Phase 2: Docker and OIDC auth

backend/Dockerfile

@@ -0,0 +1,17 @@
+FROM python:3.11-slim
+
+ENV PYTHONDONTWRITEBYTECODE=1 \
+    PYTHONUNBUFFERED=1
+
+WORKDIR /app/backend
+
+COPY backend/pyproject.toml ./pyproject.toml
+COPY backend/src ./src
+COPY backend/tests ./tests
+
+RUN pip install --no-cache-dir --upgrade pip \
+    && pip install --no-cache-dir .
+
+EXPOSE 8000
+
+CMD ["uvicorn", "media_library_viewer_api.main:app", "--host", "0.0.0.0", "--port", "8000"]

backend/README.md

@@ -1,6 +1,6 @@
 # Backend - Media Library Viewer API
 
-FastAPI backend serving the REST API for Jellyfin media browsing, SSH file inspection, and server monitoring.
+FastAPI backend serving the REST API for Jellyfin media browsing, SSH file inspection, server monitoring, and JWT-protected access.
 
 ## Project structure
 
@@ -21,10 +21,12 @@ backend/
 │       │   ├── dashboard.py
 │       │   ├── monitoring.py
 │       │   ├── media.py
+│       │   ├── users.py
 │       │   ├── files.py
 │       │   └── jobs.py
 │       ├── clients/
 │       │   ├── jellyfin.py
+│       │   ├── jellyseerr.py
 │       │   ├── resources.py
 │       │   └── ssh.py
 │       ├── domain/
@@ -52,6 +54,20 @@ JELLYFIN_URL=https://jellyfin.example.com
 JELLYFIN_API_KEY=your-api-key
 JELLYFIN_USER_ID=
 
+# Optional Jellyseerr enrichment for the Users tab
+JELLYSEERR_URL=https://requests.example.com
+JELLYSEERR_API_KEY=your-jellyseerr-api-key
+
+# Optional backend logging level
+LOG_LEVEL=INFO
+
+# Authentik / OIDC
+AUTH_ENABLED=true
+OIDC_ISSUER_URL=https://authentik.example/application/o/media-library-viewer/
+OIDC_AUDIENCE=media-library-viewer
+OIDC_JWKS_URL=
+OIDC_CLOCK_SKEW_SECONDS=30
+
 SSH_HOST=media-server.example.com
 SSH_USERNAME=username
 SSH_PORT=22
@@ -77,6 +93,10 @@ PYTHONPATH=src uvicorn media_library_viewer_api.main:app --reload --port 8000
 
 API docs available at: http://localhost:8000/docs
 
+## Docker
+
+The repository root includes a production `docker-compose.yml` and a development `docker-compose.dev.yml`.
+
 ## API Endpoints
 
 - `GET /api/dashboard/counts` — Movie/series/episode totals
@@ -96,3 +116,4 @@ API docs available at: http://localhost:8000/docs
 - `GET /api/files/resolve-path?path=` — Path resolution
 - `GET /api/jobs/templates` — Available jobs
 - `POST /api/jobs/run` — Execute a job
+- `GET /api/users` — Jellyfin users with optional Jellyseerr enrichment

backend/pyproject.toml

@@ -11,6 +11,8 @@ dependencies = [
   "requests>=2.28",
   "python-dotenv>=1.0",
   "pandas>=2.0",
+  "PyJWT[crypto]>=2.8",
+  "python-multipart>=0.0.9",
 ]
 
 [project.optional-dependencies]

backend/src/media_library_viewer_api/auth.py

@@ -0,0 +1,117 @@
+"""OIDC/JWT authentication helpers for backend API requests."""
+
+from __future__ import annotations
+
+import logging
+from functools import lru_cache
+from typing import Any
+from urllib.parse import urljoin
+
+import jwt
+import requests
+from fastapi import Request
+from fastapi.responses import JSONResponse
+from jwt import PyJWKClient
+from jwt.exceptions import InvalidTokenError
+
+from media_library_viewer_api.config import Settings, get_settings
+
+logger = logging.getLogger(__name__)
+
+EXEMPT_PATHS = {
+    "/api/health",
+    "/docs",
+    "/openapi.json",
+    "/redoc",
+}
+
+
+def _normalize_issuer_url(issuer_url: str) -> str:
+    return issuer_url.rstrip("/") + "/" if issuer_url else ""
+
+
+@lru_cache
+def get_oidc_metadata(issuer_url: str) -> dict[str, Any]:
+    normalized = _normalize_issuer_url(issuer_url)
+    discovery_url = urljoin(normalized, ".well-known/openid-configuration")
+    response = requests.get(discovery_url, timeout=10)
+    response.raise_for_status()
+    metadata = response.json()
+    if not isinstance(metadata, dict):
+        raise RuntimeError("OIDC discovery response was not a JSON object")
+    return metadata
+
+
+@lru_cache
+def get_jwk_client(jwks_url: str) -> PyJWKClient:
+    return PyJWKClient(jwks_url)
+
+
+def _split_audience(audience: str) -> list[str]:
+    return [item.strip() for item in audience.split(",") if item.strip()]
+
+
+def validate_auth_settings(settings: Settings) -> None:
+    if not settings.auth_enabled:
+        return
+    if not settings.oidc_issuer_url:
+        raise RuntimeError("AUTH_ENABLED is true but OIDC_ISSUER_URL is not configured")
+    if not settings.oidc_audience:
+        raise RuntimeError("AUTH_ENABLED is true but OIDC_AUDIENCE is not configured")
+
+
+def validate_bearer_jwt(authorization: str | None, settings: Settings | None = None) -> dict[str, Any]:
+    settings = settings or get_settings()
+    validate_auth_settings(settings)
+    if not settings.auth_enabled:
+        return {}
+
+    if not authorization:
+        raise PermissionError("Missing Authorization header")
+
+    scheme, _, token = authorization.partition(" ")
+    if scheme.lower() != "bearer" or not token.strip():
+        raise PermissionError("Authorization header must use Bearer token format")
+
+    issuer_url = _normalize_issuer_url(settings.oidc_issuer_url)
+    metadata = get_oidc_metadata(issuer_url)
+    jwks_url = settings.oidc_jwks_url.strip() or str(metadata.get("jwks_uri") or "")
+    if not jwks_url:
+        raise RuntimeError("OIDC discovery metadata does not include a JWKS URL")
+
+    jwk_client = get_jwk_client(jwks_url)
+    signing_key = jwk_client.get_signing_key_from_jwt(token).key
+    audience = _split_audience(settings.oidc_audience)
+    claims = jwt.decode(
+        token,
+        signing_key,
+        algorithms=list(metadata.get("id_token_signing_alg_values_supported") or ["RS256"]),
+        audience=audience[0] if len(audience) == 1 else audience,
+        issuer=issuer_url,
+        leeway=int(settings.oidc_clock_skew_seconds or 0),
+        options={"require": ["exp", "iss"]},
+    )
+    return claims
+
+
+async def require_jwt_auth(request: Request, call_next):
+    settings = get_settings()
+    path = request.url.path
+    if request.method == "OPTIONS" or path in EXEMPT_PATHS or not path.startswith("/api"):
+        return await call_next(request)
+
+    try:
+        claims = validate_bearer_jwt(request.headers.get("authorization"), settings)
+    except PermissionError as exc:
+        logger.warning("JWT auth rejected path=%s reason=%s", path, exc)
+        return JSONResponse(status_code=401, content={"detail": str(exc)})
+    except InvalidTokenError as exc:
+        logger.warning("JWT auth token invalid path=%s error=%s", path, exc)
+        return JSONResponse(status_code=401, content={"detail": "Invalid bearer token"})
+    except Exception as exc:  # pragma: no cover - safety net for OIDC/JWKS failures
+        logger.exception("JWT auth validation failed path=%s", path)
+        return JSONResponse(status_code=500, content={"detail": str(exc)})
+
+    request.state.jwt_claims = claims
+    request.state.jwt_subject = claims.get("sub") if isinstance(claims, dict) else None
+    return await call_next(request)

backend/src/media_library_viewer_api/clients/jellyfin.py

@@ -7,10 +7,13 @@ future FastAPI/React frontend can reuse the same client.
 
 from __future__ import annotations
 
-from typing import Any
+import logging
+from typing import Any, cast
 
 import requests
 
+logger = logging.getLogger(__name__)
+
 
 # Jellyfin validates Fields against its ItemFields enum. Keep this list to
 # documented/commonly supported optional fields; invalid names cause 400s.
@@ -54,9 +57,10 @@ class JellyfinClient:
             }
         )
 
-    def get(self, path: str, **params: Any) -> dict[str, Any]:
+    def get(self, path: str, **params: Any) -> Any:
         """GET a Jellyfin endpoint and include useful response text on errors."""
         clean_params = {k: v for k, v in params.items() if v is not None and v != ""}
+        logger.debug("Jellyfin GET %s params=%s", path, sorted(clean_params.keys()))
         response = self.session.get(
             f"{self.base_url}{path}", params=clean_params, timeout=self.timeout
         )
@@ -64,10 +68,12 @@ class JellyfinClient:
             response.raise_for_status()
         except requests.HTTPError as exc:
             detail = response.text[:500]
+            logger.warning("Jellyfin GET %s failed status=%s url=%s", path, response.status_code, response.url)
             raise requests.HTTPError(
                 f"{response.status_code} for {response.url}: {detail}",
                 response=response,
             ) from exc
+        logger.debug("Jellyfin GET %s ok status=%s", path, response.status_code)
         return response.json()
 
     def users(self) -> list[dict[str, Any]]:
@@ -77,11 +83,15 @@ class JellyfinClient:
         /Users/Me often fails with API-key auth. The user id selected here is
         then used for user-scoped library endpoints.
         """
-        return self.get("/Users")
+        users = self.get("/Users")
+        logger.info("Jellyfin returned %s visible users", len(users))
+        return users
 
     def libraries(self, user_id: str) -> list[dict[str, Any]]:
         """Return top-level library views visible to the selected Jellyfin user."""
-        return self.get(f"/Users/{user_id}/Views").get("Items", [])
+        items = self.get(f"/Users/{user_id}/Views").get("Items", [])
+        logger.info("Jellyfin returned %s libraries for user_id=%s", len(items), user_id)
+        return items
 
     def items(
         self,
@@ -101,6 +111,17 @@ class JellyfinClient:
         builder. Keep arguments close to Jellyfin's own query parameters so the
         service layer can request server-side pagination and basic sorting.
         """
+        logger.debug(
+            "Jellyfin items user_id=%s parent_id=%s start=%s limit=%s types=%s search=%s sort=%s/%s",
+            user_id,
+            parent_id or "<root>",
+            start_index,
+            limit,
+            include_item_types or "<all>",
+            search or "<none>",
+            sort_by,
+            sort_order,
+        )
         return self.get(
             f"/Users/{user_id}/Items",
             ParentId=parent_id,
@@ -123,7 +144,15 @@ class JellyfinClient:
             IncludeItemTypes=include_item_types,
             Limit=0,
         )
-        return int(response.get("TotalRecordCount", 0))
+        count = int(response.get("TotalRecordCount", 0))
+        logger.debug(
+            "Jellyfin item count user_id=%s parent_id=%s types=%s count=%s",
+            user_id,
+            parent_id or "<root>",
+            include_item_types,
+            count,
+        )
+        return count
 
     def media_counts(self, user_id: str) -> dict[str, int]:
         """Return dashboard-level counts for the main media types."""
@@ -156,11 +185,20 @@ class JellyfinClient:
             })
         return results
 
+    def sessions(self, active_within_seconds: int | None = None) -> list[dict[str, Any]]:
+        """Return Jellyfin sessions (playing and idle/logged-in).
+
+        When ``active_within_seconds`` is None, no recency filter is sent and
+        Jellyfin decides which sessions to include.
+        """
+        payload: Any = self.get("/Sessions", ActiveWithinSeconds=active_within_seconds)
+        return cast(list[dict[str, Any]], payload) if isinstance(payload, list) else []
+
     def active_sessions(self, active_within_seconds: int = 300) -> list[dict[str, Any]]:
-        """Return currently active sessions that have a now-playing item."""
-        payload = self.get("/Sessions", ActiveWithinSeconds=active_within_seconds)
-        sessions = payload if isinstance(payload, list) else []
-        return [session for session in sessions if session.get("NowPlayingItem")]
+        """Return sessions that currently have a now-playing item."""
+        sessions = [session for session in self.sessions(active_within_seconds) if session.get("NowPlayingItem")]
+        logger.info("Jellyfin active sessions within %ss: %s", active_within_seconds, len(sessions))
+        return sessions
 
     def image_url(self, item_id: str, image_type: str = "Primary") -> str:
         """Build an authenticated image URL suitable for st.image/browser use."""

backend/src/media_library_viewer_api/clients/jellyseerr.py

@@ -0,0 +1,137 @@
+"""Jellyseerr HTTP API client.
+
+Jellyseerr is optional. When configured, it can enrich the Jellyfin user list
+with email addresses, avatars, permissions, and request metadata.
+"""
+
+from __future__ import annotations
+
+import logging
+from typing import Any
+
+import requests
+
+logger = logging.getLogger(__name__)
+
+
+class JellyseerrClient:
+    """Small wrapper around the Jellyseerr REST API."""
+
+    def __init__(self, base_url: str, api_key: str, timeout: int = 30):
+        if not base_url:
+            raise ValueError("Jellyseerr URL is required")
+        if not api_key:
+            raise ValueError("Jellyseerr API key is required")
+
+        self.base_url = base_url.rstrip("/")
+        if self.base_url.endswith("/api/v1"):
+            self.base_url = self.base_url[:-7]
+        self.api_key = api_key
+        self.timeout = timeout
+        self.session = requests.Session()
+        self.session.headers.update(
+            {
+                "X-Api-Key": api_key,
+                "Accept": "application/json",
+            }
+        )
+
+    def get(self, path: str, **params: Any) -> Any:
+        """GET a Jellyseerr endpoint and include useful response text on errors."""
+        clean_params = {k: v for k, v in params.items() if v is not None and v != ""}
+        logger.debug("Jellyseerr GET %s params=%s", path, sorted(clean_params.keys()))
+        response = self.session.get(
+            f"{self.base_url}/api/v1{path}", params=clean_params, timeout=self.timeout
+        )
+        try:
+            response.raise_for_status()
+        except requests.HTTPError as exc:
+            detail = response.text[:500]
+            logger.warning(
+                "Jellyseerr GET %s failed status=%s url=%s", path, response.status_code, response.url
+            )
+            raise requests.HTTPError(
+                f"{response.status_code} for {response.url}: {detail}",
+                response=response,
+            ) from exc
+        logger.debug("Jellyseerr GET %s ok status=%s", path, response.status_code)
+        return response.json()
+
+    def absolute_url(self, path: str | None) -> str:
+        """Return an absolute URL for Jellyseerr-relative assets."""
+        if not path:
+            return ""
+        if path.startswith("http://") or path.startswith("https://"):
+            return path
+        if not path.startswith("/"):
+            path = f"/{path}"
+        return f"{self.base_url}{path}"
+
+    def jellyfin_users(self) -> list[dict[str, Any]]:
+        """Return Jellyfin-linked users known to Jellyseerr.
+
+        Jellyseerr has used both a top-level list payload and a wrapped
+        `{ "users": [...] }` payload in different versions/docs, so accept
+        either shape.
+        """
+        payload = self.get("/settings/jellyfin/users")
+        if isinstance(payload, list):
+            users = [item for item in payload if isinstance(item, dict)]
+            logger.info("Jellyseerr returned %s Jellyfin-linked users", len(users))
+            return users
+        if isinstance(payload, dict):
+            users = payload.get("users")
+            if isinstance(users, list):
+                mapped = [item for item in users if isinstance(item, dict)]
+                logger.info("Jellyseerr returned %s Jellyfin-linked users (wrapped payload)", len(mapped))
+                return mapped
+        logger.info("Jellyseerr returned no Jellyfin-linked users")
+        return []
+
+    def users(self, page_size: int = 1000) -> list[dict[str, Any]]:
+        """Return Jellyseerr users via the paginated /user list endpoint.
+
+        Jellyseerr's list endpoint uses ``take`` and ``skip`` query params,
+        not ``page``.
+        """
+        results: list[dict[str, Any]] = []
+        take = max(1, int(page_size))
+        skip = 0
+        total_results: int | None = None
+
+        while True:
+            payload = self.get("/user", take=take, skip=skip)
+            if not isinstance(payload, dict):
+                return results
+
+            page_results = payload.get("results") or []
+            page_items = [item for item in page_results if isinstance(item, dict)] if isinstance(page_results, list) else []
+            results.extend(page_items)
+
+            page_info = payload.get("pageInfo") or {}
+            if isinstance(page_info, dict):
+                try:
+                    page_total = int(page_info.get("results") or 0)
+                    if page_total:
+                        total_results = page_total
+                except (TypeError, ValueError):
+                    pass
+
+            logger.debug(
+                "Jellyseerr user page skip=%s take=%s -> %s results (total=%s)",
+                skip,
+                take,
+                len(page_items),
+                total_results if total_results is not None else "unknown",
+            )
+
+            if not page_items:
+                break
+            skip += len(page_items)
+            if len(page_items) < take:
+                break
+            if total_results is not None and skip >= total_results:
+                break
+
+        logger.info("Jellyseerr returned %s users", len(results))
+        return results

backend/src/media_library_viewer_api/clients/resources.py

@@ -9,12 +9,15 @@ Lines. This module starts/stops the collector and reads those JSONL samples.
 from __future__ import annotations
 
 import json
+import logging
 import shlex
 from dataclasses import dataclass
 from typing import Any
 
 from media_library_viewer_api.clients.ssh import RemoteSSHClient
 
+logger = logging.getLogger(__name__)
+
 # POSIX shell script copied to the remote server by start_resource_collector().
 # Keep this script bash-free because many NAS/media servers have minimal shells.
 COLLECTOR_SCRIPT = r'''#!/bin/sh
@@ -199,9 +202,14 @@ else
   echo "started pid=$(cat {shlex.quote(paths.pid_file)})"
 fi
 """
+    logger.info(
+        "Starting remote resource collector interval=%ss retention=%ss max_lines=%s", interval_seconds, retention_seconds, max_lines
+    )
     result = ssh.run(command, timeout=20)
     if result.exit_status != 0:
+        logger.warning("Failed to start remote resource collector: %s", result.stderr or result.stdout)
         raise RuntimeError(result.stderr or result.stdout or "failed to start resource collector")
+    logger.info("Remote resource collector start response: %s", result.stdout.strip())
     return result.stdout.strip()
 
 
@@ -221,9 +229,12 @@ else
   echo "not running"
 fi
 """
+    logger.info("Stopping remote resource collector")
     result = ssh.run(command, timeout=20)
     if result.exit_status != 0:
+        logger.warning("Failed to stop remote resource collector: %s", result.stderr or result.stdout)
         raise RuntimeError(result.stderr or result.stdout or "failed to stop resource collector")
+    logger.info("Remote resource collector stop response: %s", result.stdout.strip())
     return result.stdout.strip()
 
