Merge upstream/dev into feature/mcp-migration

2026-04-25 00:36:31 +02:00 · 2026-04-22 19:53:26 +02:00 · 2026-04-22 19:53:26 +02:00 · 4915675f45
commit 4915675f45
parent a4134f1f03 b067c92b4c
54 changed files with 2050 additions and 359 deletions
--- a/.github/workflows/desktop-release.yml
+++ b/.github/workflows/desktop-release.yml
@ -22,6 +22,7 @@ on:

 permissions:
  contents: write
+  id-token: write

 jobs:
  build:
@ -58,6 +59,22 @@ jobs:
          fi
          echo "VERSION=$VERSION" >> "$GITHUB_OUTPUT"

+      - name: Detect Windows signing eligibility
+        id: sign
+        shell: bash
+        run: |
+          # Sign Windows builds only on production v* tags (not beta-v*, not workflow_dispatch).
+          # This matches the single OIDC federated credential configured in Entra ID.
+          if [ "${{ matrix.os }}" = "windows-latest" ] \
+            && [ "${{ github.event_name }}" = "push" ] \
+            && [[ "$GITHUB_REF" == refs/tags/v* ]]; then
+            echo "enabled=true" >> "$GITHUB_OUTPUT"
+            echo "Windows signing: ENABLED (v* tag on windows-latest)"
+          else
+            echo "enabled=false" >> "$GITHUB_OUTPUT"
+            echo "Windows signing: skipped"
+          fi
+
      - name: Setup pnpm
        uses: pnpm/action-setup@v5

@ -98,7 +115,31 @@ jobs:

      - name: Package & Publish
        shell: bash
-        run: pnpm exec electron-builder ${{ matrix.platform }} --config electron-builder.yml --publish ${{ inputs.publish || 'always' }} -c.extraMetadata.version=${{ steps.version.outputs.VERSION }}
+        run: |
+          CMD=(pnpm exec electron-builder ${{ matrix.platform }} \
+            --config electron-builder.yml \
+            --publish "${{ inputs.publish || 'always' }}" \
+            -c.extraMetadata.version="${{ steps.version.outputs.VERSION }}")
+
+          if [ "${{ steps.sign.outputs.enabled }}" = "true" ]; then
+            CMD+=(-c.win.azureSignOptions.publisherName="$WINDOWS_PUBLISHER_NAME")
+            CMD+=(-c.win.azureSignOptions.endpoint="$AZURE_CODESIGN_ENDPOINT")
+            CMD+=(-c.win.azureSignOptions.codeSigningAccountName="$AZURE_CODESIGN_ACCOUNT")
+            CMD+=(-c.win.azureSignOptions.certificateProfileName="$AZURE_CODESIGN_PROFILE")
+          fi
+
+          "${CMD[@]}"
        working-directory: surfsense_desktop
        env:
          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          WINDOWS_PUBLISHER_NAME: ${{ vars.WINDOWS_PUBLISHER_NAME }}
+          AZURE_CODESIGN_ENDPOINT: ${{ vars.AZURE_CODESIGN_ENDPOINT }}
+          AZURE_CODESIGN_ACCOUNT: ${{ vars.AZURE_CODESIGN_ACCOUNT }}
+          AZURE_CODESIGN_PROFILE: ${{ vars.AZURE_CODESIGN_PROFILE }}
+          # Service principal credentials for Azure.Identity EnvironmentCredential used by the
+          # TrustedSigning PowerShell module. Only populated when signing is enabled.
+          # electron-builder 26 does not yet support OIDC federated tokens for Azure signing,
+          # so we fall back to client-secret auth. Rotate AZURE_CLIENT_SECRET before expiry.
+          AZURE_TENANT_ID: ${{ steps.sign.outputs.enabled == 'true' && secrets.AZURE_TENANT_ID || '' }}
+          AZURE_CLIENT_ID: ${{ steps.sign.outputs.enabled == 'true' && secrets.AZURE_CLIENT_ID || '' }}
+          AZURE_CLIENT_SECRET: ${{ steps.sign.outputs.enabled == 'true' && secrets.AZURE_CLIENT_SECRET || '' }}
--- a/2
+++ b/2
@ -1 +1 @@
-0.0.16
+0.0.19
--- a/docker/.env.example
+++ b/docker/.env.example
@ -71,6 +71,7 @@ EMBEDDING_MODEL=sentence-transformers/all-MiniLM-L6-v2
 # BACKEND_URL=https://api.yourdomain.com
 # NEXT_PUBLIC_FASTAPI_BACKEND_URL=https://api.yourdomain.com
 # NEXT_PUBLIC_ZERO_CACHE_URL=https://zero.yourdomain.com
+# FASTAPI_BACKEND_INTERNAL_URL=http://backend:8000

 # ------------------------------------------------------------------------------
 # Zero-cache (real-time sync)
--- a/docker/docker-compose.dev.yml
+++ b/docker/docker-compose.dev.yml
@ -77,6 +77,8 @@ services:
      - shared_temp:/shared_tmp
    env_file:
      - ../surfsense_backend/.env
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
    environment:
      - DATABASE_URL=${DATABASE_URL:-postgresql+asyncpg://${DB_USER:-postgres}:${DB_PASSWORD:-postgres}@${DB_HOST:-db}:${DB_PORT:-5432}/${DB_NAME:-surfsense}}
      - CELERY_BROKER_URL=${REDIS_URL:-redis://redis:6379/0}
@ -118,6 +120,8 @@ services:
      - shared_temp:/shared_tmp
    env_file:
      - ../surfsense_backend/.env
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
    environment:
      - DATABASE_URL=${DATABASE_URL:-postgresql+asyncpg://${DB_USER:-postgres}:${DB_PASSWORD:-postgres}@${DB_HOST:-db}:${DB_PORT:-5432}/${DB_NAME:-surfsense}}
      - CELERY_BROKER_URL=${REDIS_URL:-redis://redis:6379/0}
--- a/docker/docker-compose.yml
+++ b/docker/docker-compose.yml
@ -60,6 +60,8 @@ services:
      - shared_temp:/shared_tmp
    env_file:
      - .env
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
    environment:
      DATABASE_URL: ${DATABASE_URL:-postgresql+asyncpg://${DB_USER:-surfsense}:${DB_PASSWORD:-surfsense}@${DB_HOST:-db}:${DB_PORT:-5432}/${DB_NAME:-surfsense}}
      CELERY_BROKER_URL: ${REDIS_URL:-redis://redis:6379/0}
@ -100,6 +102,8 @@ services:
      - shared_temp:/shared_tmp
    env_file:
      - .env
+    extra_hosts:
+      - "host.docker.internal:host-gateway"
    environment:
      DATABASE_URL: ${DATABASE_URL:-postgresql+asyncpg://${DB_USER:-surfsense}:${DB_PASSWORD:-surfsense}@${DB_HOST:-db}:${DB_PORT:-5432}/${DB_NAME:-surfsense}}
      CELERY_BROKER_URL: ${REDIS_URL:-redis://redis:6379/0}
@ -198,6 +202,7 @@ services:
      NEXT_PUBLIC_FASTAPI_BACKEND_AUTH_TYPE: ${AUTH_TYPE:-LOCAL}
      NEXT_PUBLIC_ETL_SERVICE: ${ETL_SERVICE:-DOCLING}
      NEXT_PUBLIC_DEPLOYMENT_MODE: ${DEPLOYMENT_MODE:-self-hosted}
+      FASTAPI_BACKEND_INTERNAL_URL: ${FASTAPI_BACKEND_INTERNAL_URL:-http://backend:8000}
    labels:
      - "com.centurylinklabs.watchtower.enable=true"
    depends_on:
--- a/surfsense_backend/app/agents/new_chat/chat_deepagent.py
+++ b/surfsense_backend/app/agents/new_chat/chat_deepagent.py
@ -24,7 +24,6 @@ from deepagents.backends import StateBackend
 from deepagents.graph import BASE_AGENT_PROMPT
 from deepagents.middleware.patch_tool_calls import PatchToolCallsMiddleware
 from deepagents.middleware.subagents import GENERAL_PURPOSE_SUBAGENT
-from deepagents.middleware.summarization import create_summarization_middleware
 from langchain.agents import create_agent
 from langchain.agents.middleware import TodoListMiddleware
 from langchain_anthropic.middleware import AnthropicPromptCachingMiddleware
@ -41,6 +40,9 @@ from app.agents.new_chat.middleware import (
    MemoryInjectionMiddleware,
    SurfSenseFilesystemMiddleware,
 )
+from app.agents.new_chat.middleware.safe_summarization import (
+    create_safe_summarization_middleware,
+)
 from app.agents.new_chat.system_prompt import (
    build_configurable_system_prompt,
    build_surfsense_system_prompt,
@ -347,7 +349,7 @@ async def create_surfsense_deep_agent(
            created_by_id=user_id,
            thread_id=thread_id,
        ),
-        create_summarization_middleware(llm, StateBackend),
+        create_safe_summarization_middleware(llm, StateBackend),
        PatchToolCallsMiddleware(),
        AnthropicPromptCachingMiddleware(unsupported_model_behavior="ignore"),
    ]
@ -377,7 +379,7 @@ async def create_surfsense_deep_agent(
            thread_id=thread_id,
        ),
        SubAgentMiddleware(backend=StateBackend, subagents=[general_purpose_spec]),
-        create_summarization_middleware(llm, StateBackend),
+        create_safe_summarization_middleware(llm, StateBackend),
        PatchToolCallsMiddleware(),
        DedupHITLToolCallsMiddleware(agent_tools=tools),
        AnthropicPromptCachingMiddleware(unsupported_model_behavior="ignore"),
--- a/surfsense_backend/app/agents/new_chat/middleware/safe_summarization.py
+++ b/surfsense_backend/app/agents/new_chat/middleware/safe_summarization.py
@ -0,0 +1,123 @@
+"""Safe wrapper around deepagents' SummarizationMiddleware.
+
+Upstream issue
+--------------
+`deepagents.middleware.summarization.SummarizationMiddleware._aoffload_to_backend`
+(and its sync counterpart) call
+``get_buffer_string(filtered_messages)`` before writing the evicted history
+to the backend file. In recent ``langchain-core`` versions, ``get_buffer_string``
+accesses ``m.text`` which iterates ``self.content`` — this raises
+``TypeError: 'NoneType' object is not iterable`` whenever an ``AIMessage``
+has ``content=None`` (common when a model returns *only* tool_calls, seen
+frequently with Azure OpenAI ``gpt-5.x`` responses streamed through
+LiteLLM).
+
+The exception aborts the whole agent turn, so the user just sees "Error during
+chat" with no assistant response.
+
+Fix
+---
+We subclass ``SummarizationMiddleware`` and override
+``_filter_summary_messages`` — the only call site that feeds messages into
+``get_buffer_string`` — to return *copies* of messages whose ``content`` is
+``None`` with ``content=""``. The originals flowing through the rest of the
+agent state are untouched.
+
+We also expose a drop-in ``create_safe_summarization_middleware`` factory
+that mirrors ``deepagents.middleware.summarization.create_summarization_middleware``
+but instantiates our safe subclass.
+"""
+
+from __future__ import annotations
+
+import logging
+from typing import TYPE_CHECKING
+
+from deepagents.middleware.summarization import (
+    SummarizationMiddleware,
+    compute_summarization_defaults,
+)
+
+if TYPE_CHECKING:
+    from deepagents.backends.protocol import BACKEND_TYPES
+    from langchain_core.language_models import BaseChatModel
+    from langchain_core.messages import AnyMessage
+
+logger = logging.getLogger(__name__)
+
+
+def _sanitize_message_content(msg: AnyMessage) -> AnyMessage:
+    """Return ``msg`` with ``content`` coerced to a non-``None`` value.
+
+    ``get_buffer_string`` reads ``m.text`` which iterates ``self.content``;
+    when a provider streams back an ``AIMessage`` with only tool_calls and
+    no text, ``content`` can be ``None`` and the iteration explodes. We
+    replace ``None`` with an empty string so downstream consumers that only
+    care about text see an empty body.
+
+    The original message is left untouched — we return a copy via
+    pydantic's ``model_copy`` when available, otherwise we fall back to
+    re-setting the attribute on a shallow copy.
+    """
+
+    if getattr(msg, "content", "not-missing") is not None:
+        return msg
+
+    try:
+        return msg.model_copy(update={"content": ""})
+    except AttributeError:
+        import copy
+
+        new_msg = copy.copy(msg)
+        try:
+            new_msg.content = ""
+        except Exception:  # pragma: no cover - defensive
+            logger.debug(
+                "Could not sanitize content=None on message of type %s",
+                type(msg).__name__,
+            )
+            return msg
+        return new_msg
+
+
+class SafeSummarizationMiddleware(SummarizationMiddleware):
+    """`SummarizationMiddleware` that tolerates messages with ``content=None``.
+
+    Only ``_filter_summary_messages`` is overridden — this is the single
+    helper invoked by both the sync and async offload paths immediately
+    before ``get_buffer_string``. Normalising here means we get coverage
+    for both without having to copy the (long, rapidly-changing) offload
+    implementations from upstream.
+    """
+
+    def _filter_summary_messages(self, messages: list[AnyMessage]) -> list[AnyMessage]:
+        filtered = super()._filter_summary_messages(messages)
+        return [_sanitize_message_content(m) for m in filtered]
+
+
+def create_safe_summarization_middleware(
+    model: BaseChatModel,
+    backend: BACKEND_TYPES,
+) -> SafeSummarizationMiddleware:
+    """Drop-in replacement for ``create_summarization_middleware``.
+
+    Mirrors the defaults computed by ``deepagents`` but returns our
+    ``SafeSummarizationMiddleware`` subclass so the
+    ``content=None`` crash in ``get_buffer_string`` is avoided.
+    """
+
+    defaults = compute_summarization_defaults(model)
+    return SafeSummarizationMiddleware(
+        model=model,
+        backend=backend,
+        trigger=defaults["trigger"],
+        keep=defaults["keep"],
+        trim_tokens_to_summarize=None,
+        truncate_args_settings=defaults["truncate_args_settings"],
+    )
+
+
+__all__ = [
+    "SafeSummarizationMiddleware",
+    "create_safe_summarization_middleware",
+]
--- a/surfsense_backend/app/app.py
+++ b/surfsense_backend/app/app.py
@ -114,8 +114,19 @@ def _surfsense_error_handler(request: Request, exc: SurfSenseError) -> JSONRespo


 def _http_exception_handler(request: Request, exc: HTTPException) -> JSONResponse:
-    """Wrap FastAPI/Starlette HTTPExceptions into the standard envelope."""
+    """Wrap FastAPI/Starlette HTTPExceptions into the standard envelope.
+
+    5xx sanitization policy:
+    - 500 responses are sanitized (replaced with ``GENERIC_5XX_MESSAGE``) because
+      they usually wrap raw internal errors and may leak sensitive info.
+    - Other 5xx statuses (501, 502, 503, 504, ...) are raised explicitly by
+      route code to communicate a specific, user-safe operational state
+      (e.g. 503 "Page purchases are temporarily unavailable."). Those details
+      are preserved so the frontend can render them, but the error is still
+      logged server-side.
+    """
    rid = _get_request_id(request)
+    should_sanitize = exc.status_code == 500

    # Structured dict details (e.g. {"code": "CAPTCHA_REQUIRED", "message": "..."})
    # are preserved so the frontend can parse them.
@ -130,6 +141,7 @@ def _http_exception_handler(request: Request, exc: HTTPException) -> JSONRespons
                exc.status_code,
                message,
            )
+        if should_sanitize:
            message = GENERIC_5XX_MESSAGE
            err_code = "INTERNAL_ERROR"
        body = {
@ -158,6 +170,7 @@ def _http_exception_handler(request: Request, exc: HTTPException) -> JSONRespons
            exc.status_code,
            detail,
        )
+    if should_sanitize:
        detail = GENERIC_5XX_MESSAGE
    code = _status_to_code(exc.status_code, detail)
    return _build_error_response(exc.status_code, detail, code=code, request_id=rid)
--- a/surfsense_backend/app/services/llm_router_service.py
+++ b/surfsense_backend/app/services/llm_router_service.py
@ -133,6 +133,44 @@ PROVIDER_MAP = {
 }


+# Default ``api_base`` per LiteLLM provider prefix.  Used as a safety net when
+# a global LLM config does *not* specify ``api_base``: without this, LiteLLM
+# happily picks up provider-agnostic env vars (e.g. ``AZURE_API_BASE``,
+# ``OPENAI_API_BASE``) and routes, say, an ``openrouter/anthropic/claude-3-haiku``
+# request to an Azure endpoint, which then 404s with ``Resource not found``.
+# Only providers with a well-known, stable public base URL are listed here —
+# self-hosted / BYO-endpoint providers (ollama, custom, bedrock, vertex_ai,
+# huggingface, databricks, cloudflare, replicate) are intentionally omitted
+# so their existing config-driven behaviour is preserved.
+PROVIDER_DEFAULT_API_BASE = {
+    "openrouter": "https://openrouter.ai/api/v1",
+    "groq": "https://api.groq.com/openai/v1",
+    "mistral": "https://api.mistral.ai/v1",
+    "perplexity": "https://api.perplexity.ai",
+    "xai": "https://api.x.ai/v1",
+    "cerebras": "https://api.cerebras.ai/v1",
+    "deepinfra": "https://api.deepinfra.com/v1/openai",
+    "fireworks_ai": "https://api.fireworks.ai/inference/v1",
+    "together_ai": "https://api.together.xyz/v1",
+    "anyscale": "https://api.endpoints.anyscale.com/v1",
+    "cometapi": "https://api.cometapi.com/v1",
+    "sambanova": "https://api.sambanova.ai/v1",
+}
+
+
+# Canonical provider → base URL when a config uses a generic ``openai``-style
+# prefix but the ``provider`` field tells us which API it really is
+# (e.g. DeepSeek/Alibaba/Moonshot/Zhipu/MiniMax all use ``openai`` compat but
+# each has its own base URL).
+PROVIDER_KEY_DEFAULT_API_BASE = {
+    "DEEPSEEK": "https://api.deepseek.com/v1",
+    "ALIBABA_QWEN": "https://dashscope-intl.aliyuncs.com/compatible-mode/v1",
+    "MOONSHOT": "https://api.moonshot.ai/v1",
+    "ZHIPU": "https://open.bigmodel.cn/api/paas/v4",
+    "MINIMAX": "https://api.minimax.io/v1",
+}
+
+
 class LLMRouterService:
    """
    Singleton service for managing LiteLLM Router.
@ -224,6 +262,16 @@ class LLMRouterService:
        # hits ContextWindowExceededError.
        full_model_list, ctx_fallbacks = cls._build_context_fallback_groups(model_list)

