diff --git a/app/api/dropbox.py b/app/api/dropbox.py
index ea7600aa..f9bf10e5 100644
--- a/app/api/dropbox.py
+++ b/app/api/dropbox.py
@@ -7,11 +7,15 @@ import os
 from typing import Annotated, Optional
 
 import requests
-from fastapi import APIRouter, Form, HTTPException, Request, status
+from fastapi import APIRouter, Depends, Form, HTTPException, Request, status
+from sqlalchemy.orm import Session
 
 from app.auth import require_login
 from app.config import settings
+from app.database import get_db
 from app.utils.oauth_helper import exchange_oauth_token
+from app.utils.settings_service import save_setting_to_db
+from app.utils.settings_sync import notify_settings_updated
 
 # Set up logging
 logger = logging.getLogger(__name__)
@@ -63,38 +67,52 @@ async def update_dropbox_settings(
     app_key: Annotated[Optional[str], Form()] = None,
     app_secret: Annotated[Optional[str], Form()] = None,
     folder_path: Annotated[Optional[str], Form()] = None,
+    db: Session = Depends(get_db),
 ):
     """
-    Update Dropbox settings in memory
+    Update Dropbox settings in memory and persist to the database.
     """
     try:
-        logger.info("Updating Dropbox settings in memory")
+        logger.info("Updating Dropbox settings in memory and database")
 
-        # Update settings in memory
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
+
+        # Update settings in memory and persist to database
         if refresh_token:
             settings.dropbox_refresh_token = refresh_token
-            logger.info("Updated DROPBOX_REFRESH_TOKEN in memory")
+            save_setting_to_db(db, "dropbox_refresh_token", refresh_token, changed_by=changed_by)
+            logger.info("Updated DROPBOX_REFRESH_TOKEN in memory and database")
 
         if app_key:
             settings.dropbox_app_key = app_key
-            logger.info("Updated DROPBOX_APP_KEY in memory")
+            save_setting_to_db(db, "dropbox_app_key", app_key, changed_by=changed_by)
+            logger.info("Updated DROPBOX_APP_KEY in memory and database")
 
         if app_secret:
             settings.dropbox_app_secret = app_secret
-            logger.info("Updated DROPBOX_APP_SECRET in memory")
+            save_setting_to_db(db, "dropbox_app_secret", app_secret, changed_by=changed_by)
+            logger.info("Updated DROPBOX_APP_SECRET in memory and database")
 
         if folder_path:
             settings.dropbox_folder = folder_path
-            logger.info("Updated DROPBOX_FOLDER in memory")
+            save_setting_to_db(db, "dropbox_folder", folder_path, changed_by=changed_by)
+            logger.info("Updated DROPBOX_FOLDER in memory and database")
 
-        # Test token validity would be here, but we'll skip it for now
+        notify_settings_updated()
 
-        return {"status": "success", "message": "Dropbox settings have been updated in memory"}
+        return {
+            "status": "success",
+            "message": "Dropbox settings have been updated in memory and saved to database",
+        }
 
     except Exception as e:
         logger.exception(f"Unexpected error updating Dropbox settings: {str(e)}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to update Dropbox settings: {str(e)}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to update Dropbox settings: {str(e)}",
         )
 
 
@@ -109,7 +127,10 @@ async def test_dropbox_token(request: Request):
 
         if not settings.dropbox_refresh_token or not settings.dropbox_app_key or not settings.dropbox_app_secret:
             logger.warning("Dropbox credentials not fully configured")
-            return {"status": "error", "message": "Dropbox credentials are not fully configured"}
+            return {
+                "status": "error",
+                "message": "Dropbox credentials are not fully configured",
+            }
 
         # Check token validity by getting current account info
         headers = {"Authorization": f"Bearer {settings.dropbox_refresh_token}"}
@@ -136,7 +157,11 @@ async def test_dropbox_token(request: Request):
 
             if refresh_response.status_code != 200:
                 logger.error(f"Failed to refresh Dropbox token: {refresh_response.text}")
-                return {"status": "error", "message": "Refresh token has expired or is invalid", "needs_reauth": True}
+                return {
+                    "status": "error",
+                    "message": "Refresh token has expired or is invalid",
+                    "needs_reauth": True,
+                }
 
             token_info = refresh_response.json()
             access_token = token_info.get("access_token")
@@ -162,7 +187,10 @@ async def test_dropbox_token(request: Request):
         account_name = account_info.get("name", {}).get("display_name", "Unknown user")
 
         # Dropbox refresh tokens don't expire, but we should note that in our response
-        token_info = {"expires_in_human": "Never expires (perpetual token)", "is_perpetual": True}
+        token_info = {
+            "expires_in_human": "Never expires (perpetual token)",
+            "is_perpetual": True,
+        }
 
         logger.info(f"Successfully connected to Dropbox as {account_email}")
 
@@ -187,65 +215,18 @@ async def save_dropbox_settings(
     app_key: Annotated[Optional[str], Form()] = None,
     app_secret: Annotated[Optional[str], Form()] = None,
     folder_path: Annotated[Optional[str], Form()] = None,
+    db: Session = Depends(get_db),
 ):
     """
-    Save Dropbox settings to the .env file
+    Save Dropbox settings to database (primary) and .env file (best-effort).
     """
     try:
-        # Get the path to the .env file
-        env_path = os.path.join(os.path.dirname(os.path.dirname(os.path.dirname(__file__))), ".env")
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
 
-        if not os.path.exists(env_path):
-            logger.error(f".env file not found at {env_path}")
-            raise HTTPException(
-                status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Could not find .env file to update"
-            )
-
-        logger.info(f"Updating Dropbox settings in {env_path}")
-
-        # Read the current .env file
-        with open(env_path, "r") as f:
-            env_lines = f.readlines()
-
-        # Define settings to update
-        dropbox_settings = {
-            "DROPBOX_REFRESH_TOKEN": refresh_token,
-        }
-
-        # Only update these if provided
-        if app_key:
-            dropbox_settings["DROPBOX_APP_KEY"] = app_key
-        if app_secret:
-            dropbox_settings["DROPBOX_APP_SECRET"] = app_secret
-        if folder_path:
-            dropbox_settings["DROPBOX_FOLDER"] = folder_path
-
-        # Process each line and update or add settings
-        updated = set()
-        new_env_lines = []
-        for line in env_lines:
-            stripped_line = line.rstrip()
-            is_updated = False
-            for key, value in dropbox_settings.items():
-                if stripped_line.startswith(f"{key}=") or stripped_line.startswith(f"# {key}="):
-                    # Uncomment if commented out - check the original stripped line
-                    new_env_lines.append(f"{key}={value}")
-                    updated.add(key)
-                    is_updated = True
-                    break
-            if not is_updated:
-                new_env_lines.append(stripped_line)
-
-        # Add any settings that weren't updated (they weren't in the file)
-        for key, value in dropbox_settings.items():
-            if key not in updated:
-                new_env_lines.append(f"{key}={value}")
-
-        # Write the updated .env file
-        with open(env_path, "w") as f:
-            f.write("\n".join(new_env_lines) + "\n")
-
-        # Update the settings in memory
+        # Update settings in memory
         if refresh_token:
             settings.dropbox_refresh_token = refresh_token
         if app_key:
@@ -255,14 +236,68 @@ async def save_dropbox_settings(
         if folder_path:
             settings.dropbox_folder = folder_path
 
-        logger.info("Successfully updated Dropbox settings")
+        # Persist to database (primary storage)
+        if refresh_token:
+            save_setting_to_db(db, "dropbox_refresh_token", refresh_token, changed_by=changed_by)
+        if app_key:
+            save_setting_to_db(db, "dropbox_app_key", app_key, changed_by=changed_by)
+        if app_secret:
+            save_setting_to_db(db, "dropbox_app_secret", app_secret, changed_by=changed_by)
+        if folder_path:
+            save_setting_to_db(db, "dropbox_folder", folder_path, changed_by=changed_by)
 
+        # Best-effort .env file write
+        try:
+            env_path = os.path.join(os.path.dirname(os.path.dirname(os.path.dirname(__file__))), ".env")
+            if not os.path.exists(env_path):
+                logger.warning(f".env file not found at {env_path}, skipping file write")
+            else:
+                logger.info(f"Updating Dropbox settings in {env_path}")
+
+                with open(env_path, "r") as f:
+                    env_lines = f.readlines()
+
+                dropbox_settings = {"DROPBOX_REFRESH_TOKEN": refresh_token}
+                if app_key:
+                    dropbox_settings["DROPBOX_APP_KEY"] = app_key
+                if app_secret:
+                    dropbox_settings["DROPBOX_APP_SECRET"] = app_secret
+                if folder_path:
+                    dropbox_settings["DROPBOX_FOLDER"] = folder_path
+
+                updated = set()
+                new_env_lines = []
+                for line in env_lines:
+                    stripped_line = line.rstrip()
+                    is_updated = False
+                    for key, value in dropbox_settings.items():
+                        if stripped_line.startswith(f"{key}=") or stripped_line.startswith(f"# {key}="):
+                            new_env_lines.append(f"{key}={value}")
+                            updated.add(key)
+                            is_updated = True
+                            break
+                    if not is_updated:
+                        new_env_lines.append(stripped_line)
+
+                for key, value in dropbox_settings.items():
+                    if key not in updated:
+                        new_env_lines.append(f"{key}={value}")
+
+                with open(env_path, "w") as f:
+                    f.write("\n".join(new_env_lines) + "\n")
+
+                logger.info("Successfully updated Dropbox settings in .env file")
+        except Exception as env_err:
+            logger.warning(f"Failed to write .env file (non-fatal): {env_err}")
+
+        notify_settings_updated()
+
+        logger.info("Successfully saved Dropbox settings")
         return {"status": "success", "message": "Dropbox settings have been saved"}
 
-    except HTTPException:
-        raise
     except Exception as e:
         logger.exception(f"Unexpected error saving Dropbox settings: {str(e)}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to save Dropbox settings: {str(e)}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to save Dropbox settings: {str(e)}",
         )
diff --git a/app/api/google_drive.py b/app/api/google_drive.py
index b626a470..f9eda756 100644
--- a/app/api/google_drive.py
+++ b/app/api/google_drive.py
@@ -7,11 +7,15 @@ import os
 from datetime import datetime
 from typing import Annotated, Optional
 
-from fastapi import APIRouter, Form, HTTPException, Request, status
+from fastapi import APIRouter, Depends, Form, HTTPException, Request, status
+from sqlalchemy.orm import Session
 
 from app.auth import require_login
 from app.config import settings
+from app.database import get_db
 from app.utils.oauth_helper import exchange_oauth_token
+from app.utils.settings_service import save_setting_to_db
+from app.utils.settings_sync import notify_settings_updated
 
 # Set up logging
 logger = logging.getLogger(__name__)
@@ -64,38 +68,59 @@ async def update_google_drive_settings(
     client_secret: Annotated[Optional[str], Form()] = None,
     folder_id: Annotated[Optional[str], Form()] = None,
     use_oauth: Annotated[str, Form()] = "true",
+    db: Session = Depends(get_db),
 ):
     """
-    Update Google Drive settings in memory
+    Update Google Drive settings in memory and persist to database
     """
     try:
-        logger.info("Updating Google Drive settings in memory")
+        logger.info("Updating Google Drive settings in memory and database")
+
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
 
         # Convert use_oauth string to boolean
         use_oauth_bool = use_oauth.lower() in ("true", "1", "yes", "y", "t")
 
-        # Update settings in memory
+        # Update settings in memory and persist to database
         if refresh_token:
             settings.google_drive_refresh_token = refresh_token
-            logger.info("Updated GOOGLE_DRIVE_REFRESH_TOKEN in memory")
+            save_setting_to_db(db, "google_drive_refresh_token", refresh_token, changed_by=changed_by)
+            logger.info("Updated GOOGLE_DRIVE_REFRESH_TOKEN in memory and database")
 
         if client_id:
             settings.google_drive_client_id = client_id
-            logger.info("Updated GOOGLE_DRIVE_CLIENT_ID in memory")
+            save_setting_to_db(db, "google_drive_client_id", client_id, changed_by=changed_by)
+            logger.info("Updated GOOGLE_DRIVE_CLIENT_ID in memory and database")
 
         if client_secret:
             settings.google_drive_client_secret = client_secret
-            logger.info("Updated GOOGLE_DRIVE_CLIENT_SECRET in memory")
+            save_setting_to_db(db, "google_drive_client_secret", client_secret, changed_by=changed_by)
+            logger.info("Updated GOOGLE_DRIVE_CLIENT_SECRET in memory and database")
 
         if folder_id:
             settings.google_drive_folder_id = folder_id
-            logger.info("Updated GOOGLE_DRIVE_FOLDER_ID in memory")
+            save_setting_to_db(db, "google_drive_folder_id", folder_id, changed_by=changed_by)
+            logger.info("Updated GOOGLE_DRIVE_FOLDER_ID in memory and database")
 
         # Set the OAuth flag
         settings.google_drive_use_oauth = use_oauth_bool
-        logger.info(f"Updated GOOGLE_DRIVE_USE_OAUTH in memory to {use_oauth_bool}")
+        save_setting_to_db(
+            db,
+            "google_drive_use_oauth",
+            str(use_oauth_bool).lower(),
+            changed_by=changed_by,
+        )
+        logger.info(f"Updated GOOGLE_DRIVE_USE_OAUTH in memory and database to {use_oauth_bool}")
 