 
@@ -234,6 +245,7 @@ def restart_resource_collector(
     max_lines: int = 70_000,
     paths: ResourceMonitorPaths = ResourceMonitorPaths(),
 ) -> str:
+    logger.info("Restarting remote resource collector")
     stop_message = stop_resource_collector(ssh, paths)
     start_message = start_resource_collector(ssh, interval_seconds, retention_seconds, max_lines, paths)
     return f"{stop_message}\n{start_message}"
@@ -250,8 +262,11 @@ fi
 """
     result = ssh.run(command, timeout=10)
     if result.exit_status != 0:
+        logger.warning("Failed to read collector status: %s", result.stderr or result.stdout)
         raise RuntimeError(result.stderr or result.stdout or "failed to check collector status")
-    return result.stdout.strip()
+    status = result.stdout.strip()
+    logger.info("Resource collector status: %s", status)
+    return status
 
 
 def resource_collector_debug_info(ssh: RemoteSSHClient, paths: ResourceMonitorPaths = ResourceMonitorPaths()) -> str:
@@ -281,15 +296,20 @@ if [ -f {shlex.quote(paths.log_file)} ]; then tail -n 40 {shlex.quote(paths.log_
 echo "netdev_snapshot:"
 cat /proc/net/dev 2>&1 || true
 """
+    logger.info("Collecting resource collector diagnostics")
     result = ssh.run(command, timeout=20)
-    return (result.stdout or "") + (result.stderr or "")
+    output = (result.stdout or "") + (result.stderr or "")
+    logger.debug("Resource collector diagnostics length=%s", len(output))
+    return output
 
 
 def read_resource_metrics(ssh: RemoteSSHClient, max_lines: int = 1000, paths: ResourceMonitorPaths = ResourceMonitorPaths()) -> list[dict[str, Any]]:
     """Read recent JSONL metric samples from the remote collector file."""
     command = f"test -f {shlex.quote(paths.metrics_file)} && tail -n {int(max_lines)} {shlex.quote(paths.metrics_file)} || true"
+    logger.debug("Reading up to %s resource metric lines", max_lines)
     result = ssh.run(command, timeout=20)
     if result.exit_status != 0:
+        logger.warning("Failed to read resource metrics: %s", result.stderr or result.stdout)
         raise RuntimeError(result.stderr or result.stdout or "failed to read resource metrics")
     rows = []
     for line in result.stdout.splitlines():
@@ -310,7 +330,11 @@ def disk_space(ssh: RemoteSSHClient, path: str = "/") -> dict[str, Any]:
         + shlex.quote(path or "/")
         + " | awk 'NR==2 {printf \"{\\\"filesystem\\\":\\\"%s\\\",\\\"size\\\":%s,\\\"used\\\":%s,\\\"available\\\":%s,\\\"used_pct\\\":\\\"%s\\\",\\\"mount\\\":\\\"%s\\\"}\", $1,$2,$3,$4,$5,$6}'"
     )
+    logger.debug("Reading disk space for path=%s", path)
     result = ssh.run(command, timeout=20)
     if result.exit_status != 0 or not result.stdout.strip():
+        logger.warning("Failed to read disk space for %s: %s", path, result.stderr or result.stdout)
         raise RuntimeError(result.stderr or result.stdout or "failed to read disk space")
-    return json.loads(result.stdout)
+    data = json.loads(result.stdout)
+    logger.info("Disk space path=%s mount=%s used_pct=%s", path, data.get("mount"), data.get("used_pct"))
+    return data

backend/src/media_library_viewer_api/clients/ssh.py

@@ -10,6 +10,7 @@ commands are shell-quoted by callers. This is important for two reasons:
 from __future__ import annotations
 
 import json
+import logging
 import posixpath
 import shlex
 from dataclasses import dataclass
@@ -17,6 +18,8 @@ from typing import Any
 
 import paramiko
 
+logger = logging.getLogger(__name__)
+
 
 @dataclass
 class CommandResult:
@@ -88,14 +91,25 @@ class RemoteSSHClient:
         """
         client = self.connect()
         shell_command = f"/bin/sh -c {shlex.quote(command)}"
+        logger.debug("SSH run host=%s timeout=%s command=%s", self.host, timeout or self.timeout, command)
         stdin, stdout, stderr = client.exec_command(shell_command, timeout=timeout or self.timeout)
         exit_status = stdout.channel.recv_exit_status()
-        return CommandResult(
+        result = CommandResult(
             command=command,
             exit_status=exit_status,
             stdout=stdout.read().decode(errors="replace"),
             stderr=stderr.read().decode(errors="replace"),
         )
+        if result.exit_status == 0:
+            logger.debug("SSH command ok host=%s exit_status=%s", self.host, result.exit_status)
+        else:
+            logger.warning(
+                "SSH command failed host=%s exit_status=%s stderr=%s",
+                self.host,
+                result.exit_status,
+                result.stderr.strip() or result.stdout.strip(),
+            )
+        return result
 
     def list_dir(self, path: str) -> CommandResult:
         """List one remote directory as JSON.
@@ -123,12 +137,16 @@ class RemoteSSHClient:
                 "print(json.dumps(rows))"
             )
         )
-        return self.run(command)
+        result = self.run(command)
+        logger.info("SSH list_dir path=%s exit_status=%s", path, result.exit_status)
+        return result
 
     def stat_path(self, path: str) -> CommandResult:
         """Run stat for a remote file or directory path."""
         quoted = shlex.quote(path)
-        return self.run(f"stat --printf='%F\\n%s bytes\\n%y\\n%n\\n' {quoted}")
+        result = self.run(f"stat --printf='%F\\n%s bytes\\n%y\\n%n\\n' {quoted}")
+        logger.info("SSH stat path=%s exit_status=%s", path, result.exit_status)
+        return result
 
     def ffprobe_json(self, path: str) -> dict[str, Any]:
         """Run ffprobe and parse JSON output for a remote media file."""
@@ -137,6 +155,7 @@ class RemoteSSHClient:
             "ffprobe -v error -show_format -show_streams -print_format json " + quoted,
             timeout=60,
         )
+        logger.info("SSH ffprobe path=%s exit_status=%s", path, result.exit_status)
         if result.exit_status != 0:
             raise RuntimeError(result.stderr or result.stdout or "ffprobe failed")
         return json.loads(result.stdout)

backend/src/media_library_viewer_api/config.py

@@ -7,11 +7,16 @@ JELLYFIN_URL etc. are picked up directly without nested-model complications.
 
 from __future__ import annotations
 
+import logging
 from functools import lru_cache
 from pathlib import Path
 
 from pydantic_settings import BaseSettings
 
+from media_library_viewer_api.logging_utils import describe_settings
+
+logger = logging.getLogger(__name__)
+
 
 class Settings(BaseSettings):
     """Flat application settings read from env vars / .env file."""
@@ -21,6 +26,31 @@ class Settings(BaseSettings):
     jellyfin_api_key: str = ""
     jellyfin_user_id: str = ""
 
+    # Jellyseerr (optional)
+    jellyseerr_url: str = ""
+    jellyseerr_api_key: str = ""
+
+    # Logging
+    log_level: str = "INFO"
+
+    # Auth / OIDC (Authentik-compatible JWT validation)
+    auth_enabled: bool = False
+    oidc_issuer_url: str = ""
+    oidc_audience: str = ""
+    oidc_jwks_url: str = ""
+    oidc_clock_skew_seconds: int = 30
+
+    # SMTP (optional, used for Users -> message popup)
+    smtp_host: str = ""
+    smtp_port: int = 587
+    smtp_username: str = ""
+    smtp_password: str = ""
+    smtp_from_address: str = ""
+    smtp_from_name: str = "Media Library Viewer"
+    smtp_use_tls: bool = True
+    smtp_use_ssl: bool = False
+    smtp_timeout: int = 30
+
     # SSH
     ssh_host: str = ""
     ssh_username: str = ""
@@ -61,6 +91,10 @@ def _find_env_file() -> str | None:
 def get_settings() -> Settings:
     """Return a cached Settings instance."""
     env_file = _find_env_file()
-    if env_file:
-        return Settings(_env_file=env_file)
-    return Settings()
+    settings = Settings(_env_file=env_file) if env_file else Settings()
+    logger.info(
+        "Loaded backend settings from %s: %s",
+        env_file or "environment/defaults",
+        describe_settings(settings),
+    )
+    return settings

backend/src/media_library_viewer_api/dependencies.py

@@ -6,24 +6,53 @@ dependency system. Uses lru_cache so connections are reused across requests.
 
 from __future__ import annotations
 
+import logging
 from functools import lru_cache
 
 from media_library_viewer_api.clients.jellyfin import JellyfinClient
+from media_library_viewer_api.clients.jellyseerr import JellyseerrClient
 from media_library_viewer_api.clients.ssh import RemoteSSHClient
 from media_library_viewer_api.config import get_settings
+from media_library_viewer_api.services.mail_queue import MailQueue, get_mail_queue as _get_mail_queue
+
+logger = logging.getLogger(__name__)
 
 
 @lru_cache
 def get_jellyfin_client() -> JellyfinClient:
     """Return a cached Jellyfin client."""
     settings = get_settings()
+    logger.info("Creating Jellyfin client for %s", settings.jellyfin_url.rstrip("/") or "<unset>")
     return JellyfinClient(settings.jellyfin_url, settings.jellyfin_api_key)
 
 
+@lru_cache
+def get_jellyseerr_client() -> JellyseerrClient | None:
+    """Return a cached Jellyseerr client when configured, otherwise None."""
+    settings = get_settings()
+    if not settings.jellyseerr_url or not settings.jellyseerr_api_key:
+        logger.info(
+            "Jellyseerr client not configured (url=%s, api_key=%s)",
+            "set" if settings.jellyseerr_url else "missing",
+            "set" if settings.jellyseerr_api_key else "missing",
+        )
+        return None
+    logger.info("Creating Jellyseerr client for %s", settings.jellyseerr_url.rstrip("/") or "<unset>")
+    return JellyseerrClient(settings.jellyseerr_url, settings.jellyseerr_api_key)
+
+
 @lru_cache
 def get_ssh_client() -> RemoteSSHClient:
     """Return a cached SSH client (connects on first use)."""
     settings = get_settings()
+    logger.info(
+        "Creating SSH client host=%s user=%s port=%s key=%s password=%s",
+        settings.ssh_host or "<unset>",
+        settings.ssh_username or "<unset>",
+        settings.ssh_port,
+        settings.ssh_key_filename or "<unset>",
+        "set" if settings.ssh_password else "missing",
+    )
     client = RemoteSSHClient(
         host=settings.ssh_host,
         username=settings.ssh_username,
@@ -31,10 +60,19 @@ def get_ssh_client() -> RemoteSSHClient:
         key_filename=settings.ssh_key_filename or None,
         password=settings.ssh_password or None,
     )
-    client.connect()
+    try:
+        client.connect()
+    except Exception:
+        logger.exception("Failed to establish SSH connection to %s", settings.ssh_host or "<unset>")
+        raise
     return client
 
 
+def get_mail_queue() -> MailQueue:
+    """Return the singleton background email queue."""
+    return _get_mail_queue()
+
+
 def get_user_id() -> str:
     """Return the configured Jellyfin user ID, or discover the first available user."""
     settings = get_settings()

backend/src/media_library_viewer_api/jobs.py

@@ -7,12 +7,15 @@ confirmations/dry-runs.
 
 from __future__ import annotations
 
+import logging
 import shlex
 from dataclasses import dataclass
 from typing import Mapping
 
 from media_library_viewer_api.clients.ssh import CommandResult, RemoteSSHClient
 
+logger = logging.getLogger(__name__)
+
 
 @dataclass(frozen=True)
 class JobTemplate:
@@ -56,4 +59,5 @@ def run_job(ssh: RemoteSSHClient, job_key: str, path: str, timeout: int = 600) -
     """Render and execute a configured job template for a selected remote path."""
     template = JOB_TEMPLATES[job_key]
     command = template.render({"path": path})
+    logger.info("Executing job template key=%s path=%s timeout=%s", job_key, path, timeout)
     return ssh.run(command, timeout=timeout)

backend/src/media_library_viewer_api/logging_utils.py

@@ -0,0 +1,66 @@
+"""Logging helpers for the backend."""
+
+from __future__ import annotations
+
+import logging
+import os
+from urllib.parse import urlsplit
+
+
+def configure_logging(level_name: str | None = None) -> int:
+    """Configure root logging once and return the numeric log level."""
+    resolved_name = (level_name or os.getenv("LOG_LEVEL", "INFO")).upper()
+    level = getattr(logging, resolved_name, logging.INFO)
+    root = logging.getLogger()
+    if not root.handlers:
+        logging.basicConfig(
+            level=level,
+            format="%(asctime)s %(levelname)s %(name)s: %(message)s",
+        )
+    root.setLevel(level)
+    logging.getLogger("media_library_viewer_api").setLevel(level)
+    logging.getLogger("uvicorn").setLevel(level)
+    logging.getLogger("uvicorn.error").setLevel(level)
+    logging.getLogger("uvicorn.access").setLevel(level)
+    logging.getLogger("paramiko").setLevel(logging.WARNING)
+    logging.getLogger("urllib3").setLevel(logging.WARNING)
+    return level
+
+
+def _sanitize_url(url: str | None) -> str:
+    if not url:
+        return "<unset>"
+    parsed = urlsplit(url.strip())
+    if not parsed.scheme or not parsed.netloc:
+        return url.rstrip("/")
+    return f"{parsed.scheme}://{parsed.netloc}"
+
+
+def describe_settings(settings: object) -> dict[str, str]:
+    """Return a secret-safe summary of the current backend settings."""
+    return {
+        "log_level": str(getattr(settings, "log_level", "INFO") or "INFO").upper(),
+        "auth_enabled": str(bool(getattr(settings, "auth_enabled", True))),
+        "oidc_issuer_url": _sanitize_url(getattr(settings, "oidc_issuer_url", "")),
+        "oidc_audience": getattr(settings, "oidc_audience", "") or "<unset>",
+        "oidc_jwks_url": _sanitize_url(getattr(settings, "oidc_jwks_url", "")),
+        "jellyfin_url": _sanitize_url(getattr(settings, "jellyfin_url", "")),
+        "jellyfin_api_key": "set" if getattr(settings, "jellyfin_api_key", "") else "missing",
+        "jellyfin_user_id": getattr(settings, "jellyfin_user_id", "") or "<auto>",
+        "jellyseerr_url": _sanitize_url(getattr(settings, "jellyseerr_url", "")),
+        "jellyseerr_api_key": "set" if getattr(settings, "jellyseerr_api_key", "") else "missing",
+        "ssh_host": getattr(settings, "ssh_host", "") or "<unset>",
+        "ssh_username": getattr(settings, "ssh_username", "") or "<unset>",
+        "ssh_port": str(getattr(settings, "ssh_port", 22) or 22),
+        "ssh_key_filename": "set" if getattr(settings, "ssh_key_filename", "") else "missing",
+        "ssh_password": "set" if getattr(settings, "ssh_password", "") else "missing",
+        "smtp_host": _sanitize_url(getattr(settings, "smtp_host", "")),
+        "smtp_port": str(getattr(settings, "smtp_port", 587) or 587),
+        "smtp_username": "set" if getattr(settings, "smtp_username", "") else "missing",
+        "smtp_from_address": getattr(settings, "smtp_from_address", "") or "<unset>",
+        "smtp_from_name": getattr(settings, "smtp_from_name", "") or "<unset>",
+        "smtp_use_tls": str(bool(getattr(settings, "smtp_use_tls", True))),
+        "smtp_use_ssl": str(bool(getattr(settings, "smtp_use_ssl", False))),
+        "remote_media_root": getattr(settings, "remote_media_root", "") or "<unset>",
+        "remote_path_prefix": getattr(settings, "remote_path_prefix", "") or "<unset>",
+    }

backend/src/media_library_viewer_api/main.py

@@ -2,25 +2,41 @@
 
 from __future__ import annotations
 
+import logging
+import time
 from contextlib import asynccontextmanager
 
 import uvicorn
-from fastapi import FastAPI
+from fastapi import FastAPI, Request
 from fastapi.middleware.cors import CORSMiddleware
 
-from media_library_viewer_api.routers import dashboard, monitoring, media, files, jobs
+from media_library_viewer_api.auth import require_jwt_auth, validate_auth_settings
+from media_library_viewer_api.config import get_settings
+from media_library_viewer_api.logging_utils import configure_logging, describe_settings
+from media_library_viewer_api.routers import dashboard, monitoring, media, files, jobs, users
+from media_library_viewer_api.dependencies import get_mail_queue
+
+logger = logging.getLogger(__name__)
 
 
 @asynccontextmanager
 async def lifespan(app: FastAPI):
     """Application lifespan — startup/shutdown."""
+    settings = get_settings()
+    configure_logging(settings.log_level)
+    validate_auth_settings(settings)
+    logger.info("Backend startup complete: %s", describe_settings(settings))
+    mail_queue = get_mail_queue()
+    mail_queue.start()
     yield
+    mail_queue.stop()
+    logger.info("Backend shutdown complete")
 
 
 app = FastAPI(
     title="Media Library Viewer API",
     version="0.1.0",
-    description="Backend API for Jellyfin media browsing, SSH file inspection, and server monitoring.",
+    description="Backend API for Jellyfin media browsing, SSH file inspection, server monitoring, and JWT-protected access.",
     lifespan=lifespan,
 )
 
@@ -38,17 +54,45 @@ app.add_middleware(
     allow_headers=["*"],
 )
 
+@app.middleware("http")
+async def enforce_jwt_auth(request: Request, call_next):
+    return await require_jwt_auth(request, call_next)
+
+@app.middleware("http")
+async def log_requests(request: Request, call_next):
+    """Log every API request with timing and outcome."""
+    start = time.perf_counter()
+    client_host = request.client.host if request.client else "unknown"
+    logger.info("request start %s %s client=%s", request.method, request.url.path, client_host)
+    try:
+        response = await call_next(request)
+    except Exception:
+        logger.exception("request error %s %s client=%s", request.method, request.url.path, client_host)
+        raise
+    elapsed_ms = (time.perf_counter() - start) * 1000.0
+    logger.info(
+        "request end %s %s status=%s elapsed_ms=%.1f",
+        request.method,
+        request.url.path,
+        response.status_code,
+        elapsed_ms,
+    )
+    return response
+
+
 # Register routers
 app.include_router(dashboard.router)
 app.include_router(monitoring.router)
 app.include_router(media.router)
 app.include_router(files.router)
 app.include_router(jobs.router)
+app.include_router(users.router)
 
 
 @app.get("/api/health")
 def health_check() -> dict[str, str]:
     """Simple health check endpoint."""
+    logger.debug("health check requested")
     return {"status": "ok"}
 