+        # Build a general-purpose fallback list so NotFound/timeout/rate-limit
+        # style failures on one deployment don't bubble up as hard errors —
+        # the router retries with a sibling deployment in ``auto-large``.
+        # ``auto-large`` is the large-context subset of ``auto``; if it is
+        # empty we fall back to ``auto`` itself so the router at least picks a
+        # different deployment in the same group.
+        fallbacks: list[dict[str, list[str]]] | None = None
+        if ctx_fallbacks:
+            fallbacks = [{"auto": ["auto-large"]}]
+
        try:
            router_kwargs: dict[str, Any] = {
                "model_list": full_model_list,
@ -237,15 +285,18 @@ class LLMRouterService:
            }
            if ctx_fallbacks:
                router_kwargs["context_window_fallbacks"] = ctx_fallbacks
+            if fallbacks:
+                router_kwargs["fallbacks"] = fallbacks

            instance._router = Router(**router_kwargs)
            instance._initialized = True
            logger.info(
                "LLM Router initialized with %d deployments, "
-                "strategy: %s, context_window_fallbacks: %s",
+                "strategy: %s, context_window_fallbacks: %s, fallbacks: %s",
                len(model_list),
                final_settings.get("routing_strategy"),
                ctx_fallbacks or "none",
+                fallbacks or "none",
            )
        except Exception as e:
            logger.error(f"Failed to initialize LLM Router: {e}")
@ -348,10 +399,11 @@ class LLMRouterService:
                return None

            # Build model string
+            provider = config.get("provider", "").upper()
            if config.get("custom_provider"):
-                model_string = f"{config['custom_provider']}/{config['model_name']}"
+                provider_prefix = config["custom_provider"]
+                model_string = f"{provider_prefix}/{config['model_name']}"
            else:
-                provider = config.get("provider", "").upper()
                provider_prefix = PROVIDER_MAP.get(provider, provider.lower())
                model_string = f"{provider_prefix}/{config['model_name']}"

@ -361,9 +413,19 @@ class LLMRouterService:
                "api_key": config.get("api_key"),
            }

-            # Add optional api_base
-            if config.get("api_base"):
-                litellm_params["api_base"] = config["api_base"]
+            # Resolve ``api_base``. Config value wins; otherwise apply a
+            # provider-aware default so the deployment does not silently
+            # inherit unrelated env vars (e.g. ``AZURE_API_BASE``) and route
+            # requests to the wrong endpoint.  See ``PROVIDER_DEFAULT_API_BASE``
+            # docstring for the motivating bug (OpenRouter models 404-ing
+            # against an Azure endpoint).
+            api_base = config.get("api_base")
+            if not api_base:
+                api_base = PROVIDER_KEY_DEFAULT_API_BASE.get(provider)
+            if not api_base:
+                api_base = PROVIDER_DEFAULT_API_BASE.get(provider_prefix)
+            if api_base:
+                litellm_params["api_base"] = api_base

            # Add any additional litellm parameters
            if config.get("litellm_params"):
--- a/surfsense_backend/app/services/llm_service.py
+++ b/surfsense_backend/app/services/llm_service.py
@ -1,3 +1,4 @@
+import asyncio
 import logging

 import litellm
@ -32,6 +33,39 @@ litellm.callbacks = [token_tracker]
 logger = logging.getLogger(__name__)


+# Providers that require an interactive OAuth / device-flow login before
+# issuing any completion. LiteLLM implements these with blocking sync polling
+# (requests + time.sleep), which would freeze the FastAPI event loop if
+# invoked from validation. They are never usable from a headless backend,
+# so we reject them at the edge.
+_INTERACTIVE_AUTH_PROVIDERS: frozenset[str] = frozenset(
+    {
+        "github_copilot",
+        "github-copilot",
+        "githubcopilot",
+        "copilot",
+    }
+)
+
+# Hard upper bound for a single validation call. Must exceed the ChatLiteLLM
+# request timeout (30s) by a small margin so a well-behaved provider never
+# trips the watchdog, while any pathological/blocking provider is killed.
+_VALIDATION_TIMEOUT_SECONDS: float = 35.0
+
+
+def _is_interactive_auth_provider(
+    provider: str | None, custom_provider: str | None
+) -> bool:
+    """Return True if the given provider triggers interactive OAuth in LiteLLM."""
+    for raw in (custom_provider, provider):
+        if not raw:
+            continue
+        normalized = raw.strip().lower().replace(" ", "_")
+        if normalized in _INTERACTIVE_AUTH_PROVIDERS:
+            return True
+    return False
+
+
 class LLMRole:
    AGENT = "agent"  # For agent/chat operations
    DOCUMENT_SUMMARY = "document_summary"  # For document summarization
@ -93,6 +127,25 @@ async def validate_llm_config(
        - is_valid: True if config works, False otherwise
        - error_message: Empty string if valid, error description if invalid
    """
+    # Reject providers that require interactive OAuth/device-flow auth.
+    # LiteLLM's github_copilot provider (and similar) uses a blocking sync
+    # Authenticator that polls GitHub for up to several minutes and prints a
+    # device code to stdout. Running it on the FastAPI event loop will freeze
+    # the entire backend, so we refuse them up front.
+    if _is_interactive_auth_provider(provider, custom_provider):
+        msg = (
+            "Provider requires interactive OAuth/device-flow authentication "
+            "(e.g. github_copilot) and cannot be used in a hosted backend. "
+            "Please choose a provider that authenticates via API key."
+        )
+        logger.warning(
+            "Rejected LLM config validation for interactive-auth provider "
+            "(provider=%r, custom_provider=%r)",
+            provider,
+            custom_provider,
+        )
+        return False, msg
+
    try:
        # Build the model string for litellm
        if custom_provider:
@ -153,9 +206,30 @@ async def validate_llm_config(

        llm = SanitizedChatLiteLLM(**litellm_kwargs)

-        # Make a simple test call
+        # Run the test call in a worker thread with a hard timeout. Some
+        # LiteLLM providers have synchronous blocking code paths (e.g. OAuth
+        # authenticators that call time.sleep and requests.post) that would
+        # otherwise freeze the asyncio event loop. Offloading to a thread and
+        # bounding the wait keeps the server responsive even if a provider
+        # misbehaves.
        test_message = HumanMessage(content="Hello")
-        response = await llm.ainvoke([test_message])
+        try:
+            response = await asyncio.wait_for(
+                asyncio.to_thread(llm.invoke, [test_message]),
+                timeout=_VALIDATION_TIMEOUT_SECONDS,
+            )
+        except TimeoutError:
+            logger.warning(
+                "LLM config validation timed out after %ss for model: %s",
+                _VALIDATION_TIMEOUT_SECONDS,
+                model_string,
+            )
+            return (
+                False,
+                f"Validation timed out after {int(_VALIDATION_TIMEOUT_SECONDS)}s. "
+                "The provider is unreachable or requires interactive "
+                "authentication that is not supported by the backend.",
+            )

        # If we got here without exception, the config is valid
        if response and response.content:
--- a/surfsense_backend/pyproject.toml
+++ b/surfsense_backend/pyproject.toml
@ -1,6 +1,6 @@
 [project]
 name = "surf-new-backend"
-version = "0.0.16"
+version = "0.0.19"
 description = "SurfSense Backend"
 requires-python = ">=3.12"
 dependencies = [
@ -74,7 +74,7 @@ dependencies = [
    "deepagents>=0.4.12",
    "stripe>=15.0.0",
    "azure-ai-documentintelligence>=1.0.2",
-    "litellm>=1.83.0",
+    "litellm>=1.83.4",
    "langchain-litellm>=0.6.4",
 ]

--- a/surfsense_backend/tests/unit/test_error_contract.py
+++ b/surfsense_backend/tests/unit/test_error_contract.py
@ -70,6 +70,20 @@ def _make_test_app():
    async def raise_http_500():
        raise HTTPException(status_code=500, detail="secret db password leaked")

+    @app.get("/http-503")
+    async def raise_http_503():
+        raise HTTPException(
+            status_code=503,
+            detail="Page purchases are temporarily unavailable.",
+        )
+
+    @app.get("/http-502")
+    async def raise_http_502():
+        raise HTTPException(
+            status_code=502,
+            detail="Unable to create Stripe checkout session.",
+        )
+
    @app.get("/surfsense-connector")
    async def raise_connector():
        raise ConnectorError("GitHub API returned 401")
@ -184,6 +198,18 @@ class TestHTTPExceptionHandler:
        assert body["error"]["message"] == GENERIC_5XX_MESSAGE
        assert body["error"]["code"] == "INTERNAL_ERROR"

+    def test_503_preserves_detail(self, client):
+        # Intentional 503s (e.g. feature flag off) must surface the developer
+        # message so the frontend can render actionable copy.
+        body = _assert_envelope(client.get("/http-503"), 503)
+        assert body["error"]["message"] == "Page purchases are temporarily unavailable."
+        assert body["error"]["message"] != GENERIC_5XX_MESSAGE
+
+    def test_502_preserves_detail(self, client):
+        body = _assert_envelope(client.get("/http-502"), 502)
+        assert body["error"]["message"] == "Unable to create Stripe checkout session."
+        assert body["error"]["message"] != GENERIC_5XX_MESSAGE
+

 # ---------------------------------------------------------------------------
 # SurfSenseError hierarchy
--- a/surfsense_backend/uv.lock
+++ b/surfsense_backend/uv.lock
@ -7947,7 +7947,7 @@ wheels = [

 [[package]]
 name = "surf-new-backend"
-version = "0.0.16"
+version = "0.0.19"
 source = { editable = "." }
 dependencies = [
    { name = "alembic" },
@ -8070,7 +8070,7 @@ requires-dist = [
    { name = "langgraph", specifier = ">=1.1.3" },
    { name = "langgraph-checkpoint-postgres", specifier = ">=3.0.2" },
    { name = "linkup-sdk", specifier = ">=0.2.4" },
-    { name = "litellm", specifier = ">=1.83.0" },
+    { name = "litellm", specifier = ">=1.83.4" },
    { name = "llama-cloud-services", specifier = ">=0.6.25" },
    { name = "markdown", specifier = ">=3.7" },
    { name = "markdownify", specifier = ">=0.14.1" },
--- a/surfsense_browser_extension/package.json
+++ b/surfsense_browser_extension/package.json
@ -1,7 +1,7 @@
 {
 	"name": "surfsense_browser_extension",
 	"displayName": "Surfsense Browser Extension",
-	"version": "0.0.16",
+	"version": "0.0.19",
 	"description": "Extension to collect Browsing History for SurfSense.",
 	"author": "https://github.com/MODSetter",
 	"engines": {
--- a/surfsense_desktop/package.json
+++ b/surfsense_desktop/package.json
@ -1,6 +1,6 @@
 {
  "name": "surfsense-desktop",
-  "version": "0.0.16",
+  "version": "0.0.19",
  "description": "SurfSense Desktop App",
  "main": "dist/main.js",
  "scripts": {
--- a/surfsense_desktop/src/ipc/channels.ts
+++ b/surfsense_desktop/src/ipc/channels.ts
@ -43,4 +43,12 @@ export const IPC_CHANNELS = {
  // Active search space
  GET_ACTIVE_SEARCH_SPACE: 'search-space:get-active',
  SET_ACTIVE_SEARCH_SPACE: 'search-space:set-active',
+  // Launch on system startup
+  GET_AUTO_LAUNCH: 'auto-launch:get',
+  SET_AUTO_LAUNCH: 'auto-launch:set',
+  // Analytics (PostHog) bridge: renderer <-> main
+  ANALYTICS_IDENTIFY: 'analytics:identify',
+  ANALYTICS_RESET: 'analytics:reset',
+  ANALYTICS_CAPTURE: 'analytics:capture',
+  ANALYTICS_GET_CONTEXT: 'analytics:get-context',
 } as const;
--- a/surfsense_desktop/src/ipc/handlers.ts
+++ b/surfsense_desktop/src/ipc/handlers.ts
@ -24,10 +24,18 @@ import {
  type WatchedFolderConfig,
 } from '../modules/folder-watcher';
 import { getShortcuts, setShortcuts, type ShortcutConfig } from '../modules/shortcuts';
+import { getAutoLaunchState, setAutoLaunch } from '../modules/auto-launch';
 import { getActiveSearchSpaceId, setActiveSearchSpaceId } from '../modules/active-search-space';
 import { reregisterQuickAsk } from '../modules/quick-ask';
 import { reregisterAutocomplete } from '../modules/autocomplete';
 import { reregisterGeneralAssist } from '../modules/tray';
+import {
+  getDistinctId,
+  getMachineId,
+  identifyUser as analyticsIdentify,
+  resetUser as analyticsReset,
+  trackEvent,
+} from '../modules/analytics';

 let authTokens: { bearer: string; refresh: string } | null = null;

@ -120,6 +128,21 @@ export function registerIpcHandlers(): void {

  ipcMain.handle(IPC_CHANNELS.GET_SHORTCUTS, () => getShortcuts());

+  ipcMain.handle(IPC_CHANNELS.GET_AUTO_LAUNCH, () => getAutoLaunchState());
+
+  ipcMain.handle(
+    IPC_CHANNELS.SET_AUTO_LAUNCH,
+    async (_event, payload: { enabled: boolean; openAsHidden?: boolean }) => {
+      const next = await setAutoLaunch(payload.enabled, payload.openAsHidden);
+      trackEvent('desktop_auto_launch_toggled', {
+        enabled: next.enabled,
+        open_as_hidden: next.openAsHidden,
+        supported: next.supported,
+      });
+      return next;
+    },
+  );
+
  ipcMain.handle(IPC_CHANNELS.GET_ACTIVE_SEARCH_SPACE, () => getActiveSearchSpaceId());

  ipcMain.handle(IPC_CHANNELS.SET_ACTIVE_SEARCH_SPACE, (_event, id: string) =>
@ -131,6 +154,41 @@ export function registerIpcHandlers(): void {
    if (config.generalAssist) await reregisterGeneralAssist();
    if (config.quickAsk) await reregisterQuickAsk();
    if (config.autocomplete) await reregisterAutocomplete();
+    trackEvent('desktop_shortcut_updated', {
+      keys: Object.keys(config),
+    });
    return updated;
  });
+
+  // Analytics bridge — the renderer (web UI) hands the logged-in user down
+  // to the main process so desktop-only events are attributed to the same
+  // PostHog person, not just an anonymous machine ID.
+  ipcMain.handle(
+    IPC_CHANNELS.ANALYTICS_IDENTIFY,
+    (_event, payload: { userId: string; properties?: Record<string, unknown> }) => {
+      if (!payload?.userId) return;
+      analyticsIdentify(String(payload.userId), payload.properties);
+    }
+  );
+
+  ipcMain.handle(IPC_CHANNELS.ANALYTICS_RESET, () => {
+    analyticsReset();
+  });
+
+  ipcMain.handle(
+    IPC_CHANNELS.ANALYTICS_CAPTURE,
+    (_event, payload: { event: string; properties?: Record<string, unknown> }) => {
+      if (!payload?.event) return;
+      trackEvent(payload.event, payload.properties);
+    }
+  );
+
+  ipcMain.handle(IPC_CHANNELS.ANALYTICS_GET_CONTEXT, () => {
+    return {
+      distinctId: getDistinctId(),
+      machineId: getMachineId(),
+      appVersion: app.getVersion(),
+      platform: process.platform,
+    };
+  });
 }
--- a/surfsense_desktop/src/main.ts
+++ b/surfsense_desktop/src/main.ts
@ -1,10 +1,9 @@
-import { app, BrowserWindow } from 'electron';
+import { app } from 'electron';

-let isQuitting = false;
 import { registerGlobalErrorHandlers, showErrorDialog } from './modules/errors';
 import { startNextServer } from './modules/server';
-import { createMainWindow, getMainWindow } from './modules/window';
-import { setupDeepLinks, handlePendingDeepLink } from './modules/deep-links';
+import { createMainWindow, getMainWindow, markQuitting } from './modules/window';
+import { setupDeepLinks, handlePendingDeepLink, hasPendingDeepLink } from './modules/deep-links';
 import { setupAutoUpdater } from './modules/auto-updater';
 import { setupMenu } from './modules/menu';
 import { registerQuickAsk, unregisterQuickAsk } from './modules/quick-ask';
@ -13,6 +12,12 @@ import { registerFolderWatcher, unregisterFolderWatcher } from './modules/folder
 import { registerIpcHandlers } from './ipc/handlers';
 import { createTray, destroyTray } from './modules/tray';
 import { initAnalytics, shutdownAnalytics, trackEvent } from './modules/analytics';
+import {
+  applyAutoLaunchDefaults,
+  shouldStartHidden,
+  syncAutoLaunchOnStartup,
+  wasLaunchedAtLogin,
+} from './modules/auto-launch';

 registerGlobalErrorHandlers();

@ -24,7 +29,12 @@ registerIpcHandlers();

 app.whenReady().then(async () => {
  initAnalytics();
-  trackEvent('desktop_app_launched');
+  const launchedAtLogin = wasLaunchedAtLogin();
+  const startedHidden = shouldStartHidden();
+  trackEvent('desktop_app_launched', {
+    launched_at_login: launchedAtLogin,
+    started_hidden: startedHidden,
+  });
  setupMenu();
  try {
    await startNextServer();
@ -35,16 +45,19 @@ app.whenReady().then(async () => {
  }

  await createTray();
+  const defaultsApplied = await applyAutoLaunchDefaults();
+  if (defaultsApplied) {
+    trackEvent('desktop_auto_launch_defaulted_on');
+  }
+  await syncAutoLaunchOnStartup();

