._use_oauth and self.cloud_id:
+            # Use Atlassian API gateway with cloud_id for OAuth
+            url = f"https://api.atlassian.com/ex/jira/{self.cloud_id}/rest/api/{self.api_version}/{endpoint}"
+        else:
+            # Use direct base URL (works for both OAuth and legacy)
+            url = f"{self.base_url}/rest/api/{self.api_version}/{endpoint}"
+
         if method.upper() == "POST":
             response = requests.post(
                 url, headers=headers, json=json_payload, timeout=500
@@ -234,15 +281,24 @@ class JiraConnector:
         try:
             # Build JQL query for date range
             # Query issues that were either created OR updated within the date range
+            # Use end_date + 1 day with < operator to include the full end date
+            from datetime import datetime, timedelta
+            
+            # Parse end_date and add 1 day for inclusive end date
+            end_date_obj = datetime.strptime(end_date, "%Y-%m-%d")
+            end_date_next = (end_date_obj + timedelta(days=1)).strftime("%Y-%m-%d")
+            
+            # Check both created and updated dates to catch all relevant issues
+            # Use 'created' and 'updated' (standard JQL field names)
             date_filter = (
-                f"(createdDate >= '{start_date}' AND createdDate <= '{end_date}')"
+                f"(created >= '{start_date}' AND created < '{end_date_next}') "
+                f"OR (updated >= '{start_date}' AND updated < '{end_date_next}')"
             )
-            # TODO : This JQL needs some improvement to work as expected
 
-            jql = f"{date_filter}"
+            jql = f"{date_filter} ORDER BY created DESC"
             if project_key:
                 jql = (
-                    f'project = "{project_key}" AND {date_filter} ORDER BY created DESC'
+                    f'project = "{project_key}" AND ({date_filter}) ORDER BY created DESC'
                 )
 
             # Define fields to retrieve

surfsense_backend/app/routes/__init__.py

@@ -4,6 +4,7 @@ from .airtable_add_connector_route import (
     router as airtable_add_connector_router,
 )
 from .circleback_webhook_route import router as circleback_webhook_router
+from .discord_add_connector_route import router as discord_add_connector_router
 from .documents_routes import router as documents_router
 from .editor_routes import router as editor_router
 from .google_calendar_add_connector_route import (
@@ -15,6 +16,7 @@ from .google_drive_add_connector_route import (
 from .google_gmail_add_connector_route import (
     router as google_gmail_add_connector_router,
 )
+from .jira_add_connector_route import router as jira_add_connector_router
 from .linear_add_connector_route import router as linear_add_connector_router
 from .logs_routes import router as logs_router
 from .luma_add_connector_route import router as luma_add_connector_router
@@ -27,7 +29,6 @@ from .rbac_routes import router as rbac_router
 from .search_source_connectors_routes import router as search_source_connectors_router
 from .search_spaces_routes import router as search_spaces_router
 from .slack_add_connector_route import router as slack_add_connector_router
-from .discord_add_connector_route import router as discord_add_connector_router
 
 router = APIRouter()
 
@@ -48,6 +49,7 @@ router.include_router(luma_add_connector_router)
 router.include_router(notion_add_connector_router)
 router.include_router(slack_add_connector_router)
 router.include_router(discord_add_connector_router)
+router.include_router(jira_add_connector_router)
 router.include_router(new_llm_config_router)  # LLM configs with prompt configuration
 router.include_router(logs_router)
 router.include_router(circleback_webhook_router)  # Circleback meeting webhooks