 

backend/src/media_library_viewer_api/path_utils.py

@@ -2,8 +2,11 @@
 
 from __future__ import annotations
 
+import logging
 import posixpath
 
+logger = logging.getLogger(__name__)
+
 
 def apply_remote_path_prefix(path: str, prefix: str) -> str:
     """Apply an optional fallback prefix for Jellyfin->SSH path handoff."""
@@ -14,10 +17,16 @@ def apply_remote_path_prefix(path: str, prefix: str) -> str:
         return path
     normalized_prefix = normalized_prefix.rstrip("/")
     if path == normalized_prefix or path.startswith(normalized_prefix + "/"):
-        return posixpath.normpath(path)
+        resolved = posixpath.normpath(path)
+        logger.debug("Path prefix already applied path=%s prefix=%s resolved=%s", path, normalized_prefix, resolved)
+        return resolved
     if path.startswith("/"):
-        return posixpath.normpath(normalized_prefix + path)
-    return posixpath.normpath(posixpath.join(normalized_prefix, path))
+        resolved = posixpath.normpath(normalized_prefix + path)
+        logger.debug("Applied path prefix path=%s prefix=%s resolved=%s", path, normalized_prefix, resolved)
+        return resolved
+    resolved = posixpath.normpath(posixpath.join(normalized_prefix, path))
+    logger.debug("Joined path prefix path=%s prefix=%s resolved=%s", path, normalized_prefix, resolved)
+    return resolved
 
 
 def map_path_to_media_root(path: str, media_root: str) -> str:
@@ -39,6 +48,7 @@ def map_path_to_media_root(path: str, media_root: str) -> str:
 
     path_absolute = "/" + "/".join(raw_parts)
     if path_absolute == normalized_root or path_absolute.startswith(normalized_root + "/"):
+        logger.debug("Path already under media root path=%s media_root=%s", path, normalized_root)
         return path_absolute
 
     root_anchor = posixpath.basename(normalized_root)
@@ -48,7 +58,9 @@ def map_path_to_media_root(path: str, media_root: str) -> str:
     if root_anchor in raw_parts:
         anchor_index = raw_parts.index(root_anchor)
         remainder_parts = raw_parts[anchor_index + 1:]
-        return posixpath.join(normalized_root, *remainder_parts) if remainder_parts else normalized_root
+        resolved = posixpath.join(normalized_root, *remainder_parts) if remainder_parts else normalized_root
+        logger.debug("Mapped path to media root path=%s media_root=%s resolved=%s", path, normalized_root, resolved)
+        return resolved
 
     return path
 
@@ -64,5 +76,8 @@ def resolve_remote_media_path(path: str, media_root: str, fallback_prefix: str)
         return path
     mapped = map_path_to_media_root(path, media_root)
     if mapped and mapped != path:
+        logger.debug("Resolved media path via media root original=%s resolved=%s", path, mapped)
         return mapped
-    return apply_remote_path_prefix(mapped or path, fallback_prefix)
+    resolved = apply_remote_path_prefix(mapped or path, fallback_prefix)
+    logger.debug("Resolved media path via fallback original=%s resolved=%s", path, resolved)
+    return resolved

backend/src/media_library_viewer_api/routers/dashboard.py

@@ -1,7 +1,8 @@
-"""Dashboard router — media counts, per-library breakdown, now-playing."""
+"""Dashboard router — media counts, per-library breakdown, activity."""
 
 from __future__ import annotations
 
+import logging
 from typing import Any
 
 from fastapi import APIRouter, Depends
@@ -9,6 +10,8 @@ from fastapi import APIRouter, Depends
 from media_library_viewer_api.dependencies import get_jellyfin_client, get_user_id
 from media_library_viewer_api.clients.jellyfin import JellyfinClient
 
+logger = logging.getLogger(__name__)
+
 router = APIRouter(prefix="/api/dashboard", tags=["dashboard"])
 
 
@@ -18,7 +21,9 @@ def get_counts(
     user_id: str = Depends(get_user_id),
 ) -> dict[str, int]:
     """Return total movie/series/episode counts."""
-    return client.media_counts(user_id)
+    counts = client.media_counts(user_id)
+    logger.info("Dashboard counts user_id=%s counts=%s", user_id, counts)
+    return counts
 
 
 @router.get("/libraries")
@@ -28,26 +33,31 @@ def get_library_counts(
 ) -> list[dict[str, Any]]:
     """Return per-library item counts broken down by type."""
     libraries = client.libraries(user_id)
+    logger.info("Dashboard libraries user_id=%s count=%s", user_id, len(libraries))
     return client.library_item_counts(user_id, libraries)
 
 
-@router.get("/now-playing")
-def get_now_playing(
-    client: JellyfinClient = Depends(get_jellyfin_client),
-) -> list[dict[str, Any]]:
-    """Return currently active playback sessions with transcode info."""
-    sessions = client.active_sessions()
-    results = []
+def _map_sessions_to_activity_rows(sessions: list[dict[str, Any]]) -> list[dict[str, Any]]:
+    """Normalize Jellyfin sessions into dashboard activity rows."""
+    results: list[dict[str, Any]] = []
     for session in sessions:
         item = session.get("NowPlayingItem") or {}
         play_state = session.get("PlayState") or {}
         transcoding = session.get("TranscodingInfo") or {}
 
+        has_item = bool(item)
         series = item.get("SeriesName") or ""
-        title = f"{series} - {item.get('Name', '')}" if series else item.get("Name", "Unknown")
+        title = (
+            f"{series} - {item.get('Name', '')}" if series else item.get("Name", "Unknown")
+        ) if has_item else "(idle)"
+
+        if not has_item:
+            state_label = "idle"
+        else:
+            state_label = "paused" if play_state.get("IsPaused") else "playing"
 
         is_transcoding = bool(transcoding)
-        transcode_type = []
+        transcode_type: list[str] = []
         if is_transcoding:
             if transcoding.get("IsVideoDirect") is False:
                 transcode_type.append("video")
@@ -59,11 +69,32 @@ def get_now_playing(
         results.append({
             "user": session.get("UserName") or "Unknown",
             "title": title,
-            "type": item.get("Type", ""),
-            "state": "paused" if play_state.get("IsPaused") else "playing",
+            "type": item.get("Type", "") if has_item else "",
+            "state": state_label,
             "transcoding": "yes" if is_transcoding else "no",
             "transcoding_type": ", ".join(transcode_type),
             "device": session.get("DeviceName") or session.get("Client") or "",
             "session_id": session.get("Id") or "",
         })
     return results
+
+
+@router.get("/activity")
+def get_activity(
+    client: JellyfinClient = Depends(get_jellyfin_client),
+) -> list[dict[str, Any]]:
+    """Return activity rows for active sessions (playing and idle/logged-in)."""
+    sessions = client.sessions()
+    rows = _map_sessions_to_activity_rows(sessions)
+    state_rank = {"playing": 0, "paused": 1, "idle": 2}
+    rows.sort(key=lambda r: (state_rank.get(str(r.get("state")), 9), str(r.get("user", "")).lower()))
+    logger.info("Dashboard activity sessions=%s rows=%s", len(sessions), len(rows))
+    return rows
+
+
+@router.get("/now-playing")
+def get_now_playing(
+    client: JellyfinClient = Depends(get_jellyfin_client),
+) -> list[dict[str, Any]]:
+    """Backward-compatible alias; returns full activity rows."""
+    return get_activity(client)

backend/src/media_library_viewer_api/routers/files.py

@@ -3,15 +3,18 @@
 from __future__ import annotations
 
 import json
+import logging
 from typing import Any
 
-from fastapi import APIRouter, Depends, Query, HTTPException
+from fastapi import APIRouter, Depends, HTTPException, Query
 
-from media_library_viewer_api.dependencies import get_ssh_client
 from media_library_viewer_api.clients.ssh import RemoteSSHClient
 from media_library_viewer_api.config import get_settings
+from media_library_viewer_api.dependencies import get_ssh_client
 from media_library_viewer_api.path_utils import resolve_remote_media_path
 
+logger = logging.getLogger(__name__)
+
 router = APIRouter(prefix="/api/files", tags=["files"])
 
 
@@ -23,8 +26,10 @@ def list_directory(
     """List a remote directory."""
     result = ssh.list_dir(path)
     if result.exit_status != 0:
+        logger.warning("Files list failed path=%s exit_status=%s", path, result.exit_status)
         raise HTTPException(status_code=400, detail=result.stderr or result.stdout or "Failed to list directory")
     entries = json.loads(result.stdout)
+    logger.info("Files list path=%s entries=%s", path, len(entries))
     return {
         "path": path,
         "entries": entries,
@@ -41,7 +46,9 @@ def get_ffprobe(
     try:
         data = ssh.ffprobe_json(path)
     except RuntimeError as exc:
+        logger.warning("Files ffprobe failed path=%s error=%s", path, exc)
         raise HTTPException(status_code=400, detail=str(exc))
+    logger.info("Files ffprobe path=%s", path)
     return data
 
 
@@ -53,7 +60,9 @@ def get_stat(
     """Run stat on a remote path."""
     result = ssh.stat_path(path)
     if result.exit_status != 0:
+        logger.warning("Files stat failed path=%s exit_status=%s", path, result.exit_status)
         raise HTTPException(status_code=400, detail=result.stderr or result.stdout or "stat failed")
+    logger.info("Files stat path=%s", path)
     return {"path": path, "output": result.stdout}
 
 
@@ -64,4 +73,5 @@ def resolve_path(
     """Resolve a Jellyfin path to its SSH-visible equivalent."""
     settings = get_settings()
     resolved = resolve_remote_media_path(path, settings.media_root, settings.path_prefix)
+    logger.info("Files resolve path original=%s resolved=%s", path, resolved)
     return {"original": path, "resolved": resolved}

backend/src/media_library_viewer_api/routers/jobs.py

@@ -2,15 +2,18 @@
 
 from __future__ import annotations
 
+import logging
 from typing import Any
 
 from fastapi import APIRouter, Depends, HTTPException
 from pydantic import BaseModel
 
-from media_library_viewer_api.dependencies import get_ssh_client
 from media_library_viewer_api.clients.ssh import RemoteSSHClient
+from media_library_viewer_api.dependencies import get_ssh_client
 from media_library_viewer_api.jobs import JOB_TEMPLATES, run_job
 
+logger = logging.getLogger(__name__)
+
 router = APIRouter(prefix="/api/jobs", tags=["jobs"])
 
 
@@ -22,7 +25,7 @@ class RunJobRequest(BaseModel):
 @router.get("/templates")
 def get_templates() -> list[dict[str, str]]:
     """Return available job templates."""
-    return [
+    templates = [
         {
             "key": key,
             "name": template.name,
@@ -30,6 +33,8 @@ def get_templates() -> list[dict[str, str]]:
         }
         for key, template in JOB_TEMPLATES.items()
     ]
+    logger.info("Jobs templates requested count=%s", len(templates))
+    return templates
 
 
 @router.post("/run")
@@ -39,9 +44,12 @@ def post_run_job(
 ) -> dict[str, Any]:
     """Run a job template on a remote path."""
     if request.job_key not in JOB_TEMPLATES:
+        logger.warning("Unknown job requested key=%s path=%s", request.job_key, request.path)
         raise HTTPException(status_code=400, detail=f"Unknown job key: {request.job_key}")
 
+    logger.info("Running job key=%s path=%s", request.job_key, request.path)
     result = run_job(ssh, request.job_key, request.path)
+    logger.info("Job finished key=%s exit_status=%s path=%s", request.job_key, result.exit_status, request.path)
     return {
         "job_key": request.job_key,
         "path": request.path,

backend/src/media_library_viewer_api/routers/media.py

@@ -1,45 +1,262 @@
-"""Media router — index status, build, and query."""
+"""Media router — index status, build, stop, and query."""
 
 from __future__ import annotations
 
+import logging
+import os
+import signal
+import subprocess
+import sys
+import threading
+import time
+from pathlib import Path
 from typing import Any
 
-from fastapi import APIRouter, Depends, Query
+from fastapi import APIRouter, Depends, HTTPException, Query, status
 
-from media_library_viewer_api.dependencies import get_jellyfin_client, get_user_id
 from media_library_viewer_api.clients.jellyfin import JellyfinClient
-from media_library_viewer_api.services.media_index import MediaIndex, build_media_index
+from media_library_viewer_api.dependencies import get_jellyfin_client, get_user_id
+from media_library_viewer_api.services.media_index import MediaIndex
+
+logger = logging.getLogger(__name__)
 
 router = APIRouter(prefix="/api/media", tags=["media"])
+_build_lock = threading.Lock()
 
 
 def get_media_index() -> MediaIndex:
     return MediaIndex()
 
 
-@router.get("/status")
-def get_index_status(index: MediaIndex = Depends(get_media_index)) -> dict[str, Any]:
-    """Return media index status (exists, count, last updated, build duration)."""
+def _set_build_metadata(index: MediaIndex, state: dict[str, Any]) -> None:
+    for key, value in state.items():
+        index.set_metadata(key, "" if value is None else value)
+
+
+def _staging_db_path(index: MediaIndex) -> Path:
+    return index.db_path.with_name(f"{index.db_path.stem}.building{index.db_path.suffix}")
+
+
+def _pid_is_alive(pid: int | None) -> bool:
+    if not pid:
+        return False
+    try:
+        os.kill(pid, 0)
+        return True
+    except ProcessLookupError:
+        return False
+    except PermissionError:
+        return True
+
+
+def _clean_stale_build_state(index: MediaIndex) -> Any:
     status = index.status()
+    if status.build_running and not _pid_is_alive(status.build_pid):
+        logger.warning("Detected stale media build state pid=%s", status.build_pid)
+        _set_build_metadata(
+            index,
+            {
+                "build_running": False,
+                "build_stage": "stale",
+                "build_message": "Previous media index build stopped unexpectedly",
+                "build_cancel_requested": False,
+                "build_pid": "",
+                "build_error": "Worker process is no longer running",
+            },
+        )
+        status = index.status()
+    return status
+
+
+def _serialize_status(status: Any) -> dict[str, Any]:
     return {
         "exists": status.exists,
         "item_count": status.item_count,
         "updated_at": status.updated_at,
         "updated_at_label": status.updated_at_label,
         "build_duration_seconds": status.build_duration_seconds,
+        "build_running": status.build_running,
+        "build_stage": status.build_stage,
+        "build_message": status.build_message,
+        "build_progress": status.build_progress,
+        "build_items_processed": status.build_items_processed,
+        "build_items_total": status.build_items_total,
+        "build_current_library": status.build_current_library,
+        "build_library_index": status.build_library_index,
+        "build_libraries_total": status.build_libraries_total,
+        "build_library_progress": status.build_library_progress,
+        "build_library_items_processed": status.build_library_items_processed,
+        "build_library_items_total": status.build_library_items_total,
+        "build_elapsed_seconds": status.build_elapsed_seconds,
+        "build_eta_seconds": status.build_eta_seconds,
+        "build_library_elapsed_seconds": status.build_library_elapsed_seconds,
+        "build_library_eta_seconds": status.build_library_eta_seconds,
+        "build_cancel_requested": status.build_cancel_requested,
+        "build_pid": status.build_pid,
+        "build_error": status.build_error,
     }
 
 
-@router.post("/build")
+def _worker_command(final_db_path: Path, staging_db_path: Path) -> list[str]:
+    return [
+        sys.executable,
+        "-m",
+        "media_library_viewer_api.workers.media_index_worker",
+        "--index-path",
+        str(final_db_path),
+        "--staging-path",
+        str(staging_db_path),
+    ]
+
+
+def _start_worker(index: MediaIndex) -> subprocess.Popen[bytes]:
+    staging_path = _staging_db_path(index)
+    staging_path.unlink(missing_ok=True)
+    return subprocess.Popen(
+        _worker_command(index.db_path, staging_path),
+        start_new_session=True,
+        env=os.environ.copy(),
+    )
+
+
+@router.get("/status")
+def get_index_status(index: MediaIndex = Depends(get_media_index)) -> dict[str, Any]:
+    """Return media index status (exists, count, build progress, and errors)."""
+    with _build_lock:
+        media_status = _clean_stale_build_state(index)
+    logger.info("Media status requested running=%s stage=%s", media_status.build_running, media_status.build_stage)
+    return _serialize_status(media_status)
+
+
+@router.post("/build", status_code=status.HTTP_202_ACCEPTED)
 def post_build_index(
     client: JellyfinClient = Depends(get_jellyfin_client),
     user_id: str = Depends(get_user_id),
     index: MediaIndex = Depends(get_media_index),
 ) -> dict[str, Any]:
-    """Rebuild the media index from Jellyfin."""
-    libraries = client.libraries(user_id)
-    count = build_media_index(client, user_id, libraries, index)
-    return {"indexed_items": count}
+    """Start a media index build in a subprocess worker."""
+    with _build_lock:
+        current_status = _clean_stale_build_state(index)
+        if current_status.build_running and _pid_is_alive(current_status.build_pid):
+            logger.warning("Media build already running pid=%s", current_status.build_pid)
+            raise HTTPException(status_code=status.HTTP_409_CONFLICT, detail="Media index build already in progress")
+
+        libraries = client.libraries(user_id)
+        logger.info("Starting media index build user_id=%s libraries=%s", user_id, len(libraries))
+        process = _start_worker(index)
+        _set_build_metadata(
+            index,
+            {
+                "build_running": True,
+                "build_stage": "queued",
+                "build_message": "Media index build queued",
+                "build_progress": None,
+                "build_items_processed": 0,
+                "build_items_total": 0,
+                "build_current_library": "",
+                "build_library_index": 0,
+                "build_libraries_total": len(libraries),
+                "build_library_progress": None,
+                "build_library_items_processed": 0,
+                "build_library_items_total": 0,
+                "build_elapsed_seconds": None,
+                "build_eta_seconds": None,
+                "build_library_elapsed_seconds": None,
+                "build_library_eta_seconds": None,
+                "build_cancel_requested": False,
+                "build_pid": process.pid,
+                "build_error": "",
+            },
+        )
+        media_status = index.status()
+    logger.info("Media index build started pid=%s", process.pid)
+    return {"status": "started", **_serialize_status(media_status)}
+
+
+@router.post("/stop", status_code=status.HTTP_202_ACCEPTED)
+def stop_build(index: MediaIndex = Depends(get_media_index)) -> dict[str, Any]:
+    """Request cooperative cancellation of a running media index build."""
+    with _build_lock:
+        media_status = _clean_stale_build_state(index)
+        if not media_status.build_running:
+            logger.warning("Stop requested but no media build is running")
+            raise HTTPException(status_code=status.HTTP_409_CONFLICT, detail="No media index build is running")
+
+        logger.info("Cooperative stop requested for media build pid=%s", media_status.build_pid)
+        _set_build_metadata(
+            index,
+            {
+                "build_running": True,
+                "build_stage": "canceling",
+                "build_message": "Stopping media index build...",
+                "build_cancel_requested": True,
+                "build_error": "",
+            },
+        )
+        media_status = index.status()
+    logger.info("Media stop requested acknowledged")
+    return {"status": "stop_requested", **_serialize_status(media_status)}
+
+
+@router.post("/force-stop", status_code=status.HTTP_202_ACCEPTED)
+def force_stop_build(index: MediaIndex = Depends(get_media_index)) -> dict[str, Any]:
+    """Terminate the media index worker process if it is stuck."""
+    with _build_lock:
+        media_status = _clean_stale_build_state(index)
+        if not media_status.build_running:
+            logger.warning("Force stop requested but no media build is running")
+            raise HTTPException(status_code=status.HTTP_409_CONFLICT, detail="No media index build is running")
+
+        pid = media_status.build_pid
+        if not pid or not _pid_is_alive(pid):
+            logger.warning("Force stop requested but build worker is not alive pid=%s", pid)
+            _set_build_metadata(
+                index,
+                {
+                    "build_running": False,
+                    "build_stage": "stale",
+                    "build_message": "Media index worker is not running",
+                    "build_cancel_requested": False,
+                    "build_pid": "",
+                    "build_error": "Worker process is not running",
+                },
+            )
+            media_status = index.status()
+            return {"status": "already_stopped", **_serialize_status(media_status)}
+
+        logger.info("Force stopping media build pid=%s", pid)
+        try:
+            os.killpg(pid, signal.SIGTERM)
+        except ProcessLookupError:
+            pass
+        except PermissionError as exc:
+            raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=str(exc)) from exc
+
+        deadline = time.time() + 3.0
+        while time.time() < deadline and _pid_is_alive(pid):
+            time.sleep(0.1)
+
+        if _pid_is_alive(pid):
+            try:
+                os.killpg(pid, signal.SIGKILL)
+            except ProcessLookupError:
+                pass
+            except PermissionError as exc:
+                raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=str(exc)) from exc
+
+        _set_build_metadata(
+            index,
+            {
+                "build_running": False,
+                "build_stage": "force-stopped",
+                "build_message": "Media index build force stopped",
+                "build_cancel_requested": False,
+                "build_pid": "",
+                "build_error": "",
+            },
+        )
+        media_status = index.status()
+    return {"status": "force_stopped", **_serialize_status(media_status)}
 