-  const win = createMainWindow('/dashboard');
-
-  // Minimize to tray instead of closing the app
-  win.on('close', (e) => {
-    if (!isQuitting) {
-      e.preventDefault();
-      win.hide();
-    }
-  });
+  // When started by the OS at login we stay quietly in the tray. The window
+  // is created lazily on first user interaction (tray click / activate).
+  // Exception: if a deep link is queued, the user explicitly asked to land
+  // in the app — don't swallow it.
+  if (!startedHidden || hasPendingDeepLink()) {
+    createMainWindow('/dashboard');
+  }

  await registerQuickAsk();
  await registerAutocomplete();
@ -55,6 +68,7 @@ app.whenReady().then(async () => {

  app.on('activate', () => {
    const mw = getMainWindow();
+    trackEvent('desktop_app_activated');
    if (!mw || mw.isDestroyed()) {
      createMainWindow('/dashboard');
    } else {
@ -70,7 +84,8 @@ app.on('window-all-closed', () => {
 });

 app.on('before-quit', () => {
-  isQuitting = true;
+  markQuitting();
+  trackEvent('desktop_app_quit');
 });

 let didCleanup = false;
--- a/surfsense_desktop/src/modules/analytics.ts
+++ b/surfsense_desktop/src/modules/analytics.ts
@ -3,14 +3,27 @@ import { machineIdSync } from 'node-machine-id';
 import { app } from 'electron';

 let client: PostHog | null = null;
-let distinctId = '';
+let machineId = '';
+let currentDistinctId = '';
+let identifiedUserId: string | null = null;
+
+function baseProperties(): Record<string, unknown> {
+  return {
+    platform: 'desktop',
+    app_version: app.getVersion(),
+    os: process.platform,
+    arch: process.arch,
+    machine_id: machineId,
+  };
+}

 export function initAnalytics(): void {
  const key = process.env.POSTHOG_KEY;
  if (!key) return;

  try {
-    distinctId = machineIdSync(true);
+    machineId = machineIdSync(true);
+    currentDistinctId = machineId;
  } catch {
    return;
  }
@ -22,17 +35,92 @@ export function initAnalytics(): void {
  });
 }

-export function trackEvent(event: string, properties?: Record<string, unknown>): void {
+export function getMachineId(): string {
+  return machineId;
+}
+
+export function getDistinctId(): string {
+  return currentDistinctId;
+}
+
+/**
+ * Identify the current logged-in user in PostHog so main-process desktop
+ * events (and linked anonymous machine events) are attributed to that person.
+ *
+ * Idempotent: calling identify repeatedly with the same userId is a no-op.
+ */
+export function identifyUser(
+  userId: string,
+  properties?: Record<string, unknown>
+): void {
+  if (!client || !userId) return;
+  if (identifiedUserId === userId) {
+    // Already identified — only refresh person properties
+    try {
+      client.identify({
+        distinctId: userId,
+        properties: {
+          ...baseProperties(),
+          $set: {
+            ...(properties || {}),
+            platform: 'desktop',
+            last_seen_at: new Date().toISOString(),
+          },
+        },
+      });
+    } catch {
+      // ignore
+    }
+    return;
+  }
+
+  try {
+    // Link the anonymous machine distinct ID to the authenticated user
+    client.identify({
+      distinctId: userId,
+      properties: {
+        ...baseProperties(),
+        $anon_distinct_id: machineId,
+        $set: {
+          ...(properties || {}),
+          platform: 'desktop',
+          last_seen_at: new Date().toISOString(),
+        },
+        $set_once: {
+          first_seen_platform: 'desktop',
+        },
+      },
+    });
+
+    identifiedUserId = userId;
+    currentDistinctId = userId;
+  } catch {
+    // Analytics must never break the app
+  }
+}
+
+/**
+ * Reset user identity on logout. Subsequent events are captured anonymously
+ * against the machine ID until the user logs in again.
+ */
+export function resetUser(): void {
+  if (!client) return;
+  identifiedUserId = null;
+  currentDistinctId = machineId;
+}
+
+export function trackEvent(
+  event: string,
+  properties?: Record<string, unknown>
+): void {
  if (!client) return;

  try {
    client.capture({
-      distinctId,
+      distinctId: currentDistinctId || machineId,
      event,
      properties: {
-        platform: 'desktop',
-        app_version: app.getVersion(),
-        os: process.platform,
+        ...baseProperties(),
        ...properties,
      },
    });
--- a/surfsense_desktop/src/modules/auto-launch.ts
+++ b/surfsense_desktop/src/modules/auto-launch.ts
@ -0,0 +1,304 @@
+import { app } from 'electron';
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+
+// ---------------------------------------------------------------------------
+// Launch on system startup ("auto-launch" / "open at login").
+//
+// macOS + Windows : uses Electron's built-in `app.setLoginItemSettings()`.
+// Linux           : writes a freedesktop autostart `.desktop` file into
+//                   `~/.config/autostart/`. Electron's API is a no-op there.
+//
+// The OS is the source of truth for whether we're enabled (so a user who
+// disables us via System Settings / GNOME Tweaks isn't silently overridden).
+// We persist a small companion record in electron-store for things the OS
+// can't tell us — currently just `openAsHidden`, since on Windows we encode
+// it as a CLI arg and on Linux as part of the Exec line, but on a fresh
+// startup we still want the renderer toggle to reflect the user's intent.
+// ---------------------------------------------------------------------------
+
+const STORE_KEY = 'launchAtLogin';
+const HIDDEN_FLAG = '--hidden';
+const LINUX_DESKTOP_FILENAME = 'surfsense.desktop';
+
+export interface AutoLaunchState {
+  enabled: boolean;
+  openAsHidden: boolean;
+  supported: boolean;
+}
+
+interface PersistedState {
+  enabled: boolean;
+  openAsHidden: boolean;
+  // True once we've run the first-launch defaults (opt-in to auto-launch).
+  // We never re-apply defaults if this is set, so a user who has explicitly
+  // turned auto-launch off stays off forever.
+  defaultsApplied: boolean;
+}
+
+const DEFAULTS: PersistedState = {
+  enabled: false,
+  openAsHidden: true,
+  defaultsApplied: false,
+};
+
+// eslint-disable-next-line @typescript-eslint/no-explicit-any -- lazily imported ESM module; matches shortcuts.ts pattern
+let store: any = null;
+
+async function getStore() {
+  if (!store) {
+    const { default: Store } = await import('electron-store');
+    store = new Store({
+      name: 'auto-launch',
+      defaults: { [STORE_KEY]: DEFAULTS },
+    });
+  }
+  return store;
+}
+
+async function readPersisted(): Promise<PersistedState> {
+  const s = await getStore();
+  const stored = s.get(STORE_KEY) as Partial<PersistedState> | undefined;
+  return { ...DEFAULTS, ...(stored ?? {}) };
+}
+
+async function writePersisted(next: PersistedState): Promise<void> {
+  const s = await getStore();
+  s.set(STORE_KEY, next);
+}
+
+// ---------------------------------------------------------------------------
+// Platform support
+// ---------------------------------------------------------------------------
+
+// Auto-launch only makes sense for the packaged app — in dev `process.execPath`
+// is the local Electron binary, so registering it would point the OS at a
+// throwaway path the next time the dev server isn't running.
+function isSupported(): boolean {
+  if (!app.isPackaged) return false;
+  return ['darwin', 'win32', 'linux'].includes(process.platform);
+}
+
+// ---------------------------------------------------------------------------
+// Linux: ~/.config/autostart/surfsense.desktop
+// ---------------------------------------------------------------------------
+
+function linuxAutostartDir(): string {
+  const xdg = process.env.XDG_CONFIG_HOME;
+  const base = xdg && xdg.length > 0 ? xdg : path.join(os.homedir(), '.config');
+  return path.join(base, 'autostart');
+}
+
+function linuxAutostartFile(): string {
+  return path.join(linuxAutostartDir(), LINUX_DESKTOP_FILENAME);
+}
+
+// AppImages move around with the user — `process.execPath` points at a temp
+// mount, so we have to use the original AppImage path exposed via env.
+function linuxExecPath(): string {
+  return process.env.APPIMAGE && process.env.APPIMAGE.length > 0
+    ? process.env.APPIMAGE
+    : process.execPath;
+}
+
+function escapeDesktopExecArg(value: string): string {
+  // Freedesktop `.desktop` Exec values require quoted args when spaces are
+  // present. We keep this intentionally minimal and escape only characters
+  // that can break quoted parsing.
+  return `"${value.replace(/(["\\`$])/g, '\\$1')}"`;
+}
+
+function writeLinuxDesktopFile(openAsHidden: boolean): void {
+  const exec = escapeDesktopExecArg(linuxExecPath());
+  const args = openAsHidden ? ` ${HIDDEN_FLAG}` : '';
+  const contents = [
+    '[Desktop Entry]',
+    'Type=Application',
+    'Version=1.0',
+    'Name=SurfSense',
+    'Comment=AI-powered research assistant',
+    `Exec=${exec}${args}`,
+    'Terminal=false',
+    'Categories=Utility;Office;',
+    'X-GNOME-Autostart-enabled=true',
+    `X-GNOME-Autostart-Delay=${openAsHidden ? '5' : '0'}`,
+    '',
+  ].join('\n');
+
+  fs.mkdirSync(linuxAutostartDir(), { recursive: true });
+  fs.writeFileSync(linuxAutostartFile(), contents, { mode: 0o644 });
+}
+
+function removeLinuxDesktopFile(): void {
+  try {
+    fs.unlinkSync(linuxAutostartFile());
+  } catch (err: unknown) {
+    if ((err as NodeJS.ErrnoException)?.code !== 'ENOENT') throw err;
+  }
+}
+
+function readLinuxDesktopFile(): boolean {
+  return fs.existsSync(linuxAutostartFile());
+}
+
+// ---------------------------------------------------------------------------
+// Public API
+// ---------------------------------------------------------------------------
+
+export async function getAutoLaunchState(): Promise<AutoLaunchState> {
+  const supported = isSupported();
+  const persisted = await readPersisted();
+
+  if (!supported) {
+    return { enabled: false, openAsHidden: persisted.openAsHidden, supported: false };
+  }
+
+  // Trust the OS state — the user may have disabled it from system settings.
+  return { enabled: readOsEnabled(), openAsHidden: persisted.openAsHidden, supported: true };
+}
+
+export async function setAutoLaunch(
+  enabled: boolean,
+  openAsHidden: boolean = DEFAULTS.openAsHidden,
+): Promise<AutoLaunchState> {
+  const supported = isSupported();
+
+  if (!supported) {
+    return { enabled: false, openAsHidden, supported: false };
+  }
+
+  applySystemRegistration(enabled, openAsHidden);
+  // Preserve `defaultsApplied` (and any future fields) — and explicitly
+  // mark them as applied, since the user has now made an intentional choice.
+  await writePersisted({ enabled, openAsHidden, defaultsApplied: true });
+  return { enabled, openAsHidden, supported: true };
+}
+
+function applySystemRegistration(enabled: boolean, openAsHidden: boolean): void {
+  if (process.platform === 'linux') {
+    if (enabled) writeLinuxDesktopFile(openAsHidden);
+    else removeLinuxDesktopFile();
+    return;
+  }
+
+  if (!enabled) {
+    app.setLoginItemSettings({ openAtLogin: false });
+    return;
+  }
+
+  if (process.platform === 'win32') {
+    // On Windows we can't tell the OS to "launch hidden" — instead we pass an
+    // arg the app introspects on boot to skip showing the main window.
+    app.setLoginItemSettings({
+      openAtLogin: true,
+      args: openAsHidden ? [HIDDEN_FLAG] : [],
+    });
+    return;
+  }
+
+  // darwin
+  app.setLoginItemSettings({
+    openAtLogin: true,
+    openAsHidden,
+  });
+}
+
+// First-launch opt-in: register SurfSense as a hidden login item so the tray,
+// global shortcuts, and folder watchers are ready right after the user signs
+// in. Runs at most once per installation — the `defaultsApplied` flag is
+// flipped before we ever touch the OS so a failure to register doesn't cause
+// us to retry on every boot, and a user who turns the toggle off afterwards
+// is never silently re-enabled.
+//
+// Returns whether the defaults were actually applied this boot, so callers
+// can fire an analytics event without coupling this module to PostHog.
+export async function applyAutoLaunchDefaults(): Promise<boolean> {
+  if (!isSupported()) return false;
+  const persisted = await readPersisted();
+  if (persisted.defaultsApplied) return false;
+
+  // Mark the defaults as applied *first*. If `applySystemRegistration`
+  // throws (e.g. read-only home dir on Linux), we'd rather silently leave
+  // the user un-registered than spam them with a failed registration on
+  // every single boot.
+  const next: PersistedState = {
+    enabled: true,
+    openAsHidden: true,
+    defaultsApplied: true,
+  };
+
+  try {
+    applySystemRegistration(true, true);
+  } catch (err) {
+    console.error('[auto-launch] First-run registration failed:', err);
+    next.enabled = false;
+  }
+
+  await writePersisted(next);
+  return next.enabled;
+}
+
+// Called once at startup. Goal:
+//   * If the OS-level entry is already enabled, re-assert it so a moved
+//     binary (Windows reinstall to a new dir, Linux AppImage moved by user)
+//     gets its registered path refreshed.
+//   * If the OS-level entry has been disabled — typically because the user
+//     turned it off in System Settings / GNOME Tweaks — *respect that* and
+//     reconcile our persisted state to match. We never silently re-enable
+//     a login item the user explicitly turned off.
+export async function syncAutoLaunchOnStartup(): Promise<void> {
+  if (!isSupported()) return;
+
+  const persisted = await readPersisted();
+  const osEnabled = readOsEnabled();
+
+  if (!osEnabled) {
+    // User (or some other tool) turned us off out-of-band. Don't re-enable;
+    // just bring our persisted state in sync so the settings UI reflects
+    // reality on the next render.
+    if (persisted.enabled) {
+      await writePersisted({ ...persisted, enabled: false });
+    }
+    return;
+  }
+
+  // OS says we're enabled — refresh the registration so the recorded path /
+  // args match this binary. Idempotent on macOS; corrects path drift on
+  // Windows and Linux. If our persisted state was somehow stale we also
+  // bring it back in line.
+  try {
+    applySystemRegistration(true, persisted.openAsHidden);
+    if (!persisted.enabled) {
+      await writePersisted({ ...persisted, enabled: true });
+    }
+  } catch (err) {
+    console.error('[auto-launch] Failed to re-assert login item:', err);
+  }
+}
+
+function readOsEnabled(): boolean {
+  if (process.platform === 'linux') return readLinuxDesktopFile();
+  return app.getLoginItemSettings().openAtLogin;
+}
+
+// True when the OS launched us as part of login (used for analytics).
+export function wasLaunchedAtLogin(): boolean {
+  if (process.argv.includes(HIDDEN_FLAG)) return true;
+  if (process.platform === 'darwin') {
+    const settings = app.getLoginItemSettings();
+    return settings.wasOpenedAtLogin || settings.wasOpenedAsHidden;
+  }
+  return false;
+}
+
+// Used for boot UI behavior. On macOS we only start hidden when the OS
+// explicitly launched the app as hidden, not merely "at login".
+export function shouldStartHidden(): boolean {
+  if (process.argv.includes(HIDDEN_FLAG)) return true;
+  if (process.platform === 'darwin') {
+    const settings = app.getLoginItemSettings();
+    return settings.wasOpenedAsHidden;
+  }
+  return false;
+}
--- a/surfsense_desktop/src/modules/auto-updater.ts
+++ b/surfsense_desktop/src/modules/auto-updater.ts
@ -1,4 +1,5 @@
 import { app, dialog } from 'electron';
+import { trackEvent } from './analytics';

 const SEMVER_RE = /^\d+\.\d+\.\d+/;

@ -17,10 +18,18 @@ export function setupAutoUpdater(): void {

  autoUpdater.on('update-available', (info: { version: string }) => {
    console.log(`Update available: ${info.version}`);
+    trackEvent('desktop_update_available', {
+      current_version: version,
+      new_version: info.version,
+    });
  });

  autoUpdater.on('update-downloaded', (info: { version: string }) => {
    console.log(`Update downloaded: ${info.version}`);
+    trackEvent('desktop_update_downloaded', {
+      current_version: version,
+      new_version: info.version,
+    });
    dialog.showMessageBox({
      type: 'info',
      buttons: ['Restart', 'Later'],
@ -29,13 +38,19 @@ export function setupAutoUpdater(): void {
      message: `Version ${info.version} has been downloaded. Restart to apply the update.`,
    }).then(({ response }: { response: number }) => {
      if (response === 0) {
+        trackEvent('desktop_update_install_accepted', { new_version: info.version });
        autoUpdater.quitAndInstall();
+      } else {
+        trackEvent('desktop_update_install_deferred', { new_version: info.version });
      }
    });
  });

  autoUpdater.on('error', (err: Error) => {
    console.log('Auto-updater: update check skipped —', err.message?.split('\n')[0]);
+    trackEvent('desktop_update_error', {
+      message: err.message?.split('\n')[0],
+    });
  });

  autoUpdater.checkForUpdates().catch(() => {});
--- a/surfsense_desktop/src/modules/deep-links.ts
+++ b/surfsense_desktop/src/modules/deep-links.ts
@ -2,6 +2,7 @@ import { app } from 'electron';
 import path from 'path';
 import { getMainWindow } from './window';
 import { getServerPort } from './server';
+import { trackEvent } from './analytics';

 const PROTOCOL = 'surfsense';

@ -16,6 +17,10 @@ function handleDeepLink(url: string) {
  if (!win) return;

  const parsed = new URL(url);
+  trackEvent('desktop_deep_link_received', {
+    host: parsed.hostname,
+    path: parsed.pathname,
+  });
  if (parsed.hostname === 'auth' && parsed.pathname === '/callback') {
    const params = parsed.searchParams.toString();
    win.loadURL(`http://localhost:${getServerPort()}/auth/callback?${params}`);
@ -64,3 +69,10 @@ export function handlePendingDeepLink(): void {
    deepLinkUrl = null;
  }
 }
+
+// True when a deep link arrived before the main window existed. Callers can
+// use this to force-create a window even on a "started hidden" boot, so we
+// don't silently swallow a `surfsense://` URL the user actually clicked on.
+export function hasPendingDeepLink(): boolean {
+  return deepLinkUrl !== null;
+}
--- a/surfsense_desktop/src/modules/folder-watcher.ts
+++ b/surfsense_desktop/src/modules/folder-watcher.ts
@ -4,6 +4,7 @@ import { randomUUID } from 'crypto';
 import * as path from 'path';
 import * as fs from 'fs';
 import { IPC_CHANNELS } from '../ipc/channels';
+import { trackEvent } from './analytics';

 export interface WatchedFolderConfig {
  path: string;
@ -401,6 +402,15 @@ export async function addWatchedFolder(
    await startWatcher(config);
  }