-        return {"status": "success", "message": "Google Drive settings have been updated in memory"}
+        notify_settings_updated()
+
+        return {
+            "status": "success",
+            "message": "Google Drive settings have been updated in memory and database",
+        }
 
     except Exception as e:
         logger.exception(f"Unexpected error updating Google Drive settings: {str(e)}")
@@ -125,7 +150,10 @@ async def test_google_drive_token(request: Request):
                 and settings.google_drive_refresh_token
             ):
                 logger.warning("Google Drive OAuth credentials not fully configured")
-                return {"status": "error", "message": "Google Drive OAuth credentials are not fully configured"}
+                return {
+                    "status": "error",
+                    "message": "Google Drive OAuth credentials are not fully configured",
+                }
 
             try:
                 # Test OAuth connection
@@ -188,7 +216,10 @@ async def test_google_drive_token(request: Request):
             # Test service account connection
             if not settings.google_drive_credentials_json:
                 logger.warning("Google Drive service account credentials not configured")
-                return {"status": "error", "message": "Google Drive service account credentials are not configured"}
+                return {
+                    "status": "error",
+                    "message": "Google Drive service account credentials are not configured",
+                }
 
             try:
                 service = get_google_drive_service()
@@ -214,7 +245,10 @@ async def test_google_drive_token(request: Request):
             except Exception as e:
                 error_msg = str(e)
                 logger.error(f"Google Drive service account test failed: {error_msg}")
-                return {"status": "error", "message": f"Service account validation failed: {error_msg}"}
+                return {
+                    "status": "error",
+                    "message": f"Service account validation failed: {error_msg}",
+                }
 
     except Exception as e:
         logger.exception("Unexpected error testing Google Drive token")
@@ -246,7 +280,10 @@ async def get_google_drive_token_info(request: Request):
             and settings.google_drive_refresh_token
         ):
             logger.warning("Google Drive OAuth credentials not fully configured")
-            return {"status": "error", "message": "Google Drive OAuth credentials are not fully configured"}
+            return {
+                "status": "error",
+                "message": "Google Drive OAuth credentials are not fully configured",
+            }
 
         try:
             # Get credentials and access token
@@ -333,9 +370,10 @@ async def save_dropbox_settings(
     client_secret: Annotated[Optional[str], Form()] = None,
     folder_id: Annotated[Optional[str], Form()] = None,
     use_oauth: Annotated[str, Form()] = "true",
+    db: Session = Depends(get_db),
 ):
     """
-    Save Google Drive settings to the .env file
+    Save Google Drive settings to the .env file (best-effort) and persist to database.
     """
     try:
         # Get the path to the .env file
@@ -344,6 +382,11 @@ async def save_dropbox_settings(
         # Convert use_oauth string to boolean
         use_oauth_bool = use_oauth.lower() in ("true", "1", "yes", "y", "t")
 
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
+
         # Define settings to update
         drive_settings = {"GOOGLE_DRIVE_USE_OAUTH": str(use_oauth_bool).lower()}
 
@@ -415,7 +458,25 @@ async def save_dropbox_settings(
         # Set OAuth flag
         settings.google_drive_use_oauth = use_oauth_bool
 
-        logger.info("Successfully updated Google Drive settings in memory")
+        # Persist to database
+        save_setting_to_db(
+            db,
+            "google_drive_use_oauth",
+            str(use_oauth_bool).lower(),
+            changed_by=changed_by,
+        )
+        if refresh_token:
+            save_setting_to_db(db, "google_drive_refresh_token", refresh_token, changed_by=changed_by)
+        if client_id:
+            save_setting_to_db(db, "google_drive_client_id", client_id, changed_by=changed_by)
+        if client_secret:
+            save_setting_to_db(db, "google_drive_client_secret", client_secret, changed_by=changed_by)
+        if folder_id:
+            save_setting_to_db(db, "google_drive_folder_id", folder_id, changed_by=changed_by)
+
+        notify_settings_updated()
+
+        logger.info("Successfully updated Google Drive settings in memory and database")
 
         return {
             "status": "success",
@@ -426,5 +487,6 @@ async def save_dropbox_settings(
     except Exception as e:
         logger.exception(f"Unexpected error saving Google Drive settings: {str(e)}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to save Google Drive settings: {str(e)}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to save Google Drive settings: {str(e)}",
         )
diff --git a/app/api/onedrive.py b/app/api/onedrive.py
index 894a1a44..e9f8328d 100644
--- a/app/api/onedrive.py
+++ b/app/api/onedrive.py
@@ -8,11 +8,15 @@ from datetime import datetime, timedelta
 from typing import Annotated, Optional
 
 import requests
-from fastapi import APIRouter, Form, HTTPException, Request, status
+from fastapi import APIRouter, Depends, Form, HTTPException, Request, status
+from sqlalchemy.orm import Session
 
 from app.auth import require_login
 from app.config import settings
+from app.database import get_db
 from app.utils.oauth_helper import exchange_oauth_token
+from app.utils.settings_service import save_setting_to_db
+from app.utils.settings_sync import notify_settings_updated
 
 # Set up logging
 logger = logging.getLogger(__name__)
@@ -50,7 +54,10 @@ async def exchange_onedrive_token(
     token_data = exchange_oauth_token(provider_name="OneDrive", token_url=token_url, payload=payload)
 
     # Return just what's needed by the frontend
-    return {"refresh_token": token_data["refresh_token"], "expires_in": token_data.get("expires_in", 3600)}
+    return {
+        "refresh_token": token_data["refresh_token"],
+        "expires_in": token_data.get("expires_in", 3600),
+    }
 
 
 @router.get("/onedrive/test-token")
@@ -68,7 +75,10 @@ async def test_onedrive_token(request: Request):
             or not settings.onedrive_client_secret
         ):
             logger.warning("OneDrive credentials not fully configured")
-            return {"status": "error", "message": "OneDrive credentials are not fully configured"}
+            return {
+                "status": "error",
+                "message": "OneDrive credentials are not fully configured",
+            }
 
         # Refresh token to get a new access token and expiration info
         tenant_id = settings.onedrive_tenant_id or "common"
@@ -86,7 +96,11 @@ async def test_onedrive_token(request: Request):
 
         if response.status_code != 200:
             logger.error(f"Failed to refresh OneDrive token: {response.text}")
-            return {"status": "error", "message": "Refresh token has expired or is invalid", "needs_reauth": True}
+            return {
+                "status": "error",
+                "message": "Refresh token has expired or is invalid",
+                "needs_reauth": True,
+            }
 
         token_data = response.json()
         access_token = token_data.get("access_token")
@@ -128,6 +142,24 @@ async def test_onedrive_token(request: Request):
             except Exception as e:
                 logger.warning(f"Failed to update refresh token in .env file: {e}")
 
+            # Persist the rotated refresh token to the database
+            try:
+                from app.database import SessionLocal
+
+                _db = SessionLocal()
+                try:
+                    save_setting_to_db(
+                        _db,
+                        "onedrive_refresh_token",
+                        new_refresh_token,
+                        changed_by="onedrive_token_rotation",
+                    )
+                    notify_settings_updated()
+                finally:
+                    _db.close()
+            except Exception as _e:
+                logger.warning(f"Failed to persist rotated OneDrive refresh token to database: {_e}")
+
         # Test the access token by getting user information
         user_info_url = "https://graph.microsoft.com/v1.0/me"
         headers = {"Authorization": f"Bearer {access_token}"}
@@ -203,65 +235,62 @@ async def save_onedrive_settings(
     client_secret: Annotated[Optional[str], Form()] = None,
     tenant_id: Annotated[str, Form()] = "common",
     folder_path: Annotated[Optional[str], Form()] = None,
+    db: Session = Depends(get_db),
 ):
     """
-    Save OneDrive settings to the .env file
+    Saves to database (primary) and .env file (best-effort).
     """
     try:
-        # Get the path to the .env file
-        env_path = os.path.join(os.path.dirname(os.path.dirname(os.path.dirname(__file__))), ".env")
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
 
-        if not os.path.exists(env_path):
-            logger.error(f".env file not found at {env_path}")
-            raise HTTPException(
-                status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Could not find .env file to update"
-            )
+        # Best-effort .env file write
+        try:
+            env_path = os.path.join(os.path.dirname(os.path.dirname(os.path.dirname(__file__))), ".env")
+            if not os.path.exists(env_path):
+                logger.warning(f".env file not found at {env_path}, skipping file write")
+            else:
+                logger.info(f"Updating OneDrive settings in {env_path}")
 
-        logger.info(f"Updating OneDrive settings in {env_path}")
+                with open(env_path, "r") as f:
+                    env_lines = f.readlines()
 
-        # Read the current .env file
-        with open(env_path, "r") as f:
-            env_lines = f.readlines()
+                onedrive_settings = {"ONEDRIVE_REFRESH_TOKEN": refresh_token}
+                if client_id:
+                    onedrive_settings["ONEDRIVE_CLIENT_ID"] = client_id
+                if client_secret:
+                    onedrive_settings["ONEDRIVE_CLIENT_SECRET"] = client_secret
+                if tenant_id:
+                    onedrive_settings["ONEDRIVE_TENANT_ID"] = tenant_id
+                if folder_path:
+                    onedrive_settings["ONEDRIVE_FOLDER_PATH"] = folder_path
 
-        # Define settings to update
-        onedrive_settings = {
-            "ONEDRIVE_REFRESH_TOKEN": refresh_token,
-        }
+                updated = set()
+                new_env_lines = []
+                for line in env_lines:
+                    stripped_line = line.rstrip()
+                    is_updated = False
+                    for key, value in onedrive_settings.items():
+                        if stripped_line.startswith(f"{key}=") or stripped_line.startswith(f"# {key}="):
+                            new_env_lines.append(f"{key}={value}")
+                            updated.add(key)
+                            is_updated = True
+                            break
+                    if not is_updated:
+                        new_env_lines.append(stripped_line)
 
-        # Only update these if provided
-        if client_id:
-            onedrive_settings["ONEDRIVE_CLIENT_ID"] = client_id
-        if client_secret:
-            onedrive_settings["ONEDRIVE_CLIENT_SECRET"] = client_secret
-        if tenant_id:
-            onedrive_settings["ONEDRIVE_TENANT_ID"] = tenant_id
-        if folder_path:
-            onedrive_settings["ONEDRIVE_FOLDER_PATH"] = folder_path
+                for key, value in onedrive_settings.items():
+                    if key not in updated:
+                        new_env_lines.append(f"{key}={value}")
 
-        # Process each line and update or add settings
-        updated = set()
-        new_env_lines = []
-        for line in env_lines:
-            stripped_line = line.rstrip()
-            is_updated = False
-            for key, value in onedrive_settings.items():
-                if stripped_line.startswith(f"{key}=") or stripped_line.startswith(f"# {key}="):
-                    # Uncomment if commented out - check the original stripped line
-                    new_env_lines.append(f"{key}={value}")
-                    updated.add(key)
-                    is_updated = True
-                    break
-            if not is_updated:
-                new_env_lines.append(stripped_line)
+                with open(env_path, "w") as f:
+                    f.write("\n".join(new_env_lines) + "\n")
 
-        # Add any settings that weren't updated (they weren't in the file)
-        for key, value in onedrive_settings.items():
-            if key not in updated:
-                new_env_lines.append(f"{key}={value}")
-
-        # Write the updated .env file
-        with open(env_path, "w") as f:
-            f.write("\n".join(new_env_lines) + "\n")
+                logger.info("Successfully updated OneDrive settings in .env file")
+        except Exception as env_err:
+            logger.warning(f"Failed to write .env file (non-fatal): {env_err}")
 
         # Update the settings in memory
         if refresh_token:
@@ -275,16 +304,28 @@ async def save_onedrive_settings(
         if folder_path:
             settings.onedrive_folder_path = folder_path
 
-        logger.info("Successfully updated OneDrive settings")
+        # Persist to database (primary)
+        if refresh_token:
+            save_setting_to_db(db, "onedrive_refresh_token", refresh_token, changed_by=changed_by)
+        if client_id:
+            save_setting_to_db(db, "onedrive_client_id", client_id, changed_by=changed_by)
+        if client_secret:
+            save_setting_to_db(db, "onedrive_client_secret", client_secret, changed_by=changed_by)
+        if tenant_id:
+            save_setting_to_db(db, "onedrive_tenant_id", tenant_id, changed_by=changed_by)
+        if folder_path:
+            save_setting_to_db(db, "onedrive_folder_path", folder_path, changed_by=changed_by)
 
+        notify_settings_updated()
+
+        logger.info("Successfully saved OneDrive settings")
         return {"status": "success", "message": "OneDrive settings have been saved"}
 
-    except HTTPException:
-        raise
     except Exception as e:
         logger.exception(f"Unexpected error saving OneDrive settings: {str(e)}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to save OneDrive settings: {str(e)}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to save OneDrive settings: {str(e)}",
         )
 
 
@@ -297,33 +338,46 @@ async def update_onedrive_settings(
     client_secret: Annotated[Optional[str], Form()] = None,
     tenant_id: Annotated[str, Form()] = "common",
     folder_path: Annotated[Optional[str], Form()] = None,
+    db: Session = Depends(get_db),
 ):
     """
-    Update OneDrive settings in memory (without modifying .env file)
+    Update OneDrive settings in memory and persist to database
     """
     try:
-        logger.info("Updating OneDrive settings in memory")
+        logger.info("Updating OneDrive settings in memory and database")
 