surfsense_backend/app/routes/jira_add_connector_route.py

@@ -0,0 +1,494 @@
+"""
+Jira Connector OAuth Routes.
+
+Handles OAuth 2.0 authentication flow for Jira connector.
+Uses Atlassian OAuth 2.0 (3LO) with accessible-resources API to discover Jira instances.
+"""
+
+import logging
+from datetime import UTC, datetime, timedelta
+from uuid import UUID
+
+import httpx
+from fastapi import APIRouter, Depends, HTTPException, Request
+from fastapi.responses import RedirectResponse
+from pydantic import ValidationError
+from sqlalchemy.exc import IntegrityError
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy.future import select
+
+from app.config import config
+from app.db import (
+    SearchSourceConnector,
+    SearchSourceConnectorType,
+    User,
+    get_async_session,
+)
+from app.schemas.jira_auth_credentials import JiraAuthCredentialsBase
+from app.users import current_active_user
+from app.utils.oauth_security import OAuthStateManager, TokenEncryption
+
+logger = logging.getLogger(__name__)
+
+router = APIRouter()
+
+# Atlassian OAuth endpoints
+AUTHORIZATION_URL = "https://auth.atlassian.com/authorize"
+TOKEN_URL = "https://auth.atlassian.com/oauth/token"
+ACCESSIBLE_RESOURCES_URL = "https://api.atlassian.com/oauth/token/accessible-resources"
+
+# OAuth scopes for Jira
+SCOPES = [
+    "read:jira-work",
+    "write:jira-work",
+    "read:jira-user",
+    "offline_access",  # Required for refresh tokens
+]
+
+# Initialize security utilities
+_state_manager = None
+_token_encryption = None
+
+
+def get_state_manager() -> OAuthStateManager:
+    """Get or create OAuth state manager instance."""
+    global _state_manager
+    if _state_manager is None:
+        if not config.SECRET_KEY:
+            raise ValueError("SECRET_KEY must be set for OAuth security")
+        _state_manager = OAuthStateManager(config.SECRET_KEY)
+    return _state_manager
+
+
+def get_token_encryption() -> TokenEncryption:
+    """Get or create token encryption instance."""
+    global _token_encryption
+    if _token_encryption is None:
+        if not config.SECRET_KEY:
+            raise ValueError("SECRET_KEY must be set for token encryption")
+        _token_encryption = TokenEncryption(config.SECRET_KEY)
+    return _token_encryption
+
+
+@router.get("/auth/jira/connector/add")
+async def connect_jira(space_id: int, user: User = Depends(current_active_user)):
+    """
+    Initiate Jira OAuth flow.
+
+    Args:
+        space_id: The search space ID
+        user: Current authenticated user
+
+    Returns:
+        Authorization URL for redirect
+    """
+    try:
+        if not space_id:
+            raise HTTPException(status_code=400, detail="space_id is required")
+
+        if not config.JIRA_CLIENT_ID:
+            raise HTTPException(status_code=500, detail="Jira OAuth not configured.")
+
+        if not config.SECRET_KEY:
+            raise HTTPException(
+                status_code=500, detail="SECRET_KEY not configured for OAuth security."
+            )
+
+        # Generate secure state parameter with HMAC signature
+        state_manager = get_state_manager()
+        state_encoded = state_manager.generate_secure_state(space_id, user.id)
+
+        # Build authorization URL
+        from urllib.parse import urlencode
+
+        auth_params = {
+            "audience": "api.atlassian.com",
+            "client_id": config.JIRA_CLIENT_ID,
+            "scope": " ".join(SCOPES),
+            "redirect_uri": config.JIRA_REDIRECT_URI,
+            "state": state_encoded,
+            "response_type": "code",
+            "prompt": "consent",  # Force consent screen to get refresh token
+        }
+
+        auth_url = f"{AUTHORIZATION_URL}?{urlencode(auth_params)}"
+
+        logger.info(f"Generated Jira OAuth URL for user {user.id}, space {space_id}")
+        return {"auth_url": auth_url}
+
+    except Exception as e:
+        logger.error(f"Failed to initiate Jira OAuth: {e!s}", exc_info=True)
+        raise HTTPException(
+            status_code=500, detail=f"Failed to initiate Jira OAuth: {e!s}"
+        ) from e
+
+
+@router.get("/auth/jira/connector/callback")
+async def jira_callback(
+    request: Request,
+    code: str | None = None,
+    error: str | None = None,
+    state: str | None = None,
+    session: AsyncSession = Depends(get_async_session),
+):
+    """
+    Handle Jira OAuth callback.
+
+    Args:
+        request: FastAPI request object
+        code: Authorization code from Atlassian (if user granted access)
+        error: Error code from Atlassian (if user denied access or error occurred)
+        state: State parameter containing user/space info
+        session: Database session
+
+    Returns:
+        Redirect response to frontend
+    """
+    try:
+        # Handle OAuth errors (e.g., user denied access)
+        if error:
+            logger.warning(f"Jira OAuth error: {error}")
+            # Try to decode state to get space_id for redirect, but don't fail if it's invalid
+            space_id = None
+            if state:
+                try:
+                    state_manager = get_state_manager()
+                    data = state_manager.validate_state(state)
+                    space_id = data.get("space_id")
+                except Exception:
+                    # If state is invalid, we'll redirect without space_id
+                    logger.warning("Failed to validate state in error handler")
+
+            # Redirect to frontend with error parameter
+            if space_id:
+                return RedirectResponse(
+                    url=f"{config.NEXT_FRONTEND_URL}/dashboard/{space_id}/new-chat?modal=connectors&tab=all&error=jira_oauth_denied"
+                )
+            else:
+                return RedirectResponse(
+                    url=f"{config.NEXT_FRONTEND_URL}/dashboard?error=jira_oauth_denied"
+                )
+
+        # Validate required parameters for successful flow
+        if not code:
+            raise HTTPException(status_code=400, detail="Missing authorization code")
+        if not state:
+            raise HTTPException(status_code=400, detail="Missing state parameter")
+
+        # Validate and decode state with signature verification