 
 @router.get("/query")
@@ -57,13 +274,25 @@ def query_media(
     index: MediaIndex = Depends(get_media_index),
 ) -> dict[str, Any]:
     """Query the media index with filters, sorting, and pagination."""
-    # If no library IDs provided, use all libraries
+    # If no library IDs provided, use all libraries.
     library_ids = [lid.strip() for lid in libraries.split(",") if lid.strip()] if libraries else None
     if not library_ids:
         all_libs = client.libraries(user_id)
         library_ids = [lib["Id"] for lib in all_libs]
 
     media_types = [t.strip() for t in types.split(",") if t.strip()]
+    logger.info(
+        "Media query user_id=%s libraries=%s types=%s search=%s hdr=%s sort=%s/%s limit=%s offset=%s",
+        user_id,
+        len(library_ids or []),
+        ",".join(media_types),
+        search or "<none>",
+        hdr_filter,
+        sort_key,
+        sort_order,
+        limit,
+        offset,
+    )
 
     rows, total = index.query(
         library_ids=library_ids,
@@ -76,6 +305,7 @@ def query_media(
         offset=offset,
     )
 
+    logger.info("Media query returned total=%s rows=%s", total, len(rows))
     return {
         "items": rows,
         "total": total,

backend/src/media_library_viewer_api/routers/monitoring.py

@@ -2,13 +2,16 @@
 
 from __future__ import annotations
 
+import logging
 import time
 from typing import Any
 
 from fastapi import APIRouter, Depends
 
-from media_library_viewer_api.dependencies import get_ssh_client
 from media_library_viewer_api.clients.ssh import RemoteSSHClient
+from media_library_viewer_api.dependencies import get_ssh_client
+
+logger = logging.getLogger(__name__)
 from media_library_viewer_api.clients.resources import (
     disk_space,
     read_resource_metrics,
@@ -26,19 +29,26 @@ router = APIRouter(prefix="/api/monitoring", tags=["monitoring"])
 @router.get("/status")
 def get_status(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
     """Return collector running status."""
-    return {"status": resource_collector_status(ssh)}
+    status = resource_collector_status(ssh)
+    logger.info("Monitoring status requested: %s", status)
+    return {"status": status}
 
 
 @router.get("/metrics")
 def get_metrics(
-    max_lines: int = 1000,
-    last_seconds: int = 3600,
+    max_lines: int = 70_000,
+    last_seconds: int | None = None,
     ssh: RemoteSSHClient = Depends(get_ssh_client),
 ) -> dict[str, Any]:
     """Return resource metric samples from the remote collector."""
     rows = read_resource_metrics(ssh, max_lines=max_lines)
-    cutoff_ts = time.time() - last_seconds
-    filtered = [row for row in rows if float(row.get("ts", 0)) >= cutoff_ts]
+    if last_seconds is None:
+        filtered = rows
+        cutoff_ts = 0.0
+    else:
+        cutoff_ts = time.time() - last_seconds
+        filtered = [row for row in rows if float(row.get("ts", 0)) >= cutoff_ts]
+    logger.info("Monitoring metrics requested total=%s filtered=%s last_seconds=%s", len(rows), len(filtered), last_seconds)
     return {
         "samples": filtered,
         "total_samples": len(rows),
@@ -52,6 +62,7 @@ def get_disk_space(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str,
     """Return disk space for the configured media root."""
     settings = get_settings()
     path = settings.media_root or "/"
+    logger.info("Monitoring disk requested path=%s", path)
     return disk_space(ssh, path)
 
 
@@ -59,6 +70,7 @@ def get_disk_space(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str,
 def post_start(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
     """Start the remote resource collector."""
     message = start_resource_collector(ssh)
+    logger.info("Monitoring collector start result: %s", message)
     return {"message": message}
 
 
@@ -66,6 +78,7 @@ def post_start(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]
 def post_stop(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
     """Stop the remote resource collector."""
     message = stop_resource_collector(ssh)
+    logger.info("Monitoring collector stop result: %s", message)
     return {"message": message}
 
 
@@ -73,10 +86,13 @@ def post_stop(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
 def post_restart(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
     """Restart the remote resource collector."""
     message = restart_resource_collector(ssh)
+    logger.info("Monitoring collector restart result: %s", message)
     return {"message": message}
 
 
 @router.get("/diagnostics")
 def get_diagnostics(ssh: RemoteSSHClient = Depends(get_ssh_client)) -> dict[str, str]:
     """Return collector debug info for troubleshooting."""
-    return {"diagnostics": resource_collector_debug_info(ssh)}
+    diagnostics = resource_collector_debug_info(ssh)
+    logger.info("Monitoring diagnostics requested")
+    return {"diagnostics": diagnostics}

backend/src/media_library_viewer_api/routers/users.py

@@ -0,0 +1,394 @@
+"""Users router — Jellyfin list plus optional Jellyseerr enrichment."""
+
+from __future__ import annotations
+
+import json
+import logging
+from typing import Any
+
+from fastapi import APIRouter, Depends, File, Form, HTTPException, UploadFile, status
+
+from media_library_viewer_api.clients.jellyfin import JellyfinClient
+from media_library_viewer_api.clients.jellyseerr import JellyseerrClient
+from media_library_viewer_api.config import get_settings
+from media_library_viewer_api.dependencies import (
+    get_jellyfin_client,
+    get_jellyseerr_client,
+    get_mail_queue,
+)
+from media_library_viewer_api.services.mailer import EmailAttachment, test_smtp_connection, validate_smtp_settings
+
+logger = logging.getLogger(__name__)
+
+router = APIRouter(prefix="/api/users", tags=["users"])
+
+
+_PERMISSION_FLAGS = [
+    (2, "admin"),
+    (4, "manage_settings"),
+    (8, "manage_users"),
+    (16, "manage_requests"),
+    (32, "request"),
+    (64, "vote"),
+    (128, "auto_approve"),
+    (256, "auto_approve_movie"),
+    (512, "auto_approve_tv"),
+    (1024, "request_4k"),
+    (2048, "request_4k_movie"),
+    (4096, "request_4k_tv"),
+    (8192, "request_advanced"),
+    (16384, "request_view"),
+    (32768, "auto_approve_4k"),
+    (65536, "auto_approve_4k_movie"),
+    (131072, "auto_approve_4k_tv"),
+    (262144, "request_movie"),
+    (524288, "request_tv"),
+    (1048576, "manage_issues"),
+    (2097152, "view_issues"),
+]
+
+_USER_TYPES = {
+    1: "plex",
+    2: "local",
+    3: "jellyfin",
+    4: "emby",
+}
+
+
+def _safe_int(value: Any) -> int:
+    try:
+        return int(value)
+    except (TypeError, ValueError):
+        return 0
+
+
+def _permission_labels(permissions: int) -> list[str]:
+    labels = [label for bit, label in _PERMISSION_FLAGS if permissions & bit]
+    return labels or ["none"]
+
+
+def _role_label(permissions: int) -> str:
+    if permissions & 2:
+        return "admin"
+    if permissions & (4 | 8 | 16):
+        return "manager"
+    if permissions & (32 | 64 | 128):
+        return "requester"
+    return "user"
+
+
+def _account_type(user_type: Any) -> str:
+    return _USER_TYPES.get(_safe_int(user_type), "unknown")
+
+
+def _merge_users(
+    jellyfin_users: list[dict[str, Any]],
+    jellyseerr_jellyfin_users: list[dict[str, Any]] | None,
+    jellyseerr_users: list[dict[str, Any]] | None,
+    jellyseerr_client: JellyseerrClient | None,
+) -> dict[str, Any]:
+    def _normalize(value: Any) -> str:
+        return str(value or "").strip().lower()
+
+    def _looks_like_email(value: Any) -> bool:
+        text = str(value or "").strip()
+        return bool(text and "@" in text and " " not in text)
+
+    def _pick_source_and_value(candidates: list[tuple[str, Any]]) -> tuple[str, str]:
+        for source, value in candidates:
+            if _looks_like_email(value):
+                return source, str(value).strip()
+        return "", ""
+
+    def _first_value(candidates: list[tuple[str, Any]]) -> tuple[str, str]:
+        for source, value in candidates:
+            text = str(value or "").strip()
+            if text:
+                return source, text
+        return "", ""
+
+    def _source_summary(name_source: str, email_source: str, avatar_source: str, access_source: str) -> str:
+        return ", ".join(
+            [
+                f"name={name_source or 'none'}",
+                f"email={email_source or 'none'}",
+                f"avatar={avatar_source or 'none'}",
+                f"access={access_source or 'none'}",
+            ]
+        )
+
+    def _lookup_keys(item: dict[str, Any]) -> list[str]:
+        return [
+            _normalize(item.get("id")),
+            _normalize(item.get("Id")),
+            _normalize(item.get("userId")),
+            _normalize(item.get("user_id")),
+            _normalize(item.get("jellyfinUserId")),
+            _normalize(item.get("jellyfin_user_id")),
+            _normalize(item.get("jellyfinUsername")),
+            _normalize(item.get("jellyfin_username")),
+            _normalize(item.get("username")),
+            _normalize(item.get("displayName")),
+            _normalize(item.get("display_name")),
+        ]
+
+    linked_by_jellyfin_id: dict[str, dict[str, Any]] = {}
+    for item in jellyseerr_jellyfin_users or []:
+        for key in (
+            item.get("id"),
+            item.get("Id"),
+            item.get("userId"),
+            item.get("user_id"),
+            item.get("jellyfinUserId"),
+            item.get("jellyfin_user_id"),
+        ):
+            normalized = _normalize(key)
+            if normalized:
+                linked_by_jellyfin_id[normalized] = item
+
+    seerr_by_key: dict[str, dict[str, Any]] = {}
+    for item in jellyseerr_users or []:
+        for key in _lookup_keys(item):
+            if key:
+                seerr_by_key[key] = item
+
+    items: list[dict[str, Any]] = []
+    enriched_count = 0
+    for user in jellyfin_users:
+        jellyfin_id = str(user.get("Id") or user.get("id") or "")
+        jellyfin_name = str(user.get("Name") or user.get("name") or "")
+        jf_link = linked_by_jellyfin_id.get(_normalize(jellyfin_id))
+
+        seerr_user = None
+        for candidate in [
+            jellyfin_name,
+            (jf_link or {}).get("jellyfinUsername"),
+            (jf_link or {}).get("jellyfin_username"),
+            (jf_link or {}).get("username"),
+            (jf_link or {}).get("displayName"),
+            (jf_link or {}).get("display_name"),
+        ]:
+            seerr_user = seerr_by_key.get(_normalize(candidate))
+            if seerr_user:
+                break
+
+        email_source, email = _pick_source_and_value(
+            [
+                ("jellyseerr:user", (seerr_user or {}).get("email")),
+                ("jellyseerr:jellyfin", (jf_link or {}).get("email")),
+            ]
+        )
+        avatar_source, avatar = _first_value(
+            [
+                ("jellyseerr:user", (seerr_user or {}).get("avatar")),
+                ("jellyseerr:jellyfin", (jf_link or {}).get("thumb")),
+                ("jellyseerr:jellyfin", (jf_link or {}).get("avatar")),
+            ]
+        )
+        if avatar and jellyseerr_client:
+            avatar = jellyseerr_client.absolute_url(avatar)
+
+        permissions = _safe_int((seerr_user or {}).get("permissions"))
+        user_type = _safe_int((seerr_user or {}).get("userType") or (seerr_user or {}).get("user_type"))
+        role = _role_label(permissions)
+        access_source = "jellyseerr:user" if seerr_user else ""
+        name_source = "jellyfin"
+        summary = _source_summary(name_source, email_source, avatar_source, access_source)
+
+        if seerr_user or jf_link:
+            enriched_count += 1
+
+        items.append(
+            {
+                "jellyfin_id": jellyfin_id,
+                "username": jellyfin_name,
+                "display_name": jellyfin_name,
+                "email": email,
+                "email_source": email_source,
+                "avatar": avatar,
+                "avatar_source": avatar_source,
+                "contactable": bool(email),
+                "source": summary,
+                "source_summary": summary,
+                "name_source": name_source,
+                "access_source": access_source,
+                "jellyseerr_user_id": _safe_int((seerr_user or {}).get("id") or (seerr_user or {}).get("userId")) or None,
+                "jellyseerr_username": str(
+                    (seerr_user or {}).get("username") or (seerr_user or {}).get("jellyfinUsername") or ""
+                ),
+                "user_type": user_type or None,
+                "user_type_label": _account_type(user_type),
+                "role": role,
+                "permissions": permissions,
+                "permissions_label": ", ".join(_permission_labels(permissions)),
+                "request_count": _safe_int((seerr_user or {}).get("requestCount")) or None,
+            }
+        )
+
+    logger.info(
+        "Users merged jellyfin=%s jellyseerr_jellyfin=%s jellyseerr_users=%s enriched=%s",
+        len(jellyfin_users),
+        len(jellyseerr_jellyfin_users or []),
+        len(jellyseerr_users or []),
+        enriched_count,
+    )
+    return {
+        "items": items,
+        "total": len(items),
+        "jellyseerr_configured": jellyseerr_client is not None,
+        "jellyseerr_available": bool(jellyseerr_users or jellyseerr_jellyfin_users),
+        "jellyseerr_jellyfin_user_count": len(jellyseerr_jellyfin_users or []),
+        "jellyseerr_user_count": len(jellyseerr_users or []),
+        "enriched_count": enriched_count,
+    }
+
+
+@router.get("")
+def get_users(
+    jellyfin: JellyfinClient = Depends(get_jellyfin_client),
+    jellyseerr: JellyseerrClient | None = Depends(get_jellyseerr_client),
+) -> dict[str, Any]:
+    """Return the known users, enriched with Jellyseerr data when available."""
+    jellyfin_users = jellyfin.users()
+    logger.info("Users endpoint fetched %s Jellyfin users", len(jellyfin_users))
+    jellyseerr_jellyfin_users: list[dict[str, Any]] | None = None
+    jellyseerr_users: list[dict[str, Any]] | None = None
+    jellyseerr_error = ""
+    if jellyseerr:
+        try:
+            jellyseerr_jellyfin_users = jellyseerr.jellyfin_users()
+        except Exception as exc:  # pragma: no cover - network fallback
+            logger.exception("Jellyseerr Jellyfin-linked user fetch failed")
+            jellyseerr_error = f"Jellyseerr Jellyfin users fetch failed: {exc}"
+        try:
+            jellyseerr_users = jellyseerr.users()
+        except Exception as exc:  # pragma: no cover - network fallback
+            logger.exception("Jellyseerr user list fetch failed")
+            jellyseerr_error = (
+                f"{jellyseerr_error}; " if jellyseerr_error else ""
+            ) + f"Jellyseerr user list fetch failed: {exc}"
+
+    result = _merge_users(jellyfin_users, jellyseerr_jellyfin_users, jellyseerr_users, jellyseerr)
+    result["jellyseerr_error"] = jellyseerr_error
+    logger.info(
+        "Users response total=%s configured=%s available=%s enriched=%s error=%s",
+        result["total"],
+        result["jellyseerr_configured"],
+        result["jellyseerr_available"],
+        result["enriched_count"],
+        bool(jellyseerr_error),
+    )
+    return result
+
+
+@router.get("/message/status")
+def get_user_message_status(mail_queue=Depends(get_mail_queue)) -> dict[str, Any]:
+    """Return the current background email queue status."""
+    return mail_queue.status()
+
+
+@router.post("/message/test-smtp")
+def test_user_message_smtp() -> dict[str, Any]:
+    """Test the configured SMTP connection without sending an email."""
+    settings = get_settings()
+    return test_smtp_connection(settings)
+
+
+@router.post("/message", status_code=status.HTTP_202_ACCEPTED)
+async def post_user_message(
+    recipient_ids: str = Form(...),
+    subject: str = Form(...),
+    html_body: str = Form(""),
+    text_body: str = Form(""),
+    attachments: list[UploadFile] | None = File(default=None),
+    jellyfin: JellyfinClient = Depends(get_jellyfin_client),
+    jellyseerr: JellyseerrClient | None = Depends(get_jellyseerr_client),
+    mail_queue=Depends(get_mail_queue),
+) -> dict[str, Any]:
+    """Queue a single email to the selected users without blocking the API."""
+    try:
+        requested_ids = json.loads(recipient_ids)
+    except json.JSONDecodeError as exc:
+        raise HTTPException(status_code=400, detail=f"recipient_ids must be valid JSON: {exc}") from exc
+
+    if not isinstance(requested_ids, list):
+        raise HTTPException(status_code=400, detail="recipient_ids must be a JSON list")
+
+    cleaned_ids = [str(item).strip() for item in requested_ids if str(item).strip()]
+    if not cleaned_ids:
+        raise HTTPException(status_code=400, detail="At least one recipient is required")
+
+    subject = subject.strip()
+    if not subject:
+        raise HTTPException(status_code=400, detail="Subject is required")
+
+    directory = get_users(jellyfin=jellyfin, jellyseerr=jellyseerr)
+    users_by_id = {str(item.get("jellyfin_id") or ""): item for item in directory.get("items", [])}
+
+    recipients: list[str] = []
+    recipient_labels: list[str] = []
+    skipped: list[dict[str, str]] = []
+    for user_id in cleaned_ids:
+        item = users_by_id.get(user_id)
+        if not item:
+            skipped.append({"jellyfin_id": user_id, "reason": "not found"})
+            continue
+        email = str(item.get("email") or "").strip()
+        if not email:
+            skipped.append({"jellyfin_id": user_id, "reason": "missing email"})
+            continue
+        recipients.append(email)
+        recipient_labels.append(f"{item.get('display_name') or item.get('username') or user_id} <{email}>")
+
+    if not recipients:
+        raise HTTPException(status_code=400, detail="No selected users have a deliverable email address")
+
+    settings = get_settings()
+    validate_smtp_settings(settings)
+
+    queue_status = mail_queue.status()
+    if not queue_status["worker_running"]:
+        raise HTTPException(status_code=503, detail="Email queue worker is not running")
+
+    attachment_payloads: list[EmailAttachment] = []
+    for upload in attachments or []:
+        data = await upload.read()
+        if not data:
+            continue
+        attachment_payloads.append(
+            EmailAttachment(
+                filename=upload.filename or "attachment",
+                content_type=upload.content_type or "application/octet-stream",
+                data=data,
+            )
+        )
+
+    request_id = mail_queue.enqueue(
+        settings=settings,
+        recipients=recipients,
+        subject=subject,
+        html_body=html_body,
+        text_body=text_body,
+        attachments=attachment_payloads,
+    )
+    from_address = str(getattr(settings, "smtp_from_address", "") or "").strip() or str(
+        getattr(settings, "smtp_username", "") or ""
+    ).strip()
+    logger.info(
+        "Users message queued request_id=%s subject=%s recipients=%s attachments=%s skipped=%s",
+        request_id,
+        subject,
+        len(recipients),
+        len(attachment_payloads),
+        len(skipped),
+    )
+    return {
+        "status": "queued",
+        "request_id": request_id,
+        "from_address": from_address,
+        "recipient_count": len(recipients),
+        "attachment_count": len(attachment_payloads),
+        "subject": subject,
+        "recipient_labels": recipient_labels,
+        "skipped": skipped,
+    }