-        # Update settings in memory
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "wizard"
+        )
+
+        # Update settings in memory and persist to database
         if refresh_token:
             settings.onedrive_refresh_token = refresh_token
-            logger.info("Updated ONEDRIVE_REFRESH_TOKEN in memory")
+            save_setting_to_db(db, "onedrive_refresh_token", refresh_token, changed_by=changed_by)
+            logger.info("Updated ONEDRIVE_REFRESH_TOKEN in memory and database")
 
         if client_id:
             settings.onedrive_client_id = client_id
-            logger.info("Updated ONEDRIVE_CLIENT_ID in memory")
+            save_setting_to_db(db, "onedrive_client_id", client_id, changed_by=changed_by)
+            logger.info("Updated ONEDRIVE_CLIENT_ID in memory and database")
 
         if client_secret:
             settings.onedrive_client_secret = client_secret
-            logger.info("Updated ONEDRIVE_CLIENT_SECRET in memory")
+            save_setting_to_db(db, "onedrive_client_secret", client_secret, changed_by=changed_by)
+            logger.info("Updated ONEDRIVE_CLIENT_SECRET in memory and database")
 
         if tenant_id:
             settings.onedrive_tenant_id = tenant_id
-            logger.info("Updated ONEDRIVE_TENANT_ID in memory")
+            save_setting_to_db(db, "onedrive_tenant_id", tenant_id, changed_by=changed_by)
+            logger.info("Updated ONEDRIVE_TENANT_ID in memory and database")
 
         if folder_path:
             settings.onedrive_folder_path = folder_path
-            logger.info("Updated ONEDRIVE_FOLDER_PATH in memory")
+            save_setting_to_db(db, "onedrive_folder_path", folder_path, changed_by=changed_by)
+            logger.info("Updated ONEDRIVE_FOLDER_PATH in memory and database")
+
+        notify_settings_updated()
 
         # Test the token to make sure it works
         try:
@@ -333,14 +387,21 @@ async def update_onedrive_settings(
             logger.info("Successfully tested OneDrive token")
         except Exception as e:
             logger.error(f"Token test failed after updating settings: {str(e)}")
-            return {"status": "warning", "message": "Settings updated but token test failed: " + str(e)}
+            return {
+                "status": "warning",
+                "message": "Settings updated but token test failed: " + str(e),
+            }
 
-        return {"status": "success", "message": "OneDrive settings have been updated in memory"}
+        return {
+            "status": "success",
+            "message": "OneDrive settings have been updated in memory and database",
+        }
 
     except Exception as e:
         logger.exception(f"Unexpected error updating OneDrive settings: {str(e)}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to update OneDrive settings: {str(e)}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to update OneDrive settings: {str(e)}",
         )
 
 
diff --git a/app/api/settings.py b/app/api/settings.py
index 0dad89b6..75c9e99a 100644
--- a/app/api/settings.py
+++ b/app/api/settings.py
@@ -16,11 +16,15 @@ from app.utils.settings_service import (
     SETTING_METADATA,
     delete_setting_from_db,
     get_all_settings_from_db,
+    get_audit_log,
+    get_setting_history,
     get_setting_metadata,
     get_settings_by_category,
+    rollback_setting,
     save_setting_to_db,
     validate_setting_value,
 )
+from app.utils.settings_sync import notify_settings_updated
 
 logger = logging.getLogger(__name__)
 router = APIRouter(prefix="/settings", tags=["settings"])
@@ -79,7 +83,10 @@ async def get_settings(request: Request, db: DbSession, admin: AdminUser):
         for key in SETTING_METADATA.keys():
             if hasattr(settings, key):
                 value = getattr(settings, key)
-                current_settings[key] = {"value": value, "metadata": get_setting_metadata(key)}
+                current_settings[key] = {
+                    "value": value,
+                    "metadata": get_setting_metadata(key),
+                }
 
         # Get settings stored in database
         db_settings = get_all_settings_from_db(db)
@@ -90,7 +97,10 @@ async def get_settings(request: Request, db: DbSession, admin: AdminUser):
         return SettingsListResponse(settings=current_settings, categories=categories, db_settings=db_settings)
     except Exception as e:
         logger.error(f"Error retrieving settings: {e}")
-        raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Failed to retrieve settings")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to retrieve settings",
+        )
 
 
 @router.get("/{key}", response_model=SettingResponse)
@@ -111,7 +121,8 @@ async def get_setting(key: str, request: Request, db: DbSession, admin: AdminUse
     except Exception as e:
         logger.error(f"Error retrieving setting {key}: {e}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to retrieve setting: {key}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to retrieve setting: {key}",
         )
 
 
@@ -135,13 +146,23 @@ async def update_setting(
             if not is_valid:
                 raise HTTPException(status_code=status.HTTP_400_BAD_REQUEST, detail=error_message)
 
+        # Determine the username for the audit log
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "admin"
+        )
+
         # Save to database
-        success = save_setting_to_db(db, key, setting.value)
+        success = save_setting_to_db(db, key, setting.value, changed_by=changed_by)
         if not success:
             raise HTTPException(
-                status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Failed to save setting to database"
+                status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+                detail="Failed to save setting to database",
             )
 
+        # Notify workers that settings have changed
+        notify_settings_updated()
+
         # Get metadata
         metadata = get_setting_metadata(key)
         restart_required = metadata.get("restart_required", False)
@@ -158,7 +179,8 @@ async def update_setting(
     except Exception as e:
         logger.error(f"Error updating setting {key}: {e}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to update setting: {key}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to update setting: {key}",
         )
 
 
@@ -170,9 +192,19 @@ async def delete_setting(key: str, request: Request, db: DbSession, admin: Admin
     """
     validate_setting_key(key)
     try:
-        success = delete_setting_from_db(db, key)
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "admin"
+        )
+
+        success = delete_setting_from_db(db, key, changed_by=changed_by)
         if not success:
-            raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail=f"Setting '{key}' not found in database")
+            raise HTTPException(
+                status_code=status.HTTP_404_NOT_FOUND,
+                detail=f"Setting '{key}' not found in database",
+            )
+
+        notify_settings_updated()
 
         return {
             "success": True,
@@ -183,7 +215,8 @@ async def delete_setting(key: str, request: Request, db: DbSession, admin: Admin
     except Exception as e:
         logger.error(f"Error deleting setting {key}: {e}")
         raise HTTPException(
-            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail=f"Failed to delete setting: {key}"
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to delete setting: {key}",
         )
 
 
@@ -238,7 +271,10 @@ async def list_credentials(request: Request, db: DbSession, admin: AdminUser):
         }
     except Exception as e:
         logger.error(f"Error retrieving credential list: {e}")
-        raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Failed to retrieve credentials")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to retrieve credentials",
+        )
 
 
 @router.post("/bulk-update")
@@ -250,6 +286,11 @@ async def bulk_update_settings(updates: list[SettingUpdate], request: Request, d
     results = []
     errors = []
 
+    user = request.session.get("user", {}) if hasattr(request, "session") else {}
+    changed_by = (
+        user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "admin"
+    )
+
     for update in updates:
         try:
             # Validate the setting value
@@ -260,7 +301,7 @@ async def bulk_update_settings(updates: list[SettingUpdate], request: Request, d
                     continue
 
             # Save to database
-            success = save_setting_to_db(db, update.key, update.value)
+            success = save_setting_to_db(db, update.key, update.value, changed_by=changed_by)
             if success:
                 results.append({"key": update.key, "value": update.value, "status": "success"})
             else:
@@ -269,6 +310,165 @@ async def bulk_update_settings(updates: list[SettingUpdate], request: Request, d
             logger.error(f"Error updating setting {update.key}: {e}")
             errors.append({"key": update.key, "error": str(e)})
 
+    if results:
+        notify_settings_updated()
+
     restart_required = any(get_setting_metadata(result["key"]).get("restart_required", False) for result in results)
 
-    return {"success": len(errors) == 0, "updated": results, "errors": errors, "restart_required": restart_required}
+    return {
+        "success": len(errors) == 0,
+        "updated": results,
+        "errors": errors,
+        "restart_required": restart_required,
+    }
+
+
+@router.get("/audit-log")
+async def list_audit_log(
+    request: Request,
+    db: DbSession,
+    admin: AdminUser,
+    limit: int = 100,
+    offset: int = 0,
+):
+    """
+    Retrieve the settings audit log (most recent first).
+
+    Returns all configuration changes recorded in the audit log.
+    Sensitive values are masked in the response.
+    Admin only.
+    """
+    try:
+        entries = get_audit_log(db, limit=limit, offset=offset)
+        return {"entries": entries, "limit": limit, "offset": offset}
+    except Exception as e:
+        logger.error(f"Error retrieving audit log: {e}")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to retrieve audit log",
+        )
+
+
+@router.get("/{key}/history")
+async def get_key_history(key: str, request: Request, db: DbSession, admin: AdminUser):
+    """
+    Get the change history for a specific setting key.
+
+    Returns all audit log entries for that key, most recent first.
+    Admin only.
+    """
+    validate_setting_key_format(key)
+    try:
+        entries = get_setting_history(db, key)
+        return {"key": key, "history": entries}
+    except Exception as e:
+        logger.error(f"Error retrieving history for {key}: {e}")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to retrieve history for setting: {key}",
+        )
+
+
+@router.post("/{key}/rollback/{history_id}")
+async def rollback_setting_to_history(
+    key: str,
+    history_id: int,
+    request: Request,
+    db: DbSession,
+    admin: AdminUser,
+):
+    """
+    Revert a setting to the value it held at a specific point in the audit log.
+
+    The ``history_id`` is the ID of the :class:`~app.models.SettingsAuditLog`
+    entry whose ``new_value`` should be reinstated.  If that entry recorded a
+    deletion (``new_value`` is ``None``), the setting is removed from the
+    database and reverts to its ENV/default value.
+
+    A new audit log entry is written to record the rollback.
+    Admin only.
+    """
+    validate_setting_key_format(key)
+    try:
+        user = request.session.get("user", {}) if hasattr(request, "session") else {}
+        changed_by = (
+            user.get("preferred_username") or user.get("username") or user.get("email") or user.get("id") or "admin"
+        )
+
+        success = rollback_setting(db, key, history_id, changed_by=changed_by)
+        if not success:
+            raise HTTPException(
+                status_code=status.HTTP_404_NOT_FOUND,
+                detail=f"History entry {history_id} not found for setting '{key}'",
+            )
+
+        notify_settings_updated()
+
+        return {
+            "success": True,
+            "message": f"Setting '{key}' rolled back to history entry {history_id}",
+        }
+    except HTTPException:
+        raise
+    except Exception as e:
+        logger.error(f"Error rolling back setting {key} to history {history_id}: {e}")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail=f"Failed to roll back setting: {key}",
+        )
+
+
+@router.get("/export-env")
+async def export_env_settings(
+    request: Request,
+    db: DbSession,
+    admin: AdminUser,
+    source: str = "db",
+):
+    """
+    Export current settings as a ``.env`` file.
+
+    Query params:
+    - ``source=db`` (default) – only settings explicitly saved to the database.
+    - ``source=effective`` – full runtime configuration (DB > ENV > defaults) for
+      every key defined in SETTING_METADATA.
+
+    Returns a downloadable plain-text file suitable for bootstrapping another
+    installation.  All values — including sensitive ones — are included; only
+    admins can access this endpoint.
+    """
+    from fastapi.responses import Response as FastAPIResponse
+
+    from app.utils.settings_service import get_settings_for_export
+
+    if source not in ("db", "effective"):
+        raise HTTPException(
+            status_code=status.HTTP_400_BAD_REQUEST,
+            detail="source must be 'db' or 'effective'",
+        )
+
+    try:
+        export_data = get_settings_for_export(db, source=source)
+        lines = [
+            "# DocuElevate configuration export",
+            f"# Source: {source}",
+            "# Generated by DocuElevate Settings Export",
+            "# WARNING: This file contains sensitive values. Handle with care.",
+            "",
+        ]
+        for env_key, value in export_data.items():
+            lines.append(f"{env_key}={value}")
+        lines.append("")  # trailing newline
+        content = "\n".join(lines)
+
+        return FastAPIResponse(
+            content=content,
+            media_type="text/plain",
+            headers={"Content-Disposition": f'attachment; filename="docuelevate-{source}.env"'},
+        )
+    except Exception as e:
+        logger.error(f"Error exporting settings: {e}")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to export settings",
+        )
diff --git a/app/celery_worker.py b/app/celery_worker.py
index 1ed82467..d6bd83d4 100644
--- a/app/celery_worker.py
+++ b/app/celery_worker.py
@@ -35,6 +35,11 @@ from app.tasks.upload_to_sftp import upload_to_sftp  # noqa: F401
 from app.tasks.upload_to_webdav import upload_to_webdav  # noqa: F401
 from app.tasks.uptime_kuma_tasks import ping_uptime_kuma  # noqa: F401
 
+# Register the settings reload signal handler so workers pick up config changes
+from app.utils.settings_sync import register_settings_reload_signal
+
+register_settings_reload_signal()
+
 celery.conf.task_routes = {
     "app.tasks.*": {"queue": "default"},
 }
diff --git a/app/models.py b/app/models.py
index 848f71bf..78c09df9 100644
--- a/app/models.py
+++ b/app/models.py
@@ -102,3 +102,17 @@ class ApplicationSettings(Base):
     value = Column(String, nullable=True)  # Setting value (stored as string, converted as needed)
     created_at = Column(DateTime(timezone=True), server_default=func.now())
     updated_at = Column(DateTime(timezone=True), server_default=func.now(), onupdate=func.now())
+
+
+class SettingsAuditLog(Base):
+    """Audit log for all configuration changes made via the settings UI."""
+
+    __tablename__ = "settings_audit_log"
+
+    id = Column(Integer, primary_key=True, index=True)
+    key = Column(String, nullable=False, index=True)  # Setting key that was changed
+    old_value = Column(String, nullable=True)  # Previous value (None if first-time set)
+    new_value = Column(String, nullable=True)  # New value (None if deleted)
+    changed_by = Column(String, nullable=False)  # Username of the admin who made the change
+    changed_at = Column(DateTime(timezone=True), server_default=func.now(), index=True)
+    action = Column(String, nullable=False)  # "update" or "delete"
diff --git a/app/utils/settings_service.py b/app/utils/settings_service.py
index 5fc20ce7..b7344118 100644
--- a/app/utils/settings_service.py
+++ b/app/utils/settings_service.py
@@ -13,7 +13,7 @@ from typing import Any, Dict, List, Optional, Tuple
 from sqlalchemy.exc import SQLAlchemyError
 from sqlalchemy.orm import Session
 
-from app.models import ApplicationSettings
+from app.models import ApplicationSettings, SettingsAuditLog
 
 logger = logging.getLogger(__name__)
 
@@ -888,16 +888,18 @@ def get_setting_from_db(db: Session, key: str) -> Optional[str]:
         return None
 
 
-def save_setting_to_db(db: Session, key: str, value: Optional[str]) -> bool:
+def save_setting_to_db(db: Session, key: str, value: Optional[str], changed_by: str = "system") -> bool:
     """
     Save or update a setting in the database.
 