+        state_manager = get_state_manager()
+        try:
+            data = state_manager.validate_state(state)
+        except HTTPException:
+            raise
+        except Exception as e:
+            raise HTTPException(
+                status_code=400, detail=f"Invalid state parameter: {e!s}"
+            ) from e
+
+        user_id = UUID(data["user_id"])
+        space_id = data["space_id"]
+
+        # Validate redirect URI (security: ensure it matches configured value)
+        if not config.JIRA_REDIRECT_URI:
+            raise HTTPException(
+                status_code=500, detail="JIRA_REDIRECT_URI not configured"
+            )
+
+        # Exchange authorization code for access token
+        token_data = {
+            "grant_type": "authorization_code",
+            "client_id": config.JIRA_CLIENT_ID,
+            "client_secret": config.JIRA_CLIENT_SECRET,
+            "code": code,
+            "redirect_uri": config.JIRA_REDIRECT_URI,
+        }
+
+        async with httpx.AsyncClient() as client:
+            token_response = await client.post(
+                TOKEN_URL,
+                data=token_data,
+                headers={"Content-Type": "application/x-www-form-urlencoded"},
+                timeout=30.0,
+            )
+
+        if token_response.status_code != 200:
+            error_detail = token_response.text
+            try:
+                error_json = token_response.json()
+                error_detail = error_json.get("error_description", error_json.get("error", error_detail))
+            except Exception:
+                pass
+            raise HTTPException(
+                status_code=400, detail=f"Token exchange failed: {error_detail}"
+            )
+
+        token_json = token_response.json()
+
+        # Encrypt sensitive tokens before storing
+        token_encryption = get_token_encryption()
+        access_token = token_json.get("access_token")
+        refresh_token = token_json.get("refresh_token")
+
+        if not access_token:
+            raise HTTPException(
+                status_code=400, detail="No access token received from Atlassian"
+            )
+
+        # Fetch accessible resources to get Jira instance information
+        async with httpx.AsyncClient() as client:
+            resources_response = await client.get(
+                ACCESSIBLE_RESOURCES_URL,
+                headers={"Authorization": f"Bearer {access_token}"},
+                timeout=30.0,
+            )
+
+        if resources_response.status_code != 200:
+            error_detail = resources_response.text
+            logger.error(f"Failed to fetch accessible resources: {error_detail}")
+            raise HTTPException(
+                status_code=400,
+                detail=f"Failed to fetch Jira instances: {error_detail}",
+            )
+
+        resources = resources_response.json()
+
+        # Filter for Jira instances (resources with type "jira" or id field)
+        jira_instances = [
+            r
+            for r in resources
+            if r.get("id") and (r.get("name") or r.get("url"))
+        ]
+
+        if not jira_instances:
+            raise HTTPException(
+                status_code=400,
+                detail="No accessible Jira instances found. Please ensure you have access to at least one Jira instance.",
+            )
+
+        # For now, use the first Jira instance
+        # TODO: Support multiple instances by letting user choose during OAuth
+        jira_instance = jira_instances[0]
+        cloud_id = jira_instance["id"]
+        base_url = jira_instance.get("url")
+        
+        # If URL is not provided, construct it from cloud_id
+        if not base_url:
+            # Try to extract from name or construct default format
+            instance_name = jira_instance.get("name", "").lower().replace(" ", "")
+            if instance_name:
+                base_url = f"https://{instance_name}.atlassian.net"
+            else:
+                # Fallback: use cloud_id directly (though this may not work)
+                base_url = f"https://{cloud_id}.atlassian.net"
+
+        # Calculate expiration time (UTC, tz-aware)
+        expires_at = None
+        expires_in = token_json.get("expires_in")
+        if expires_in:
+            now_utc = datetime.now(UTC)
+            expires_at = now_utc + timedelta(seconds=int(expires_in))
+
+        # Store the encrypted access token and refresh token in connector config
+        connector_config = {
+            "access_token": token_encryption.encrypt_token(access_token),
+            "refresh_token": token_encryption.encrypt_token(refresh_token)
+            if refresh_token
+            else None,
+            "token_type": token_json.get("token_type", "Bearer"),
+            "expires_in": expires_in,
+            "expires_at": expires_at.isoformat() if expires_at else None,
+            "scope": token_json.get("scope"),
+            "cloud_id": cloud_id,
+            "base_url": base_url.rstrip("/") if base_url else None,
+            # Mark that tokens are encrypted for backward compatibility
+            "_token_encrypted": True,
+        }
+
+        # Check if connector already exists for this search space and user
+        existing_connector_result = await session.execute(
+            select(SearchSourceConnector).filter(
+                SearchSourceConnector.search_space_id == space_id,
+                SearchSourceConnector.user_id == user_id,
+                SearchSourceConnector.connector_type
+                == SearchSourceConnectorType.JIRA_CONNECTOR,
+            )
+        )
+        existing_connector = existing_connector_result.scalars().first()
+
+        if existing_connector:
+            # Update existing connector
+            existing_connector.config = connector_config
+            existing_connector.name = "Jira Connector"
+            existing_connector.is_indexable = True
+            logger.info(
+                f"Updated existing Jira connector for user {user_id} in space {space_id}"
+            )
+        else:
+            # Create new connector
+            new_connector = SearchSourceConnector(
+                name="Jira Connector",