+  trackEvent('desktop_folder_watch_added', {
+    search_space_id: config.searchSpaceId,
+    root_folder_id: config.rootFolderId,
+    active: config.active,
+    has_exclude_patterns: (config.excludePatterns?.length ?? 0) > 0,
+    has_extension_filter: !!config.fileExtensions && config.fileExtensions.length > 0,
+    is_update: existing >= 0,
+  });
+
  return folders;
 }

@ -409,6 +419,7 @@ export async function removeWatchedFolder(
 ): Promise<WatchedFolderConfig[]> {
  const s = await getStore();
  const folders: WatchedFolderConfig[] = s.get(STORE_KEY, []);
+  const removed = folders.find((f: WatchedFolderConfig) => f.path === folderPath);
  const updated = folders.filter((f: WatchedFolderConfig) => f.path !== folderPath);
  s.set(STORE_KEY, updated);

@ -418,6 +429,13 @@ export async function removeWatchedFolder(
  const ms = await getMtimeStore();
  ms.delete(folderPath);

+  if (removed) {
+    trackEvent('desktop_folder_watch_removed', {
+      search_space_id: removed.searchSpaceId,
+      root_folder_id: removed.rootFolderId,
+    });
+  }
+
  return updated;
 }

--- a/surfsense_desktop/src/modules/tray.ts
+++ b/surfsense_desktop/src/modules/tray.ts
@ -2,6 +2,7 @@ import { app, globalShortcut, Menu, nativeImage, Tray } from 'electron';
 import path from 'path';
 import { getMainWindow, createMainWindow } from './window';
 import { getShortcuts } from './shortcuts';
+import { trackEvent } from './analytics';

 let tray: Tray | null = null;
 let currentShortcut: string | null = null;
@ -15,14 +16,16 @@ function getTrayIcon(): nativeImage {
  return img.resize({ width: 16, height: 16 });
 }

-function showMainWindow(): void {
-  let win = getMainWindow();
-  if (!win || win.isDestroyed()) {
-    win = createMainWindow('/dashboard');
+function showMainWindow(source: 'tray_click' | 'tray_menu' | 'shortcut' = 'tray_click'): void {
+  const existing = getMainWindow();
+  const reopened = !existing || existing.isDestroyed();
+  if (reopened) {
+    createMainWindow('/dashboard');
  } else {
-    win.show();
-    win.focus();
+    existing.show();
+    existing.focus();
  }
+  trackEvent('desktop_main_window_shown', { source, reopened });
 }

 function registerShortcut(accelerator: string): void {
@ -32,7 +35,7 @@ function registerShortcut(accelerator: string): void {
  }
  if (!accelerator) return;
  try {
-    const ok = globalShortcut.register(accelerator, showMainWindow);
+    const ok = globalShortcut.register(accelerator, () => showMainWindow('shortcut'));
    if (ok) {
      currentShortcut = accelerator;
    } else {
@ -50,13 +53,19 @@ export async function createTray(): Promise<void> {
  tray.setToolTip('SurfSense');

  const contextMenu = Menu.buildFromTemplate([
-    { label: 'Open SurfSense', click: showMainWindow },
+    { label: 'Open SurfSense', click: () => showMainWindow('tray_menu') },
    { type: 'separator' },
-    { label: 'Quit', click: () => { app.exit(0); } },
+    {
+      label: 'Quit',
+      click: () => {
+        trackEvent('desktop_tray_quit_clicked');
+        app.exit(0);
+      },
+    },
  ]);

  tray.setContextMenu(contextMenu);
-  tray.on('double-click', showMainWindow);
+  tray.on('double-click', () => showMainWindow('tray_click'));

  const shortcuts = await getShortcuts();
  registerShortcut(shortcuts.generalAssist);
--- a/surfsense_desktop/src/modules/window.ts
+++ b/surfsense_desktop/src/modules/window.ts
@ -8,11 +8,18 @@ const isDev = !app.isPackaged;
 const HOSTED_FRONTEND_URL = process.env.HOSTED_FRONTEND_URL as string;

 let mainWindow: BrowserWindow | null = null;
+let isQuitting = false;

 export function getMainWindow(): BrowserWindow | null {
  return mainWindow;
 }

+// Called from main.ts on `before-quit` so the close-to-tray handler knows
+// to actually let the window die instead of hiding it.
+export function markQuitting(): void {
+  isQuitting = true;
+}
+
 export function createMainWindow(initialPath = '/dashboard'): BrowserWindow {
  mainWindow = new BrowserWindow({
    width: 1280,
@ -70,6 +77,16 @@ export function createMainWindow(initialPath = '/dashboard'): BrowserWindow {
    mainWindow.webContents.openDevTools();
  }

+  // Hide-to-tray on close (don't actually destroy the window unless the
+  // user really is quitting). Applies to every instance — including the one
+  // created lazily after a launch-at-login boot.
+  mainWindow.on('close', (e) => {
+    if (!isQuitting && mainWindow) {
+      e.preventDefault();
+      mainWindow.hide();
+    }
+  });
+
  mainWindow.on('closed', () => {
    mainWindow = null;
  });
--- a/surfsense_desktop/src/preload.ts
+++ b/surfsense_desktop/src/preload.ts
@ -82,8 +82,23 @@ contextBridge.exposeInMainWorld('electronAPI', {
  setShortcuts: (config: Record<string, string>) =>
    ipcRenderer.invoke(IPC_CHANNELS.SET_SHORTCUTS, config),

+  // Launch on system startup
+  getAutoLaunch: () => ipcRenderer.invoke(IPC_CHANNELS.GET_AUTO_LAUNCH),
+  setAutoLaunch: (enabled: boolean, openAsHidden?: boolean) =>
+    ipcRenderer.invoke(IPC_CHANNELS.SET_AUTO_LAUNCH, { enabled, openAsHidden }),
+
  // Active search space
  getActiveSearchSpace: () => ipcRenderer.invoke(IPC_CHANNELS.GET_ACTIVE_SEARCH_SPACE),
  setActiveSearchSpace: (id: string) =>
    ipcRenderer.invoke(IPC_CHANNELS.SET_ACTIVE_SEARCH_SPACE, id),
+
+  // Analytics bridge — lets posthog-js running inside the Next.js renderer
+  // mirror identify/reset/capture into the Electron main-process PostHog
+  // client so desktop-only events are attributed to the logged-in user.
+  analyticsIdentify: (userId: string, properties?: Record<string, unknown>) =>
+    ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_IDENTIFY, { userId, properties }),
+  analyticsReset: () => ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_RESET),
+  analyticsCapture: (event: string, properties?: Record<string, unknown>) =>
+    ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_CAPTURE, { event, properties }),
+  getAnalyticsContext: () => ipcRenderer.invoke(IPC_CHANNELS.ANALYTICS_GET_CONTEXT),
 });
--- a/surfsense_web/app/(home)/free/[model_slug]/page.tsx
+++ b/surfsense_web/app/(home)/free/[model_slug]/page.tsx
@ -41,7 +41,7 @@ async function getAllModels(): Promise<AnonModel[]> {

 function buildSeoTitle(model: AnonModel): string {
 	if (model.seo_title) return model.seo_title;
-	return `${model.name} Free Online Without Login | No Sign-Up AI Chat | SurfSense`;
+	return `Chat with ${model.name} Free, No Login | SurfSense`;
 }

 function buildSeoDescription(model: AnonModel): string {
--- a/surfsense_web/app/(home)/free/page.tsx
+++ b/surfsense_web/app/(home)/free/page.tsx
@ -18,7 +18,7 @@ import type { AnonModel } from "@/contracts/types/anonymous-chat.types";
 import { BACKEND_URL } from "@/lib/env-config";

 export const metadata: Metadata = {
-	title: "ChatGPT Free Online Without Login | Chat GPT No Login, Claude AI Free | SurfSense",
+	title: "Free AI Chat, No Login Required | SurfSense",
 	description:
 		"Use ChatGPT free online without login. Chat with GPT-4, Claude AI, Gemini and more for free. No sign-up required. Open source NotebookLM alternative with free AI chat and document Q&A.",
 	keywords: [
@ -67,7 +67,7 @@ export const metadata: Metadata = {
 		canonical: "https://surfsense.com/free",
 	},
 	openGraph: {
-		title: "ChatGPT Free Online Without Login | Claude AI Free No Login | SurfSense",
+		title: "Free AI Chat, No Login Required | SurfSense",
 		description:
 			"Use ChatGPT free online without login. Chat with GPT-4, Claude AI, Gemini and 100+ AI models. Open source NotebookLM alternative.",
 		url: "https://surfsense.com/free",
@ -84,7 +84,7 @@ export const metadata: Metadata = {
 	},
 	twitter: {
 		card: "summary_large_image",
-		title: "ChatGPT Free Online Without Login | Claude AI Free No Login | SurfSense",
+		title: "Free AI Chat, No Login Required | SurfSense",
 		description:
 			"Use ChatGPT free online without login. Chat with GPT-4, Claude AI, Gemini and more. No sign-up needed.",
 		images: ["/og-image.png"],
--- a/surfsense_web/app/api/zero/query/route.ts
+++ b/surfsense_web/app/api/zero/query/route.ts
@ -5,7 +5,10 @@ import type { Context } from "@/types/zero";
 import { queries } from "@/zero/queries";
 import { schema } from "@/zero/schema";

-const backendURL = process.env.NEXT_PUBLIC_FASTAPI_BACKEND_URL || "http://localhost:8000";
+const backendURL =
+	process.env.FASTAPI_BACKEND_INTERNAL_URL ||
+	process.env.NEXT_PUBLIC_FASTAPI_BACKEND_URL ||
+	"http://localhost:8000";

 async function authenticateRequest(
 	request: Request
--- a/surfsense_web/app/dashboard/[search_space_id]/user-settings/components/DesktopContent.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/user-settings/components/DesktopContent.tsx
@ -1,6 +1,6 @@
 "use client";

-import { BrainCog, Rocket, Zap } from "lucide-react";
+import { BrainCog, Power, Rocket, Zap } from "lucide-react";
 import { useEffect, useState } from "react";
 import { toast } from "sonner";
 import { DEFAULT_SHORTCUTS, ShortcutRecorder } from "@/components/desktop/shortcut-recorder";
@ -30,6 +30,10 @@ export function DesktopContent() {
 	const [searchSpaces, setSearchSpaces] = useState<SearchSpace[]>([]);
 	const [activeSpaceId, setActiveSpaceId] = useState<string | null>(null);

+	const [autoLaunchEnabled, setAutoLaunchEnabled] = useState(false);
+	const [autoLaunchHidden, setAutoLaunchHidden] = useState(true);
+	const [autoLaunchSupported, setAutoLaunchSupported] = useState(false);
+
 	useEffect(() => {
 		if (!api) {
 			setLoading(false);
@ -38,19 +42,28 @@ export function DesktopContent() {
 		}

 		let mounted = true;
+		const hasAutoLaunchApi =
+			typeof api.getAutoLaunch === "function" && typeof api.setAutoLaunch === "function";
+		setAutoLaunchSupported(hasAutoLaunchApi);

 		Promise.all([
 			api.getAutocompleteEnabled(),
 			api.getShortcuts?.() ?? Promise.resolve(null),
 			api.getActiveSearchSpace?.() ?? Promise.resolve(null),
 			searchSpacesApiService.getSearchSpaces(),
+			hasAutoLaunchApi ? api.getAutoLaunch() : Promise.resolve(null),
 		])
-			.then(([autoEnabled, config, spaceId, spaces]) => {
+			.then(([autoEnabled, config, spaceId, spaces, autoLaunch]) => {
 				if (!mounted) return;
 				setEnabled(autoEnabled);
 				if (config) setShortcuts(config);
 				setActiveSpaceId(spaceId);
 				if (spaces) setSearchSpaces(spaces);
+				if (autoLaunch) {
+					setAutoLaunchEnabled(autoLaunch.enabled);
+					setAutoLaunchHidden(autoLaunch.openAsHidden);
+					setAutoLaunchSupported(autoLaunch.supported);
+				}
 				setLoading(false);
 				setShortcutsLoaded(true);
 			})
@ -106,6 +119,40 @@ export function DesktopContent() {
 		updateShortcut(key, DEFAULT_SHORTCUTS[key]);
 	};

+	const handleAutoLaunchToggle = async (checked: boolean) => {
+		if (!autoLaunchSupported || !api.setAutoLaunch) {
+			toast.error("Please update the desktop app to configure launch on startup");
+			return;
+		}
+		setAutoLaunchEnabled(checked);
+		try {
+			const next = await api.setAutoLaunch(checked, autoLaunchHidden);
+			if (next) {
+				setAutoLaunchEnabled(next.enabled);
+				setAutoLaunchHidden(next.openAsHidden);
+				setAutoLaunchSupported(next.supported);
+			}
+			toast.success(checked ? "SurfSense will launch on startup" : "Launch on startup disabled");
+		} catch {
+			setAutoLaunchEnabled(!checked);
+			toast.error("Failed to update launch on startup");
+		}
+	};
+
+	const handleAutoLaunchHiddenToggle = async (checked: boolean) => {
+		if (!autoLaunchSupported || !api.setAutoLaunch) {
+			toast.error("Please update the desktop app to configure startup behavior");
+			return;
+		}
+		setAutoLaunchHidden(checked);
+		try {
+			await api.setAutoLaunch(autoLaunchEnabled, checked);
+		} catch {
+			setAutoLaunchHidden(!checked);
+			toast.error("Failed to update startup behavior");
+		}
+	};
+
 	const handleSearchSpaceChange = (value: string) => {
 		setActiveSpaceId(value);
 		api.setActiveSearchSpace?.(value);
@ -145,6 +192,59 @@ export function DesktopContent() {
 				</CardContent>
 			</Card>

+			{/* Launch on Startup */}
+			<Card>
+				<CardHeader className="px-3 md:px-6 pt-3 md:pt-6 pb-2 md:pb-3">
+					<CardTitle className="text-base md:text-lg flex items-center gap-2">
+						<Power className="h-4 w-4" />
+						Launch on Startup
+					</CardTitle>
+					<CardDescription className="text-xs md:text-sm">
+						Automatically start SurfSense when you sign in to your computer so global shortcuts and
+						folder sync are always available.
+					</CardDescription>
+				</CardHeader>
+				<CardContent className="px-3 md:px-6 pb-3 md:pb-6 space-y-3">
+					<div className="flex items-center justify-between rounded-lg border p-4">
+						<div className="space-y-0.5">
+							<Label htmlFor="auto-launch-toggle" className="text-sm font-medium cursor-pointer">
+								Open SurfSense at login
+							</Label>
+							<p className="text-xs text-muted-foreground">
+								{autoLaunchSupported
+									? "Adds SurfSense to your system's login items."
+									: "Only available in the packaged desktop app."}
+							</p>
+						</div>
+						<Switch
+							id="auto-launch-toggle"
+							checked={autoLaunchEnabled}
+							onCheckedChange={handleAutoLaunchToggle}
+							disabled={!autoLaunchSupported}
+						/>
+					</div>
+					<div className="flex items-center justify-between rounded-lg border p-4">
+						<div className="space-y-0.5">
+							<Label
+								htmlFor="auto-launch-hidden-toggle"
+								className="text-sm font-medium cursor-pointer"
+							>
+								Start minimized to tray
+							</Label>
+							<p className="text-xs text-muted-foreground">
+								Skip the main window on boot — SurfSense lives in the system tray until you need it.
+							</p>
+						</div>
+						<Switch
+							id="auto-launch-hidden-toggle"
+							checked={autoLaunchHidden}
+							onCheckedChange={handleAutoLaunchHiddenToggle}
+							disabled={!autoLaunchSupported || !autoLaunchEnabled}
+						/>
+					</div>
+				</CardContent>
+			</Card>
+
 			{/* Keyboard Shortcuts */}
 			<Card>
 				<CardHeader className="px-3 md:px-6 pt-3 md:pt-6 pb-2 md:pb-3">
--- a/surfsense_web/app/dashboard/[search_space_id]/user-settings/components/PurchaseHistoryContent.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/user-settings/components/PurchaseHistoryContent.tsx
@ -1,7 +1,8 @@
 "use client";

-import { useQuery } from "@tanstack/react-query";
-import { ReceiptText } from "lucide-react";
+import { useQueries } from "@tanstack/react-query";
+import { Coins, FileText, ReceiptText } from "lucide-react";
+import { useMemo } from "react";
 import { Badge } from "@/components/ui/badge";
 import { Spinner } from "@/components/ui/spinner";
 import {
@ -12,10 +13,26 @@ import {
 	TableHeader,
 	TableRow,
 } from "@/components/ui/table";
-import type { PagePurchase, PagePurchaseStatus } from "@/contracts/types/stripe.types";
+import type {
+	PagePurchase,
+	PagePurchaseStatus,
+	TokenPurchase,
+} from "@/contracts/types/stripe.types";
 import { stripeApiService } from "@/lib/apis/stripe-api.service";
 import { cn } from "@/lib/utils";

+type PurchaseKind = "pages" | "tokens";
+
+type UnifiedPurchase = {
+	id: string;
+	kind: PurchaseKind;
+	created_at: string;
+	status: PagePurchaseStatus;
+	granted: number;
+	amount_total: number | null;
+	currency: string | null;
+};
+
 const STATUS_STYLES: Record<PagePurchaseStatus, { label: string; className: string }> = {
 	completed: {
 		label: "Completed",
@ -31,6 +48,22 @@ const STATUS_STYLES: Record<PagePurchaseStatus, { label: string; className: stri
 	},
 };

+const KIND_META: Record<
+	PurchaseKind,
+	{ label: string; icon: React.ComponentType<{ className?: string }>; iconClass: string }
+> = {
+	pages: {
+		label: "Pages",
+		icon: FileText,
+		iconClass: "text-sky-500",
+	},
+	tokens: {
+		label: "Premium Tokens",
+		icon: Coins,
+		iconClass: "text-amber-500",
+	},
+};
+
 function formatDate(iso: string): string {
 	return new Date(iso).toLocaleDateString(undefined, {
 		year: "numeric",
@ -39,19 +72,63 @@ function formatDate(iso: string): string {
 	});
 }