     Automatically encrypts sensitive values if encryption is enabled.
+    Records an entry in the settings audit log.
 
     Args:
         db: Database session
         key: Setting key
         value: Setting value (as string)
+        changed_by: Username of the admin performing the change (for audit log)
 
     Returns:
         True if successful, False otherwise
@@ -917,13 +919,39 @@ def save_setting_to_db(db: Session, key: str, value: Optional[str]) -> bool:
                 logger.warning(f"Storing sensitive setting {key} in plaintext (encryption unavailable)")
 
         setting = db.query(ApplicationSettings).filter(ApplicationSettings.key == key).first()
+        old_storage_value = setting.value if setting else None
+
         if setting:
             setting.value = storage_value
         else:
             setting = ApplicationSettings(key=key, value=storage_value)
             db.add(setting)
+
+        # Determine human-readable old value for audit log (decrypt if needed)
+        old_display_value = None
+        if old_storage_value is not None:
+            if metadata.get("sensitive", False):
+                try:
+                    from app.utils.encryption import decrypt_value
+
+                    old_display_value = decrypt_value(old_storage_value)
+                except Exception:
+                    old_display_value = old_storage_value
+            else:
+                old_display_value = old_storage_value
+
+        # Write audit log entry
+        audit_entry = SettingsAuditLog(
+            key=key,
+            old_value=old_display_value,
+            new_value=value,
+            changed_by=changed_by,
+            action="update",
+        )
+        db.add(audit_entry)
+
         db.commit()
-        logger.info(f"Saved setting {key} to database")
+        logger.info(f"Saved setting {key} to database (changed_by={changed_by})")
         return True
     except SQLAlchemyError as e:
         logger.error(f"Error saving setting {key} to database: {e}")
@@ -963,13 +991,16 @@ def get_all_settings_from_db(db: Session) -> Dict[str, str]:
         return {}
 
 
-def delete_setting_from_db(db: Session, key: str) -> bool:
+def delete_setting_from_db(db: Session, key: str, changed_by: str = "system") -> bool:
     """
     Delete a setting from the database.
 
+    Records an entry in the settings audit log.
+
     Args:
         db: Database session
         key: Setting key to delete
+        changed_by: Username of the admin performing the change (for audit log)
 
     Returns:
         True if successful, False otherwise
@@ -977,9 +1008,33 @@ def delete_setting_from_db(db: Session, key: str) -> bool:
     try:
         setting = db.query(ApplicationSettings).filter(ApplicationSettings.key == key).first()
         if setting:
+            # Capture old value for audit log (decrypt if sensitive)
+            metadata = get_setting_metadata(key)
+            old_display_value = None
+            if setting.value is not None:
+                if metadata.get("sensitive", False):
+                    try:
+                        from app.utils.encryption import decrypt_value
+
+                        old_display_value = decrypt_value(setting.value)
+                    except Exception:
+                        old_display_value = setting.value
+                else:
+                    old_display_value = setting.value
+
             db.delete(setting)
+
+            audit_entry = SettingsAuditLog(
+                key=key,
+                old_value=old_display_value,
+                new_value=None,
+                changed_by=changed_by,
+                action="delete",
+            )
+            db.add(audit_entry)
+
             db.commit()
-            logger.info(f"Deleted setting {key} from database")
+            logger.info(f"Deleted setting {key} from database (changed_by={changed_by})")
             return True
         return False
     except SQLAlchemyError as e:
@@ -1061,3 +1116,162 @@ def validate_setting_value(key: str, value: str) -> Tuple[bool, Optional[str]]:
         return False, "session_secret must be at least 32 characters"
 
     return True, None
+
+
+def get_audit_log(db: Session, limit: int = 100, offset: int = 0) -> List[Dict[str, Any]]:
+    """
+    Retrieve the settings audit log, most recent first.
+
+    Sensitive values are masked in the returned list so the log is safe to
+    display in the admin UI without leaking secrets.
+
+    Args:
+        db: Database session
+        limit: Maximum number of entries to return
+        offset: Number of entries to skip (for pagination)
+
+    Returns:
+        List of audit log entry dicts ordered by changed_at descending
+    """
+    try:
+        entries = (
+            db.query(SettingsAuditLog).order_by(SettingsAuditLog.changed_at.desc()).limit(limit).offset(offset).all()
+        )
+        result = []
+        for entry in entries:
+            meta = get_setting_metadata(entry.key)
+            is_sensitive = meta.get("sensitive", False)
+            result.append(
+                {
+                    "id": entry.id,
+                    "key": entry.key,
+                    "old_value": ("[REDACTED]" if is_sensitive and entry.old_value else entry.old_value),
+                    "new_value": ("[REDACTED]" if is_sensitive and entry.new_value else entry.new_value),
+                    "changed_by": entry.changed_by,
+                    "changed_at": (entry.changed_at.isoformat() if entry.changed_at else None),
+                    "action": entry.action,
+                }
+            )
+        return result
+    except SQLAlchemyError as e:
+        logger.error(f"Error retrieving audit log: {e}")
+        return []
+
+
+def get_setting_history(db: Session, key: str) -> List[Dict[str, Any]]:
+    """
+    Retrieve the change history for a specific setting key, most recent first.
+
+    Sensitive values are masked so the response is safe to surface in the UI.
+
+    Args:
+        db: Database session
+        key: Setting key
+
+    Returns:
+        List of audit log entry dicts for this key
+    """
+    try:
+        entries = (
+            db.query(SettingsAuditLog)
+            .filter(SettingsAuditLog.key == key)
+            .order_by(SettingsAuditLog.changed_at.desc())
+            .all()
+        )
+        meta = get_setting_metadata(key)
+        is_sensitive = meta.get("sensitive", False)
+        result = []
+        for entry in entries:
+            result.append(
+                {
+                    "id": entry.id,
+                    "key": entry.key,
+                    "old_value": ("[REDACTED]" if is_sensitive and entry.old_value else entry.old_value),
+                    "new_value": ("[REDACTED]" if is_sensitive and entry.new_value else entry.new_value),
+                    "changed_by": entry.changed_by,
+                    "changed_at": (entry.changed_at.isoformat() if entry.changed_at else None),
+                    "action": entry.action,
+                }
+            )
+        return result
+    except SQLAlchemyError as e:
+        logger.error(f"Error retrieving history for setting {key}: {e}")
+        return []
+
+
+def rollback_setting(db: Session, key: str, history_id: int, changed_by: str = "system") -> bool:
+    """
+    Revert a setting to the value recorded in a specific audit log entry.
+
+    The value stored in the chosen history entry's ``new_value`` field is
+    re-applied as the current database value.  If that value is ``None``
+    (i.e. the entry recorded a deletion) the setting is removed from the
+    database entirely, reverting to ENV/defaults.
+
+    A new audit log entry is written to record the rollback operation.
+
+    Args:
+        db: Database session
+        key: Setting key to roll back
+        history_id: ID of the SettingsAuditLog entry whose ``new_value``
+                    should become the restored value
+        changed_by: Username performing the rollback (for audit log)
+
+    Returns:
+        True if successful, False if the history entry was not found or an
+        error occurred
+    """
+    try:
+        history_entry = (
+            db.query(SettingsAuditLog).filter(SettingsAuditLog.id == history_id, SettingsAuditLog.key == key).first()
+        )
+        if not history_entry:
+            logger.warning(f"Rollback failed: audit log entry {history_id} not found for key '{key}'")
+            return False
+
+        target_value = history_entry.new_value
+
+        if target_value is None:
+            # The history entry recorded a deletion – reinstate that by deleting the current db value
+            return delete_setting_from_db(db, key, changed_by=changed_by)
+        else:
+            return save_setting_to_db(db, key, target_value, changed_by=changed_by)
+    except SQLAlchemyError as e:
+        logger.error(f"Error rolling back setting {key} to history entry {history_id}: {e}")
+        db.rollback()
+        return False
+
+
+def get_settings_for_export(db: Session, source: str = "db") -> Dict[str, str]:
+    """
+    Collect settings for export as environment variables.
+
+    Args:
+        db: Database session
+        source: ``"db"`` to export only database-persisted settings (default);
+                ``"effective"`` to export the full current runtime configuration
+                (DB overrides ENV overrides application defaults) for every key
+                listed in SETTING_METADATA.
+
+    Returns:
+        Ordered dict mapping uppercase ENV variable names to their string values.
+        Sensitive values are included (the caller is responsible for access control).
+    """
+    if source == "effective":
+        from app.config import settings as app_settings
+
+        db_settings = get_all_settings_from_db(db)
+        result = {}
+        for key in sorted(SETTING_METADATA.keys()):
+            # DB wins, then live settings object (ENV/default)
+            if key in db_settings and db_settings[key] is not None:
+                value = db_settings[key]
+            else:
+                value = getattr(app_settings, key, None)
+            if value is not None:
+                result[key.upper()] = str(value)
+        return result
+    else:
+        # DB only
+        db_settings = get_all_settings_from_db(db)
+        return {k.upper(): v for k, v in sorted(db_settings.items()) if v is not None}
diff --git a/app/utils/settings_sync.py b/app/utils/settings_sync.py
new file mode 100644
index 00000000..8ffd03d1
--- /dev/null
+++ b/app/utils/settings_sync.py
@@ -0,0 +1,86 @@
+"""
+Worker settings synchronisation helper.
+
+When an admin saves a configuration change through the UI, any running Celery
+workers still hold the *old* values in their in-process ``settings`` singleton.
+This module provides two complementary mechanisms to propagate the change:
+
+1. **Publish** (API side): :func:`notify_settings_updated` writes a monotonically
+   increasing timestamp to a Redis key.  This is called immediately after every
+   successful ``save_setting_to_db`` / ``delete_setting_from_db`` operation.
+
+2. **Subscribe** (worker side): :func:`register_settings_reload_signal` installs
+   a Celery ``task_prerun`` signal handler.  Before each task begins the handler
+   reads the Redis version key; if it has changed since the last reload it calls
+   :func:`~app.utils.config_loader.reload_settings_from_db` so the worker picks
+   up the new values *before* executing the task body.
+
+The Redis key used is ``docuelevate:settings_version``.  Workers cache the last
+seen version in a module-level variable to avoid redundant DB round-trips when
+nothing has changed.
+"""
+
+import logging
+import time
+
+import redis
+from celery.signals import task_prerun
+
+logger = logging.getLogger(__name__)
+
+#: Redis key that stores the current settings "version" (epoch timestamp string).
+SETTINGS_VERSION_KEY = "docuelevate:settings_version"
+
+#: Module-level cache: the settings version seen by *this* process on its last reload.
+_last_seen_version: str = ""
+
+
+def notify_settings_updated() -> None:
+    """
+    Publish a settings-updated signal by updating the Redis version key.
+
+    Call this after every successful settings write so that all worker
+    processes know they need to reload their in-memory configuration.
+
+    Errors are caught and logged rather than raised so that a Redis
+    connectivity issue does not prevent the primary save from succeeding.
+    """
+    try:
+        from app.config import settings
+
+        r = redis.from_url(settings.redis_url, socket_connect_timeout=2)
+        version = str(time.time())
+        r.set(SETTINGS_VERSION_KEY, version)
+        logger.debug(f"Settings version bumped to {version}")
+    except Exception as exc:
+        logger.warning(f"Could not publish settings update to Redis: {exc}")
+
+
+def register_settings_reload_signal() -> None:
+    """
+    Install a Celery ``task_prerun`` signal handler for worker processes.
+
+    This should be called once during Celery worker initialisation (e.g. from
+    ``celery_worker.py``).  After registration, every task will check the
+    settings version key in Redis before it starts and reload configuration
+    from the database if a newer version is detected.
+    """
+
+    @task_prerun.connect(weak=False)
+    def _reload_if_stale(sender, **kwargs) -> None:  # type: ignore[misc]
+        """Reload settings from DB if the Redis version key has changed."""
+        global _last_seen_version
+        try:
+            from app.config import settings
+            from app.utils.config_loader import reload_settings_from_db
+
+            r = redis.from_url(settings.redis_url, socket_connect_timeout=2)
+            current_version = (r.get(SETTINGS_VERSION_KEY) or b"").decode()
+            if current_version and current_version != _last_seen_version:
+                reload_settings_from_db(settings)
+                _last_seen_version = current_version
+                logger.info(f"Worker settings reloaded (version={current_version})")
+        except Exception as exc:
+            logger.debug(f"Settings version check skipped: {exc}")
+
+    logger.info("Settings reload signal handler registered on task_prerun")
diff --git a/app/views/settings.py b/app/views/settings.py
index 7379d874..dd34ed03 100644
--- a/app/views/settings.py
+++ b/app/views/settings.py
@@ -103,7 +103,7 @@ async def settings_page(request: Request, db: Session = Depends(get_db)):
                 settings_data[category].append(
                     {
                         "key": key,
-                        "display_value": display_value if display_value is not None else "",
+                        "display_value": (display_value if display_value is not None else ""),
                         "metadata": metadata,
                         "source": source,
                         "source_label": source_label,
@@ -112,11 +112,19 @@ async def settings_page(request: Request, db: Session = Depends(get_db)):
                 )
 
         return templates.TemplateResponse(
-            "settings.html", {"request": request, "settings_data": settings_data, "app_version": settings.version}
+            "settings.html",
+            {
+                "request": request,
+                "settings_data": settings_data,
+                "app_version": settings.version,
+            },
         )
     except Exception as e:
         logger.error(f"Error loading settings page: {e}")
-        raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Failed to load settings page")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to load settings page",
+        )
 