+                connector_type=SearchSourceConnectorType.JIRA_CONNECTOR,
+                is_indexable=True,
+                config=connector_config,
+                search_space_id=space_id,
+                user_id=user_id,
+            )
+            session.add(new_connector)
+            logger.info(
+                f"Created new Jira connector for user {user_id} in space {space_id}"
+            )
+
+        try:
+            await session.commit()
+            logger.info(f"Successfully saved Jira connector for user {user_id}")
+
+            # Redirect to the frontend with success params
+            return RedirectResponse(
+                url=f"{config.NEXT_FRONTEND_URL}/dashboard/{space_id}/new-chat?modal=connectors&tab=all&success=true&connector=jira-connector"
+            )
+
+        except ValidationError as e:
+            await session.rollback()
+            raise HTTPException(
+                status_code=422, detail=f"Validation error: {e!s}"
+            ) from e
+        except IntegrityError as e:
+            await session.rollback()
+            raise HTTPException(
+                status_code=409,
+                detail=f"Integrity error: A connector with this type already exists. {e!s}",
+            ) from e
+        except Exception as e:
+            logger.error(f"Failed to create search source connector: {e!s}")
+            await session.rollback()
+            raise HTTPException(
+                status_code=500,
+                detail=f"Failed to create search source connector: {e!s}",
+            ) from e
+
+    except HTTPException:
+        raise
+    except Exception as e:
+        logger.error(f"Failed to complete Jira OAuth: {e!s}", exc_info=True)
+        raise HTTPException(
+            status_code=500, detail=f"Failed to complete Jira OAuth: {e!s}"
+        ) from e
+
+
+async def refresh_jira_token(
+    session: AsyncSession, connector: SearchSourceConnector
+) -> SearchSourceConnector:
+    """
+    Refresh the Jira access token for a connector.
+
+    Args:
+        session: Database session
+        connector: Jira connector to refresh
+
+    Returns:
+        Updated connector object
+    """
+    try:
+        logger.info(f"Refreshing Jira token for connector {connector.id}")
+
+        credentials = JiraAuthCredentialsBase.from_dict(connector.config)
+
+        # Decrypt tokens if they are encrypted
+        token_encryption = get_token_encryption()
+        is_encrypted = connector.config.get("_token_encrypted", False)
+
+        refresh_token = credentials.refresh_token
+        if is_encrypted and refresh_token:
+            try:
+                refresh_token = token_encryption.decrypt_token(refresh_token)
+            except Exception as e:
+                logger.error(f"Failed to decrypt refresh token: {e!s}")
+                raise HTTPException(
+                    status_code=500, detail="Failed to decrypt stored refresh token"
+                ) from e
+
+        if not refresh_token:
+            raise HTTPException(
+                status_code=400,
+                detail="No refresh token available. Please re-authenticate.",
+            )
+
+        # Prepare token refresh data
+        refresh_data = {
+            "grant_type": "refresh_token",
+            "client_id": config.JIRA_CLIENT_ID,
+            "client_secret": config.JIRA_CLIENT_SECRET,
+            "refresh_token": refresh_token,
+        }
+
+        async with httpx.AsyncClient() as client:
+            token_response = await client.post(
+                TOKEN_URL,
+                data=refresh_data,
+                headers={"Content-Type": "application/x-www-form-urlencoded"},
+                timeout=30.0,
+            )
+
+        if token_response.status_code != 200:
+            error_detail = token_response.text
+            try:
+                error_json = token_response.json()
+                error_detail = error_json.get("error_description", error_json.get("error", error_detail))
+            except Exception:
+                pass
+            raise HTTPException(
+                status_code=400, detail=f"Token refresh failed: {error_detail}"
+            )
+
+        token_json = token_response.json()
+
+        # Calculate expiration time (UTC, tz-aware)
+        expires_at = None
+        expires_in = token_json.get("expires_in")
+        if expires_in:
+            now_utc = datetime.now(UTC)
+            expires_at = now_utc + timedelta(seconds=int(expires_in))
+
+        # Encrypt new tokens before storing
+        access_token = token_json.get("access_token")
+        new_refresh_token = token_json.get("refresh_token")
+
+        if not access_token:
+            raise HTTPException(
+                status_code=400, detail="No access token received from Jira refresh"
+            )
+
+        # Update credentials object with encrypted tokens
+        credentials.access_token = token_encryption.encrypt_token(access_token)
+        if new_refresh_token:
+            credentials.refresh_token = token_encryption.encrypt_token(
+                new_refresh_token
+            )
+        credentials.expires_in = expires_in
+        credentials.expires_at = expires_at
+        credentials.scope = token_json.get("scope")
+
+        # Preserve cloud_id and base_url
+        if not credentials.cloud_id:
+            credentials.cloud_id = connector.config.get("cloud_id")
+        if not credentials.base_url:
+            credentials.base_url = connector.config.get("base_url")
+
+        # Update connector config with encrypted tokens
+        credentials_dict = credentials.to_dict()
+        credentials_dict["_token_encrypted"] = True
+        connector.config = credentials_dict
+        await session.commit()
+        await session.refresh(connector)
+
+        logger.info(f"Successfully refreshed Jira token for connector {connector.id}")
+
+        return connector
+    except HTTPException:
+        raise
+    except Exception as e:
+        logger.error(f"Failed to refresh Jira token: {e!s}", exc_info=True)
+        raise HTTPException(
+            status_code=500, detail=f"Failed to refresh Jira token: {e!s}"
+        ) from e