-function formatAmount(purchase: PagePurchase): string {
-	if (purchase.amount_total == null) return "—";
-	const dollars = purchase.amount_total / 100;
-	const currency = (purchase.currency ?? "usd").toUpperCase();
-	return `$${dollars.toFixed(2)} ${currency}`;
+function formatAmount(amount: number | null, currency: string | null): string {
+	if (amount == null) return "—";
+	const dollars = amount / 100;
+	const code = (currency ?? "usd").toUpperCase();
+	return `$${dollars.toFixed(2)} ${code}`;
+}
+
+function normalizePagePurchase(p: PagePurchase): UnifiedPurchase {
+	return {
+		id: p.id,
+		kind: "pages",
+		created_at: p.created_at,
+		status: p.status,
+		granted: p.pages_granted,
+		amount_total: p.amount_total,
+		currency: p.currency,
+	};
+}
+
+function normalizeTokenPurchase(p: TokenPurchase): UnifiedPurchase {
+	return {
+		id: p.id,
+		kind: "tokens",
+		created_at: p.created_at,
+		status: p.status,
+		granted: p.tokens_granted,
+		amount_total: p.amount_total,
+		currency: p.currency,
+	};
 }

 export function PurchaseHistoryContent() {
-	const { data, isLoading } = useQuery({
-		queryKey: ["stripe-purchases"],
-		queryFn: () => stripeApiService.getPurchases(),
+	const results = useQueries({
+		queries: [
+			{
+				queryKey: ["stripe-purchases"],
+				queryFn: () => stripeApiService.getPurchases(),
+			},
+			{
+				queryKey: ["stripe-token-purchases"],
+				queryFn: () => stripeApiService.getTokenPurchases(),
+			},
+		],
 	});

+	const [pagesQuery, tokensQuery] = results;
+	const isLoading = pagesQuery.isLoading || tokensQuery.isLoading;
+
+	const purchases = useMemo<UnifiedPurchase[]>(() => {
+		const pagePurchases = pagesQuery.data?.purchases ?? [];
+		const tokenPurchases = tokensQuery.data?.purchases ?? [];
+		return [
+			...pagePurchases.map(normalizePagePurchase),
+			...tokenPurchases.map(normalizeTokenPurchase),
+		].sort((a, b) => new Date(b.created_at).getTime() - new Date(a.created_at).getTime());
+	}, [pagesQuery.data, tokensQuery.data]);
+
 	if (isLoading) {
 		return (
 			<div className="flex items-center justify-center py-12">
@ -60,15 +137,13 @@ export function PurchaseHistoryContent() {
 		);
 	}

-	const purchases = data?.purchases ?? [];
-
 	if (purchases.length === 0) {
 		return (
 			<div className="flex flex-col items-center justify-center gap-2 py-16 text-center">
 				<ReceiptText className="h-8 w-8 text-muted-foreground" />
 				<p className="text-sm font-medium">No purchases yet</p>
 				<p className="text-xs text-muted-foreground">
-					Your page-pack purchases will appear here after checkout.
+					Your page and premium token purchases will appear here after checkout.
 				</p>
 			</div>
 		);
@ -81,25 +156,36 @@ export function PurchaseHistoryContent() {
 					<TableHeader>
 						<TableRow>
 							<TableHead>Date</TableHead>
-							<TableHead className="text-right">Pages</TableHead>
+							<TableHead>Type</TableHead>
+							<TableHead className="text-right">Granted</TableHead>
 							<TableHead className="text-right">Amount</TableHead>
 							<TableHead className="text-center">Status</TableHead>
 						</TableRow>
 					</TableHeader>
 					<TableBody>
 						{purchases.map((p) => {
-							const style = STATUS_STYLES[p.status];
+							const statusStyle = STATUS_STYLES[p.status];
+							const kind = KIND_META[p.kind];
+							const KindIcon = kind.icon;
 							return (
-								<TableRow key={p.id}>
+								<TableRow key={`${p.kind}-${p.id}`}>
 									<TableCell className="text-sm">{formatDate(p.created_at)}</TableCell>
-									<TableCell className="text-right tabular-nums text-sm">
-										{p.pages_granted.toLocaleString()}
+									<TableCell className="text-sm">
+										<div className="flex items-center gap-2">
+											<KindIcon className={cn("h-4 w-4", kind.iconClass)} />
+											<span>{kind.label}</span>
+										</div>
 									</TableCell>
 									<TableCell className="text-right tabular-nums text-sm">
-										{formatAmount(p)}
+										{p.granted.toLocaleString()}
+									</TableCell>
+									<TableCell className="text-right tabular-nums text-sm">
+										{formatAmount(p.amount_total, p.currency)}
 									</TableCell>
 									<TableCell className="text-center">
-										<Badge className={cn("text-[10px]", style.className)}>{style.label}</Badge>
+										<Badge className={cn("text-[10px]", statusStyle.className)}>
+											{statusStyle.label}
+										</Badge>
 									</TableCell>
 								</TableRow>
 							);
@ -108,7 +194,8 @@ export function PurchaseHistoryContent() {
 				</Table>
 			</div>
 			<p className="text-center text-xs text-muted-foreground">
-				Showing your {purchases.length} most recent purchase{purchases.length !== 1 ? "s" : ""}.
+				Showing your {purchases.length} most recent purchase
+				{purchases.length !== 1 ? "s" : ""}.
 			</p>
 		</div>
 	);
--- a/surfsense_web/app/layout.tsx
+++ b/surfsense_web/app/layout.tsx
@ -45,7 +45,7 @@ export const metadata: Metadata = {
 	alternates: {
 		canonical: "https://surfsense.com",
 	},
-	title: "SurfSense - NotebookLM Alternative | Free ChatGPT & Claude AI",
+	title: "SurfSense – Open Source, Privacy-Focused NotebookLM Alternative for Teams",
 	description:
 		"Open source NotebookLM alternative for teams with no data limits. Use ChatGPT, Claude AI, and any AI model for free.",
 	keywords: [
@ -87,7 +87,7 @@ export const metadata: Metadata = {
 		"SurfSense",
 	],
 	openGraph: {
-		title: "SurfSense - NotebookLM Alternative | Free ChatGPT & Claude AI",
+		title: "SurfSense – Open Source, Privacy-Focused NotebookLM Alternative for Teams",
 		description:
 			"Open source NotebookLM alternative for teams with no data limits. Use ChatGPT, Claude, and any AI model for free.",
 		url: "https://surfsense.com",
@ -105,7 +105,7 @@ export const metadata: Metadata = {
 	},
 	twitter: {
 		card: "summary_large_image",
-		title: "SurfSense - NotebookLM Alternative | Free ChatGPT & Claude AI",
+		title: "SurfSense – Open Source, Privacy-Focused NotebookLM Alternative for Teams",
 		description:
 			"Open source NotebookLM alternative for teams with no data limits. Use ChatGPT, Claude AI, and any AI model for free.",
 		creator: "@SurfSenseAI",
--- a/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts
+++ b/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts
@ -303,5 +303,79 @@ export const AUTO_INDEX_DEFAULTS: Record<string, AutoIndexConfig> = {

 export const AUTO_INDEX_CONNECTOR_TYPES = new Set<string>(Object.keys(AUTO_INDEX_DEFAULTS));

+// ============================================================================
+// CONNECTOR TELEMETRY REGISTRY
+// ----------------------------------------------------------------------------
+// Single source of truth for "what does this connector_type look like in
+// analytics?". Any connector added to the lists above is automatically
+// picked up here, so adding a new integration does NOT require touching
+// `lib/posthog/events.ts` or per-connector tracking code.
+// ============================================================================
+
+export type ConnectorTelemetryGroup = "oauth" | "composio" | "crawler" | "other" | "unknown";
+
+export interface ConnectorTelemetryMeta {
+	connector_type: string;
+	connector_title: string;
+	connector_group: ConnectorTelemetryGroup;
+	is_oauth: boolean;
+}
+
+const CONNECTOR_TELEMETRY_REGISTRY: ReadonlyMap<string, ConnectorTelemetryMeta> = (() => {
+	const map = new Map<string, ConnectorTelemetryMeta>();
+
+	for (const c of OAUTH_CONNECTORS) {
+		map.set(c.connectorType, {
+			connector_type: c.connectorType,
+			connector_title: c.title,
+			connector_group: "oauth",
+			is_oauth: true,
+		});
+	}
+	for (const c of COMPOSIO_CONNECTORS) {
+		map.set(c.connectorType, {
+			connector_type: c.connectorType,
+			connector_title: c.title,
+			connector_group: "composio",
+			is_oauth: true,
+		});
+	}
+	for (const c of CRAWLERS) {
+		map.set(c.connectorType, {
+			connector_type: c.connectorType,
+			connector_title: c.title,
+			connector_group: "crawler",
+			is_oauth: false,
+		});
+	}
+	for (const c of OTHER_CONNECTORS) {
+		map.set(c.connectorType, {
+			connector_type: c.connectorType,
+			connector_title: c.title,
+			connector_group: "other",
+			is_oauth: false,
+		});
+	}
+
+	return map;
+})();
+
+/**
+ * Returns telemetry metadata for a connector_type, or a minimal "unknown"
+ * record so tracking never no-ops for connectors that exist in the backend
+ * but were forgotten in the UI registry.
+ */
+export function getConnectorTelemetryMeta(connectorType: string): ConnectorTelemetryMeta {
+	const hit = CONNECTOR_TELEMETRY_REGISTRY.get(connectorType);
+	if (hit) return hit;
+
+	return {
+		connector_type: connectorType,
+		connector_title: connectorType,
+		connector_group: "unknown",
+		is_oauth: false,
+	};
+}
+
 // Re-export IndexingConfigState from schemas for backward compatibility
 export type { IndexingConfigState } from "./connector-popup.schemas";
--- a/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts
+++ b/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts
@ -24,6 +24,8 @@ import { isSelfHosted } from "@/lib/env-config";
 import {
 	trackConnectorConnected,
 	trackConnectorDeleted,
+	trackConnectorSetupFailure,
+	trackConnectorSetupStarted,
 	trackIndexWithDateRangeOpened,
 	trackIndexWithDateRangeStarted,
 	trackPeriodicIndexingStarted,
@ -232,10 +234,20 @@ export const useConnectorDialog = () => {

 		if (result.error) {
 			const oauthConnector = result.connector
-				? OAUTH_CONNECTORS.find((c) => c.id === result.connector)
+				? OAUTH_CONNECTORS.find((c) => c.id === result.connector) ||
+					COMPOSIO_CONNECTORS.find((c) => c.id === result.connector)
 				: null;
 			const name = oauthConnector?.title || "connector";

+			if (oauthConnector) {
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					oauthConnector.connectorType,
+					result.error,
+					"oauth_callback"
+				);
+			}
+
 			if (result.error === "duplicate_account") {
 				toast.error(`This ${name} account is already connected`, {
 					description: "Please use a different account or manage the existing connection.",
@ -351,6 +363,8 @@ export const useConnectorDialog = () => {
 			// Set connecting state immediately to disable button and show spinner
 			setConnectingId(connector.id);

+			trackConnectorSetupStarted(Number(searchSpaceId), connector.connectorType, "oauth_click");
+
 			try {
 				// Check if authEndpoint already has query parameters
 				const separator = connector.authEndpoint.includes("?") ? "&" : "?";
@ -372,6 +386,12 @@ export const useConnectorDialog = () => {
 				window.location.href = validatedData.auth_url;
 			} catch (error) {
 				console.error(`Error connecting to ${connector.title}:`, error);
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					connector.connectorType,
+					error instanceof Error ? error.message : "oauth_initiation_failed",
+					"oauth_init"
+				);
 				if (error instanceof Error && error.message.includes("Invalid auth URL")) {
 					toast.error(`Invalid response from ${connector.title} OAuth endpoint`);
 				} else {
@ -395,6 +415,11 @@ export const useConnectorDialog = () => {
 		if (!searchSpaceId) return;

 		setConnectingId("webcrawler-connector");
+		trackConnectorSetupStarted(
+			Number(searchSpaceId),
+			EnumConnectorName.WEBCRAWLER_CONNECTOR,
+			"webcrawler_quick_add"
+		);
 		try {
 			await createConnector({
 				data: {
@ -444,6 +469,12 @@ export const useConnectorDialog = () => {
 			}
 		} catch (error) {
 			console.error("Error creating webcrawler connector:", error);
+			trackConnectorSetupFailure(
+				Number(searchSpaceId),
+				EnumConnectorName.WEBCRAWLER_CONNECTOR,
+				error instanceof Error ? error.message : "webcrawler_create_failed",
+				"webcrawler_quick_add"
+			);
 			toast.error("Failed to create web crawler connector");
 		} finally {
 			setConnectingId(null);
@ -455,6 +486,8 @@ export const useConnectorDialog = () => {
 		(connectorType: string) => {
 			if (!searchSpaceId) return;

+			trackConnectorSetupStarted(Number(searchSpaceId), connectorType, "non_oauth_click");
+
 			// Handle Obsidian specifically on Desktop & Cloud
 			if (connectorType === EnumConnectorName.OBSIDIAN_CONNECTOR && !selfHosted && isDesktop) {
 				setIsOpen(false);
@ -683,6 +716,12 @@ export const useConnectorDialog = () => {
 				}
 			} catch (error) {
 				console.error("Error creating connector:", error);
+				trackConnectorSetupFailure(
+					Number(searchSpaceId),
+					connectingConnectorType ?? formData.connector_type,
+					error instanceof Error ? error.message : "connector_create_failed",
+					"non_oauth_form"
+				);
 				toast.error(error instanceof Error ? error.message : "Failed to create connector");
 			} finally {
 				isCreatingConnectorRef.current = false;
--- a/surfsense_web/components/documents/CreateFolderDialog.tsx
+++ b/surfsense_web/components/documents/CreateFolderDialog.tsx
@ -1,6 +1,6 @@
 "use client";

-import { useCallback, useEffect, useRef, useState } from "react";
+import { useCallback, useRef, useState } from "react";
 import { Button } from "@/components/ui/button";
 import {
 	Dialog,
@ -29,12 +29,16 @@ export function CreateFolderDialog({
 	const [name, setName] = useState("");
 	const inputRef = useRef<HTMLInputElement>(null);

-	useEffect(() => {
-		if (open) {
-			setName("");
-			setTimeout(() => inputRef.current?.focus(), 0);
-		}
-	}, [open]);
+	const handleOpenChange = useCallback(
+		(next: boolean) => {
+			if (next) {
+				setName("");
+				setTimeout(() => inputRef.current?.focus(), 0);
+			}
+			onOpenChange(next);
+		},
+		[onOpenChange]
+	);

 	const handleSubmit = useCallback(
 		(e?: React.FormEvent) => {
@ -50,7 +54,7 @@ export function CreateFolderDialog({
 	const isSubfolder = !!parentFolderName;

 	return (
-		<Dialog open={open} onOpenChange={onOpenChange}>
+		<Dialog open={open} onOpenChange={handleOpenChange}>
 			<DialogContent className="select-none max-w-[90vw] sm:max-w-sm p-4 sm:p-5 data-[state=open]:animate-none data-[state=closed]:animate-none">
 				<DialogHeader className="space-y-2 pb-2">
 					<div className="flex items-center gap-2 sm:gap-3">
--- a/surfsense_web/components/documents/FolderPickerDialog.tsx
+++ b/surfsense_web/components/documents/FolderPickerDialog.tsx
@ -1,7 +1,7 @@
 "use client";

 import { ChevronDown, ChevronRight, Folder, FolderOpen, Home } from "lucide-react";
-import { useCallback, useEffect, useMemo, useState } from "react";
+import { useCallback, useMemo, useState } from "react";
 import { Button } from "@/components/ui/button";
 import {
 	Dialog,
@ -36,12 +36,16 @@ export function FolderPickerDialog({
 	const [selectedId, setSelectedId] = useState<number | null>(null);
 	const [expandedIds, setExpandedIds] = useState<Set<number>>(new Set());

-	useEffect(() => {
-		if (open) {
-			setSelectedId(null);
-			setExpandedIds(new Set());
-		}
-	}, [open]);
+	const handleOpenChange = useCallback(
+		(next: boolean) => {
+			if (next) {
+				setSelectedId(null);
+				setExpandedIds(new Set());
+			}
+			onOpenChange(next);
+		},
+		[onOpenChange]
+	);

 	const foldersByParent = useMemo(() => {
 		const map: Record<string, FolderDisplay[]> = {};
@ -123,7 +127,7 @@ export function FolderPickerDialog({
 	}

 	return (
-		<Dialog open={open} onOpenChange={onOpenChange}>
+		<Dialog open={open} onOpenChange={handleOpenChange}>
 			<DialogContent className="select-none max-w-[90vw] sm:max-w-sm p-4 sm:p-5 data-[state=open]:animate-none data-[state=closed]:animate-none">
 				<DialogHeader className="space-y-2 pb-2">
 					<div className="flex items-center gap-2 sm:gap-3">
--- a/surfsense_web/components/free-chat/anonymous-chat.tsx
+++ b/surfsense_web/components/free-chat/anonymous-chat.tsx
@ -5,6 +5,7 @@ import { useCallback, useEffect, useRef, useState } from "react";
 import type { AnonModel, AnonQuotaResponse } from "@/contracts/types/anonymous-chat.types";
 import { anonymousChatApiService } from "@/lib/apis/anonymous-chat-api.service";
 import { readSSEStream } from "@/lib/chat/streaming-state";
+import { trackAnonymousChatMessageSent } from "@/lib/posthog/events";
 import { cn } from "@/lib/utils";
 import { QuotaBar } from "./quota-bar";
 import { QuotaWarningBanner } from "./quota-warning-banner";
@ -61,6 +62,12 @@ export function AnonymousChat({ model }: AnonymousChatProps) {
 			textareaRef.current.style.height = "auto";
 		}

+		trackAnonymousChatMessageSent({
+			modelSlug: model.seo_slug,
+			messageLength: trimmed.length,
+			surface: "free_model_page",
+		});
+
 		const controller = new AbortController();
 		abortRef.current = controller;