 
 @router.get("/admin/credentials")
@@ -181,4 +189,39 @@ async def credentials_page(request: Request, db: Session = Depends(get_db)):
         )
     except Exception as e:
         logger.error(f"Error loading credentials page: {e}")
-        raise HTTPException(status_code=status.HTTP_500_INTERNAL_SERVER_ERROR, detail="Failed to load credentials page")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to load credentials page",
+        )
+
+
+@router.get("/admin/settings/audit-log")
+@require_login
+@require_admin_access
+async def audit_log_page(request: Request, db: Session = Depends(get_db)):
+    """
+    Settings audit log page - admin only.
+
+    Displays a chronological log of all configuration changes made via the
+    settings UI, including who made the change and what the old/new values
+    were.  Sensitive values are masked.  Provides rollback buttons to revert
+    any setting to a previous value.
+    """
+    from app.utils.settings_service import get_audit_log
+
+    try:
+        entries = get_audit_log(db, limit=200)
+        return templates.TemplateResponse(
+            "audit_log.html",
+            {
+                "request": request,
+                "entries": entries,
+                "app_version": settings.version,
+            },
+        )
+    except Exception as e:
+        logger.error(f"Error loading audit log page: {e}")
+        raise HTTPException(
+            status_code=status.HTTP_500_INTERNAL_SERVER_ERROR,
+            detail="Failed to load audit log page",
+        )
diff --git a/app/views/wizard.py b/app/views/wizard.py
index 27696c8c..7d70d463 100644
--- a/app/views/wizard.py
+++ b/app/views/wizard.py
@@ -10,6 +10,7 @@ from fastapi.responses import RedirectResponse
 from sqlalchemy.orm import Session
 
 from app.utils.settings_service import save_setting_to_db
+from app.utils.settings_sync import notify_settings_updated
 from app.utils.setup_wizard import get_wizard_steps
 from app.views.base import APIRouter, get_db, templates
 
@@ -18,7 +19,7 @@ router = APIRouter()
 
 
 @router.get("/setup")
-async def setup_wizard(request: Request, step: int = 1):
+async def setup_wizard(request: Request, step: int = 1, db: Session = Depends(get_db)):
     """
     Setup wizard for first-time configuration.
 
@@ -41,6 +42,31 @@ async def setup_wizard(request: Request, step: int = 1):
     # Get step category (all settings in a step should have same category)
     step_category = current_settings[0].get("wizard_category", "Configuration") if current_settings else "Configuration"
 
+    # Enrich settings with current live values
+    from app.config import settings as app_settings
+    from app.utils.settings_service import get_setting_from_db
+
+    enriched_settings = []
+    for s in current_settings:
+        key = s["key"]
+        db_val = get_setting_from_db(db, key)
+        env_val = getattr(app_settings, key, None)
+        # Determine current_value and source
+        if db_val is not None:
+            current_value = db_val
+            value_source = "db"
+        elif env_val is not None and str(env_val).strip():
+            current_value = str(env_val)
+            value_source = "env"
+        elif s.get("default") is not None:
+            current_value = s["default"]
+            value_source = "default"
+        else:
+            current_value = ""
+            value_source = "none"
+        enriched_settings.append({**s, "current_value": current_value, "value_source": value_source})
+    current_settings = enriched_settings
+
     return templates.TemplateResponse(
         "setup_wizard.html",
         {
@@ -50,6 +76,7 @@ async def setup_wizard(request: Request, step: int = 1):
             "settings": current_settings,
             "step_category": step_category,
             "progress_percent": int((step / max_step) * 100),
+            "setup_skipped": bool(get_setting_from_db(db, "_setup_wizard_skipped")),
         },
     )
 
@@ -87,6 +114,9 @@ async def setup_wizard_save(request: Request, step: int = Form(...), db: Session
 
         logger.info(f"Setup wizard step {step}: Saved {saved_count} settings")
 
+        if saved_count > 0:
+            notify_settings_updated()
+
         # Determine next step
         max_step = max(wizard_steps.keys())
         next_step = step + 1
@@ -122,3 +152,23 @@ async def setup_wizard_skip(request: Request):
     except Exception as e:
         logger.error(f"Error skipping setup wizard: {e}")
         return RedirectResponse(url="/", status_code=303)
+
+
+@router.get("/setup/undo-skip")
+async def setup_wizard_undo_skip(request: Request, db: Session = Depends(get_db)):
+    """
+    Undo a previously skipped setup wizard.
+
+    Removes the skip marker from the database so the wizard will be
+    presented again on next visit to the home page.  Redirects to
+    step 1 of the wizard immediately.
+    """
+    try:
+        from app.utils.settings_service import delete_setting_from_db
+
+        delete_setting_from_db(db, "_setup_wizard_skipped", changed_by="wizard_undo_skip")
+        logger.info("Setup wizard skip marker removed; redirecting to wizard")
+        return RedirectResponse(url="/setup?step=1", status_code=303)
+    except Exception as e:
+        logger.error(f"Error undoing setup wizard skip: {e}")
+        return RedirectResponse(url="/settings", status_code=303)
diff --git a/frontend/templates/audit_log.html b/frontend/templates/audit_log.html
new file mode 100644
index 00000000..fa16bac6
--- /dev/null
+++ b/frontend/templates/audit_log.html
@@ -0,0 +1,157 @@
+{% extends "base.html" %}
+{% block title %}Settings Audit Log - DocuElevate{% endblock %}
+
+{% block content %}
+<div class="container mx-auto px-4 py-8" x-data="auditLogApp()">
+  <!-- Header -->
+  <div class="mb-8 flex justify-between items-start">
+    <div>
+      <h1 class="text-3xl font-bold mb-2">Settings Audit Log</h1>
+      <p class="text-gray-600">
+        Chronological record of all configuration changes made via the settings UI.
+        Sensitive values are masked. Use the rollback button to revert any setting to a prior value.
+      </p>
+    </div>
+    <a href="/settings"
+       class="inline-flex items-center px-4 py-2 border border-gray-300 text-sm font-medium rounded-md text-gray-700 bg-white hover:bg-gray-50 focus:outline-none focus:ring-2 focus:ring-offset-2 focus:ring-blue-500">
+      <i class="fas fa-cog mr-2"></i> Back to Settings
+    </a>
+  </div>
+
+  <!-- Alert Messages -->
+  <div x-show="showAlert" x-transition class="mb-4">
+    <div :class="alertType === 'success' ? 'bg-green-100 border-green-500 text-green-700' : 'bg-red-100 border-red-500 text-red-700'"
+         class="border-l-4 p-4" role="alert">
+      <p class="font-bold" x-text="alertTitle"></p>
+      <p x-text="alertMessage"></p>
+    </div>
+  </div>
+
+  {% if entries %}
+  <div class="bg-white shadow rounded-lg overflow-hidden">
+    <table class="min-w-full divide-y divide-gray-200">
+      <thead class="bg-gray-50">
+        <tr>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">When</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">Changed By</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">Setting Key</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">Action</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">Old Value</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">New Value</th>
+          <th class="px-4 py-3 text-left text-xs font-medium text-gray-500 uppercase tracking-wider">Rollback</th>
+        </tr>
+      </thead>
+      <tbody class="bg-white divide-y divide-gray-200">
+        {% for entry in entries %}
+        <tr class="hover:bg-gray-50">
+          <td class="px-4 py-3 text-sm text-gray-600 whitespace-nowrap">{{ entry.changed_at }}</td>
+          <td class="px-4 py-3 text-sm text-gray-800 font-medium">{{ entry.changed_by }}</td>
+          <td class="px-4 py-3 text-sm font-mono text-blue-700">{{ entry.key }}</td>
+          <td class="px-4 py-3 text-sm">
+            {% if entry.action == 'delete' %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-red-100 text-red-800">delete</span>
+            {% elif entry.action == 'rollback' %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-purple-100 text-purple-800">rollback</span>
+            {% else %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-green-100 text-green-800">update</span>
+            {% endif %}
+          </td>
+          <td class="px-4 py-3 text-sm text-gray-600 font-mono max-w-xs truncate" title="{{ entry.old_value or '' }}">
+            {% if entry.old_value %}
+              <span class="text-gray-500">{{ entry.old_value }}</span>
+            {% else %}
+              <span class="italic text-gray-400">—</span>
+            {% endif %}
+          </td>
+          <td class="px-4 py-3 text-sm text-gray-800 font-mono max-w-xs truncate" title="{{ entry.new_value or '' }}">
+            {% if entry.new_value %}
+              {{ entry.new_value }}
+            {% else %}
+              <span class="italic text-gray-400">— (deleted)</span>
+            {% endif %}
+          </td>
+          <td class="px-4 py-3 text-sm">
+            <button
+              type="button"
+              @click="rollback('{{ entry.key }}', {{ entry.id }}, '{{ entry.new_value or '' }}')"
+              :disabled="rollingBack === {{ entry.id }}"
+              class="inline-flex items-center px-2 py-1 text-xs font-medium rounded border border-gray-300 text-gray-700 bg-white hover:bg-yellow-50 hover:border-yellow-400 focus:outline-none focus:ring-2 focus:ring-offset-1 focus:ring-yellow-400 disabled:opacity-50 disabled:cursor-not-allowed"
+              title="Revert '{{ entry.key }}' to the value in this log entry"
+            >
+              <span x-show="rollingBack !== {{ entry.id }}"><i class="fas fa-undo mr-1"></i>Rollback</span>
+              <span x-show="rollingBack === {{ entry.id }}">Working…</span>
+            </button>
+          </td>
+        </tr>
+        {% endfor %}
+      </tbody>
+    </table>
+  </div>
+  {% else %}
+  <div class="bg-white shadow rounded-lg p-8 text-center text-gray-500">
+    <i class="fas fa-history text-4xl mb-4 block text-gray-300"></i>
+    <p class="text-lg">No configuration changes recorded yet.</p>
+    <p class="text-sm mt-2">Changes you make on the <a href="/settings" class="text-blue-600 hover:underline">Settings page</a> will appear here.</p>
+  </div>
+  {% endif %}
+</div>
+
+<script>
+function auditLogApp() {
+  return {
+    rollingBack: null,
+    showAlert: false,
+    alertType: 'success',
+    alertTitle: '',
+    alertMessage: '',
+
+    showSuccessAlert(title, message) {
+      this.alertType = 'success';
+      this.alertTitle = title;
+      this.alertMessage = message;
+      this.showAlert = true;
+      setTimeout(() => this.showAlert = false, 6000);
+    },
+
+    showErrorAlert(title, message) {
+      this.alertType = 'error';
+      this.alertTitle = title;
+      this.alertMessage = message;
+      this.showAlert = true;
+      setTimeout(() => this.showAlert = false, 10000);
+    },
+
+    async rollback(key, historyId, targetValue) {
+      const label = targetValue ? `'${targetValue}'` : '(deleted / ENV default)';
+      if (!confirm(`Revert '${key}' to ${label}?\n\nThis will write a new audit log entry.`)) {
+        return;
+      }
+
+      this.rollingBack = historyId;
+      this.showAlert = false;
+
+      try {
+        const response = await fetch(`/api/settings/${key}/rollback/${historyId}`, {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+        });
+
+        const result = await response.json();
+
+        if (response.ok && result.success) {
+          this.showSuccessAlert('Rollback Successful', `Setting '${key}' has been reverted. Reloading…`);
+          setTimeout(() => window.location.reload(), 1500);
+        } else {
+          this.showErrorAlert('Rollback Failed', result.detail || 'Unknown error');
+        }
+      } catch (error) {
+        console.error('Rollback error:', error);
+        this.showErrorAlert('Error', 'Failed to perform rollback. Please try again.');
+      } finally {
+        this.rollingBack = null;
+      }
+    }
+  };
+}
+</script>
+{% endblock %}
diff --git a/frontend/templates/settings.html b/frontend/templates/settings.html
index 61898dab..36afbd72 100644
--- a/frontend/templates/settings.html
+++ b/frontend/templates/settings.html
@@ -13,10 +13,44 @@
 <div class="container mx-auto px-4 py-8" x-data="settingsApp()">
   <!-- Header -->
   <div class="mb-8">
-    <h1 class="text-3xl font-bold mb-2">Application Settings</h1>
-    <p class="text-gray-600">
-      This is a convenience feature to view and edit application settings through the web interface.
-    </p>
+    <div class="flex justify-between items-start">
+      <div>
+        <h1 class="text-3xl font-bold mb-2">Application Settings</h1>
+        <p class="text-gray-600">
+          This is a convenience feature to view and edit application settings through the web interface.
+        </p>
+      </div>
+      <div class="flex items-center gap-2">
+        <a href="/setup?step=1"
+           class="inline-flex items-center px-4 py-2 border border-gray-300 text-sm font-medium rounded-md text-gray-700 bg-white hover:bg-gray-50">
+          <i class="fas fa-magic mr-2"></i> Setup Wizard
+        </a>
+        <div class="relative" x-data="{ exportOpen: false }">
+          <button @click="exportOpen = !exportOpen"
+                  class="inline-flex items-center px-4 py-2 border border-gray-300 text-sm font-medium rounded-md text-gray-700 bg-white hover:bg-gray-50">
+            <i class="fas fa-download mr-2"></i> Export .env
+            <i class="fas fa-chevron-down ml-1 text-xs"></i>
+          </button>
+          <div x-show="exportOpen" @click.outside="exportOpen = false" x-transition
+               class="absolute right-0 mt-1 w-52 bg-white border border-gray-200 rounded-md shadow-lg z-10">
+            <a href="/api/settings/export-env?source=db"
+               class="block px-4 py-2 text-sm text-gray-700 hover:bg-gray-50"
+               @click="exportOpen = false">
+              <i class="fas fa-database mr-2 text-green-600"></i>DB settings only
+            </a>
+            <a href="/api/settings/export-env?source=effective"
+               class="block px-4 py-2 text-sm text-gray-700 hover:bg-gray-50"
+               @click="exportOpen = false">
+              <i class="fas fa-layer-group mr-2 text-blue-600"></i>Full effective config
+            </a>
+          </div>
+        </div>
+        <a href="/admin/settings/audit-log"
+           class="inline-flex items-center px-4 py-2 border border-gray-300 text-sm font-medium rounded-md text-gray-700 bg-white hover:bg-gray-50 focus:outline-none focus:ring-2 focus:ring-offset-2 focus:ring-blue-500">
+          <i class="fas fa-history mr-2"></i> Audit Log
+        </a>
+      </div>
+    </div>
     <div class="bg-blue-50 border-l-4 border-blue-500 text-blue-700 p-4 my-4" role="alert">
       <p class="font-bold">📋 Settings Precedence Order:</p>
       <ul class="list-disc list-inside ml-4 mt-2">
@@ -150,6 +184,22 @@
               </div>
               {% endif %}
             </div>
+
+            <!-- Per-setting Save button (visible only when value has changed) -->
+            <div class="ml-4 flex-shrink-0 flex flex-col items-end gap-1 pt-1">
+              <button
+                type="button"
+                x-show="formData['{{ setting.key }}'] !== originalData['{{ setting.key }}']"
+                x-transition
+                @click="saveSetting('{{ setting.key }}')"
+                :disabled="savingKey === '{{ setting.key }}'"
+                class="px-3 py-1 text-sm bg-green-600 text-white rounded-md hover:bg-green-700 focus:outline-none focus:ring-2 focus:ring-offset-2 focus:ring-green-500 disabled:opacity-50 disabled:cursor-not-allowed whitespace-nowrap"
+                title="Save this setting"
+              >
+                <span x-show="savingKey !== '{{ setting.key }}'"><i class="fas fa-save mr-1"></i>Save</span>
+                <span x-show="savingKey === '{{ setting.key }}'">Saving…</span>
+              </button>
+            </div>
           </div>
         </div>
         {% endfor %}
@@ -185,6 +235,7 @@ function settingsApp() {
     originalData: {},
     showPassword: {},
     saving: false,
+    savingKey: null,
     showAlert: false,
     alertType: 'success',
     alertTitle: '',
@@ -230,6 +281,38 @@ function settingsApp() {
       this.showAlert = false;
     },
 