backend/src/media_library_viewer_api/services/mail_queue.py

@@ -0,0 +1,232 @@
+"""In-process background queue for outbound user emails.
+
+The queue keeps SMTP delivery off the request path so message composition
+returns quickly and the rest of the API remains responsive while the worker
+thread performs the blocking SMTP call.
+"""
+
+from __future__ import annotations
+
+import logging
+import queue
+import threading
+import time
+import uuid
+from dataclasses import dataclass, field
+from typing import Any
+
+from media_library_viewer_api.services.mailer import EmailAttachment, describe_smtp_error, send_email_message
+
+logger = logging.getLogger(__name__)
+
+
+@dataclass(frozen=True)
+class QueuedEmailMessage:
+    """A queued outbound email request."""
+
+    request_id: str
+    settings: Any
+    recipients: list[str]
+    subject: str
+    html_body: str
+    text_body: str
+    attachments: list[EmailAttachment] = field(default_factory=list)
+    created_at: float = field(default_factory=time.time)
+
+
+class MailQueue:
+    """Single-worker in-process queue for SMTP delivery."""
+
+    def __init__(self) -> None:
+        self._queue: queue.Queue[QueuedEmailMessage | None] = queue.Queue()
+        self._thread: threading.Thread | None = None
+        self._stop_event = threading.Event()
+        self._lock = threading.Lock()
+        self._pending_count = 0
+        self._active_request_id: str | None = None
+        self._last_request_id: str | None = None
+        self._last_result: str | None = None
+        self._last_error = ""
+        self._last_error_at: float | None = None
+        self._last_success_at: float | None = None
+        self._last_activity_at: float | None = None
+        self._sent_count = 0
+        self._failed_count = 0
+
+    def start(self) -> None:
+        """Start the worker thread if it is not already running."""
+        with self._lock:
+            if self._thread and self._thread.is_alive():
+                return
+            self._stop_event.clear()
+            self._thread = threading.Thread(target=self._run, name="mail-queue-worker", daemon=True)
+            self._thread.start()
+            logger.info("Mail queue worker started")
+
+    def stop(self, timeout: float = 5.0) -> None:
+        """Stop the worker thread and wait briefly for shutdown."""
+        with self._lock:
+            thread = self._thread
+            if not thread:
+                return
+            self._stop_event.set()
+            self._queue.put(None)
+        thread.join(timeout=timeout)
+        if thread.is_alive():
+            logger.warning("Mail queue worker did not stop within %.1fs", timeout)
+        else:
+            logger.info("Mail queue worker stopped")
+        with self._lock:
+            if self._thread is thread:
+                self._thread = None
+
+    def enqueue(
+        self,
+        *,
+        settings: Any,
+        recipients: list[str],
+        subject: str,
+        html_body: str,
+        text_body: str = "",
+        attachments: list[EmailAttachment] | None = None,
+    ) -> str:
+        """Queue an outbound email and return a request identifier."""
+        request_id = uuid.uuid4().hex
+        message = QueuedEmailMessage(
+            request_id=request_id,
+            settings=settings,
+            recipients=list(recipients),
+            subject=subject,
+            html_body=html_body,
+            text_body=text_body,
+            attachments=list(attachments or []),
+        )
+        with self._lock:
+            self._pending_count += 1
+            self._last_request_id = request_id
+            self._last_result = "queued"
+            self._last_activity_at = time.time()
+        self._queue.put(message)
+        logger.info(
+            "Queued email request_id=%s recipients=%s attachments=%s subject=%s",
+            request_id,
+            len(message.recipients),
+            len(message.attachments),
+            subject,
+        )
+        return request_id
+
+    def status(self) -> dict[str, Any]:
+        """Return a snapshot of the queue state for health/status endpoints."""
+        with self._lock:
+            worker_running = bool(self._thread and self._thread.is_alive())
+            stop_requested = self._stop_event.is_set()
+            pending_count = self._pending_count
+            active_request_id = self._active_request_id
+            last_request_id = self._last_request_id
+            last_result = self._last_result
+            last_error = self._last_error
+            last_error_at = self._last_error_at
+            last_success_at = self._last_success_at
+            last_activity_at = self._last_activity_at
+            sent_count = self._sent_count
+            failed_count = self._failed_count
+
+        if not worker_running:
+            state = "stopped" if stop_requested else "error"
+        elif active_request_id or pending_count > 0:
+            state = "busy"
+        elif last_result == "failed" and last_error:
+            state = "error"
+        else:
+            state = "idle"
+
+        return {
+            "state": state,
+            "worker_running": worker_running,
+            "stop_requested": stop_requested,
+            "pending_count": pending_count,
+            "active_request_id": active_request_id,
+            "last_request_id": last_request_id,
+            "last_result": last_result,
+            "last_error": last_error,
+            "last_error_at": last_error_at,
+            "last_success_at": last_success_at,
+            "last_activity_at": last_activity_at,
+            "sent_count": sent_count,
+            "failed_count": failed_count,
+        }
+
+    def _run(self) -> None:
+        while not self._stop_event.is_set():
+            try:
+                message = self._queue.get(timeout=0.5)
+            except queue.Empty:
+                continue
+
+            try:
+                if message is None:
+                    continue
+
+                with self._lock:
+                    self._pending_count = max(0, self._pending_count - 1)
+                    self._active_request_id = message.request_id
+                    self._last_request_id = message.request_id
+                    self._last_result = "sending"
+                    self._last_activity_at = time.time()
+
+                logger.info(
+                    "Mail queue sending request_id=%s recipients=%s attachments=%s subject=%s",
+                    message.request_id,
+                    len(message.recipients),
+                    len(message.attachments),
+                    message.subject,
+                )
+                result: dict[str, Any] = send_email_message(
+                    message.settings,
+                    recipients=message.recipients,
+                    subject=message.subject,
+                    html_body=message.html_body,
+                    text_body=message.text_body,
+                    attachments=message.attachments,
+                )
+                with self._lock:
+                    self._active_request_id = None
+                    self._last_result = "sent"
+                    self._last_success_at = time.time()
+                    self._last_activity_at = self._last_success_at
+                    self._last_error = ""
+                    self._last_error_at = None
+                    self._sent_count += 1
+                logger.info(
+                    "Mail queue sent request_id=%s mode=%s auth_user=%s recipient_count=%s attachment_count=%s",
+                    message.request_id,
+                    (result.get("selected_mode") or {}).get("label", "<unknown>"),
+                    result.get("authenticated_as") or "<none>",
+                    result.get("recipient_count", 0),
+                    result.get("attachment_count", 0),
+                )
+            except Exception as exc:
+                friendly_error = describe_smtp_error(exc)
+                with self._lock:
+                    self._active_request_id = None
+                    self._last_result = "failed"
+                    self._last_error = friendly_error
+                    self._last_error_at = time.time()
+                    self._last_activity_at = self._last_error_at
+                    self._failed_count += 1
+                logger.exception(
+                    "Mail queue delivery failed request_id=%s error=%s",
+                    getattr(message, "request_id", "unknown"),
+                    friendly_error,
+                )
+            finally:
+                self._queue.task_done()
+
+
+_MAIL_QUEUE = MailQueue()
+
+
+def get_mail_queue() -> MailQueue:
+    """Return the singleton mail queue."""
+    return _MAIL_QUEUE

backend/src/media_library_viewer_api/services/mailer.py

@@ -0,0 +1,540 @@
+"""SMTP email sending helpers for user communication workflows."""
+
+from __future__ import annotations
+
+import logging
+import mimetypes
+import socket
+import smtplib
+import ssl
+from dataclasses import dataclass
+from email.message import EmailMessage
+from email.utils import formataddr
+from html.parser import HTMLParser
+from typing import Any, Iterable
+
+
+logger = logging.getLogger(__name__)
+
+
+@dataclass(frozen=True)
+class EmailAttachment:
+    """Attachment payload passed from the API layer."""
+
+    filename: str
+    content_type: str
+    data: bytes
+
+
+class _HTMLToTextParser(HTMLParser):
+    """Small HTML-to-text helper for plain-text fallback bodies."""
+
+    block_tags = {"p", "div", "section", "article", "header", "footer", "li", "tr", "td", "th", "br"}
+
+    def __init__(self) -> None:
+        super().__init__()
+        self.parts: list[str] = []
+
+    def handle_starttag(self, tag: str, attrs):  # type: ignore[override]
+        if tag.lower() in self.block_tags and self.parts and not self.parts[-1].endswith("\n"):
+            self.parts.append("\n")
+
+    def handle_endtag(self, tag: str) -> None:
+        if tag.lower() in self.block_tags and self.parts and not self.parts[-1].endswith("\n"):
+            self.parts.append("\n")
+
+    def handle_data(self, data: str) -> None:
+        if data:
+            self.parts.append(data)
+
+    def text(self) -> str:
+        return "".join(self.parts)
+
+
+def html_to_text(html: str) -> str:
+    """Convert a small HTML body to readable plain text."""
+    parser = _HTMLToTextParser()
+    parser.feed(html or "")
+    text = parser.text()
+    lines = [line.rstrip() for line in text.splitlines()]
+    return "\n".join(line for line in lines if line).strip()
+
+
+def _from_address(settings: object) -> str:
+    from_address = str(getattr(settings, "smtp_from_address", "") or "").strip()
+    if from_address:
+        return from_address
+    smtp_username = str(getattr(settings, "smtp_username", "") or "").strip()
+    if smtp_username:
+        return smtp_username
+    raise ValueError("SMTP from address is required (set SMTP_FROM_ADDRESS or SMTP_USERNAME)")
+
+
+def validate_smtp_settings(settings: object) -> None:
+    """Validate that the SMTP configuration is sufficient to send mail."""
+    smtp_host = str(getattr(settings, "smtp_host", "") or "").strip()
+    if not smtp_host:
+        raise ValueError("SMTP host is required")
+    _from_address(settings)
+
+
+def _smtp_settings(settings: object) -> dict[str, object]:
+    smtp_host = str(getattr(settings, "smtp_host", "") or "").strip()
+    if not smtp_host:
+        raise ValueError("SMTP host is required")
+    smtp_port = int(getattr(settings, "smtp_port", 587) or 587)
+    smtp_username = str(getattr(settings, "smtp_username", "") or "").strip()
+    smtp_password = str(getattr(settings, "smtp_password", "") or "")
+    use_tls = bool(getattr(settings, "smtp_use_tls", True))
+    use_ssl = bool(getattr(settings, "smtp_use_ssl", False))
+    smtp_timeout = int(getattr(settings, "smtp_timeout", 30) or 30)
+    return {
+        "smtp_host": smtp_host,
+        "smtp_port": smtp_port,
+        "smtp_username": smtp_username,
+        "smtp_password": smtp_password,
+        "use_tls": use_tls,
+        "use_ssl": use_ssl,
+        "smtp_timeout": smtp_timeout,
+    }
+
+
+def _smtp_mode_label(mode: dict[str, object]) -> str:
+    transport = "SSL" if mode["use_ssl"] else "STARTTLS" if mode["use_tls"] else "plain SMTP"
+    return f"{mode['smtp_host']}:{mode['smtp_port']} via {transport}"
+
+
+def _smtp_mode_candidates(settings: object) -> list[dict[str, Any]]:
+    base = _smtp_settings(settings)
+    candidates = [dict(base, mode_label="configured")]
+    smtp_host = str(base["smtp_host"]).lower()
+    if "fastmail.com" in smtp_host:
+        fastmail_ssl = {
+            **base,
+            "smtp_port": 465,
+            "use_tls": False,
+            "use_ssl": True,
+            "mode_label": "Fastmail SSL 465",
+        }
+        fastmail_tls = {
+            **base,
+            "smtp_port": 587,
+            "use_tls": True,
+            "use_ssl": False,
+            "mode_label": "Fastmail STARTTLS 587",
+        }
+        for mode in (fastmail_ssl, fastmail_tls):
+            if not any(
+                candidate["smtp_port"] == mode["smtp_port"]
+                and candidate["use_tls"] == mode["use_tls"]
+                and candidate["use_ssl"] == mode["use_ssl"]
+                for candidate in candidates
+            ):
+                candidates.append(mode)
+    return candidates
+
+
+def _probe_smtp_connection(mode: dict[str, Any]) -> None:
+    context = ssl.create_default_context()
+    smtp_host = str(mode["smtp_host"])
+    smtp_port = int(mode["smtp_port"])
+    smtp_username = str(mode["smtp_username"])
+    smtp_password = str(mode["smtp_password"])
+    use_tls = bool(mode["use_tls"])
+    use_ssl = bool(mode["use_ssl"])
+    smtp_timeout = int(mode["smtp_timeout"])
+
+    if use_ssl:
+        smtp_connection = smtplib.SMTP_SSL(smtp_host, smtp_port, timeout=smtp_timeout)
+    else:
+        smtp_connection = smtplib.SMTP(smtp_host, smtp_port, timeout=smtp_timeout)
+
+    with smtp_connection as smtp:
+        if use_tls and not use_ssl:
+            smtp.ehlo()
+            smtp.starttls(context=context)
+            smtp.ehlo()
+        else:
+            smtp.ehlo()
+        if smtp_username:
+            smtp.login(smtp_username, smtp_password)
+        smtp.noop()
+
+
+def _smtp_sender_not_authorized(error: Exception) -> bool:
+    code = getattr(error, "smtp_code", None)
+    raw_error = getattr(error, "smtp_error", b"")
+    if isinstance(raw_error, bytes):
+        raw_error_text = raw_error.decode(errors="ignore")
+    else:
+        raw_error_text = str(raw_error)
+    text = f"{code} {raw_error_text} {error}".lower()
+    return code in {551, 553} or "not authorised to send from this header address" in text or "not authorized to send from this header address" in text
+
+
+def _smtp_attempt_metadata(mode: dict[str, Any]) -> dict[str, Any]:
+    transport = "SSL" if mode["use_ssl"] else "STARTTLS" if mode["use_tls"] else "plain SMTP"
+    return {
+        "label": str(mode.get("mode_label") or _smtp_mode_label(mode)),
+        "smtp_host": str(mode["smtp_host"]),
+        "smtp_port": int(mode["smtp_port"]),
+        "use_tls": bool(mode["use_tls"]),
+        "use_ssl": bool(mode["use_ssl"]),
+        "transport": transport,
+        "auth_user": str(mode.get("smtp_username") or "") or "<none>",
+    }
+
+
+def describe_smtp_error(error: Exception) -> str:
+    """Convert SMTP failures into operator-friendly messages."""
+    chain: list[Exception] = []
+    current: Exception | None = error
+    while current is not None and current not in chain:
+        chain.append(current)
+        current = current.__cause__ if isinstance(current.__cause__, Exception) else None
+
+    for item in chain:
+        text = str(item).strip()
+        lowered = text.lower()
+        if isinstance(item, (TimeoutError, socket.timeout)) or "timed out" in lowered:
+            return (
+                "SMTP connection timed out while waiting for the server greeting. "
+                "Check host, port, network access, and SMTP_TIMEOUT."
+            )
+        if isinstance(item, smtplib.SMTPAuthenticationError):
+            return (
+                "SMTP authentication failed. Check SMTP_USERNAME and SMTP_PASSWORD "
+                "(Fastmail and similar providers usually require an app password)."
+            )
+        if isinstance(item, (smtplib.SMTPDataError, smtplib.SMTPResponseException)):
+            smtp_code = getattr(item, "smtp_code", None)
+            if smtp_code in {551, 553} or "not authorised to send from this header address" in lowered or "not authorized to send from this header address" in lowered:
+                return (
+                    "SMTP server rejected the configured From address. Use an authorized alias "
+                    "for this account or change SMTP_FROM_ADDRESS to a sender the provider allows."
+                )
+        if isinstance(item, smtplib.SMTPConnectError):
+            return "SMTP connection was rejected by the server. Check the host and port."
+        if isinstance(item, smtplib.SMTPServerDisconnected) and "timed out" in lowered:
+            return (
+                "SMTP connection timed out while waiting for the server greeting. "
+                "Check host, port, network access, and SMTP_TIMEOUT."
+            )
+
+    return f"SMTP delivery failed: {error}"
+
+
+def test_smtp_connection(settings: object) -> dict[str, object]:
+    """Validate SMTP connectivity and authentication without sending a message."""
+    try:
+        base = _smtp_settings(settings)
+    except ValueError as exc:
+        return {
+            "status": "error",
+            "message": str(exc),
+            "attempts": [],
+            "selected_mode": None,
+            "from_address": "",
+            "from_name": str(getattr(settings, "smtp_from_name", "") or "").strip() or "Media Library Viewer",
+            "smtp_host": str(getattr(settings, "smtp_host", "") or "").strip(),
+            "smtp_port": int(getattr(settings, "smtp_port", 587) or 587),
+            "use_tls": bool(getattr(settings, "smtp_use_tls", True)),
+            "use_ssl": bool(getattr(settings, "smtp_use_ssl", False)),
+            "authenticated": False,
+        }
+
+    from_address = _from_address(settings)
+    from_name = str(getattr(settings, "smtp_from_name", "") or "").strip() or "Media Library Viewer"
+    attempts: list[dict[str, Any]] = []
+    last_error = ""
+    logger.info(
+        "SMTP test requested from_address=%s auth_user=%s",
+        from_address,
+        base["smtp_username"] or "<none>",
+    )
+
+    for mode in _smtp_mode_candidates(settings):
+        meta = _smtp_attempt_metadata(mode)
+        logger.info(
+            "SMTP test attempting label=%s host=%s port=%s transport=%s auth_user=%s",
+            meta["label"],
+            meta["smtp_host"],
+            meta["smtp_port"],
+            meta["transport"],
+            meta["auth_user"],
+        )
+        try:
+            _probe_smtp_connection(mode)
+            attempts.append(
+                {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                    "status": "ok",
+                }
+            )
+            logger.info(
+                "SMTP test succeeded label=%s host=%s port=%s transport=%s auth_user=%s",
+                meta["label"],
+                meta["smtp_host"],
+                meta["smtp_port"],
+                meta["transport"],
+                meta["auth_user"],
+            )
+            return {
+                "status": "ok",
+                "message": f"SMTP connection successful using {meta['label']}",
+                "from_address": from_address,
+                "from_name": from_name,
+                "smtp_host": meta["smtp_host"],
+                "smtp_port": meta["smtp_port"],
+                "use_tls": meta["use_tls"],
+                "use_ssl": meta["use_ssl"],
+                "authenticated": bool(str(mode["smtp_username"])),
+                "selected_mode": {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                },
+                "attempts": attempts,
+            }
+        except Exception as exc:
+            last_error = describe_smtp_error(exc)
+            attempts.append(
+                {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                    "status": "failed",
+                    "error": last_error,
+                }
+            )
+            logger.warning(
+                "SMTP test failed label=%s host=%s port=%s transport=%s auth_user=%s error=%s",
+                meta["label"],
+                meta["smtp_host"],
+                meta["smtp_port"],
+                meta["transport"],
+                meta["auth_user"],
+                last_error,
+            )
+
+    logger.error(
+        "SMTP test exhausted attempts=%s error=%s",
+        [attempt["label"] for attempt in attempts],
+        last_error or "SMTP test failed.",
+    )
+    return {
+        "status": "error",
+        "message": last_error or "SMTP test failed.",
+        "from_address": from_address,
+        "from_name": from_name,
+        "smtp_host": base["smtp_host"],
+        "smtp_port": base["smtp_port"],
+        "use_tls": base["use_tls"],
+        "use_ssl": base["use_ssl"],
+        "authenticated": bool(base["smtp_username"]),
+        "selected_mode": None,
+        "attempts": attempts,
+    }
+
+
+def build_email_message(
+    settings: object,
+    recipients: list[str],
+    subject: str,
+    html_body: str,
+    text_body: str,
+    attachments: Iterable[EmailAttachment] = (),
+    *,
+    sender_address: str | None = None,
+    reply_to_address: str | None = None,
+) -> tuple[EmailMessage, str]:
+    """Build a MIME email message with HTML and attachments."""
+    from_address = sender_address or _from_address(settings)
+    from_name = str(getattr(settings, "smtp_from_name", "") or "").strip() or "Media Library Viewer"
+    msg = EmailMessage()
+    msg["Subject"] = subject
+    msg["From"] = formataddr((from_name, from_address))
+    msg["To"] = "Undisclosed recipients:;"
+    msg["Reply-To"] = reply_to_address or from_address
+
+    plain_text = text_body.strip() or html_to_text(html_body)
+    if html_body.strip():
+        msg.set_content(plain_text or " ")
+        msg.add_alternative(html_body, subtype="html")
+    else:
+        msg.set_content(plain_text or "")
+
+    for attachment in attachments:
+        content_type = attachment.content_type or mimetypes.guess_type(attachment.filename)[0] or "application/octet-stream"
+        maintype, subtype = content_type.split("/", 1) if "/" in content_type else ("application", "octet-stream")
+        msg.add_attachment(
+            attachment.data,
+            maintype=maintype,
+            subtype=subtype,
+            filename=attachment.filename or "attachment",
+        )
+
+    return msg, from_address
+
+
+def _send_email_via_mode(
+    mode: dict[str, Any],
+    message: EmailMessage,
+    recipients: list[str],
+    from_address: str,
+) -> None:
+    context = ssl.create_default_context()
+    smtp_host = str(mode["smtp_host"])
+    smtp_port = int(mode["smtp_port"])
+    smtp_username = str(mode["smtp_username"])
+    smtp_password = str(mode["smtp_password"])
+    use_tls = bool(mode["use_tls"])
+    use_ssl = bool(mode["use_ssl"])
+    smtp_timeout = int(mode["smtp_timeout"])
+
+    if use_ssl:
+        smtp_connection = smtplib.SMTP_SSL(smtp_host, smtp_port, timeout=smtp_timeout)
+    else:
+        smtp_connection = smtplib.SMTP(smtp_host, smtp_port, timeout=smtp_timeout)
+
+    with smtp_connection as smtp:
+        if use_tls and not use_ssl:
+            smtp.ehlo()
+            smtp.starttls(context=context)
+            smtp.ehlo()
+        else:
+            smtp.ehlo()
+        if smtp_username:
+            smtp.login(smtp_username, smtp_password)
+        smtp.send_message(message, from_addr=from_address, to_addrs=recipients)
+
+
+def send_email_message(
+    settings: object,
+    recipients: list[str],
+    subject: str,
+    html_body: str,
+    text_body: str = "",
+    attachments: Iterable[EmailAttachment] = (),
+) -> dict[str, object]:
+    """Send a single outbound email to a recipient list via SMTP BCC."""
+    if not recipients:
+        raise ValueError("At least one recipient is required")
+
+    attachment_list = list(attachments)
+    preferred_from_address = _from_address(settings)
+    smtp_username = str(getattr(settings, "smtp_username", "") or "").strip()
+    message, from_address = build_email_message(
+        settings,
+        recipients,
+        subject,
+        html_body,
+        text_body,
+        attachment_list,
+        sender_address=preferred_from_address,
+        reply_to_address=preferred_from_address,
+    )
+
+    logger.info(
+        "SMTP send requested subject=%s recipients=%s from_address=%s auth_user=%s attachments=%s",
+        subject,
+        len(recipients),
+        from_address,
+        smtp_username or "<none>",
+        len(attachment_list),
+    )
+
+    attempts: list[dict[str, Any]] = []
+    last_error = ""
+    for mode in _smtp_mode_candidates(settings):
+        meta = _smtp_attempt_metadata(mode)
+        logger.info(
+            "SMTP send attempting label=%s host=%s port=%s transport=%s auth_user=%s from_address=%s",
+            meta["label"],
+            meta["smtp_host"],
+            meta["smtp_port"],
+            meta["transport"],
+            meta["auth_user"],
+            from_address,
+        )
+        try:
+            _send_email_via_mode(mode, message, recipients, from_address)
+            attempts.append(
+                {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                    "status": "ok",
+                }
+            )
+            logger.info(
+                "SMTP send succeeded label=%s host=%s port=%s transport=%s auth_user=%s from_address=%s",
+                meta["label"],
+                meta["smtp_host"],
+                meta["smtp_port"],
+                meta["transport"],
+                meta["auth_user"],
+                from_address,
+            )
+            return {
+                "from_address": from_address,
+                "recipient_count": len(recipients),
+                "attachment_count": len(attachment_list),
+                "subject": subject,
+                "authenticated_as": smtp_username or None,
+                "selected_mode": {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                },
+                "attempts": attempts,
+            }
+        except Exception as exc:
+            last_error = describe_smtp_error(exc)
+            attempts.append(
+                {
+                    "label": meta["label"],
+                    "smtp_host": meta["smtp_host"],
+                    "smtp_port": meta["smtp_port"],
+                    "use_tls": meta["use_tls"],
+                    "use_ssl": meta["use_ssl"],
+                    "status": "failed",
+                    "error": last_error,
+                }
+            )
+            if _smtp_sender_not_authorized(exc):
+                logger.warning(
+                    "SMTP send sender rejected label=%s host=%s port=%s transport=%s auth_user=%s from_address=%s error=%s",
+                    meta["label"],
+                    meta["smtp_host"],
+                    meta["smtp_port"],
+                    meta["transport"],
+                    meta["auth_user"],
+                    from_address,
+                    last_error,
+                )
+            else:
+                logger.warning(
+                    "SMTP send failed label=%s host=%s port=%s transport=%s auth_user=%s from_address=%s error=%s",
+                    meta["label"],
+                    meta["smtp_host"],
+                    meta["smtp_port"],
+                    meta["transport"],
+                    meta["auth_user"],
+                    from_address,
+                    last_error,
+                )
+
+    raise RuntimeError(last_error or "SMTP delivery failed")