--- a/surfsense_web/components/free-chat/free-chat-page.tsx
+++ b/surfsense_web/components/free-chat/free-chat-page.tsx
@ -28,6 +28,7 @@ import {
 	updateToolCall,
 } from "@/lib/chat/streaming-state";
 import { BACKEND_URL } from "@/lib/env-config";
+import { trackAnonymousChatMessageSent } from "@/lib/posthog/events";
 import { FreeModelSelector } from "./free-model-selector";
 import { FreeThread } from "./free-thread";

@ -206,6 +207,13 @@ export function FreeChatPage() {
 			}
 			if (!userQuery.trim()) return;

+			trackAnonymousChatMessageSent({
+				modelSlug,
+				messageLength: userQuery.trim().length,
+				hasUploadedDoc: anonMode.isAnonymous && anonMode.uploadedDoc !== null ? true : false,
+				surface: "free_chat_page",
+			});
+
 			const userMsgId = `msg-user-${Date.now()}`;
 			setMessages((prev) => [
 				...prev,
--- a/surfsense_web/components/free-chat/free-model-selector.tsx
+++ b/surfsense_web/components/free-chat/free-model-selector.tsx
@ -27,13 +27,14 @@ export function FreeModelSelector({ className }: { className?: string }) {
 		anonymousChatApiService.getModels().then(setModels).catch(console.error);
 	}, []);

-	useEffect(() => {
-		if (open) {
+	const handleOpenChange = useCallback((next: boolean) => {
+		if (next) {
 			setSearchQuery("");
 			setFocusedIndex(-1);
 			requestAnimationFrame(() => searchInputRef.current?.focus());
 		}
-	}, [open]);
+		setOpen(next);
+	}, []);

 	const currentModel = useMemo(
 		() => models.find((m) => m.seo_slug === currentSlug) ?? null,
@ -94,7 +95,7 @@ export function FreeModelSelector({ className }: { className?: string }) {
 	);

 	return (
-		<Popover open={open} onOpenChange={setOpen}>
+		<Popover open={open} onOpenChange={handleOpenChange}>
 			<PopoverTrigger asChild>
 				<Button
 					variant="ghost"
--- a/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
+++ b/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
@ -65,16 +65,15 @@ function EmailsTagField({
 		setTags((prev) => (typeof newTags === "function" ? newTags(prev) : newTags));
 	}, []);

-	const handleAddTag = useCallback(
-		(text: string) => {
-			const trimmed = text.trim();
-			if (!trimmed) return;
-			if (tags.some((tag) => tag.text === trimmed)) return;
+	const handleAddTag = useCallback((text: string) => {
+		const trimmed = text.trim();
+		if (!trimmed) return;
+		setTags((prev) => {
+			if (prev.some((tag) => tag.text === trimmed)) return prev;
 			const newTag: TagType = { id: Date.now().toString(), text: trimmed };
-			setTags((prev) => [...prev, newTag]);
-		},
-		[tags]
-	);
+			return [...prev, newTag];
+		});
+	}, []);

 	return (
 		<TagInput
--- a/surfsense_web/components/homepage/features-bento-grid.tsx
+++ b/surfsense_web/components/homepage/features-bento-grid.tsx
@ -426,15 +426,50 @@ const AiSortIllustration = () => (
 			<title>AI File Sorting illustration showing automatic folder organization</title>
 			{/* Scattered documents on the left */}
 			<g opacity="0.5">
-				<rect x="20" y="40" width="35" height="45" rx="4" className="fill-neutral-200 dark:fill-neutral-700" transform="rotate(-8 37 62)" />
-				<rect x="50" y="80" width="35" height="45" rx="4" className="fill-neutral-200 dark:fill-neutral-700" transform="rotate(5 67 102)" />
-				<rect x="15" y="110" width="35" height="45" rx="4" className="fill-neutral-200 dark:fill-neutral-700" transform="rotate(-3 32 132)" />
+				<rect
+					x="20"
+					y="40"
+					width="35"
+					height="45"
+					rx="4"
+					className="fill-neutral-200 dark:fill-neutral-700"
+					transform="rotate(-8 37 62)"
+				/>
+				<rect
+					x="50"
+					y="80"
+					width="35"
+					height="45"
+					rx="4"
+					className="fill-neutral-200 dark:fill-neutral-700"
+					transform="rotate(5 67 102)"
+				/>
+				<rect
+					x="15"
+					y="110"
+					width="35"
+					height="45"
+					rx="4"
+					className="fill-neutral-200 dark:fill-neutral-700"
+					transform="rotate(-3 32 132)"
+				/>
 			</g>

 			{/* AI sparkle / magic in the center */}
 			<g transform="translate(140, 90)">
-				<path d="M 0,-18 L 4,-6 L 16,-4 L 6,4 L 8,16 L 0,10 L -8,16 L -6,4 L -16,-4 L -4,-6 Z" className="fill-emerald-500 dark:fill-emerald-400" opacity="0.85">
-					<animateTransform attributeName="transform" type="rotate" from="0" to="360" dur="10s" repeatCount="indefinite" />
+				<path
+					d="M 0,-18 L 4,-6 L 16,-4 L 6,4 L 8,16 L 0,10 L -8,16 L -6,4 L -16,-4 L -4,-6 Z"
+					className="fill-emerald-500 dark:fill-emerald-400"
+					opacity="0.85"
+				>
+					<animateTransform
+						attributeName="transform"
+						type="rotate"
+						from="0"
+						to="360"
+						dur="10s"
+						repeatCount="indefinite"
+					/>
 				</path>
 				<circle cx="0" cy="0" r="3" className="fill-white dark:fill-emerald-200">
 					<animate attributeName="opacity" values="0.5;1;0.5" dur="2s" repeatCount="indefinite" />
@ -442,51 +477,208 @@ const AiSortIllustration = () => (
 			</g>

 			{/* Animated sorting arrows */}
-			<g className="stroke-emerald-500 dark:stroke-emerald-400" strokeWidth="2" fill="none" opacity="0.6">
+			<g
+				className="stroke-emerald-500 dark:stroke-emerald-400"
+				strokeWidth="2"
+				fill="none"
+				opacity="0.6"
+			>
 				<path d="M 100 70 Q 140 60, 180 50" strokeDasharray="4,4">
-					<animate attributeName="stroke-dashoffset" from="8" to="0" dur="1s" repeatCount="indefinite" />
+					<animate
+						attributeName="stroke-dashoffset"
+						from="8"
+						to="0"
+						dur="1s"
+						repeatCount="indefinite"
+					/>
 				</path>
 				<path d="M 100 100 Q 140 100, 180 100" strokeDasharray="4,4">
-					<animate attributeName="stroke-dashoffset" from="8" to="0" dur="1s" repeatCount="indefinite" />
+					<animate
+						attributeName="stroke-dashoffset"
+						from="8"
+						to="0"
+						dur="1s"
+						repeatCount="indefinite"
+					/>
 				</path>
 				<path d="M 100 130 Q 140 140, 180 150" strokeDasharray="4,4">
-					<animate attributeName="stroke-dashoffset" from="8" to="0" dur="1s" repeatCount="indefinite" />
+					<animate
+						attributeName="stroke-dashoffset"
+						from="8"
+						to="0"
+						dur="1s"
+						repeatCount="indefinite"
+					/>
 				</path>
 			</g>

 			{/* Organized folder tree on the right */}
 			{/* Root folder */}
 			<g>
-				<rect x="220" y="30" width="160" height="28" rx="6" className="fill-white dark:fill-neutral-800" opacity="0.9" />
-				<rect x="228" y="36" width="16" height="14" rx="3" className="fill-emerald-500 dark:fill-emerald-400" />
-				<line x1="252" y1="43" x2="330" y2="43" className="stroke-neutral-400 dark:stroke-neutral-500" strokeWidth="2.5" strokeLinecap="round" />
+				<rect
+					x="220"
+					y="30"
+					width="160"
+					height="28"
+					rx="6"
+					className="fill-white dark:fill-neutral-800"
+					opacity="0.9"
+				/>
+				<rect
+					x="228"
+					y="36"
+					width="16"
+					height="14"
+					rx="3"
+					className="fill-emerald-500 dark:fill-emerald-400"
+				/>
+				<line
+					x1="252"
+					y1="43"
+					x2="330"
+					y2="43"
+					className="stroke-neutral-400 dark:stroke-neutral-500"
+					strokeWidth="2.5"
+					strokeLinecap="round"
+				/>
 			</g>

 			{/* Subfolder 1 */}
 			<g>
-				<line x1="240" y1="58" x2="240" y2="76" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<line x1="240" y1="76" x2="250" y2="76" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<rect x="250" y="64" width="130" height="24" rx="5" className="fill-white dark:fill-neutral-800" opacity="0.85" />
-				<rect x="257" y="70" width="12" height="11" rx="2" className="fill-teal-400 dark:fill-teal-500" />
-				<line x1="276" y1="76" x2="340" y2="76" className="stroke-neutral-400 dark:stroke-neutral-500" strokeWidth="2" strokeLinecap="round" />
+				<line
+					x1="240"
+					y1="58"
+					x2="240"
+					y2="76"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<line
+					x1="240"
+					y1="76"
+					x2="250"
+					y2="76"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<rect
+					x="250"
+					y="64"
+					width="130"
+					height="24"
+					rx="5"
+					className="fill-white dark:fill-neutral-800"
+					opacity="0.85"
+				/>
+				<rect
+					x="257"
+					y="70"
+					width="12"
+					height="11"
+					rx="2"
+					className="fill-teal-400 dark:fill-teal-500"
+				/>
+				<line
+					x1="276"
+					y1="76"
+					x2="340"
+					y2="76"
+					className="stroke-neutral-400 dark:stroke-neutral-500"
+					strokeWidth="2"
+					strokeLinecap="round"
+				/>
 			</g>

 			{/* Subfolder 2 */}
 			<g>
-				<line x1="240" y1="76" x2="240" y2="108" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<line x1="240" y1="108" x2="250" y2="108" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<rect x="250" y="96" width="130" height="24" rx="5" className="fill-white dark:fill-neutral-800" opacity="0.85" />
-				<rect x="257" y="102" width="12" height="11" rx="2" className="fill-cyan-400 dark:fill-cyan-500" />
-				<line x1="276" y1="108" x2="350" y2="108" className="stroke-neutral-400 dark:stroke-neutral-500" strokeWidth="2" strokeLinecap="round" />
+				<line
+					x1="240"
+					y1="76"
+					x2="240"
+					y2="108"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<line
+					x1="240"
+					y1="108"
+					x2="250"
+					y2="108"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<rect
+					x="250"
+					y="96"
+					width="130"
+					height="24"
+					rx="5"
+					className="fill-white dark:fill-neutral-800"
+					opacity="0.85"
+				/>
+				<rect
+					x="257"
+					y="102"
+					width="12"
+					height="11"
+					rx="2"
+					className="fill-cyan-400 dark:fill-cyan-500"
+				/>
+				<line
+					x1="276"
+					y1="108"
+					x2="350"
+					y2="108"
+					className="stroke-neutral-400 dark:stroke-neutral-500"
+					strokeWidth="2"
+					strokeLinecap="round"
+				/>
 			</g>

 			{/* Subfolder 3 */}
 			<g>
-				<line x1="240" y1="108" x2="240" y2="140" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<line x1="240" y1="140" x2="250" y2="140" className="stroke-neutral-300 dark:stroke-neutral-600" strokeWidth="1.5" />
-				<rect x="250" y="128" width="130" height="24" rx="5" className="fill-white dark:fill-neutral-800" opacity="0.85" />
-				<rect x="257" y="134" width="12" height="11" rx="2" className="fill-emerald-400 dark:fill-emerald-500" />
-				<line x1="276" y1="140" x2="325" y2="140" className="stroke-neutral-400 dark:stroke-neutral-500" strokeWidth="2" strokeLinecap="round" />
+				<line
+					x1="240"
+					y1="108"
+					x2="240"
+					y2="140"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<line
+					x1="240"
+					y1="140"
+					x2="250"
+					y2="140"
+					className="stroke-neutral-300 dark:stroke-neutral-600"
+					strokeWidth="1.5"
+				/>
+				<rect
+					x="250"
+					y="128"
+					width="130"
+					height="24"
+					rx="5"
+					className="fill-white dark:fill-neutral-800"
+					opacity="0.85"
+				/>
+				<rect
+					x="257"
+					y="134"
+					width="12"
+					height="11"
+					rx="2"
+					className="fill-emerald-400 dark:fill-emerald-500"
+				/>
+				<line
+					x1="276"
+					y1="140"
+					x2="325"
+					y2="140"
+					className="stroke-neutral-400 dark:stroke-neutral-500"
+					strokeWidth="2"
+					strokeLinecap="round"
+				/>
 			</g>

 			{/* Sparkle accents */}
@ -495,10 +687,22 @@ const AiSortIllustration = () => (
 					<animate attributeName="opacity" values="0;1;0" dur="2s" repeatCount="indefinite" />
 				</circle>
 				<circle cx="190" cy="155" r="1.5" className="fill-teal-400">
-					<animate attributeName="opacity" values="0;1;0" dur="2.5s" begin="0.8s" repeatCount="indefinite" />
+					<animate
+						attributeName="opacity"
+						values="0;1;0"
+						dur="2.5s"
+						begin="0.8s"
+						repeatCount="indefinite"
+					/>
 				</circle>
 				<circle cx="155" cy="120" r="1.5" className="fill-cyan-400">
-					<animate attributeName="opacity" values="0;1;0" dur="3s" begin="0.4s" repeatCount="indefinite" />
+					<animate
+						attributeName="opacity"
+						values="0;1;0"
+						dur="3s"
+						begin="0.4s"
+						repeatCount="indefinite"
+					/>
 				</circle>
 			</g>
 		</svg>
--- a/surfsense_web/components/layout/ui/shell/LayoutShell.tsx
+++ b/surfsense_web/components/layout/ui/shell/LayoutShell.tsx
@ -2,8 +2,10 @@

 import { useAtomValue } from "jotai";
 import { AnimatePresence, motion } from "motion/react";
+import dynamic from "next/dynamic";
 import { useCallback, useMemo, useState } from "react";
 import { activeTabAtom, type Tab } from "@/atoms/tabs/tabs.atom";
+import { Spinner } from "@/components/ui/spinner";
 import { TooltipProvider } from "@/components/ui/tooltip";
 import type { InboxItem } from "@/hooks/use-inbox";
 import { useIsMobile } from "@/hooks/use-mobile";
@ -25,9 +27,20 @@ import {
 	Sidebar,
 } from "../sidebar";
 import { SidebarSlideOutPanel } from "../sidebar/SidebarSlideOutPanel";
-import { DocumentTabContent } from "../tabs/DocumentTabContent";
 import { TabBar } from "../tabs/TabBar";

+const DocumentTabContent = dynamic(
+	() => import("../tabs/DocumentTabContent").then((m) => ({ default: m.DocumentTabContent })),
+	{
+		ssr: false,
+		loading: () => (
+			<div className="flex-1 flex items-center justify-center h-full">
+				<Spinner size="lg" />
+			</div>
+		),
+	}
+);
+
 // Per-tab data source
 interface TabDataSource {
 	items: InboxItem[];
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@ -478,7 +478,7 @@ function AuthenticatedDocumentsSidebar({
 		setFolderPickerOpen(true);
 	}, []);

-	const [, setIsExportingKB] = useState(false);
+	const isExportingKBRef = useRef(false);
 	const [exportWarningOpen, setExportWarningOpen] = useState(false);
 	const [exportWarningContext, setExportWarningContext] = useState<{
 		folder: FolderDisplay;
@ -508,7 +508,7 @@ function AuthenticatedDocumentsSidebar({
 		const ctx = exportWarningContext;
 		if (!ctx?.folder) return;

-		setIsExportingKB(true);
+		isExportingKBRef.current = true;
 		try {
 			const safeName =
 				ctx.folder.name
@ -524,7 +524,7 @@ function AuthenticatedDocumentsSidebar({
 			console.error("Folder export failed:", err);
 			toast.error(err instanceof Error ? err.message : "Export failed");
 		} finally {
-			setIsExportingKB(false);
+			isExportingKBRef.current = false;
 		}
 		setExportWarningContext(null);
 	}, [exportWarningContext, searchSpaceId, doExport]);
@ -560,7 +560,7 @@ function AuthenticatedDocumentsSidebar({
 				return;
 			}

-			setIsExportingKB(true);
+			isExportingKBRef.current = true;
 			try {
 				const safeName =
 					folder.name
@ -576,7 +576,7 @@ function AuthenticatedDocumentsSidebar({
 				console.error("Folder export failed:", err);
 				toast.error(err instanceof Error ? err.message : "Export failed");
 			} finally {
-				setIsExportingKB(false);
+				isExportingKBRef.current = false;
 			}
 		},
 		[searchSpaceId, getPendingCountInSubtree, doExport]
--- a/surfsense_web/components/new-chat/model-selector.tsx
+++ b/surfsense_web/components/new-chat/model-selector.tsx
@ -269,6 +269,34 @@ export function ModelSelector({
 	const searchInputRef = useRef<HTMLInputElement>(null);
 	const isMobile = useIsMobile();

+	const handleOpenChange = useCallback(
+		(next: boolean) => {
+			if (next) {
+				setSearchQuery("");
+				setSelectedProvider("all");
+				if (!isMobile) {
+					requestAnimationFrame(() => searchInputRef.current?.focus());
+				}
+			}
+			setOpen(next);
+		},
+		[isMobile]
+	);
+
+	const handleTabChange = useCallback(
+		(next: "llm" | "image" | "vision") => {
+			setActiveTab(next);
+			setSelectedProvider("all");
+			setSearchQuery("");
+			setFocusedIndex(-1);
+			setModelScrollPos("top");
+			if (open && !isMobile) {
+				requestAnimationFrame(() => searchInputRef.current?.focus());
+			}
+		},
+		[open, isMobile]
+	);
+
 	const handleModelListScroll = useCallback((e: React.UIEvent<HTMLDivElement>) => {
 		const el = e.currentTarget;
 		const atTop = el.scrollTop <= 2;
@ -292,43 +320,19 @@ export function ModelSelector({
 		[isMobile]
 	);