surfsense_backend/app/schemas/jira_auth_credentials.py

@@ -0,0 +1,72 @@
+from datetime import UTC, datetime
+
+from pydantic import BaseModel, field_validator
+
+
+class JiraAuthCredentialsBase(BaseModel):
+    access_token: str
+    refresh_token: str | None = None
+    token_type: str = "Bearer"
+    expires_in: int | None = None
+    expires_at: datetime | None = None
+    scope: str | None = None
+    cloud_id: str | None = None
+    base_url: str | None = None
+
+    @property
+    def is_expired(self) -> bool:
+        """Check if the credentials have expired."""
+        if self.expires_at is None:
+            return False
+        return self.expires_at <= datetime.now(UTC)
+
+    @property
+    def is_refreshable(self) -> bool:
+        """Check if the credentials can be refreshed."""
+        return self.refresh_token is not None
+
+    def to_dict(self) -> dict:
+        """Convert credentials to dictionary for storage."""
+        return {
+            "access_token": self.access_token,
+            "refresh_token": self.refresh_token,
+            "token_type": self.token_type,
+            "expires_in": self.expires_in,
+            "expires_at": self.expires_at.isoformat() if self.expires_at else None,
+            "scope": self.scope,
+            "cloud_id": self.cloud_id,
+            "base_url": self.base_url,
+        }
+
+    @classmethod
+    def from_dict(cls, data: dict) -> "JiraAuthCredentialsBase":
+        """Create credentials from dictionary."""
+        expires_at = None
+        if data.get("expires_at"):
+            expires_at = datetime.fromisoformat(data["expires_at"])
+
+        return cls(
+            access_token=data["access_token"],
+            refresh_token=data.get("refresh_token"),
+            token_type=data.get("token_type", "Bearer"),
+            expires_in=data.get("expires_in"),
+            expires_at=expires_at,
+            scope=data.get("scope"),
+            cloud_id=data.get("cloud_id"),
+            base_url=data.get("base_url"),
+        )
+
+    @field_validator("expires_at", mode="before")
+    @classmethod
+    def ensure_aware_utc(cls, v):
+        # Strings like "2025-08-26T14:46:57.367184"
+        if isinstance(v, str):
+            # add +00:00 if missing tz info
+            if v.endswith("Z"):
+                return datetime.fromisoformat(v.replace("Z", "+00:00"))
+            dt = datetime.fromisoformat(v)
+            return dt if dt.tzinfo else dt.replace(tzinfo=UTC)
+        # datetime objects
+        if isinstance(v, datetime):
+            return v if v.tzinfo else v.replace(tzinfo=UTC)
+        return v