backend/src/media_library_viewer_api/services/media_index.py

@@ -7,14 +7,18 @@ through FastAPI to a React frontend without rewriting Jellyfin indexing logic.
 
 from __future__ import annotations
 
+import logging
 import sqlite3
 import time
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Any, Iterable
+from typing import Any, Callable, Iterable
 
 from media_library_viewer_api.clients.jellyfin import JellyfinClient
 from media_library_viewer_api.domain.media import display_media_row, normalize_media_item
+from media_library_viewer_api.path_utils import resolve_remote_media_path
+
+logger = logging.getLogger(__name__)
 
 # Local generated database. It is ignored by git and can be rebuilt from
 # Jellyfin metadata whenever needed.
@@ -42,6 +46,19 @@ SORT_COLUMNS = {
 }
 
 
+def _estimate_remaining_seconds(elapsed_seconds: float, progress: float | None) -> float | None:
+    if progress is None:
+        return None
+    progress = max(0.0, min(1.0, progress))
+    if progress <= 0.0:
+        return None
+    return max(0.0, elapsed_seconds * (1.0 - progress) / progress)
+
+
+class MediaIndexBuildCancelled(Exception):
+    """Raised when a media index build is requested to stop."""
+
+
 @dataclass(frozen=True)
 class MediaIndexStatus:
     """Lightweight status object displayed by the Media tab."""
@@ -51,6 +68,25 @@ class MediaIndexStatus:
     updated_at: int | None = None
     updated_at_label: str = ""
     build_duration_seconds: float | None = None
+    build_running: bool = False
+    build_stage: str = ""
+    build_message: str = ""
+    build_progress: float | None = None
+    build_items_processed: int = 0
+    build_items_total: int = 0
+    build_current_library: str = ""
+    build_library_index: int = 0
+    build_libraries_total: int = 0
+    build_library_progress: float | None = None
+    build_library_items_processed: int = 0
+    build_library_items_total: int = 0
+    build_elapsed_seconds: float | None = None
+    build_eta_seconds: float | None = None
+    build_library_elapsed_seconds: float | None = None
+    build_library_eta_seconds: float | None = None
+    build_cancel_requested: bool = False
+    build_pid: int | None = None
+    build_error: str = ""
 
 
 class MediaIndex:
@@ -66,8 +102,10 @@ class MediaIndex:
 
     def connect(self) -> sqlite3.Connection:
         """Open a sqlite connection configured to return Row objects."""
-        conn = sqlite3.connect(self.db_path)
+        conn = sqlite3.connect(self.db_path, timeout=30)
         conn.row_factory = sqlite3.Row
+        conn.execute("PRAGMA journal_mode=WAL")
+        conn.execute("PRAGMA busy_timeout=30000")
         return conn
 
     def init_schema(self) -> None:
@@ -170,24 +208,68 @@ class MediaIndex:
         try:
             with self.connect() as conn:
                 item_count = int(conn.execute("SELECT COUNT(*) FROM media_items").fetchone()[0])
-                updated_row = conn.execute("SELECT value FROM index_metadata WHERE key='updated_at'").fetchone()
-                duration_row = conn.execute("SELECT value FROM index_metadata WHERE key='build_duration_seconds'").fetchone()
+                meta = {
+                    row[0]: row[1]
+                    for row in conn.execute("SELECT key, value FROM index_metadata").fetchall()
+                }
         except sqlite3.Error:
             return MediaIndexStatus(exists=False)
-        updated_at = int(updated_row[0]) if updated_row and str(updated_row[0]).isdigit() else None
+        updated_at_raw = meta.get("updated_at", "")
+        updated_at = int(updated_at_raw) if str(updated_at_raw).isdigit() else None
         label = time.strftime("%Y-%m-%d %H:%M:%S", time.localtime(updated_at)) if updated_at else ""
+        duration_raw = meta.get("build_duration_seconds")
         build_duration = None
-        if duration_row:
+        if duration_raw is not None:
             try:
-                build_duration = float(duration_row[0])
+                build_duration = float(duration_raw)
             except (TypeError, ValueError):
                 build_duration = None
+
+        def _bool(key: str, default: bool = False) -> bool:
+            value = str(meta.get(key, str(default))).strip().lower()
+            return value in {"1", "true", "yes", "on"}
+
+        def _int(key: str, default: int = 0) -> int:
+            value = meta.get(key, default)
+            try:
+                return int(value)
+            except (TypeError, ValueError):
+                return default
+
+        def _float(key: str) -> float | None:
+            value = meta.get(key)
+            if value in (None, ""):
+                return None
+            try:
+                return float(value)
+            except (TypeError, ValueError):
+                return None
+
         return MediaIndexStatus(
             exists=True,
             item_count=item_count,
             updated_at=updated_at,
             updated_at_label=label,
             build_duration_seconds=build_duration,
+            build_running=_bool("build_running"),
+            build_stage=str(meta.get("build_stage", "")),
+            build_message=str(meta.get("build_message", "")),
+            build_progress=_float("build_progress"),
+            build_items_processed=_int("build_items_processed"),
+            build_items_total=_int("build_items_total"),
+            build_current_library=str(meta.get("build_current_library", "")),
+            build_library_index=_int("build_library_index"),
+            build_libraries_total=_int("build_libraries_total"),
+            build_library_progress=_float("build_library_progress"),
+            build_library_items_processed=_int("build_library_items_processed"),
+            build_library_items_total=_int("build_library_items_total"),
+            build_elapsed_seconds=_float("build_elapsed_seconds"),
+            build_eta_seconds=_float("build_eta_seconds"),
+            build_library_elapsed_seconds=_float("build_library_elapsed_seconds"),
+            build_library_eta_seconds=_float("build_library_eta_seconds"),
+            build_cancel_requested=_bool("build_cancel_requested"),
+            build_pid=_int("build_pid") or None,
+            build_error=str(meta.get("build_error", "")),
         )
 
     def query(
@@ -245,18 +327,79 @@ def build_media_index(
     libraries: list[dict[str, Any]],
     index: MediaIndex | None = None,
     page_size: int = 500,
+    media_root: str = "",
+    fallback_prefix: str = "",
+    progress_callback: Callable[[dict[str, Any]], None] | None = None,
+    should_cancel: Callable[[], bool] | None = None,
 ) -> int:
     """Fetch Jellyfin pages for all selected libraries and rebuild the index."""
     index = index or MediaIndex()
     started_at = time.perf_counter()
     normalized_rows: list[dict[str, Any]] = []
-    for library in libraries:
+    processed_total = 0
+    expected_total = 0
+    current_library_name = ""
+    current_library_index = 0
+    current_library_processed = 0
+    current_library_total = 0
+    current_library_started_at = started_at
+
+    def ensure_not_cancelled() -> None:
+        if should_cancel and should_cancel():
+            raise MediaIndexBuildCancelled()
+
+    def emit(stage: str, message: str) -> None:
+        if not progress_callback:
+            return
+        elapsed_seconds = time.perf_counter() - started_at
+        library_elapsed_seconds = time.perf_counter() - current_library_started_at
+        overall_progress = (processed_total / expected_total) if expected_total else None
+        library_progress = (current_library_processed / current_library_total) if current_library_total else None
+        progress_callback(
+            {
+                "stage": stage,
+                "message": message,
+                "processed": processed_total,
+                "total": expected_total,
+                "progress": overall_progress,
+                "elapsed_seconds": elapsed_seconds,
+                "eta_seconds": _estimate_remaining_seconds(elapsed_seconds, overall_progress),
+                "library": current_library_name,
+                "library_index": current_library_index,
+                "libraries_total": len(libraries),
+                "library_processed": current_library_processed,
+                "library_total": current_library_total,
+                "library_progress": library_progress,
+                "library_elapsed_seconds": library_elapsed_seconds if current_library_total else None,
+                "library_eta_seconds": _estimate_remaining_seconds(library_elapsed_seconds, library_progress),
+            }
+        )
+
+    ensure_not_cancelled()
+    logger.info("Media index build starting libraries=%s page_size=%s", len(libraries), page_size)
+    emit("starting", "Starting media index build")
+    for library_index, library in enumerate(libraries, start=1):
         library_id = library.get("Id")
-        library_name = library.get("Name", "")
+        current_library_name = library.get("Name", "")
+        current_library_index = library_index
+        current_library_processed = 0
+        current_library_total = 0
+        current_library_started_at = time.perf_counter()
         if not library_id:
             continue
+        ensure_not_cancelled()
+        logger.info(
+            "Media index scanning library index=%s/%s name=%s id=%s",
+            library_index,
+            len(libraries),
+            current_library_name or "Library",
+            library_id,
+        )
+        emit("library-starting", f"Scanning {current_library_name or 'Library'}")
         start = 0
+        discovered_library_total = None
         while True:
+            ensure_not_cancelled()
             response = client.items(
                 user_id=user_id,
                 parent_id=library_id,
@@ -267,12 +410,49 @@ def build_media_index(
                 sort_by="SortName",
                 sort_order="Ascending",
             )
+            ensure_not_cancelled()
             items = response.get("Items", [])
-            normalized_rows.extend(normalize_media_item(item, library_id, library_name) for item in items)
+            if discovered_library_total is None:
+                discovered_library_total = int(response.get("TotalRecordCount", len(items)))
+                current_library_total = max(discovered_library_total, 0)
+                expected_total += current_library_total
+            normalized_rows.extend(
+                {
+                    **row,
+                    "path": resolve_remote_media_path(row.get("path", ""), media_root, fallback_prefix),
+                }
+                for row in (
+                    normalize_media_item(item, library_id, current_library_name)
+                    for item in items
+                )
+            )
+            processed_total += len(items)
+            current_library_processed += len(items)
             start += len(items)
+            ensure_not_cancelled()
+            emit(
+                "building",
+                f"{current_library_name or 'Library'}: {current_library_processed} / {current_library_total or '?'} items",
+            )
+            logger.debug(
+                "Media index progress library=%s processed=%s/%s total_processed=%s",
+                current_library_name or "Library",
+                current_library_processed,
+                current_library_total,
+                processed_total,
+            )
             total = int(response.get("TotalRecordCount", start))
             if not items or start >= total:
                 break
+    ensure_not_cancelled()
+    logger.info("Media index finalizing rows=%s", len(normalized_rows))
+    emit("finalizing", "Writing index to disk")
+    ensure_not_cancelled()
     count = index.replace_items(normalized_rows)
-    index.set_metadata("build_duration_seconds", f"{time.perf_counter() - started_at:.3f}")
+    duration = time.perf_counter() - started_at
+    index.set_metadata("build_duration_seconds", f"{duration:.3f}")
+    processed_total = count
+    current_library_processed = current_library_total
+    emit("completed", f"Indexed {count} items in {duration:.1f}s")
+    logger.info("Media index build completed count=%s duration=%.2fs", count, duration)
     return count

backend/src/media_library_viewer_api/workers/__init__.py

@@ -0,0 +1 @@
+"""Worker entrypoints for background tasks."""