-	// Reset search + provider when tab changes
-	// biome-ignore lint/correctness/useExhaustiveDependencies: activeTab is intentionally used as a trigger
-	useEffect(() => {
-		setSelectedProvider("all");
-		setSearchQuery("");
-		setFocusedIndex(-1);
-		setModelScrollPos("top");
-	}, [activeTab]);
-
-	// Reset on open
-	useEffect(() => {
-		if (open) {
-			setSearchQuery("");
-			setSelectedProvider("all");
-		}
-	}, [open]);
-
 	// Cmd/Ctrl+M shortcut (desktop only)
 	useEffect(() => {
 		if (isMobile) return;
 		const handler = (e: KeyboardEvent) => {
 			if ((e.metaKey || e.ctrlKey) && e.key === "m") {
 				e.preventDefault();
-				setOpen((prev) => !prev);
+				// setOpen((prev) => !prev);
+				handleOpenChange(!open);
 			}
 		};
 		document.addEventListener("keydown", handler);
 		return () => document.removeEventListener("keydown", handler);
-	}, [isMobile]);
-
-	// Focus search input on open
-	// biome-ignore lint/correctness/useExhaustiveDependencies: activeTab is intentionally used as a trigger to re-focus on tab switch
-	useEffect(() => {
-		if (open && !isMobile) {
-			requestAnimationFrame(() => searchInputRef.current?.focus());
-		}
-	}, [open, isMobile, activeTab]);
+	}, [isMobile, open, handleOpenChange]);

 	// ─── Data ───
 	const { data: llmUserConfigs, isLoading: llmUserLoading } = useAtomValue(newLLMConfigsAtom);
@ -971,7 +975,8 @@ export function ModelSelector({
 							<button
 								key={value}
 								type="button"
-								onClick={() => setActiveTab(value)}
+								// onClick={() => setActiveTab(value)}
+								onClick={() => handleTabChange(value)}
 								className={cn(
 									"flex items-center justify-center gap-1.5 text-sm font-medium transition-all duration-200 border-b-[1.5px]",
 									activeTab === value
@ -1208,7 +1213,7 @@ export function ModelSelector({
 	// ─── Shell: Drawer on mobile, Popover on desktop ───
 	if (isMobile) {
 		return (
-			<Drawer open={open} onOpenChange={setOpen}>
+			<Drawer open={open} onOpenChange={handleOpenChange}>
 				<DrawerTrigger asChild>{triggerButton}</DrawerTrigger>
 				<DrawerContent className="max-h-[85vh]">
 					<DrawerHandle />
@ -1222,7 +1227,7 @@ export function ModelSelector({
 	}

 	return (
-		<Popover open={open} onOpenChange={setOpen}>
+		<Popover open={open} onOpenChange={handleOpenChange}>
 			<PopoverTrigger asChild>{triggerButton}</PopoverTrigger>
 			<PopoverContent
 				className="w-[300px] md:w-[380px] p-0 rounded-lg shadow-lg overflow-hidden bg-white border-border/60 dark:bg-neutral-900 dark:border dark:border-white/5 select-none"
--- a/surfsense_web/components/sources/DocumentUploadTab.tsx
+++ b/surfsense_web/components/sources/DocumentUploadTab.tsx
@ -546,35 +546,36 @@ export function DocumentUploadTab({
 						</button>
 					)
 				) : (
-				<div
-					role="button"
-					tabIndex={0}
-					className="flex flex-col items-center gap-4 py-12 px-4 cursor-pointer w-full bg-transparent outline-none select-none"
-					onClick={() => {
-						if (!isElectron) fileInputRef.current?.click();
-					}}
-					onKeyDown={(e) => {
-						if (e.key === "Enter" || e.key === " ") {
-							e.preventDefault();
+					// biome-ignore lint/a11y/useSemanticElements: cannot use <button> here because the contents include nested interactive elements (renderBrowseButton renders a Button), which would be invalid HTML.
+					<div
+						role="button"
+						tabIndex={0}
+						className="flex flex-col items-center gap-4 py-12 px-4 cursor-pointer w-full bg-transparent outline-none select-none"
+						onClick={() => {
 							if (!isElectron) fileInputRef.current?.click();
-						}
-					}}
-				>
-					<Upload className="h-10 w-10 text-muted-foreground" />
-					<div className="text-center space-y-1.5">
-						<p className="text-base font-medium">
-							{isElectron ? t("select_files_or_folder") : t("tap_select_files_or_folder")}
-						</p>
-						<p className="text-sm text-muted-foreground">{t("file_size_limit")}</p>
-					</div>
-					<fieldset
-						className="w-full mt-1 border-none p-0 m-0"
-						onClick={(e) => e.stopPropagation()}
-						onKeyDown={(e) => e.stopPropagation()}
+						}}
+						onKeyDown={(e) => {
+							if (e.key === "Enter" || e.key === " ") {
+								e.preventDefault();
+								if (!isElectron) fileInputRef.current?.click();
+							}
+						}}
 					>
-						{renderBrowseButton({ fullWidth: true })}
-					</fieldset>
-				</div>
+						<Upload className="h-10 w-10 text-muted-foreground" />
+						<div className="text-center space-y-1.5">
+							<p className="text-base font-medium">
+								{isElectron ? t("select_files_or_folder") : t("tap_select_files_or_folder")}
+							</p>
+							<p className="text-sm text-muted-foreground">{t("file_size_limit")}</p>
+						</div>
+						<fieldset
+							className="w-full mt-1 border-none p-0 m-0"
+							onClick={(e) => e.stopPropagation()}
+							onKeyDown={(e) => e.stopPropagation()}
+						>
+							{renderBrowseButton({ fullWidth: true })}
+						</fieldset>
+					</div>
 				)}
 			</div>

--- a/surfsense_web/components/theme/theme-toggle.tsx
+++ b/surfsense_web/components/theme/theme-toggle.tsx
@ -586,7 +586,7 @@ export const useThemeToggle = ({
 	}, []);

 	const toggleTheme = useCallback(() => {
-		setIsDark(!isDark);
+		setIsDark((prev) => !prev);

 		const animation = createAnimation(variant, start, blur, gifUrl);

@ -604,7 +604,7 @@ export const useThemeToggle = ({
 		}

 		document.startViewTransition(switchTheme);
-	}, [theme, setTheme, variant, start, blur, gifUrl, updateStyles, isDark]);
+	}, [theme, setTheme, variant, start, blur, gifUrl, updateStyles]);

 	const setCrazyLightTheme = useCallback(() => {
 		setIsDark(false);
--- a/surfsense_web/content/docs/how-to/meta.json
+++ b/surfsense_web/content/docs/how-to/meta.json
@ -1,6 +1,6 @@
 {
 	"title": "How to",
-	"pages": ["zero-sync", "realtime-collaboration", "web-search"],
+	"pages": ["zero-sync", "realtime-collaboration", "web-search", "ollama"],
 	"icon": "Compass",
 	"defaultOpen": false
 }
--- a/surfsense_web/content/docs/how-to/ollama.mdx
+++ b/surfsense_web/content/docs/how-to/ollama.mdx
@ -0,0 +1,90 @@
+---
+title: Connect Ollama
+description: Simple setup guide for using Ollama with SurfSense across local, Docker, remote, and cloud setups
+---
+
+# Connect Ollama
+
+Use this page to choose the correct **API Base URL** when adding an Ollama provider in SurfSense.
+
+## 1) Pick your API Base URL
+
+| Ollama location | SurfSense location | API Base URL |
+|---|---|---|
+| Same machine | No Docker | `http://localhost:11434` |
+| Host machine (macOS/Windows) | Docker Desktop | `http://host.docker.internal:11434` |
+| Host machine (Linux) | Docker Compose | `http://host.docker.internal:11434` |
+| Same Docker Compose stack | Docker Compose | `http://ollama:11434` |
+| Another machine in your network | Any | `http://<lan-ip>:11434` |
+| Public Ollama endpoint / proxy / cloud | Any | `http(s)://<your-domain-or-endpoint>` |
+
+If SurfSense runs in Docker, do not use `localhost` unless Ollama is in the same container.
+
+## 2) Add Ollama in SurfSense
+
+Go to **Search Space Settings -> Agent Models -> Add Model** and set:
+
+- Provider: `OLLAMA`
+- Model name: your model tag, for example `llama3.2` or `qwen3:8b`
+- API Base URL: from the table above
+- API key:
+  - local/self-hosted Ollama: any non-empty value
+  - Ollama cloud/proxied auth: real key or token required by that endpoint
+
+Save. SurfSense validates the connection immediately.
+
+## 3) Common setups
+
+### A) SurfSense in Docker Desktop, Ollama on your host
+
+Use:
+
+```text
+http://host.docker.internal:11434
+```
+
+### B) Ollama as a service in the same Compose
+
+Use API Base URL:
+
+```text
+http://ollama:11434
+```
+
+Minimal service example:
+
+```yaml
+ollama:
+  image: ollama/ollama:latest
+  volumes:
+    - ollama_data:/root/.ollama
+  ports:
+    - "11434:11434"
+```
+
+### C) Ollama on another machine
+
+Ollama binds to `127.0.0.1` by default. Make it reachable on the network:
+
+- Set `OLLAMA_HOST=0.0.0.0:11434` on the machine/service running Ollama
+- Open firewall port `11434`
+- Use `http://<lan-ip>:11434` in SurfSense's API Base URL
+
+## 4) Quick troubleshooting
+
+| Error | Cause | Fix |
+|---|---|---|
+| `Cannot connect to host localhost:11434` | Wrong URL from Dockerized backend | Use `host.docker.internal` or `ollama` |
+| `Cannot connect to host <lan-ip>:11434` | Ollama not exposed on network or firewall blocked | Set `OLLAMA_HOST=0.0.0.0:11434`, allow port 11434 |
+| URL starts with `/%20http://...` | Leading space in URL | Re-enter API Base URL without spaces |
+| `model not found` | Model not pulled on Ollama | Run `ollama pull <model>` |
+
+If needed, test from the backend container using the same host you put in **API Base URL**:
+
+```bash
+docker compose exec backend curl -v <YOUR_API_BASE_URL>/api/tags
+```
+
+## See also
+
+- [Docker Installation](/docs/docker-installation/docker-compose)
--- a/surfsense_web/contracts/types/stripe.types.ts
+++ b/surfsense_web/contracts/types/stripe.types.ts
@ -49,6 +49,8 @@ export const tokenStripeStatusResponse = z.object({
 	premium_tokens_remaining: z.number().default(0),
 });

+export const tokenPurchaseStatusEnum = pagePurchaseStatusEnum;
+
 export const tokenPurchase = z.object({
 	id: z.uuid(),
 	stripe_checkout_session_id: z.string(),
@ -57,7 +59,7 @@ export const tokenPurchase = z.object({
 	tokens_granted: z.number(),
 	amount_total: z.number().nullable(),
 	currency: z.string().nullable(),
-	status: z.string(),
+	status: tokenPurchaseStatusEnum,
 	completed_at: z.string().nullable(),
 	created_at: z.string(),
 });
@ -75,5 +77,6 @@ export type GetPagePurchasesResponse = z.infer<typeof getPagePurchasesResponse>;
 export type CreateTokenCheckoutSessionRequest = z.infer<typeof createTokenCheckoutSessionRequest>;
 export type CreateTokenCheckoutSessionResponse = z.infer<typeof createTokenCheckoutSessionResponse>;
 export type TokenStripeStatusResponse = z.infer<typeof tokenStripeStatusResponse>;
+export type TokenPurchaseStatus = z.infer<typeof tokenPurchaseStatusEnum>;
 export type TokenPurchase = z.infer<typeof tokenPurchase>;
 export type GetTokenPurchasesResponse = z.infer<typeof getTokenPurchasesResponse>;
--- a/surfsense_web/instrumentation-client.ts
+++ b/surfsense_web/instrumentation-client.ts
@ -1,18 +1,65 @@
 import posthog from "posthog-js";

-function initPostHog() {
+/**
+ * PostHog initialisation for the Next.js renderer.
+ *
+ * The same bundle ships in two contexts:
+ *   1. A normal browser session on surfsense.com  -> platform = "web"
+ *   2. The Electron desktop app (renders the Next app from localhost)
+ *      -> platform = "desktop"
+ *
+ * When running inside Electron we also seed `posthog-js` with the main
+ * process's machine distinctId so that events fired from both the renderer
+ * (e.g. `chat_message_sent`, page views) and the Electron main process
+ * (e.g. `desktop_quick_ask_opened`) share a single PostHog person before
+ * login, and can be merged into the authenticated user afterwards.
+ */
+
+function isElectron(): boolean {
+	return typeof window !== "undefined" && !!window.electronAPI;
+}
+
+function currentPlatform(): "desktop" | "web" {
+	return isElectron() ? "desktop" : "web";
+}
+
+async function resolveBootstrapDistinctId(): Promise<string | undefined> {
+	if (!isElectron() || !window.electronAPI?.getAnalyticsContext) return undefined;
+	try {
+		const ctx = await window.electronAPI.getAnalyticsContext();
+		return ctx?.machineId || ctx?.distinctId || undefined;
+	} catch {
+		return undefined;
+	}
+}
+
+async function initPostHog() {
 	try {
 		if (!process.env.NEXT_PUBLIC_POSTHOG_KEY) return;

+		const platform = currentPlatform();
+		const bootstrapDistinctId = await resolveBootstrapDistinctId();
+
 		posthog.init(process.env.NEXT_PUBLIC_POSTHOG_KEY, {
 			api_host: "https://assets.surfsense.com",
 			ui_host: "https://us.posthog.com",
 			defaults: "2026-01-30",
 			capture_pageview: "history_change",
 			capture_pageleave: true,
+			...(bootstrapDistinctId
+				? {
+						bootstrap: {
+							distinctID: bootstrapDistinctId,
+							isIdentifiedID: false,
+						},
+					}
+				: {}),
 			before_send: (event) => {
 				if (event?.properties) {
-					event.properties.platform = "web";
+					event.properties.platform = platform;
+					if (platform === "desktop") {
+						event.properties.is_desktop = true;
+					}

 					const params = new URLSearchParams(window.location.search);
 					const ref = params.get("ref");
@ -30,9 +77,14 @@ function initPostHog() {

 					event.properties.$set = {
 						...event.properties.$set,
-						platform: "web",
+						platform,
 						last_seen_at: new Date().toISOString(),
 					};
+
+					event.properties.$set_once = {
+						...event.properties.$set_once,
+						first_seen_platform: platform,
+					};
 				}
 				return event;
 			},
@ -51,8 +103,12 @@ if (typeof window !== "undefined") {
 	window.posthog = posthog;

 	if ("requestIdleCallback" in window) {
-		requestIdleCallback(initPostHog);
+		requestIdleCallback(() => {
+			void initPostHog();
+		});
 	} else {
-		setTimeout(initPostHog, 3500);
+		setTimeout(() => {
+			void initPostHog();
+		}, 3500);
 	}
 }
--- a/surfsense_web/lib/posthog/events.ts
+++ b/surfsense_web/lib/posthog/events.ts
@ -1,4 +1,5 @@
 import posthog from "posthog-js";
+import { getConnectorTelemetryMeta } from "@/components/assistant-ui/connector-popup/constants/connector-constants";

 /**
 * PostHog Analytics Event Definitions
@ -13,8 +14,8 @@ import posthog from "posthog-js";
 * - auth: Authentication events
 * - search_space: Search space management
 * - document: Document management
- * - chat: Chat and messaging
- * - connector: External connector events
+ * - chat: Chat and messaging (authenticated + anonymous)
+ * - connector: External connector events (all lifecycle stages)
 * - contact: Contact form events
 * - settings: Settings changes
 * - marketing: Marketing/referral tracking
@ -28,6 +29,17 @@ function safeCapture(event: string, properties?: Record<string, unknown>) {
 	}
 }

+/**
+ * Drop undefined values so PostHog doesn't log `"foo": undefined` noise.
+ */
+function compact<T extends Record<string, unknown>>(obj: T): Record<string, unknown> {
+	const out: Record<string, unknown> = {};
+	for (const [k, v] of Object.entries(obj)) {
+		if (v !== undefined) out[k] = v;
+	}
+	return out;
+}
+
 // ============================================
 // AUTH EVENTS
 // ============================================
@ -127,6 +139,28 @@ export function trackChatError(searchSpaceId: number, chatId: number, error?: st
 	});
 }

+/**
+ * Track a message sent from the unauthenticated "free" / anonymous chat
+ * flow. This is intentionally a separate event from `chat_message_sent`
+ * so WAU / retention queries on the authenticated event stay clean while
+ * still giving us visibility into top-of-funnel usage on /free/*.
+ */
+export function trackAnonymousChatMessageSent(options: {
+	modelSlug: string;
+	messageLength?: number;
+	hasUploadedDoc?: boolean;
+	webSearchEnabled?: boolean;
+	surface?: "free_chat_page" | "free_model_page";
+}) {
+	safeCapture("anonymous_chat_message_sent", {
+		model_slug: options.modelSlug,
+		message_length: options.messageLength,
+		has_uploaded_doc: options.hasUploadedDoc ?? false,
+		web_search_enabled: options.webSearchEnabled,
+		surface: options.surface,
+	});
+}
+
 // ============================================
 // DOCUMENT EVENTS
 // ============================================
@ -179,37 +213,88 @@ export function trackYouTubeImport(searchSpaceId: number, url: string) {
 }

 // ============================================
-// CONNECTOR EVENTS
+// CONNECTOR EVENTS (generic lifecycle dispatcher)
 // ============================================
+//
+// All connector events go through `trackConnectorEvent`. The connector's
+// human-readable title and its group (oauth/composio/crawler/other) are
+// auto-attached from the shared registry in `connector-constants.ts`, so
+// adding a new connector to that list is the only change required for it
+// to show up correctly in PostHog dashboards.