surfsense_backend/app/tasks/connector_indexers/jira_indexer.py

@@ -84,31 +84,137 @@ async def index_jira_issues(
             return 0, f"Connector with ID {connector_id} not found"
 
         # Get the Jira credentials from the connector config
-        jira_email = connector.config.get("JIRA_EMAIL")
-        jira_api_token = connector.config.get("JIRA_API_TOKEN")
-        jira_base_url = connector.config.get("JIRA_BASE_URL")
+        # Support both OAuth (preferred) and legacy API token authentication
+        config_data = connector.config.copy()
+        is_oauth = config_data.get("_token_encrypted", False) or config_data.get("access_token")
 
-        if not jira_email or not jira_api_token or not jira_base_url:
-            await task_logger.log_task_failure(
+        if is_oauth:
+            # OAuth 2.0 authentication
+            from app.utils.oauth_security import TokenEncryption
+
+            if not config.SECRET_KEY:
+                await task_logger.log_task_failure(
+                    log_entry,
+                    f"SECRET_KEY not configured but tokens are marked as encrypted for connector {connector_id}",
+                    "Missing SECRET_KEY for token decryption",
+                    {"error_type": "MissingSecretKey"},
+                )
+                return 0, "SECRET_KEY not configured but tokens are marked as encrypted"
+            
+            try:
+                token_encryption = TokenEncryption(config.SECRET_KEY)
+
+                # Decrypt access_token
+                if config_data.get("access_token"):
+                    config_data["access_token"] = token_encryption.decrypt_token(
+                        config_data["access_token"]
+                    )
+                    logger.info(
+                        f"Decrypted Jira access token for connector {connector_id}"
+                    )
+
+                # Decrypt refresh_token if present
+                if config_data.get("refresh_token"):
+                    config_data["refresh_token"] = token_encryption.decrypt_token(
+                        config_data["refresh_token"]
+                    )
+                    logger.info(
+                        f"Decrypted Jira refresh token for connector {connector_id}"
+                    )
+            except Exception as e:
+                await task_logger.log_task_failure(
+                    log_entry,
+                    f"Failed to decrypt Jira tokens for connector {connector_id}: {e!s}",
+                    "Token decryption failed",
+                    {"error_type": "TokenDecryptionError"},
+                )
+                return 0, f"Failed to decrypt Jira tokens: {e!s}"
+
+            try:
+                from app.schemas.jira_auth_credentials import JiraAuthCredentialsBase
+                credentials = JiraAuthCredentialsBase.from_dict(config_data)
+            except Exception as e:
+                await task_logger.log_task_failure(
+                    log_entry,
+                    f"Invalid Jira OAuth credentials in connector {connector_id}",
+                    str(e),
+                    {"error_type": "InvalidCredentials"},
+                )
+                return 0, f"Invalid Jira OAuth credentials: {e!s}"
+
+            # Check if credentials are expired and refresh if needed
+            if credentials.is_expired:
+                await task_logger.log_task_progress(
+                    log_entry,
+                    f"Jira credentials expired for connector {connector_id}, refreshing token",
+                    {"stage": "token_refresh"},
+                )
+
+                from app.routes.jira_add_connector_route import refresh_jira_token
+
+                try:
+                    connector = await refresh_jira_token(session, connector)
+                    # Re-fetch credentials after refresh
+                    config_data = connector.config.copy()
+                    if config_data.get("access_token"):
+                        config_data["access_token"] = token_encryption.decrypt_token(
+                            config_data["access_token"]
+                        )
+                    credentials = JiraAuthCredentialsBase.from_dict(config_data)
+                except Exception as e:
+                    await task_logger.log_task_failure(
+                        log_entry,
+                        f"Failed to refresh Jira token for connector {connector_id}: {e!s}",
+                        "Token refresh failed",
+                        {"error_type": "TokenRefreshError"},
+                    )
+                    return 0, f"Failed to refresh Jira token: {e!s}"
+
+            # Initialize Jira client with OAuth credentials
+            await task_logger.log_task_progress(
                 log_entry,
-                f"Jira credentials not found in connector config for connector {connector_id}",
-                "Missing Jira credentials",
-                {"error_type": "MissingCredentials"},
+                f"Initializing Jira client with OAuth for connector {connector_id}",
+                {"stage": "client_initialization"},
             )
-            return 0, "Jira credentials not found in connector config"
 