backend/src/media_library_viewer_api/workers/media_index_worker.py

@@ -0,0 +1,200 @@
+"""Subprocess worker that builds the media index.
+
+The FastAPI app starts this worker as a separate Python process so the build can
+be cooperatively canceled or force-killed without taking down the API server.
+"""
+
+from __future__ import annotations
+
+import argparse
+import logging
+import os
+import time
+from pathlib import Path
+from typing import Any
+
+from media_library_viewer_api.config import get_settings
+from media_library_viewer_api.dependencies import get_jellyfin_client, get_user_id
+from media_library_viewer_api.services.media_index import (
+    MediaIndex,
+    MediaIndexBuildCancelled,
+    build_media_index,
+)
+from media_library_viewer_api.logging_utils import configure_logging, describe_settings
+
+logger = logging.getLogger(__name__)
+
+
+def _set_build_metadata(index: MediaIndex, state: dict[str, Any]) -> None:
+    for key, value in state.items():
+        index.set_metadata(key, "" if value is None else value)
+
+
+def _cancel_requested(index: MediaIndex) -> bool:
+    return index.status().build_cancel_requested
+
+
+def _start_state(index: MediaIndex, pid: int, library_count: int) -> None:
+    _set_build_metadata(
+        index,
+        {
+            "build_running": True,
+            "build_stage": "starting",
+            "build_message": "Starting media index build",
+            "build_progress": None,
+            "build_items_processed": 0,
+            "build_items_total": 0,
+            "build_current_library": "",
+            "build_library_index": 0,
+            "build_libraries_total": library_count,
+            "build_library_progress": None,
+            "build_library_items_processed": 0,
+            "build_library_items_total": 0,
+            "build_elapsed_seconds": None,
+            "build_eta_seconds": None,
+            "build_library_elapsed_seconds": None,
+            "build_library_eta_seconds": None,
+            "build_cancel_requested": False,
+            "build_pid": pid,
+            "build_error": "",
+        },
+    )
+
+
+def _progress_callback(index: MediaIndex, pid: int, state: dict[str, Any]) -> None:
+    _set_build_metadata(
+        index,
+        {
+            "build_running": True,
+            "build_stage": state.get("stage", ""),
+            "build_message": state.get("message", ""),
+            "build_progress": state.get("progress"),
+            "build_items_processed": state.get("processed", 0),
+            "build_items_total": state.get("total", 0),
+            "build_current_library": state.get("library", ""),
+            "build_library_index": state.get("library_index", 0),
+            "build_libraries_total": state.get("libraries_total", 0),
+            "build_library_progress": state.get("library_progress"),
+            "build_library_items_processed": state.get("library_processed", 0),
+            "build_library_items_total": state.get("library_total", 0),
+            "build_elapsed_seconds": state.get("elapsed_seconds"),
+            "build_eta_seconds": state.get("eta_seconds"),
+            "build_library_elapsed_seconds": state.get("library_elapsed_seconds"),
+            "build_library_eta_seconds": state.get("library_eta_seconds"),
+            "build_cancel_requested": False,
+            "build_pid": pid,
+            "build_error": "",
+        },
+    )
+
+
+def run_build(final_index_path: str | Path, staging_index_path: str | Path) -> int:
+    """Run the media index build in a subprocess."""
+    settings = get_settings()
+    configure_logging(settings.log_level)
+    logger.info("Media index worker starting: %s", describe_settings(settings))
+    client = get_jellyfin_client()
+    user_id = get_user_id()
+    libraries = client.libraries(user_id)
+
+    final_index = MediaIndex(final_index_path)
+    staging_index = MediaIndex(staging_index_path)
+    pid = os.getpid()
+    started_at = time.perf_counter()
+
+    staging_path = Path(staging_index.db_path)
+    staging_path.unlink(missing_ok=True)
+    logger.info("Media index worker pid=%s libraries=%s", pid, len(libraries))
+    _start_state(final_index, pid, len(libraries))
+
+    try:
+        count = build_media_index(
+            client,
+            user_id,
+            libraries,
+            index=staging_index,
+            media_root=settings.media_root,
+            fallback_prefix=settings.path_prefix,
+            progress_callback=lambda state: _progress_callback(final_index, pid, state),
+            should_cancel=lambda: _cancel_requested(final_index),
+        )
+        # Swap the staging database into place atomically.
+        os.replace(staging_index.db_path, final_index.db_path)
+        completed_index = MediaIndex(final_index.db_path)
+        logger.info("Media index worker completed count=%s", count)
+        elapsed = time.perf_counter() - started_at
+        completed_status = completed_index.status()
+        _set_build_metadata(
+            completed_index,
+            {
+                "build_running": False,
+                "build_stage": "completed",
+                "build_message": "Media index build complete",
+                "build_progress": 1.0,
+                "build_items_processed": count,
+                "build_items_total": count,
+                "build_current_library": "",
+                "build_library_index": len(libraries),
+                "build_libraries_total": len(libraries),
+                "build_library_progress": 1.0,
+                "build_library_items_processed": 0,
+                "build_library_items_total": 0,
+                "build_elapsed_seconds": elapsed,
+                "build_eta_seconds": 0.0,
+                "build_library_elapsed_seconds": 0.0,
+                "build_library_eta_seconds": 0.0,
+                "build_cancel_requested": False,
+                "build_pid": "",
+                "build_error": "",
+                # Keep the duration reported by the staging build.
+                "build_duration_seconds": completed_status.build_duration_seconds or elapsed,
+            },
+        )
+        return 0
+    except MediaIndexBuildCancelled:
+        logger.info("Media index worker canceled")
+        _set_build_metadata(
+            final_index,
+            {
+                "build_running": False,
+                "build_stage": "canceled",
+                "build_message": "Media index build canceled",
+                "build_cancel_requested": False,
+                "build_pid": "",
+                "build_error": "",
+            },
+        )
+        return 130
+    except Exception as exc:  # pragma: no cover - defensive subprocess error handling
+        logger.exception("Media index worker failed")
+        _set_build_metadata(
+            final_index,
+            {
+                "build_running": False,
+                "build_stage": "error",
+                "build_message": "Media index build failed",
+                "build_cancel_requested": False,
+                "build_pid": "",
+                "build_error": str(exc),
+            },
+        )
+        return 1
+    finally:
+        # If the build did not complete successfully, the staging DB is disposable.
+        if staging_path.exists() and staging_path != Path(final_index.db_path):
+            try:
+                staging_path.unlink()
+            except OSError:
+                pass
+
+
+def main() -> int:
+    parser = argparse.ArgumentParser(description="Build the media index in a worker process")
+    parser.add_argument("--index-path", required=True)
+    parser.add_argument("--staging-path", required=True)
+    args = parser.parse_args()
+    return run_build(args.index_path, args.staging_path)
+
+
+if __name__ == "__main__":  # pragma: no cover
+    raise SystemExit(main())

backend/tests/test_api.py

@@ -5,14 +5,23 @@ without requiring real remote connections.
 """
 
 import json
+from types import SimpleNamespace
 from unittest.mock import MagicMock, patch
 
 import pytest
 from fastapi.testclient import TestClient
 
 from media_library_viewer_api.main import app
-from media_library_viewer_api.dependencies import get_ssh_client, get_jellyfin_client, get_user_id
+from media_library_viewer_api.dependencies import (
+    get_ssh_client,
+    get_jellyfin_client,
+    get_jellyseerr_client,
+    get_mail_queue,
+    get_user_id,
+)
 from media_library_viewer_api.clients.ssh import CommandResult
+from media_library_viewer_api.routers.media import get_media_index
+from media_library_viewer_api.services.media_index import MediaIndex
 
 
 # --- Fixtures ---
@@ -26,11 +35,15 @@ def mock_jellyfin():
         {"Id": "lib1", "Name": "Movies", "CollectionType": "movies"},
         {"Id": "lib2", "Name": "TV Shows", "CollectionType": "tvshows"},
     ]
+    client.users.return_value = [
+        {"Id": "jf1", "Name": "alex"},
+        {"Id": "jf2", "Name": "sam"},
+    ]
     client.library_item_counts.return_value = [
         {"library": "Movies", "type": "movies", "movies": 100, "series": 0, "episodes": 0, "total": 100},
         {"library": "TV Shows", "type": "tvshows", "movies": 0, "series": 20, "episodes": 500, "total": 520},
     ]
-    client.active_sessions.return_value = [
+    client.sessions.return_value = [
         {
             "Id": "sess1",
             "UserName": "alex",
@@ -38,11 +51,51 @@ def mock_jellyfin():
             "NowPlayingItem": {"Name": "Test Movie", "Type": "Movie"},
             "PlayState": {"IsPaused": False},
             "TranscodingInfo": {"IsVideoDirect": True, "IsAudioDirect": False},
-        }
+        },
+        {
+            "Id": "sess2",
+            "UserName": "sam",
+            "DeviceName": "Android",
+            "NowPlayingItem": None,
+            "PlayState": {},
+            "TranscodingInfo": None,
+        },
     ]
     return client
 
 
+@pytest.fixture
+def mock_jellyseerr():
+    """Mock Jellyseerr client."""
+    client = MagicMock()
+    client.jellyfin_users.return_value = [
+        {"id": "jf1", "username": "alex", "thumb": "/avatarproxy/alex", "email": "alex@example.com"},
+        {"id": "jf2", "username": "sam", "thumb": "/avatarproxy/sam", "email": "sam@example.com"},
+    ]
+    client.users.return_value = [
+        {
+            "id": 7,
+            "username": "alex",
+            "email": "alex@example.com",
+            "avatar": "/avatarproxy/alex",
+            "userType": 3,
+            "permissions": 10,
+            "requestCount": 3,
+        },
+        {
+            "id": 8,
+            "username": "sam",
+            "email": "sam@example.com",
+            "avatar": "/avatarproxy/sam",
+            "userType": 2,
+            "permissions": 32,
+            "requestCount": 1,
+        },
+    ]
+    client.absolute_url.side_effect = lambda path: f"https://requests.example.com{path}"
+    return client
+
+
 @pytest.fixture
 def mock_ssh():
     """Mock SSH client."""
@@ -73,9 +126,10 @@ def mock_ssh():
 
 
 @pytest.fixture
-def test_client(mock_jellyfin, mock_ssh):
+def test_client(mock_jellyfin, mock_jellyseerr, mock_ssh):
     """FastAPI test client with mocked dependencies."""
     app.dependency_overrides[get_jellyfin_client] = lambda: mock_jellyfin
+    app.dependency_overrides[get_jellyseerr_client] = lambda: mock_jellyseerr
     app.dependency_overrides[get_ssh_client] = lambda: mock_ssh
     app.dependency_overrides[get_user_id] = lambda: "user123"
     client = TestClient(app)
@@ -111,17 +165,244 @@ class TestDashboard:
         assert data[0]["library"] == "Movies"
         assert data[1]["library"] == "TV Shows"
 
-    def test_now_playing(self, test_client):
+    def test_activity(self, test_client):
+        response = test_client.get("/api/dashboard/activity")
+        assert response.status_code == 200
+        data = response.json()
+        assert len(data) == 2
+
+        playing_row = next(row for row in data if row["user"] == "alex")
+        assert playing_row["title"] == "Test Movie"
+        assert playing_row["state"] == "playing"
+        assert playing_row["transcoding"] == "yes"
+        assert "audio" in playing_row["transcoding_type"]
+
+        idle_row = next(row for row in data if row["user"] == "sam")
+        assert idle_row["state"] == "idle"
+        assert idle_row["title"] == "(idle)"
+
+    def test_now_playing_alias(self, test_client):
         response = test_client.get("/api/dashboard/now-playing")
         assert response.status_code == 200
         data = response.json()
-        assert len(data) == 1
-        assert data[0]["user"] == "alex"
-        assert data[0]["title"] == "Test Movie"
-        assert data[0]["transcoding"] == "yes"
-        assert "audio" in data[0]["transcoding_type"]
+        assert len(data) == 2
 
 
+# --- Users ---
+
+class TestUsers:
+    def test_users_list_enriched(self, test_client):
+        response = test_client.get("/api/users")
+        assert response.status_code == 200
+        data = response.json()
+        assert data["total"] == 2
+        assert data["jellyseerr_configured"] is True
+        assert data["jellyseerr_available"] is True
+        assert data["jellyseerr_error"] == ""
+
+        alex = next(item for item in data["items"] if item["username"] == "alex")
+        assert alex["email"] == "alex@example.com"
+        assert alex["email_source"] == "jellyseerr:user"
+        assert alex["contactable"] is True
+        assert alex["avatar"].startswith("https://requests.example.com/")
+        assert alex["avatar_source"] == "jellyseerr:user"
+        assert alex["permissions"] == 10
+        assert alex["permissions_label"] == "admin, manage_users"
+        assert alex["role"] == "admin"
+        assert alex["user_type_label"] == "jellyfin"
+        assert alex["request_count"] == 3
+        assert "name=jellyfin" in alex["source_summary"]
+        assert "email=jellyseerr:user" in alex["source_summary"]
+
+        sam = next(item for item in data["items"] if item["username"] == "sam")
+        assert sam["role"] == "requester"
+        assert sam["user_type_label"] == "local"
+        assert sam["email"] == "sam@example.com"
+
+    def test_users_message_status(self, test_client):
+        mail_queue = MagicMock()
+        mail_queue.status.return_value = {
+            "state": "idle",
+            "worker_running": True,
+            "stop_requested": False,
+            "pending_count": 0,
+            "active_request_id": None,
+            "last_request_id": None,
+            "last_result": None,
+            "last_error": "",
+            "last_error_at": None,
+            "last_success_at": None,
+            "last_activity_at": None,
+            "sent_count": 0,
+            "failed_count": 0,
+        }
+        app.dependency_overrides[get_mail_queue] = lambda: mail_queue
+        try:
+            response = test_client.get("/api/users/message/status")
+        finally:
+            app.dependency_overrides.pop(get_mail_queue, None)
+        assert response.status_code == 200
+        assert response.json()["state"] == "idle"
+        assert response.json()["pending_count"] == 0
+
+    def test_users_message_test_smtp(self, test_client):
+        settings = SimpleNamespace(
+            smtp_host="smtp.fastmail.com",
+            smtp_port=587,
+            smtp_username="main@fastmail.com",
+            smtp_password="app-password",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+        app.dependency_overrides[get_mail_queue] = lambda: MagicMock()
+        try:
+            with patch("media_library_viewer_api.routers.users.get_settings", return_value=settings), patch(
+                "media_library_viewer_api.routers.users.test_smtp_connection",
+                return_value={
+                    "status": "ok",
+                    "message": "SMTP connection successful using Fastmail STARTTLS 587",
+                    "from_address": "alias@example.com",
+                    "from_name": "Media Library Viewer",
+                    "smtp_host": "smtp.fastmail.com",
+                    "smtp_port": 587,
+                    "use_tls": True,
+                    "use_ssl": False,
+                    "authenticated": True,
+                    "selected_mode": {
+                        "label": "Fastmail STARTTLS 587",
+                        "smtp_host": "smtp.fastmail.com",
+                        "smtp_port": 587,
+                        "use_tls": True,
+                        "use_ssl": False,
+                    },
+                    "attempts": [
+                        {
+                            "label": "Fastmail STARTTLS 587",
+                            "smtp_host": "smtp.fastmail.com",
+                            "smtp_port": 587,
+                            "use_tls": True,
+                            "use_ssl": False,
+                            "status": "ok",
+                        }
+                    ],
+                },
+            ):
+                response = test_client.post("/api/users/message/test-smtp")
+        finally:
+            app.dependency_overrides.pop(get_mail_queue, None)
+        assert response.status_code == 200
+        data = response.json()
+        assert data["status"] == "ok"
+        assert data["smtp_host"] == "smtp.fastmail.com"
+        assert data["selected_mode"]["label"] == "Fastmail STARTTLS 587"
+
+    def test_users_message_test_smtp_timeout_message(self, test_client):
+        settings = SimpleNamespace(
+            smtp_host="smtp.fastmail.com",
+            smtp_port=587,
+            smtp_username="main@fastmail.com",
+            smtp_password="app-password",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+        app.dependency_overrides[get_mail_queue] = lambda: MagicMock()
+        try:
+            with patch("media_library_viewer_api.routers.users.get_settings", return_value=settings), patch(
+                "media_library_viewer_api.routers.users.test_smtp_connection",
+                return_value={
+                    "status": "error",
+                    "message": "SMTP connection timed out while waiting for the server greeting. Check host, port, network access, and SMTP_TIMEOUT.",
+                    "from_address": "alias@example.com",
+                    "from_name": "Media Library Viewer",
+                    "smtp_host": "smtp.fastmail.com",
+                    "smtp_port": 587,
+                    "use_tls": True,
+                    "use_ssl": False,
+                    "authenticated": True,
+                    "selected_mode": None,
+                    "attempts": [
+                        {
+                            "label": "configured",
+                            "smtp_host": "smtp.fastmail.com",
+                            "smtp_port": 587,
+                            "use_tls": True,
+                            "use_ssl": False,
+                            "status": "failed",
+                            "error": "SMTP connection timed out while waiting for the server greeting. Check host, port, network access, and SMTP_TIMEOUT.",
+                        }
+                    ],
+                },
+            ):
+                response = test_client.post("/api/users/message/test-smtp")
+        finally:
+            app.dependency_overrides.pop(get_mail_queue, None)
+        assert response.status_code == 200
+        assert response.json()["status"] == "error"
+        assert "timed out" in response.json()["message"].lower()
+
+    def test_users_message_is_queued(self, test_client):
+        mail_queue = MagicMock()
+        mail_queue.status.return_value = {
+            "state": "idle",
+            "worker_running": True,
+            "stop_requested": False,
+            "pending_count": 0,
+            "active_request_id": None,
+            "last_request_id": None,
+            "last_result": None,
+            "last_error": "",
+            "last_error_at": None,
+            "last_success_at": None,
+            "last_activity_at": None,
+            "sent_count": 0,
+            "failed_count": 0,
+        }
+        mail_queue.enqueue.return_value = "mail-123456"
+        app.dependency_overrides[get_mail_queue] = lambda: mail_queue
+        settings = SimpleNamespace(
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="mailer@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+
+        try:
+            with patch("media_library_viewer_api.routers.users.get_settings", return_value=settings):
+                response = test_client.post(
+                    "/api/users/message",
+                    data={
+                        "recipient_ids": json.dumps(["jf1", "jf2"]),
+                        "subject": "Hello team",
+                        "html_body": "<p>Hi there</p>",
+                        "text_body": "Hi there",
+                    },
+                )
+        finally:
+            app.dependency_overrides.pop(get_mail_queue, None)
+
+        assert response.status_code == 202
+        data = response.json()
+        assert data["status"] == "queued"
+        assert data["request_id"] == "mail-123456"
+        assert data["recipient_count"] == 2
+        assert data["attachment_count"] == 0
+        mail_queue.enqueue.assert_called_once()
+        kwargs = mail_queue.enqueue.call_args.kwargs
+        assert kwargs["recipients"] == ["alex@example.com", "sam@example.com"]
+        assert kwargs["subject"] == "Hello team"
+        assert kwargs["settings"] is settings
+
 # --- Files ---
 
 class TestFiles:
@@ -163,6 +444,135 @@ class TestFiles:
         assert "Permission denied" in response.text
 