-export function trackConnectorSetupStarted(searchSpaceId: number, connectorType: string) {
-	safeCapture("connector_setup_started", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
+export type ConnectorEventStage =
+	| "setup_started"
+	| "setup_success"
+	| "setup_failure"
+	| "oauth_initiated"
+	| "connected"
+	| "deleted"
+	| "synced";
+
+export interface ConnectorEventOptions {
+	searchSpaceId?: number | null;
+	connectorId?: number | null;
+	/** Source of the action (e.g. "oauth_callback", "non_oauth_form", "webcrawler_quick_add"). */
+	source?: string;
+	/** Free-form error message for failure events. */
+	error?: string;
+	/** Extra properties specific to the stage (e.g. frequency_minutes for sync events). */
+	extra?: Record<string, unknown>;
+}
+
+/**
+ * Generic connector lifecycle tracker. Every connector analytics event
+ * should funnel through here so the enrichment stays consistent.
+ */
+export function trackConnectorEvent(
+	stage: ConnectorEventStage,
+	connectorType: string,
+	options: ConnectorEventOptions = {}
+) {
+	const meta = getConnectorTelemetryMeta(connectorType);
+	safeCapture(`connector_${stage}`, {
+		...compact({
+			search_space_id: options.searchSpaceId ?? undefined,
+			connector_id: options.connectorId ?? undefined,
+			source: options.source,
+			error: options.error,
+		}),
+		connector_type: meta.connector_type,
+		connector_title: meta.connector_title,
+		connector_group: meta.connector_group,
+		is_oauth: meta.is_oauth,
+		...(options.extra ?? {}),
 	});
 }

+// ---- Convenience wrappers kept for backward compatibility ----
+
+export function trackConnectorSetupStarted(
+	searchSpaceId: number,
+	connectorType: string,
+	source?: string
+) {
+	trackConnectorEvent("setup_started", connectorType, { searchSpaceId, source });
+}
+
 export function trackConnectorSetupSuccess(
 	searchSpaceId: number,
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_setup_success", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("setup_success", connectorType, { searchSpaceId, connectorId });
 }

 export function trackConnectorSetupFailure(
-	searchSpaceId: number,
+	searchSpaceId: number | null | undefined,
 	connectorType: string,
-	error?: string
+	error?: string,
+	source?: string
 ) {
-	safeCapture("connector_setup_failure", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
+	trackConnectorEvent("setup_failure", connectorType, {
+		searchSpaceId: searchSpaceId ?? undefined,
 		error,
+		source,
 	});
 }

@ -218,11 +303,7 @@ export function trackConnectorDeleted(
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_deleted", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("deleted", connectorType, { searchSpaceId, connectorId });
 }

 export function trackConnectorSynced(
@ -230,11 +311,7 @@ export function trackConnectorSynced(
 	connectorType: string,
 	connectorId: number
 ) {
-	safeCapture("connector_synced", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
-	});
+	trackConnectorEvent("synced", connectorType, { searchSpaceId, connectorId });
 }

 // ============================================
@ -345,10 +422,9 @@ export function trackConnectorConnected(
 	connectorType: string,
 	connectorId?: number
 ) {
-	safeCapture("connector_connected", {
-		search_space_id: searchSpaceId,
-		connector_type: connectorType,
-		connector_id: connectorId,
+	trackConnectorEvent("connected", connectorType, {
+		searchSpaceId,
+		connectorId: connectorId ?? undefined,
 	});
 }

@ -467,8 +543,13 @@ export function trackReferralLanding(refCode: string, landingUrl: string) {
 // ============================================

 /**
- * Identify a user for PostHog analytics
- * Call this after successful authentication
+ * Identify a user for PostHog analytics.
+ * Call this after successful authentication.
+ *
+ * In the Electron desktop app the same call is mirrored into the
+ * main-process PostHog client so desktop-only events (e.g.
+ * `desktop_quick_ask_opened`, `desktop_autocomplete_accepted`) are
+ * attributed to the logged-in user rather than an anonymous machine ID.
 */
 export function identifyUser(userId: string, properties?: Record<string, unknown>) {
 	try {
@ -476,10 +557,19 @@ export function identifyUser(userId: string, properties?: Record<string, unknown
 	} catch {
 		// Silently ignore – ad-blockers may break posthog
 	}
+
+	try {
+		if (typeof window !== "undefined" && window.electronAPI?.analyticsIdentify) {
+			void window.electronAPI.analyticsIdentify(userId, properties);
+		}
+	} catch {
+		// IPC errors must never break the app
+	}
 }

 /**
- * Reset user identity (call on logout)
+ * Reset user identity (call on logout). Mirrors the reset into the
+ * Electron main process when running inside the desktop app.
 */
 export function resetUser() {
 	try {
@ -487,4 +577,12 @@ export function resetUser() {
 	} catch {
 		// Silently ignore – ad-blockers may break posthog
 	}
+
+	try {
+		if (typeof window !== "undefined" && window.electronAPI?.analyticsReset) {
+			void window.electronAPI.analyticsReset();
+		}
+	} catch {
+		// IPC errors must never break the app
+	}
 }
--- a/surfsense_web/package.json
+++ b/surfsense_web/package.json
@ -1,6 +1,6 @@
 {
 	"name": "surfsense_web",
-	"version": "0.0.16",
+	"version": "0.0.19",
 	"private": true,
 	"description": "SurfSense Frontend",
 	"scripts": {
--- a/surfsense_web/pnpm-lock.yaml
+++ b/surfsense_web/pnpm-lock.yaml
@ -1088,10 +1088,6 @@ packages:
    peerDependencies:
      '@babel/core': ^7.0.0-0

-  '@babel/runtime@7.28.6':
-    resolution: {integrity: sha512-05WQkdpL9COIMz4LjTxGpPNCdlpyimKppYNoJ5Di5EUObifl8t4tuLuUBBZEpoLYOmfvIWrsp9fCl0HoPRVTdA==}
-    engines: {node: '>=6.9.0'}
-
  '@babel/runtime@7.29.2':
    resolution: {integrity: sha512-JiDShH45zKHWyGe4ZNVRrCjBz8Nh9TMmZG1kh4QTK8hCBTWBi8Da+i7s1fJw7/lYpM4ccepSNfqzZ/QvABBi5g==}
    engines: {node: '>=6.9.0'}
@ -2188,12 +2184,6 @@ packages:
    peerDependencies:
      '@opentelemetry/api': '>=1.0.0 <1.10.0'

-  '@opentelemetry/core@2.5.1':
-    resolution: {integrity: sha512-Dwlc+3HAZqpgTYq0MUyZABjFkcrKTePwuiFVLjahGD8cx3enqihmpAmdgNFO1R4m/sIe5afjJrA25Prqy4NXlA==}
-    engines: {node: ^18.19.0 || >=20.6.0}
-    peerDependencies:
-      '@opentelemetry/api': '>=1.0.0 <1.10.0'
-
  '@opentelemetry/core@2.6.0':
    resolution: {integrity: sha512-HLM1v2cbZ4TgYN6KEOj+Bbj8rAKriOdkF9Ed3tG25FoprSiQl7kYc+RRT6fUZGOvx0oMi5U67GoFdT+XUn8zEg==}
    engines: {node: ^18.19.0 || >=20.6.0}
@ -2606,12 +2596,6 @@ packages:
    peerDependencies:
      '@opentelemetry/api': '>=1.3.0 <1.10.0'

-  '@opentelemetry/resources@2.5.1':
-    resolution: {integrity: sha512-BViBCdE/GuXRlp9k7nS1w6wJvY5fnFX5XvuEtWsTAOQFIO89Eru7lGW3WbfbxtCuZ/GbrJfAziXG0w0dpxL7eQ==}
-    engines: {node: ^18.19.0 || >=20.6.0}
-    peerDependencies:
-      '@opentelemetry/api': '>=1.3.0 <1.10.0'
-
  '@opentelemetry/resources@2.6.0':
    resolution: {integrity: sha512-D4y/+OGe3JSuYUCBxtH5T9DSAWNcvCb/nQWIga8HNtXTVPQn59j0nTBAgaAXxUVBDl40mG3Tc76b46wPlZaiJQ==}
    engines: {node: ^18.19.0 || >=20.6.0}
@ -4372,8 +4356,8 @@ packages:
    peerDependencies:
      react: '>= 16'

-  '@tabler/icons@3.37.1':
-    resolution: {integrity: sha512-neLCWkuyNHEPXCyYu6nbN4S3g/59BTa4qyITAugYVpq1YzYNDOZooW7/vRWH98ZItXAudxdKU8muFT7y1PqzuA==}
+  '@tabler/icons@3.41.1':
+    resolution: {integrity: sha512-OaRnVbRmH2nHtFeg+RmMJ/7m2oBIF9XCJAUD5gQnMrpK9f05ydj8MZrAf3NZQqOXyxGN1UBL0D5IKLLEUfr74Q==}

  '@tailwindcss/node@4.2.1':
    resolution: {integrity: sha512-jlx6sLk4EOwO6hHe1oCGm1Q4AN/s0rSrTTPBGPM0/RQ6Uylwq17FuU8IeJJKEjtc6K6O07zsvP+gDO6MMWo7pg==}
@ -4814,6 +4798,7 @@ packages:
  '@xmldom/xmldom@0.8.11':
    resolution: {integrity: sha512-cQzWCtO6C8TQiYl1ruKNn2U6Ao4o4WBBcbL61yJl84x+j5sOWWFU9X7DpND8XZG3daDppSsigMdfAIl2upQBRw==}
    engines: {node: '>=10.0.0'}
+    deprecated: this version has critical issues, please update to the latest version

  abstract-logging@2.0.1:
    resolution: {integrity: sha512-2BjRTZxTPvheOvGbBslFSYOUkr+SjPtOnrLP33f+VIWLzezQpZcqVg7ja3L4dBXmzzgwT+a029jRx5PCi3JuiA==}
@ -7012,11 +6997,6 @@ packages:
    engines: {node: ^10 || ^12 || ^13.7 || ^14 || >=15.0.1}
    hasBin: true

-  nanoid@5.1.6:
-    resolution: {integrity: sha512-c7+7RQ+dMB5dPwwCp4ee1/iV/q2P6aK1mTZcfr1BTuVlyW9hJYiMPybJCcnBlQtuSmTIWNeazm/zqNoZSSElBg==}
-    engines: {node: ^18 || >=20}
-    hasBin: true
-
  nanoid@5.1.7:
    resolution: {integrity: sha512-ua3NDgISf6jdwezAheMOk4mbE1LXjm1DfMUDMuJf4AqxLFK3ccGpgWizwa5YV7Yz9EpXwEaWoRXSb/BnV0t5dQ==}
    engines: {node: ^18 || >=20}
@ -7421,8 +7401,8 @@ packages:
  property-information@7.1.0:
    resolution: {integrity: sha512-TwEZ+X+yCJmYfL7TPUOcvBZ4QfoT5YenQiJuX//0th53DE6w0xxLEtfK3iyryQFddXuvkIk51EEgrJQ0WJkOmQ==}

-  protobufjs@7.5.4:
-    resolution: {integrity: sha512-CvexbZtbov6jW2eXAvLukXjXUW1TzFaivC46BpWc/3BpcCysb5Vffu+B3XHMm8lVEuy2Mm4XGex8hBSg1yapPg==}
+  protobufjs@7.5.5:
+    resolution: {integrity: sha512-3wY1AxV+VBNW8Yypfd1yQY9pXnqTAN+KwQxL8iYm3/BjKYMNg4i0owhEe26PWDOMaIrzeeF98Lqd5NGz4omiIg==}
    engines: {node: '>=12.0.0'}

  proxy-compare@2.6.0:
@ -9387,8 +9367,6 @@ snapshots:
    transitivePeerDependencies:
      - supports-color

-  '@babel/runtime@7.28.6': {}
-
  '@babel/runtime@7.29.2': {}

  '@babel/standalone@7.29.2': {}
@ -9886,7 +9864,7 @@ snapshots:
    dependencies:
      lodash.camelcase: 4.3.0
      long: 5.3.2
-      protobufjs: 7.5.4
+      protobufjs: 7.5.5
      yargs: 17.7.2

  '@hookform/resolvers@5.2.2(react-hook-form@7.71.2(react@19.2.4))':
@ -10246,7 +10224,7 @@ snapshots:
      '@opentelemetry/resource-detector-azure': 0.10.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/resource-detector-container': 0.7.11(@opentelemetry/api@1.9.0)
      '@opentelemetry/resource-detector-gcp': 0.37.0(@opentelemetry/api@1.9.0)
-      '@opentelemetry/resources': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/resources': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/sdk-node': 0.203.0(@opentelemetry/api@1.9.0)
    transitivePeerDependencies:
      - encoding
@ -10270,11 +10248,6 @@ snapshots:
      '@opentelemetry/api': 1.9.0
      '@opentelemetry/semantic-conventions': 1.39.0

-  '@opentelemetry/core@2.5.1(@opentelemetry/api@1.9.0)':
-    dependencies:
-      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/semantic-conventions': 1.39.0
-
  '@opentelemetry/core@2.6.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
@ -10397,7 +10370,7 @@ snapshots:
  '@opentelemetry/instrumentation-amqplib@0.50.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/semantic-conventions': 1.39.0
    transitivePeerDependencies:
@ -10415,7 +10388,7 @@ snapshots:
  '@opentelemetry/instrumentation-aws-sdk@0.58.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/semantic-conventions': 1.39.0
    transitivePeerDependencies:
@ -10441,7 +10414,7 @@ snapshots:
  '@opentelemetry/instrumentation-connect@0.47.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/semantic-conventions': 1.39.0
      '@types/connect': 3.4.38
@ -10473,7 +10446,7 @@ snapshots:
  '@opentelemetry/instrumentation-express@0.52.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/semantic-conventions': 1.39.0
    transitivePeerDependencies:
@ -10482,7 +10455,7 @@ snapshots:
  '@opentelemetry/instrumentation-fastify@0.48.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/semantic-conventions': 1.39.0
    transitivePeerDependencies:
@ -10491,7 +10464,7 @@ snapshots:
  '@opentelemetry/instrumentation-fs@0.23.0(@opentelemetry/api@1.9.0)':
    dependencies:
      '@opentelemetry/api': 1.9.0
-      '@opentelemetry/core': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/core': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/instrumentation': 0.203.0(@opentelemetry/api@1.9.0)
    transitivePeerDependencies:
      - supports-color
@ -10521,7 +10494,7 @@ snapshots:
  '@opentelemetry/instrumentation-hapi@0.50.0(@opentelemetry/api@1.9.0)':
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@ -12389,7 +12356,7 @@ snapshots:
      '@opentelemetry/api-logs': 0.203.0
      '@opentelemetry/auto-instrumentations-node': 0.62.2(@opentelemetry/api@1.9.0)(@opentelemetry/core@2.6.0(@opentelemetry/api@1.9.0))
      '@opentelemetry/exporter-metrics-otlp-http': 0.203.0(@opentelemetry/api@1.9.0)
-      '@opentelemetry/resources': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/resources': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/sdk-metrics': 2.2.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/sdk-node': 0.203.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/sdk-trace-node': 2.6.0(@opentelemetry/api@1.9.0)
@ -12417,7 +12384,7 @@ snapshots:
      js-xxhash: 4.0.0
      json-custom-numbers: 3.1.1
      kasi: 1.1.2
-      nanoid: 5.1.6
+      nanoid: 5.1.7
      parse-prometheus-text-format: 1.1.1
      pg-format: pg-format-fix@1.0.5
      postgres: 3.4.7
@ -12756,10 +12723,10 @@ snapshots:

  '@tabler/icons-react@3.37.1(react@19.2.4)':
    dependencies:
-      '@tabler/icons': 3.37.1
+      '@tabler/icons': 3.41.1
      react: 19.2.4

-  '@tabler/icons@3.37.1': {}
+  '@tabler/icons@3.41.1': {}

  '@tailwindcss/node@4.2.1':
    dependencies:
@ -15875,8 +15842,6 @@ snapshots:

  nanoid@3.3.11: {}

-  nanoid@5.1.6: {}
-
  nanoid@5.1.7: {}

  napi-build-utils@2.0.0: {}
@ -16256,7 +16221,7 @@ snapshots:
      '@opentelemetry/api': 1.9.0
      '@opentelemetry/api-logs': 0.208.0
      '@opentelemetry/exporter-logs-otlp-http': 0.208.0(@opentelemetry/api@1.9.0)
-      '@opentelemetry/resources': 2.5.1(@opentelemetry/api@1.9.0)
+      '@opentelemetry/resources': 2.6.0(@opentelemetry/api@1.9.0)
      '@opentelemetry/sdk-logs': 0.208.0(@opentelemetry/api@1.9.0)
      '@posthog/core': 1.23.1
      '@posthog/types': 1.352.1
@ -16323,7 +16288,7 @@ snapshots:

  property-information@7.1.0: {}

-  protobufjs@7.5.4:
+  protobufjs@7.5.5:
    dependencies:
      '@protobufjs/aspromise': 1.1.2
      '@protobufjs/base64': 1.1.2
@ -16560,7 +16525,7 @@ snapshots:

  react-syntax-highlighter@15.6.6(react@19.2.4):
    dependencies:
-      '@babel/runtime': 7.28.6
+      '@babel/runtime': 7.29.2
      highlight.js: 10.7.3
      highlightjs-vue: 1.0.0
      lowlight: 1.20.0
@ -16645,7 +16610,7 @@ snapshots:

  redux@4.2.1:
    dependencies:
-      '@babel/runtime': 7.28.6
+      '@babel/runtime': 7.29.2

  reflect.getprototypeof@1.0.10:
    dependencies:
--- a/surfsense_web/types/window.d.ts
+++ b/surfsense_web/types/window.d.ts
@ -102,9 +102,29 @@ interface ElectronAPI {
 	setShortcuts: (
 		config: Partial<{ generalAssist: string; quickAsk: string; autocomplete: string }>
 	) => Promise<{ generalAssist: string; quickAsk: string; autocomplete: string }>;
+	// Launch on system startup
+	getAutoLaunch: () => Promise<{
+		enabled: boolean;
+		openAsHidden: boolean;
+		supported: boolean;
+	}>;
+	setAutoLaunch: (
+		enabled: boolean,
+		openAsHidden?: boolean
+	) => Promise<{ enabled: boolean; openAsHidden: boolean; supported: boolean }>;
 	// Active search space
 	getActiveSearchSpace: () => Promise<string | null>;
 	setActiveSearchSpace: (id: string) => Promise<void>;
+	// Analytics bridge (PostHog mirror into the Electron main process)
+	analyticsIdentify: (userId: string, properties?: Record<string, unknown>) => Promise<void>;
+	analyticsReset: () => Promise<void>;
+	analyticsCapture: (event: string, properties?: Record<string, unknown>) => Promise<void>;
+	getAnalyticsContext: () => Promise<{
+		distinctId: string;
+		machineId: string;
+		appVersion: string;
+		platform: string;
+	}>;
 }

 declare global {
 @ -1 +1 @@
 .0.16
 .0.19