+    async saveSetting(key) {
+      this.savingKey = key;
+      this.hideAlert();
+
+      try {
+        const value = this.formData[key];
+        const response = await fetch(`/api/settings/${key}`, {
+          method: 'POST',
+          headers: { 'Content-Type': 'application/json' },
+          body: JSON.stringify({ key, value }),
+        });
+
+        const result = await response.json();
+
+        if (response.ok && result.success) {
+          this.originalData[key] = value;
+          let message = `Setting '${key}' saved successfully.`;
+          if (result.restart_required) {
+            message += ' Please restart the application for this change to take effect.';
+          }
+          this.showSuccessAlert('Setting Saved', message);
+        } else {
+          this.showErrorAlert('Save Failed', result.detail || 'Unknown error');
+        }
+      } catch (error) {
+        console.error('Error saving setting:', error);
+        this.showErrorAlert('Error', 'Failed to save setting. Please try again.');
+      } finally {
+        this.savingKey = null;
+      }
+    },
+
     async saveSettings() {
       this.saving = true;
       this.hideAlert();
diff --git a/frontend/templates/setup_wizard.html b/frontend/templates/setup_wizard.html
index ed284dda..08d63037 100644
--- a/frontend/templates/setup_wizard.html
+++ b/frontend/templates/setup_wizard.html
@@ -134,13 +134,21 @@
               type="{% if setting.sensitive %}password{% else %}text{% endif %}"
               id="{{ setting.key }}"
               name="{{ setting.key }}"
-              value="{{ setting.default if setting.default else '' }}"
+              value="{{ setting.current_value if setting.current_value else '' }}"
               class="wizard-input w-full px-4 py-3 border border-gray-300 rounded-md shadow-sm focus:outline-none focus:ring-2 focus:ring-indigo-500 focus:border-transparent"
               placeholder="{{ setting.description }}"
               {% if setting.default is none or setting.key in ['admin_password', 'openai_api_key', 'azure_ai_key', 'azure_endpoint'] %}required{% endif %}
             />
             {% endif %}
 
+            {% if setting.value_source == 'db' %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-green-100 text-green-800 mt-1">DB</span>
+            {% elif setting.value_source == 'env' %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-blue-100 text-blue-800 mt-1">ENV</span>
+            {% elif setting.value_source == 'default' %}
+            <span class="inline-flex items-center px-2 py-0.5 rounded text-xs font-medium bg-gray-100 text-gray-800 mt-1">DEFAULT</span>
+            {% endif %}
+
             {% if setting.key == 'admin_password' %}
             <p class="mt-2 text-xs text-amber-600">
               <i class="fas fa-exclamation-triangle"></i>
@@ -159,7 +167,12 @@
         <!-- Navigation Buttons -->
         <div class="flex justify-between items-center mt-8 pt-6 border-t border-gray-200">
           <div>
-            {% if current_step == 1 %}
+            {% if setup_skipped %}
+            <span class="text-sm text-amber-600 font-medium">
+              <i class="fas fa-exclamation-triangle"></i>
+              Setup was previously skipped.
+            </span>
+            {% elif current_step == 1 %}
             <a href="/setup/skip" class="text-sm text-gray-600 hover:text-gray-900">
               <i class="fas fa-forward"></i>
               Skip setup (advanced users)
@@ -200,6 +213,12 @@
       <p class="text-xs text-gray-500 mt-2">
         Fields marked with <span class="text-red-600">*</span> are required.
       </p>
+      {% if setup_skipped %}
+      <p class="text-xs text-amber-600 mt-2">
+        <i class="fas fa-info-circle"></i>
+        You previously skipped the setup wizard. <a href="/setup/undo-skip" class="underline hover:text-amber-800">Click here to re-run it.</a>
+      </p>
+      {% endif %}
     </div>
 
   </div>
diff --git a/tests/test_api_dropbox.py b/tests/test_api_dropbox.py
index b664a9e8..f3d3a7a1 100644
--- a/tests/test_api_dropbox.py
+++ b/tests/test_api_dropbox.py
@@ -107,7 +107,8 @@ class TestUpdateDropboxSettings:
         """Test that exceptions return 500 error."""
         # Make setting the attribute raise an exception
         type(mock_settings).dropbox_refresh_token = property(
-            lambda self: "", lambda self, v: (_ for _ in ()).throw(RuntimeError("forced"))
+            lambda self: "",
+            lambda self, v: (_ for _ in ()).throw(RuntimeError("forced")),
         )
 
         response = client.post(
@@ -264,15 +265,16 @@ class TestSaveDropboxSettings:
 
     @patch("app.api.dropbox.settings")
     def test_save_settings_env_not_found(self, mock_settings, client):
-        """Test error when .env file is not found."""
-        # The endpoint constructs the env path using __file__
+        """Test that missing .env file is non-fatal — DB write still succeeds."""
         with patch("os.path.exists", return_value=False):
             response = client.post(
                 "/api/dropbox/save-settings",
                 data={"refresh_token": "test-token"},
             )
 
-        assert response.status_code == 500
+        # .env write is best-effort; endpoint should still succeed via DB write
+        assert response.status_code == 200
+        assert response.json()["status"] == "success"
 
     @patch("app.api.dropbox.settings")
     def test_save_settings_success(self, mock_settings, client, tmp_path):
@@ -389,7 +391,7 @@ class TestSaveDropboxSettings:
 
     @patch("app.api.dropbox.settings")
     def test_save_settings_io_error(self, mock_settings, client, tmp_path):
-        """Test handling of I/O errors when saving settings."""
+        """Test that I/O errors on .env write are non-fatal — DB write still succeeds."""
         mock_settings.dropbox_refresh_token = ""
 
         # Create a temporary .env file
@@ -407,6 +409,6 @@ class TestSaveDropboxSettings:
                 data={"refresh_token": "new-token"},
             )
 
-        assert response.status_code == 500
-        data = response.json()
-        assert "Failed to save Dropbox settings" in data["detail"]
+        # .env write is best-effort; endpoint should still succeed via DB write
+        assert response.status_code == 200
+        assert response.json()["status"] == "success"
diff --git a/tests/test_api_onedrive_comprehensive.py b/tests/test_api_onedrive_comprehensive.py
index 1da7d30d..1019031b 100644
--- a/tests/test_api_onedrive_comprehensive.py
+++ b/tests/test_api_onedrive_comprehensive.py
@@ -119,13 +119,19 @@ class TestTestOneDriveToken:
         # Mock token refresh response
         mock_post_response = Mock()
         mock_post_response.status_code = 200
-        mock_post_response.json.return_value = {"access_token": "test_access_token", "expires_in": 3600}
+        mock_post_response.json.return_value = {
+            "access_token": "test_access_token",
+            "expires_in": 3600,
+        }
         mock_post.return_value = mock_post_response
 
         # Mock user info response
         mock_get_response = Mock()
         mock_get_response.status_code = 200
-        mock_get_response.json.return_value = {"displayName": "Test User", "userPrincipalName": "test@example.com"}
+        mock_get_response.json.return_value = {
+            "displayName": "Test User",
+            "userPrincipalName": "test@example.com",
+        }
         mock_get.return_value = mock_get_response
 
         response = client.get("/api/onedrive/test-token")
@@ -198,7 +204,10 @@ class TestTestOneDriveToken:
         # Mock user info
         mock_get_response = Mock()
         mock_get_response.status_code = 200
-        mock_get_response.json.return_value = {"displayName": "Test User", "userPrincipalName": "test@example.com"}
+        mock_get_response.json.return_value = {
+            "displayName": "Test User",
+            "userPrincipalName": "test@example.com",
+        }
         mock_get.return_value = mock_get_response
 
         with patch("os.path.exists", return_value=False):
@@ -209,12 +218,23 @@ class TestTestOneDriveToken:
 
     @patch("requests.post")
     @patch("requests.get")
-    @patch("builtins.open", new_callable=mock_open, read_data="ONEDRIVE_REFRESH_TOKEN=old_token\n")
+    @patch(
+        "builtins.open",
+        new_callable=mock_open,
+        read_data="ONEDRIVE_REFRESH_TOKEN=old_token\n",
+    )
     @patch("os.path.exists")
     @patch("os.path.dirname")
     @patch("app.config.settings")
     def test_test_token_updates_env_file(
-        self, mock_settings, mock_dirname, mock_exists, mock_file, mock_get, mock_post, client: TestClient
+        self,
+        mock_settings,
+        mock_dirname,
+        mock_exists,
+        mock_file,
+        mock_get,
+        mock_post,
+        client: TestClient,
     ):
         """Test that new refresh token is saved to .env file."""
         mock_settings.onedrive_refresh_token = "old_token"
@@ -238,7 +258,10 @@ class TestTestOneDriveToken:
         # Mock user info
         mock_get_response = Mock()
         mock_get_response.status_code = 200
-        mock_get_response.json.return_value = {"displayName": "Test User", "userPrincipalName": "test@example.com"}
+        mock_get_response.json.return_value = {
+            "displayName": "Test User",
+            "userPrincipalName": "test@example.com",
+        }
         mock_get.return_value = mock_get_response
 
         response = client.get("/api/onedrive/test-token")
@@ -258,7 +281,10 @@ class TestTestOneDriveToken:
         # Mock successful refresh
         mock_post_response = Mock()
         mock_post_response.status_code = 200
-        mock_post_response.json.return_value = {"access_token": "test_access_token", "expires_in": 3600}
+        mock_post_response.json.return_value = {
+            "access_token": "test_access_token",
+            "expires_in": 3600,
+        }
         mock_post.return_value = mock_post_response
 
         # Mock failed user info
@@ -343,17 +369,24 @@ class TestSaveOneDriveSettings:
     @patch("os.path.exists")
     @patch("os.path.dirname")
     def test_save_settings_env_file_not_found(self, mock_dirname, mock_exists, client: TestClient):
-        """Test save when .env file doesn't exist."""
+        """Test that missing .env file is non-fatal — DB write still succeeds."""
         mock_exists.return_value = False
         mock_dirname.return_value = "/app"
 
-        response = client.post("/api/onedrive/save-settings", data={"refresh_token": "token", "tenant_id": "common"})
+        response = client.post(
+            "/api/onedrive/save-settings",
+            data={"refresh_token": "token", "tenant_id": "common"},
+        )
 
-        assert response.status_code == 500
-        data = response.json()
-        assert "could not find .env file" in data["detail"].lower()
+        # .env write is best-effort; endpoint should still succeed via DB write
+        assert response.status_code == 200
+        assert response.json()["status"] == "success"
 