 
+# --- Media index build ---
+
+class TestMediaIndexApi:
+    def test_status_includes_build_progress(self, test_client, tmp_path):
+        index = MediaIndex(tmp_path / "index.sqlite")
+        index.init_schema()
+        index.set_metadata("build_running", "true")
+        index.set_metadata("build_stage", "building")
+        index.set_metadata("build_message", "3 / 10 items")
+        index.set_metadata("build_progress", "0.3")
+        index.set_metadata("build_items_processed", "3")
+        index.set_metadata("build_items_total", "10")
+        index.set_metadata("build_current_library", "Movies")
+        index.set_metadata("build_library_index", "1")
+        index.set_metadata("build_libraries_total", "2")
+        index.set_metadata("build_library_progress", "0.5")
+        index.set_metadata("build_library_items_processed", "1")
+        index.set_metadata("build_library_items_total", "2")
+        index.set_metadata("build_elapsed_seconds", "12.0")
+        index.set_metadata("build_eta_seconds", "28.0")
+        index.set_metadata("build_library_elapsed_seconds", "4.0")
+        index.set_metadata("build_library_eta_seconds", "4.0")
+        index.set_metadata("build_pid", "4321")
+        app.dependency_overrides[get_media_index] = lambda: index
+        with patch("media_library_viewer_api.routers.media._pid_is_alive", return_value=True):
+            response = test_client.get("/api/media/status")
+            assert response.status_code == 200
+            data = response.json()
+            assert data["build_running"] is True
+            assert data["build_stage"] == "building"
+            assert data["build_message"] == "3 / 10 items"
+            assert data["build_progress"] == 0.3
+            assert data["build_items_processed"] == 3
+            assert data["build_items_total"] == 10
+            assert data["build_current_library"] == "Movies"
+            assert data["build_library_index"] == 1
+            assert data["build_libraries_total"] == 2
+            assert data["build_library_progress"] == 0.5
+            assert data["build_library_items_processed"] == 1
+            assert data["build_library_items_total"] == 2
+            assert data["build_elapsed_seconds"] == 12.0
+            assert data["build_eta_seconds"] == 28.0
+            assert data["build_library_elapsed_seconds"] == 4.0
+            assert data["build_library_eta_seconds"] == 4.0
+            assert data["build_pid"] == 4321
+
+    def test_build_returns_started_when_background_build_is_queued(self, test_client, tmp_path, mock_jellyfin):
+        index = MediaIndex(tmp_path / "index.sqlite")
+        app.dependency_overrides[get_media_index] = lambda: index
+
+        class FakeProcess:
+            pid = 4321
+
+        with patch("media_library_viewer_api.routers.media._start_worker", return_value=FakeProcess()) as start_worker:
+            try:
+                response = test_client.post("/api/media/build")
+                assert response.status_code == 202
+                data = response.json()
+                assert data["status"] == "started"
+                assert data["build_running"] is True
+                assert data["build_stage"] == "queued"
+                assert data["build_libraries_total"] == len(mock_jellyfin.libraries.return_value)
+                assert data["build_pid"] == 4321
+                start_worker.assert_called_once()
+            finally:
+                app.dependency_overrides.pop(get_media_index, None)
+
+    def test_stop_requests_cancel(self, test_client, tmp_path):
+        index = MediaIndex(tmp_path / "index.sqlite")
+        index.init_schema()
+        index.set_metadata("build_running", "true")
+        index.set_metadata("build_stage", "building")
+        index.set_metadata("build_pid", "4321")
+        app.dependency_overrides[get_media_index] = lambda: index
+
+        with patch("media_library_viewer_api.routers.media._pid_is_alive", return_value=True):
+            try:
+                response = test_client.post("/api/media/stop")
+                assert response.status_code == 202
+                data = response.json()
+                assert data["status"] == "stop_requested"
+                assert data["build_cancel_requested"] is True
+                status = test_client.get("/api/media/status").json()
+                assert status["build_cancel_requested"] is True
+                assert status["build_stage"] == "canceling"
+            finally:
+                app.dependency_overrides.pop(get_media_index, None)
+
+    def test_force_stop_terminates_worker(self, test_client, tmp_path):
+        index = MediaIndex(tmp_path / "index.sqlite")
+        index.init_schema()
+        index.set_metadata("build_running", "true")
+        index.set_metadata("build_stage", "building")
+        index.set_metadata("build_pid", "4321")
+        app.dependency_overrides[get_media_index] = lambda: index
+
+        alive_calls = {"count": 0}
+
+        def fake_pid_is_alive(pid):
+            alive_calls["count"] += 1
+            return alive_calls["count"] <= 2
+
+        with patch("media_library_viewer_api.routers.media._pid_is_alive", side_effect=fake_pid_is_alive), patch(
+            "media_library_viewer_api.routers.media.os.killpg"
+        ) as killpg, patch("media_library_viewer_api.routers.media.time.sleep", return_value=None):
+            try:
+                response = test_client.post("/api/media/force-stop")
+                assert response.status_code == 202
+                data = response.json()
+                assert data["status"] == "force_stopped"
+                killpg.assert_called()
+                status = test_client.get("/api/media/status").json()
+                assert status["build_running"] is False
+                assert status["build_stage"] == "force-stopped"
+            finally:
+                app.dependency_overrides.pop(get_media_index, None)
+
+    def test_force_stop_returns_conflict_when_idle(self, test_client, tmp_path):
+        index = MediaIndex(tmp_path / "index.sqlite")
+        index.init_schema()
+        app.dependency_overrides[get_media_index] = lambda: index
+
+        try:
+            response = test_client.post("/api/media/force-stop")
+            assert response.status_code == 409
+        finally:
+            app.dependency_overrides.pop(get_media_index, None)
+
+
 # --- Jobs ---
 
 class TestJobs:

backend/tests/test_config.py

@@ -12,12 +12,17 @@ class TestSettings:
             assert settings.ssh_host == ""
             assert settings.ssh_port == 22
             assert settings.jellyfin_url == ""
+            assert settings.jellyseerr_url == ""
+            assert settings.log_level == "INFO"
             assert settings.remote_media_root == ""
 
     def test_from_env(self):
         env = {
             "JELLYFIN_URL": "https://test.example.com",
             "JELLYFIN_API_KEY": "key123",
+            "JELLYSEERR_URL": "https://requests.example.com",
+            "JELLYSEERR_API_KEY": "seerr123",
+            "LOG_LEVEL": "DEBUG",
             "SSH_HOST": "192.168.1.1",
             "SSH_USERNAME": "testuser",
             "SSH_PORT": "2222",
@@ -27,6 +32,9 @@ class TestSettings:
             settings = Settings(_env_file=None)
             assert settings.jellyfin_url == "https://test.example.com"
             assert settings.jellyfin_api_key == "key123"
+            assert settings.jellyseerr_url == "https://requests.example.com"
+            assert settings.jellyseerr_api_key == "seerr123"
+            assert settings.log_level == "DEBUG"
             assert settings.ssh_host == "192.168.1.1"
             assert settings.ssh_username == "testuser"
             assert settings.ssh_port == 2222

backend/tests/test_jellyseerr_client.py

@@ -0,0 +1,81 @@
+"""Unit tests for the Jellyseerr client."""
+
+from __future__ import annotations
+
+import unittest
+from unittest.mock import MagicMock
+
+from media_library_viewer_api.clients.jellyseerr import JellyseerrClient
+
+
+class JellyseerrClientTests(unittest.TestCase):
+    def setUp(self) -> None:
+        self.client = JellyseerrClient("https://requests.example.com/api/v1", "api-key")
+        self.session = MagicMock()
+        self.client.session = self.session
+
+    def test_jellyfin_users_accepts_wrapped_payload(self) -> None:
+        response = MagicMock()
+        response.raise_for_status.return_value = None
+        response.json.return_value = {
+            "users": [
+                {"id": "jf1", "username": "alex", "email": "alex@example.com", "thumb": "/avatar"},
+                {"id": "jf2", "username": "sam", "email": "sam@example.com", "thumb": "/avatar2"},
+            ]
+        }
+        self.session.get.return_value = response
+
+        users = self.client.jellyfin_users()
+
+        self.assertEqual(len(users), 2)
+        self.assertEqual(users[0]["email"], "alex@example.com")
+        self.assertEqual(users[1]["username"], "sam")
+        self.session.get.assert_called_once()
+
+    def test_jellyfin_users_accepts_list_payload(self) -> None:
+        response = MagicMock()
+        response.raise_for_status.return_value = None
+        response.json.return_value = [
+            {"id": "jf1", "username": "alex"},
+            {"id": "jf2", "username": "sam"},
+        ]
+        self.session.get.return_value = response
+
+        users = self.client.jellyfin_users()
+
+        self.assertEqual([u["username"] for u in users], ["alex", "sam"])
+
+    def test_users_uses_take_and_skip(self) -> None:
+        first = MagicMock()
+        first.raise_for_status.return_value = None
+        first.json.return_value = {
+            "pageInfo": {"results": 3, "pages": 2, "pageSize": 2, "page": 1},
+            "results": [
+                {"id": 1, "username": "alex", "email": "alex@example.com"},
+                {"id": 2, "username": "sam", "email": "sam@example.com"},
+            ],
+        }
+        second = MagicMock()
+        second.raise_for_status.return_value = None
+        second.json.return_value = {
+            "pageInfo": {"results": 3, "pages": 2, "pageSize": 2, "page": 2},
+            "results": [
+                {"id": 3, "username": "max", "email": "max@example.com"},
+            ],
+        }
+        self.session.get.side_effect = [first, second]
+
+        users = self.client.users(page_size=2)
+
+        self.assertEqual([u["username"] for u in users], ["alex", "sam", "max"])
+        self.assertEqual(self.session.get.call_args_list[0].kwargs["params"], {"take": 2, "skip": 0})
+        self.assertEqual(self.session.get.call_args_list[1].kwargs["params"], {"take": 2, "skip": 2})
+
+    def test_absolute_url_normalizes_relative_paths(self) -> None:
+        self.assertEqual(self.client.absolute_url("/avatar.png"), "https://requests.example.com/avatar.png")
+        self.assertEqual(self.client.absolute_url("avatar.png"), "https://requests.example.com/avatar.png")
+        self.assertEqual(self.client.absolute_url("https://cdn.example.com/x.png"), "https://cdn.example.com/x.png")
+
+
+if __name__ == "__main__":
+    unittest.main()

backend/tests/test_mailer.py

@@ -0,0 +1,207 @@
+"""Unit tests for SMTP mail helpers."""
+
+from __future__ import annotations
+
+import smtplib
+import unittest
+from types import SimpleNamespace
+from unittest.mock import MagicMock, patch
+
+from media_library_viewer_api.services.mailer import (
+    EmailAttachment,
+    describe_smtp_error,
+    html_to_text,
+    send_email_message,
+    test_smtp_connection as smtp_connection_probe,
+)
+
+
+class _SMTPContext:
+    def __init__(self, smtp: MagicMock):
+        self.smtp = smtp
+
+    def __enter__(self):
+        return self.smtp
+
+    def __exit__(self, exc_type, exc, tb):
+        return False
+
+
+class MailerTests(unittest.TestCase):
+    def test_html_to_text_strips_tags(self) -> None:
+        text = html_to_text("<p>Hello <strong>world</strong></p><p>Line 2</p>")
+        self.assertIn("Hello", text)
+        self.assertIn("world", text)
+        self.assertIn("Line 2", text)
+
+    def test_send_email_message_uses_smtp_with_attachments(self) -> None:
+        settings = SimpleNamespace(
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="mailer@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+        smtp = MagicMock()
+        smtp.send_message.return_value = {}
+        smtp_factory = MagicMock(return_value=_SMTPContext(smtp))
+
+        with patch("media_library_viewer_api.services.mailer.smtplib.SMTP", smtp_factory), patch(
+            "media_library_viewer_api.services.mailer.smtplib.SMTP_SSL"
+        ) as smtp_ssl:
+            result = send_email_message(
+                settings,
+                recipients=["alex@example.com", "sam@example.com"],
+                subject="Hello",
+                html_body="<p><strong>Hi</strong> there</p>",
+                attachments=[EmailAttachment(filename="note.txt", content_type="text/plain", data=b"note")],
+            )
+
+        smtp_ssl.assert_not_called()
+        smtp.starttls.assert_called_once()
+        smtp.login.assert_called_once_with("mailer@example.com", "secret")
+        smtp.send_message.assert_called_once()
+        message = smtp.send_message.call_args.args[0]
+        self.assertEqual(message["Subject"], "Hello")
+        self.assertEqual(message["From"], "Media Library Viewer <mailer@example.com>")
+        self.assertEqual(result["recipient_count"], 2)
+        self.assertEqual(result["attachment_count"], 1)
+
+    def test_test_smtp_connection_uses_starttls_and_login(self) -> None:
+        settings = SimpleNamespace(
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+        smtp = MagicMock()
+        smtp_factory = MagicMock(return_value=_SMTPContext(smtp))
+
+        with patch("media_library_viewer_api.services.mailer.smtplib.SMTP", smtp_factory), patch(
+            "media_library_viewer_api.services.mailer.smtplib.SMTP_SSL"
+        ) as smtp_ssl:
+            result = smtp_connection_probe(settings)
+
+        smtp_ssl.assert_not_called()
+        smtp.ehlo.assert_called()
+        smtp.starttls.assert_called_once()
+        smtp.login.assert_called_once_with("mailer@example.com", "secret")
+        smtp.noop.assert_called_once()
+        self.assertEqual(result["status"], "ok")
+        self.assertEqual(result["from_address"], "alias@example.com")
+        self.assertEqual(result["smtp_host"], "smtp.example.com")
+        self.assertEqual(result["selected_mode"]["label"], "configured")
+
+    def test_test_smtp_connection_falls_back_to_fastmail_mode(self) -> None:
+        settings = SimpleNamespace(
+            smtp_host="smtp.fastmail.com",
+            smtp_port=465,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=False,
+            smtp_use_ssl=True,
+            smtp_timeout=15,
+        )
+        smtp_ssl = MagicMock(side_effect=TimeoutError("timed out"))
+        fallback_smtp = MagicMock()
+        smtp_factory = MagicMock(return_value=_SMTPContext(fallback_smtp))
+
+        with patch("media_library_viewer_api.services.mailer.smtplib.SMTP_SSL", smtp_ssl), patch(
+            "media_library_viewer_api.services.mailer.smtplib.SMTP",
+            smtp_factory,
+        ):
+            result = smtp_connection_probe(settings)
+
+        self.assertEqual(result["status"], "ok")
+        self.assertEqual(result["selected_mode"]["label"], "Fastmail STARTTLS 587")
+        self.assertEqual(len(result["attempts"]), 2)
+        self.assertEqual(result["attempts"][0]["status"], "failed")
+        self.assertEqual(result["attempts"][1]["status"], "ok")
+        fallback_smtp.starttls.assert_called_once()
+        fallback_smtp.login.assert_called_once_with("mailer@example.com", "secret")
+
+    def test_send_email_message_falls_back_to_fastmail_mode(self) -> None:
+        settings = SimpleNamespace(
+            smtp_host="smtp.fastmail.com",
+            smtp_port=465,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=False,
+            smtp_use_ssl=True,
+            smtp_timeout=15,
+        )
+        smtp_ssl_factory = MagicMock(side_effect=TimeoutError("timed out"))
+        fallback_smtp = MagicMock()
+        fallback_factory = MagicMock(return_value=_SMTPContext(fallback_smtp))
+
+        with patch("media_library_viewer_api.services.mailer.smtplib.SMTP_SSL", smtp_ssl_factory), patch(
+            "media_library_viewer_api.services.mailer.smtplib.SMTP",
+            fallback_factory,
+        ):
+            result = send_email_message(
+                settings,
+                recipients=["alex@example.com"],
+                subject="Hello",
+                html_body="<p>Hello</p>",
+            )
+
+        self.assertEqual(result["selected_mode"]["label"], "Fastmail STARTTLS 587")
+        self.assertEqual(result["authenticated_as"], "mailer@example.com")
+        self.assertEqual(len(result["attempts"]), 2)
+        self.assertEqual(result["attempts"][0]["status"], "failed")
+        self.assertEqual(result["attempts"][1]["status"], "ok")
+        fallback_smtp.send_message.assert_called_once()
+
+    def test_send_email_message_rejects_unauthorized_from_address(self) -> None:
+        settings = SimpleNamespace(
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            smtp_username="mailer@example.com",
+            smtp_password="secret",
+            smtp_from_address="alias@example.com",
+            smtp_from_name="Media Library Viewer",
+            smtp_use_tls=True,
+            smtp_use_ssl=False,
+            smtp_timeout=15,
+        )
+        smtp = MagicMock()
+        smtp.send_message.side_effect = smtplib.SMTPDataError(
+            551, b"5.7.1 Not authorised to send from this header address"
+        )
+        smtp_factory = MagicMock(return_value=_SMTPContext(smtp))
+
+        with patch("media_library_viewer_api.services.mailer.smtplib.SMTP", smtp_factory), patch(
+            "media_library_viewer_api.services.mailer.smtplib.SMTP_SSL"
+        ) as smtp_ssl:
+            with self.assertRaises(RuntimeError) as ctx:
+                send_email_message(
+                    settings,
+                    recipients=["alex@example.com"],
+                    subject="Hello",
+                    html_body="<p>Hello</p>",
+                )
+
+        smtp_ssl.assert_not_called()
+        self.assertIn("authorized alias", str(ctx.exception).lower())
+        self.assertEqual(smtp.send_message.call_count, 1)
+
+    def test_describe_smtp_error_handles_timeout(self) -> None:
+        detail = describe_smtp_error(TimeoutError("timed out"))
+        self.assertIn("timed out", detail.lower())
+
+
+if __name__ == "__main__":
+    unittest.main()

backend/tests/test_media_index.py

@@ -3,7 +3,12 @@
 import pytest
 import tempfile
 from pathlib import Path
-from media_library_viewer_api.services.media_index import MediaIndex
+from typing import Any
+from media_library_viewer_api.services.media_index import (
+    MediaIndex,
+    MediaIndexBuildCancelled,
+    build_media_index,
+)
 
 
 @pytest.fixture
@@ -242,3 +247,126 @@ class TestMediaIndexMetadata:
         index.set_metadata("build_duration_seconds", "12.5")
         status = index.status()
         assert status.build_duration_seconds == 12.5
+
+
+class TestMediaIndexBuildPaths:
+    def test_build_media_index_patches_remote_media_root(self, tmp_path):
+        class FakeClient:
+            def items(self, **kwargs):
+                return {
+                    "Items": [
+                        {
+                            "Id": "m1",
+                            "Name": "Movie One",
+                            "Type": "Movie",
+                            "Path": "/media/movies/Movie One/file.mkv",
+                        }
+                    ],
+                    "TotalRecordCount": 1,
+                }
+
+        index = MediaIndex(tmp_path / "index.sqlite")
+        count = build_media_index(
+            FakeClient(),
+            "user1",
+            [{"Id": "lib1", "Name": "Movies"}],
+            index,
+            media_root="/srv/media",
+            fallback_prefix="",
+        )
+        assert count == 1
+        rows, total = index.query(library_ids=["lib1"], media_types=["Movie"])
+        assert total == 1
+        assert rows[0]["path"] == "/srv/media/movies/Movie One/file.mkv"
+
+    def test_build_media_index_reports_progress(self, tmp_path):
+        class FakeClient:
+            def __init__(self):
+                self.calls = []
+
+            def items(self, **kwargs):
+                self.calls.append(kwargs.get("start_index", 0))
+                if kwargs.get("start_index", 0) == 0:
+                    return {
+                        "Items": [
+                            {"Id": "m1", "Name": "Movie One", "Type": "Movie", "Path": "/media/a.mkv"}
+                        ],
+                        "TotalRecordCount": 2,
+                    }
+                return {
+                    "Items": [
+                        {"Id": "m2", "Name": "Movie Two", "Type": "Movie", "Path": "/media/b.mkv"}
+                    ],
+                    "TotalRecordCount": 2,
+                }
+
+        events: list[dict[str, Any]] = []
+        index = MediaIndex(tmp_path / "index.sqlite")
+        count = build_media_index(
+            FakeClient(),
+            "user1",
+            [{"Id": "lib1", "Name": "Movies"}],
+            index,
+            page_size=1,
+            progress_callback=events.append,
+        )
+        assert count == 2
+        assert events[0]["stage"] == "starting"
+        assert events[0]["progress"] is None
+        assert any(event["stage"] == "building" for event in events)
+        building_event = next(event for event in events if event["stage"] == "building")
+        assert building_event["library"] == "Movies"
+        assert building_event["library_progress"] in (0.5, 1.0)
+        assert "elapsed_seconds" in building_event
+        assert "eta_seconds" in building_event
+        assert events[-1]["stage"] == "completed"
+        assert events[-1]["progress"] == 1.0
+        assert events[-1]["library_progress"] == 1.0
+
+    def test_build_media_index_can_be_cancelled(self, tmp_path):
+        class FakeClient:
+            def __init__(self):
+                self.calls = []
+
+            def items(self, **kwargs):
+                self.calls.append(kwargs.get("start_index", 0))
+                if kwargs.get("start_index", 0) == 0:
+                    return {
+                        "Items": [
+                            {"Id": "m1", "Name": "Movie One", "Type": "Movie", "Path": "/media/a.mkv"}
+                        ],
+                        "TotalRecordCount": 2,
+                    }
+                return {
+                    "Items": [
+                        {"Id": "m2", "Name": "Movie Two", "Type": "Movie", "Path": "/media/b.mkv"}
+                    ],
+                    "TotalRecordCount": 2,
+                }
+
+        events: list[dict[str, Any]] = []
+        cancel_after_building = [False]
+
+        def progress_callback(state: dict[str, Any]) -> None:
+            events.append(state)
+            if state["stage"] == "building":
+                cancel_after_building[0] = True
+
+        def should_cancel() -> bool:
+            return cancel_after_building[0]
+
+        index = MediaIndex(tmp_path / "index.sqlite")
+        client = FakeClient()
+        with pytest.raises(MediaIndexBuildCancelled):
+            build_media_index(
+                client,
+                "user1",
+                [{"Id": "lib1", "Name": "Movies"}],
+                index,
+                page_size=1,
+                progress_callback=progress_callback,
+                should_cancel=should_cancel,
+            )
+        assert any(event["stage"] == "building" for event in events)
+        assert events[-1]["stage"] == "building"
+        assert client.calls == [0]