-        # Initialize Jira client
-        await task_logger.log_task_progress(
-            log_entry,
-            f"Initializing Jira client for connector {connector_id}",
-            {"stage": "client_initialization"},
-        )
+            jira_client = JiraConnector(
+                base_url=credentials.base_url,
+                access_token=credentials.access_token,
+                cloud_id=credentials.cloud_id,
+            )
+        else:
+            # Legacy API token authentication
+            jira_email = config_data.get("JIRA_EMAIL")
+            jira_api_token = config_data.get("JIRA_API_TOKEN")
+            jira_base_url = config_data.get("JIRA_BASE_URL")
 
-        jira_client = JiraConnector(
-            base_url=jira_base_url, email=jira_email, api_token=jira_api_token
-        )
+            if not jira_email or not jira_api_token or not jira_base_url:
+                await task_logger.log_task_failure(
+                    log_entry,
+                    f"Jira credentials not found in connector config for connector {connector_id}",
+                    "Missing Jira credentials",
+                    {"error_type": "MissingCredentials"},
+                )
+                return 0, "Jira credentials not found in connector config"
+
+            # Initialize Jira client with legacy credentials
+            await task_logger.log_task_progress(
+                log_entry,
+                f"Initializing Jira client with API token for connector {connector_id}",
+                {"stage": "client_initialization"},
+            )
+
+            jira_client = JiraConnector(
+                base_url=jira_base_url, email=jira_email, api_token=jira_api_token
+            )
 
         # Calculate date range
+        # Handle "undefined" strings from frontend
+        if start_date == "undefined" or start_date == "":
+            start_date = None
+        if end_date == "undefined" or end_date == "":
+            end_date = None
+
         start_date_str, end_date_str = calculate_date_range(
             connector, start_date, end_date, default_days_back=365
         )
@@ -422,4 +528,4 @@ async def index_jira_issues(
             {"error_type": type(e).__name__},
         )
         logger.error(f"Failed to index JIRA issues: {e!s}", exc_info=True)
-        return 0, f"Failed to index JIRA issues: {e!s}"
+        return 0, f"Failed to index JIRA issues: {e!s}"

surfsense_backend/app/utils/validators.py

@@ -538,13 +538,13 @@ def validate_connector_config(
             },
         },
         # "DISCORD_CONNECTOR": {"required": ["DISCORD_BOT_TOKEN"], "validators": {}},
-        "JIRA_CONNECTOR": {
-            "required": ["JIRA_EMAIL", "JIRA_API_TOKEN", "JIRA_BASE_URL"],
-            "validators": {
-                "JIRA_EMAIL": lambda: validate_email_field("JIRA_EMAIL", "JIRA"),
-                "JIRA_BASE_URL": lambda: validate_url_field("JIRA_BASE_URL", "JIRA"),
-            },
-        },
+        # "JIRA_CONNECTOR": {
+        #     "required": ["JIRA_EMAIL", "JIRA_API_TOKEN", "JIRA_BASE_URL"],
+        #     "validators": {
+        #         "JIRA_EMAIL": lambda: validate_email_field("JIRA_EMAIL", "JIRA"),
+        #         "JIRA_BASE_URL": lambda: validate_url_field("JIRA_BASE_URL", "JIRA"),
+        #     },
+        # },
         "CONFLUENCE_CONNECTOR": {
             "required": [
                 "CONFLUENCE_BASE_URL",