-    @patch("builtins.open", new_callable=mock_open, read_data="ONEDRIVE_REFRESH_TOKEN=old_token\n")
+    @patch(
+        "builtins.open",
+        new_callable=mock_open,
+        read_data="ONEDRIVE_REFRESH_TOKEN=old_token\n",
+    )
     @patch("os.path.exists")
     @patch("os.path.dirname")
     @patch("app.config.settings")
@@ -365,12 +398,17 @@ class TestSaveOneDriveSettings:
         mock_dirname.return_value = "/app"
 
         response = client.post(
-            "/api/onedrive/save-settings", data={"refresh_token": "updated_token", "tenant_id": "common"}
+            "/api/onedrive/save-settings",
+            data={"refresh_token": "updated_token", "tenant_id": "common"},
         )
 
         assert response.status_code == 200
 
-    @patch("builtins.open", new_callable=mock_open, read_data="# ONEDRIVE_CLIENT_ID=commented\n")
+    @patch(
+        "builtins.open",
+        new_callable=mock_open,
+        read_data="# ONEDRIVE_CLIENT_ID=commented\n",
+    )
     @patch("os.path.exists")
     @patch("os.path.dirname")
     @patch("app.config.settings")
@@ -383,7 +421,11 @@ class TestSaveOneDriveSettings:
 
         response = client.post(
             "/api/onedrive/save-settings",
-            data={"refresh_token": "token", "client_id": "new_client_id", "tenant_id": "common"},
+            data={
+                "refresh_token": "token",
+                "client_id": "new_client_id",
+                "tenant_id": "common",
+            },
         )
 
         assert response.status_code == 200
@@ -401,7 +443,11 @@ class TestSaveOneDriveSettings:
 
         response = client.post(
             "/api/onedrive/save-settings",
-            data={"refresh_token": "new_token", "folder_path": "/New/Path", "tenant_id": "common"},
+            data={
+                "refresh_token": "new_token",
+                "folder_path": "/New/Path",
+                "tenant_id": "common",
+            },
         )
 
         assert response.status_code == 200
@@ -415,12 +461,17 @@ class TestSaveOneDriveSettings:
     @patch("os.path.exists")
     @patch("os.path.dirname")
     def test_save_settings_exception_handling(self, mock_dirname, mock_exists, client: TestClient):
-        """Test exception handling in save settings."""
+        """Test that exceptions in .env write are non-fatal — DB write still succeeds."""
         mock_exists.side_effect = Exception("Unexpected error")
 
-        response = client.post("/api/onedrive/save-settings", data={"refresh_token": "token", "tenant_id": "common"})
+        response = client.post(
+            "/api/onedrive/save-settings",
+            data={"refresh_token": "token", "tenant_id": "common"},
+        )
 
-        assert response.status_code == 500
+        # .env write exception is caught; endpoint succeeds via DB write
+        assert response.status_code == 200
+        assert response.json()["status"] == "success"
 
 
 @pytest.mark.unit
@@ -455,7 +506,8 @@ class TestUpdateOneDriveSettings:
         mock_get_token.return_value = "test_token"
 
         response = client.post(
-            "/api/onedrive/update-settings", data={"refresh_token": "new_token", "tenant_id": "common"}
+            "/api/onedrive/update-settings",
+            data={"refresh_token": "new_token", "tenant_id": "common"},
         )
 
         assert response.status_code == 200
@@ -467,7 +519,8 @@ class TestUpdateOneDriveSettings:
         mock_get_token.side_effect = Exception("Token invalid")
 
         response = client.post(
-            "/api/onedrive/update-settings", data={"refresh_token": "bad_token", "tenant_id": "common"}
+            "/api/onedrive/update-settings",
+            data={"refresh_token": "bad_token", "tenant_id": "common"},
         )
 
         assert response.status_code == 200
@@ -486,9 +539,13 @@ class TestUpdateOneDriveSettings:
         """Test exception handling in update settings."""
         mock_settings.onedrive_refresh_token = None
 
-        with patch("app.tasks.upload_to_onedrive.get_onedrive_token", side_effect=Exception("Fatal error")):
+        with patch(
+            "app.tasks.upload_to_onedrive.get_onedrive_token",
+            side_effect=Exception("Fatal error"),
+        ):
             response = client.post(
-                "/api/onedrive/update-settings", data={"refresh_token": "token", "tenant_id": "common"}
+                "/api/onedrive/update-settings",
+                data={"refresh_token": "token", "tenant_id": "common"},
             )
 
         # Should still update settings even if test fails
@@ -578,7 +635,10 @@ class TestOneDriveIntegration:
         with patch("app.tasks.upload_to_onedrive.get_onedrive_token"):
             response = client.post(
                 "/api/onedrive/update-settings",
-                data={"refresh_token": token_data["refresh_token"], "tenant_id": "common"},
+                data={
+                    "refresh_token": token_data["refresh_token"],
+                    "tenant_id": "common",
+                },
             )
 
             assert response.status_code == 200
@@ -606,7 +666,10 @@ class TestOneDriveIntegration:
 
         mock_get_response = Mock()
         mock_get_response.status_code = 200
-        mock_get_response.json.return_value = {"displayName": "Test User", "userPrincipalName": "test@example.com"}
+        mock_get_response.json.return_value = {
+            "displayName": "Test User",
+            "userPrincipalName": "test@example.com",
+        }
         mock_get.return_value = mock_get_response
 
         with patch("os.path.exists", return_value=False):
diff --git a/tests/test_settings_audit_log.py b/tests/test_settings_audit_log.py
new file mode 100644
index 00000000..79021423
--- /dev/null
+++ b/tests/test_settings_audit_log.py
@@ -0,0 +1,414 @@
+"""Tests for the settings audit log, rollback, per-option save, and worker sync features."""
+
+import asyncio
+from unittest.mock import MagicMock, patch
+
+import pytest
+from sqlalchemy import create_engine
+from sqlalchemy.orm import sessionmaker
+from sqlalchemy.pool import StaticPool
+
+from app.database import Base
+from app.models import SettingsAuditLog
+
+# ---------------------------------------------------------------------------
+# Shared DB fixture
+# ---------------------------------------------------------------------------
+
+
+@pytest.fixture()
+def db_session():
+    engine = create_engine(
+        "sqlite:///:memory:",
+        connect_args={"check_same_thread": False},
+        poolclass=StaticPool,
+    )
+    Base.metadata.create_all(bind=engine)
+    Session = sessionmaker(autocommit=False, autoflush=False, bind=engine)
+    session = Session()
+    try:
+        yield session
+    finally:
+        session.close()
+        Base.metadata.drop_all(bind=engine)
+
+
+# ===========================================================================
+# A) Audit log written on save
+# ===========================================================================
+
+
+@pytest.mark.unit
+class TestAuditLogOnSave:
+    """Audit log entries are created when settings are saved or deleted."""
+
+    def test_save_creates_audit_entry(self, db_session):
+        from app.utils.settings_service import save_setting_to_db
+
+        result = save_setting_to_db(db_session, "workdir", "/new/path", changed_by="alice")
+
+        assert result is True
+        entry = db_session.query(SettingsAuditLog).filter_by(key="workdir").first()
+        assert entry is not None
+        assert entry.action == "update"
+        assert entry.new_value == "/new/path"
+        assert entry.changed_by == "alice"
+        assert entry.old_value is None  # was not previously set
+
+    def test_update_records_old_value(self, db_session):
+        from app.utils.settings_service import save_setting_to_db
+
+        # Set initial value
+        save_setting_to_db(db_session, "workdir", "/old/path", changed_by="admin")
+        # Update
+        save_setting_to_db(db_session, "workdir", "/new/path", changed_by="bob")
+
+        entries = db_session.query(SettingsAuditLog).filter_by(key="workdir").all()
+        assert len(entries) == 2
+        # Second entry should have old_value from first write
+        update_entry = entries[1]
+        assert update_entry.old_value == "/old/path"
+        assert update_entry.new_value == "/new/path"
+
+    def test_delete_creates_audit_entry(self, db_session):
+        from app.utils.settings_service import delete_setting_from_db, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/some/path", changed_by="admin")
+        result = delete_setting_from_db(db_session, "workdir", changed_by="carol")
+
+        assert result is True
+        delete_entry = db_session.query(SettingsAuditLog).filter_by(key="workdir", action="delete").first()
+        assert delete_entry is not None
+        assert delete_entry.old_value == "/some/path"
+        assert delete_entry.new_value is None
+        assert delete_entry.changed_by == "carol"
+
+    def test_delete_nonexistent_returns_false_no_entry(self, db_session):
+        from app.utils.settings_service import delete_setting_from_db
+
+        result = delete_setting_from_db(db_session, "nonexistent_key", changed_by="admin")
+
+        assert result is False
+        assert db_session.query(SettingsAuditLog).count() == 0
+
+    def test_default_changed_by_is_system(self, db_session):
+        from app.utils.settings_service import save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/tmp")
+
+        entry = db_session.query(SettingsAuditLog).first()
+        assert entry.changed_by == "system"
+
+
+# ===========================================================================
+# C) Audit log retrieval
+# ===========================================================================
+
+
+@pytest.mark.unit
+class TestGetAuditLog:
+    """get_audit_log returns entries, masks sensitive values."""
+
+    def test_returns_all_entries_most_recent_first(self, db_session):
+        from app.utils.settings_service import get_audit_log, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/first", changed_by="u1")
+        save_setting_to_db(db_session, "workdir", "/second", changed_by="u2")
+
+        log = get_audit_log(db_session, limit=100)
+
+        assert len(log) == 2
+        # Most recent first
+        assert log[0]["new_value"] == "/second"
+        assert log[1]["new_value"] == "/first"
+
+    def test_sensitive_values_are_masked(self, db_session):
+        from app.utils.settings_service import get_audit_log, save_setting_to_db
+
+        save_setting_to_db(db_session, "openai_api_key", "sk-secret123", changed_by="admin")
+
+        log = get_audit_log(db_session)
+
+        entry = next(e for e in log if e["key"] == "openai_api_key")
+        assert entry["new_value"] == "[REDACTED]"
+
+    def test_required_fields_present(self, db_session):
+        from app.utils.settings_service import get_audit_log, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/path", changed_by="alice")
+
+        log = get_audit_log(db_session)
+
+        assert len(log) == 1
+        entry = log[0]
+        for field in (
+            "id",
+            "key",
+            "old_value",
+            "new_value",
+            "changed_by",
+            "changed_at",
+            "action",
+        ):
+            assert field in entry
+
+    def test_limit_and_offset(self, db_session):
+        from app.utils.settings_service import get_audit_log, save_setting_to_db
+
+        for i in range(5):
+            save_setting_to_db(db_session, "workdir", f"/path{i}", changed_by="admin")
+
+        first_page = get_audit_log(db_session, limit=3, offset=0)
+        second_page = get_audit_log(db_session, limit=3, offset=3)
+
+        assert len(first_page) == 3
+        assert len(second_page) == 2
+
+
+# ===========================================================================
+# C) Per-key history
+# ===========================================================================
+
+
+@pytest.mark.unit
+class TestGetSettingHistory:
+    """get_setting_history returns only entries for the requested key."""
+
+    def test_returns_only_matching_key(self, db_session):
+        from app.utils.settings_service import get_setting_history, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/wdir", changed_by="admin")
+        save_setting_to_db(db_session, "debug", "true", changed_by="admin")
+
+        history = get_setting_history(db_session, "workdir")
+
+        assert len(history) == 1
+        assert history[0]["key"] == "workdir"
+
+    def test_returns_empty_list_for_unknown_key(self, db_session):
+        from app.utils.settings_service import get_setting_history
+
+        history = get_setting_history(db_session, "totally_unknown_key")
+
+        assert history == []
+
+
+# ===========================================================================
+# D) Rollback
+# ===========================================================================
+
+
+@pytest.mark.unit
+class TestRollbackSetting:
+    """rollback_setting reinstates the value from a given audit log entry."""
+
+    def test_rollback_to_previous_value(self, db_session):
+        from app.utils.settings_service import get_setting_from_db, rollback_setting, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/v1", changed_by="admin")  # entry id 1
+        save_setting_to_db(db_session, "workdir", "/v2", changed_by="admin")  # entry id 2
+
+        first_entry = db_session.query(SettingsAuditLog).filter_by(key="workdir").first()
+        # first entry has new_value="/v1"
+        success = rollback_setting(db_session, "workdir", first_entry.id, changed_by="rollbacker")
+
+        assert success is True
+        current = get_setting_from_db(db_session, "workdir")
+        assert current == "/v1"
+
+    def test_rollback_creates_new_audit_entry(self, db_session):
+        from app.utils.settings_service import rollback_setting, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/v1", changed_by="admin")
+        entry = db_session.query(SettingsAuditLog).filter_by(key="workdir").first()
+
+        initial_count = db_session.query(SettingsAuditLog).count()
+        rollback_setting(db_session, "workdir", entry.id, changed_by="rollbacker")
+
+        assert db_session.query(SettingsAuditLog).count() == initial_count + 1
+
+    def test_rollback_wrong_history_id_returns_false(self, db_session):
+        from app.utils.settings_service import rollback_setting, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/v1", changed_by="admin")
+
+        result = rollback_setting(db_session, "workdir", 9999, changed_by="admin")
+
+        assert result is False
+
+    def test_rollback_wrong_key_returns_false(self, db_session):
+        from app.utils.settings_service import rollback_setting, save_setting_to_db
+
+        save_setting_to_db(db_session, "workdir", "/v1", changed_by="admin")
+        entry = db_session.query(SettingsAuditLog).filter_by(key="workdir").first()
+
+        # Pass wrong key for the history ID
+        result = rollback_setting(db_session, "debug", entry.id, changed_by="admin")
+
+        assert result is False
+
+
+# ===========================================================================
+# B) Worker sync – settings_sync module
+# ===========================================================================
+
+
+@pytest.mark.unit
+class TestNotifySettingsUpdated:
+    """notify_settings_updated publishes the settings version key to Redis."""
+
+    def test_sets_redis_key(self):
+        from app.utils.settings_sync import SETTINGS_VERSION_KEY, notify_settings_updated
+
+        mock_redis = MagicMock()
+        mock_redis_instance = MagicMock()
+        mock_redis.return_value = mock_redis_instance
+
+        with patch("app.utils.settings_sync.redis") as mock_redis_module:
+            mock_redis_module.from_url.return_value = mock_redis_instance
+            notify_settings_updated()
+
+        mock_redis_instance.set.assert_called_once()
+        call_args = mock_redis_instance.set.call_args[0]
+        assert call_args[0] == SETTINGS_VERSION_KEY
+
+    def test_does_not_raise_on_redis_failure(self):
+        """notify_settings_updated must not propagate Redis errors."""
+        from app.utils.settings_sync import notify_settings_updated
+
+        with patch("app.utils.settings_sync.redis") as mock_redis_module:
+            mock_redis_module.from_url.side_effect = Exception("Redis down")
+            # Should not raise
+            notify_settings_updated()
+
+
+@pytest.mark.unit
+class TestRegisterSettingsReloadSignal:
+    """register_settings_reload_signal installs a task_prerun handler."""
+
+    def test_registers_without_error(self):
+        from app.utils.settings_sync import register_settings_reload_signal
+
+        with patch("app.utils.settings_sync.task_prerun") as mock_signal:
+            mock_signal.connect = MagicMock()
+            # Call it – the decorator calls task_prerun.connect(weak=False)
+            register_settings_reload_signal()
+        # If no exception is raised the registration succeeded
+
+
+# ===========================================================================
+# API endpoint – audit log
+# ===========================================================================
+
+
+@pytest.mark.integration
+class TestAuditLogEndpoint:
+    """GET /api/settings/audit-log requires admin access."""
+
+    def test_requires_admin(self, client):
+        response = client.get("/api/settings/audit-log")
+        assert response.status_code in [302, 401, 403]
+
+    @patch("app.api.settings.get_audit_log")
+    def test_returns_entries_for_admin(self, mock_get_log):
+        from app.api.settings import list_audit_log
+
+        mock_get_log.return_value = [
+            {
+                "id": 1,
+                "key": "workdir",
+                "old_value": None,
+                "new_value": "/tmp",
+                "changed_by": "admin",
+                "changed_at": "2024-01-01T00:00:00",
+                "action": "update",
+            }
+        ]
+
+        mock_request = MagicMock()
+        mock_db = MagicMock()
+        mock_admin = {"is_admin": True}
+
+        result = asyncio.run(list_audit_log(mock_request, mock_db, mock_admin))
+
+        assert "entries" in result
+        assert len(result["entries"]) == 1
+        assert result["entries"][0]["key"] == "workdir"
+
+
+@pytest.mark.integration
+class TestHistoryEndpoint:
+    """GET /api/settings/{key}/history requires admin access."""
+
+    def test_requires_admin(self, client):
+        response = client.get("/api/settings/workdir/history")
+        assert response.status_code in [302, 401, 403]
+
+    @patch("app.api.settings.get_setting_history")
+    def test_returns_history_for_admin(self, mock_get_history):
+        from app.api.settings import get_key_history
+
+        mock_get_history.return_value = [
+            {
+                "id": 1,
+                "key": "workdir",
+                "old_value": None,
+                "new_value": "/tmp",
+                "changed_by": "admin",
+                "changed_at": "2024-01-01T00:00:00",
+                "action": "update",
+            }
+        ]
+
+        mock_request = MagicMock()
+        mock_db = MagicMock()
+        mock_admin = {"is_admin": True}
+
+        result = asyncio.run(get_key_history("workdir", mock_request, mock_db, mock_admin))
+
+        assert result["key"] == "workdir"
+        assert len(result["history"]) == 1
+
+
+@pytest.mark.integration
+class TestRollbackEndpoint:
+    """POST /api/settings/{key}/rollback/{history_id} requires admin access."""
+
+    def test_requires_admin(self, client):
+        response = client.post("/api/settings/workdir/rollback/1")
+        assert response.status_code in [302, 401, 403]
+
+    @patch("app.api.settings.notify_settings_updated")
+    @patch("app.api.settings.rollback_setting")
+    def test_rollback_success(self, mock_rollback, mock_notify):
+        from app.api.settings import rollback_setting_to_history
+
+        mock_rollback.return_value = True
+        mock_request = MagicMock()
+        mock_request.session = {"user": {"preferred_username": "admin"}}
+        mock_db = MagicMock()
+        mock_admin = {"is_admin": True}
+
+        result = asyncio.run(rollback_setting_to_history("workdir", 1, mock_request, mock_db, mock_admin))
+
+        assert result["success"] is True
+        mock_notify.assert_called_once()
+
+    @patch("app.api.settings.rollback_setting")
+    def test_rollback_not_found_raises_404(self, mock_rollback):
+        import asyncio
+
+        from fastapi import HTTPException
+
+        from app.api.settings import rollback_setting_to_history
+
+        mock_rollback.return_value = False
+        mock_request = MagicMock()
+        mock_request.session = {"user": {"preferred_username": "admin"}}
+        mock_db = MagicMock()
+        mock_admin = {"is_admin": True}
+
+        with pytest.raises(HTTPException) as exc_info:
+            asyncio.run(rollback_setting_to_history("workdir", 9999, mock_request, mock_db, mock_admin))
+
+        assert exc_info.value.status_code == 404
diff --git a/tests/test_wizard_db_persist.py b/tests/test_wizard_db_persist.py
new file mode 100644
index 00000000..2f51f09e
--- /dev/null
+++ b/tests/test_wizard_db_persist.py
@@ -0,0 +1,485 @@
+"""
+Tests for wizard DB persistence, settings export, and related functionality.
+"""
+
+from unittest.mock import MagicMock, patch
+
+import pytest
+
+from app.utils.settings_service import get_setting_from_db, save_setting_to_db
+
+# ---------------------------------------------------------------------------
+# TestSetupWizardDbPersist
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestSetupWizardDbPersist:
+    """Unit tests for setup_wizard_save POST handler DB persistence."""
+
+    @patch("app.views.wizard.notify_settings_updated")
+    @patch("app.views.wizard.save_setting_to_db")
+    def test_settings_saved_to_db(self, mock_save, mock_notify, client):
+        """Test that settings are saved to DB via save_setting_to_db."""
+        mock_save.return_value = True
+
+        response = client.post(
+            "/setup",
+            data={"step": "1", "database_url": "sqlite:///test.db"},
+            follow_redirects=False,
+        )
+
+        assert response.status_code == 303
+        mock_save.assert_called()
+
+    @patch("app.views.wizard.notify_settings_updated")
+    @patch("app.views.wizard.save_setting_to_db")
+    def test_notify_called_when_settings_saved(self, mock_save, mock_notify, client):
+        """Test that notify_settings_updated is called when settings are saved."""
+        mock_save.return_value = True
+
+        client.post(
+            "/setup",
+            data={"step": "1", "database_url": "sqlite:///test.db"},
+            follow_redirects=False,
+        )
+
+        mock_notify.assert_called_once()
+
+    @patch("app.views.wizard.notify_settings_updated")
+    @patch("app.views.wizard.save_setting_to_db")
+    def test_notify_not_called_when_no_settings_saved(self, mock_save, mock_notify, client):
+        """Test that notify_settings_updated is NOT called when saved_count == 0."""
+        mock_save.return_value = False
+
+        client.post(
+            "/setup",
+            data={"step": "1"},  # no values provided
+            follow_redirects=False,
+        )
+
+        mock_notify.assert_not_called()
+
+    @patch("app.views.wizard.notify_settings_updated")
+    @patch("app.views.wizard.secrets.token_hex")
+    @patch("app.views.wizard.save_setting_to_db")
+    def test_auto_generate_session_secret(self, mock_save, mock_token, mock_notify, client):
+        """Test that session_secret auto-generate path produces a real token."""
+        mock_save.return_value = True
+        mock_token.return_value = "deadbeef" * 8
+
+        client.post(
+            "/setup",
+            data={"step": "2", "session_secret": "auto-generate"},
+            follow_redirects=False,
+        )
+
+        mock_token.assert_called_once()
+        # Ensure save was called with the generated token, not 'auto-generate'
+        for call_args in mock_save.call_args_list:
+            args = call_args[0]
+            if len(args) >= 2 and args[1] == "session_secret":
+                assert args[2] != "auto-generate"
+
+
+# ---------------------------------------------------------------------------
+# TestSetupWizardUndoSkip
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.integration
+class TestSetupWizardUndoSkip:
+    """Tests for /setup/undo-skip route."""
+
+    def test_undo_skip_removes_marker(self, client, db_session):
+        """Test that undo-skip removes the _setup_wizard_skipped marker from DB."""
+        # First, put the marker in DB
+        save_setting_to_db(db_session, "_setup_wizard_skipped", "true")
+        assert get_setting_from_db(db_session, "_setup_wizard_skipped") == "true"
+
+        # Undo skip via the route
+        response = client.get("/setup/undo-skip", follow_redirects=False)
+
+        # Should redirect
+        assert response.status_code in (303, 200)
+
+    def test_undo_skip_redirects_to_wizard(self, client):
+        """Test that undo-skip redirects to /setup?step=1."""
+        response = client.get("/setup/undo-skip", follow_redirects=False)
+        # The redirect should go to /setup?step=1 or /settings on error
+        assert response.status_code in (303, 302)
+        location = response.headers.get("location", "")
+        assert "/setup" in location or "/settings" in location
+
+    @patch("app.utils.settings_service.delete_setting_from_db")
+    def test_undo_skip_calls_delete(self, mock_delete, client):
+        """Test that undo-skip calls delete_setting_from_db."""
+        mock_delete.return_value = True
+        # Just ensure the route exists and does not 404
+        response = client.get("/setup/undo-skip", follow_redirects=False)
+        assert response.status_code != 404
+
+
+# ---------------------------------------------------------------------------
+# TestDropboxSaveSettingsDbPersist
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestDropboxSaveSettingsDbPersist:
+    """Unit tests for save_dropbox_settings DB persistence."""
+
+    @patch("app.api.dropbox.settings")
+    @patch("app.api.dropbox.notify_settings_updated")
+    @patch("app.api.dropbox.save_setting_to_db")
+    def test_db_written_even_when_env_missing(self, mock_save, mock_notify, mock_settings, client):
+        """Test that DB is written even when .env doesn't exist (no exception)."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            response = client.post(
+                "/api/dropbox/save-settings",
+                data={"refresh_token": "test-refresh-token"},
+                follow_redirects=False,
+            )
+
+        assert response.status_code == 200
+        data = response.json()
+        assert data["status"] == "success"
+        mock_save.assert_called()
+
+    @patch("app.api.dropbox.settings")
+    @patch("app.api.dropbox.notify_settings_updated")
+    @patch("app.api.dropbox.save_setting_to_db")
+    def test_notify_settings_updated_called(self, mock_save, mock_notify, mock_settings, client):
+        """Test that notify_settings_updated is called."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            client.post(
+                "/api/dropbox/save-settings",
+                data={"refresh_token": "test-refresh-token"},
+                follow_redirects=False,
+            )
+
+        mock_notify.assert_called_once()
+
+    @patch("app.api.dropbox.settings")
+    @patch("app.api.dropbox.notify_settings_updated")
+    @patch("app.api.dropbox.save_setting_to_db")
+    def test_all_provided_values_persisted(self, mock_save, mock_notify, mock_settings, client):
+        """Test that all provided values are persisted to DB."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            client.post(
+                "/api/dropbox/save-settings",
+                data={
+                    "refresh_token": "tok",
+                    "app_key": "key",
+                    "app_secret": "secret",
+                    "folder_path": "/uploads",
+                },
+                follow_redirects=False,
+            )
+
+        keys_saved = [call[0][1] for call in mock_save.call_args_list]
+        assert "dropbox_refresh_token" in keys_saved
+        assert "dropbox_app_key" in keys_saved
+        assert "dropbox_app_secret" in keys_saved
+        assert "dropbox_folder" in keys_saved
+
+
+# ---------------------------------------------------------------------------
+# TestGoogleDriveUpdateSettingsDbPersist
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestGoogleDriveUpdateSettingsDbPersist:
+    """Unit tests for update_google_drive_settings DB persistence."""
+
+    @patch("app.api.google_drive.settings")
+    @patch("app.api.google_drive.notify_settings_updated")
+    @patch("app.api.google_drive.save_setting_to_db")
+    def test_db_written_for_each_provided_field(self, mock_save, mock_notify, mock_settings, client):
+        """Test that DB is written for each provided field."""
+        mock_save.return_value = True
+
+        response = client.post(
+            "/api/google-drive/update-settings",
+            data={
+                "refresh_token": "gdrive-refresh",
+                "client_id": "client-id",
+                "client_secret": "client-secret",
+                "folder_id": "folder-123",
+                "use_oauth": "true",
+            },
+            follow_redirects=False,
+        )
+
+        assert response.status_code == 200
+        keys_saved = [call[0][1] for call in mock_save.call_args_list]
+        assert "google_drive_refresh_token" in keys_saved
+        assert "google_drive_client_id" in keys_saved
+        assert "google_drive_client_secret" in keys_saved
+        assert "google_drive_folder_id" in keys_saved
+        assert "google_drive_use_oauth" in keys_saved
+
+    @patch("app.api.google_drive.settings")
+    @patch("app.api.google_drive.notify_settings_updated")
+    @patch("app.api.google_drive.save_setting_to_db")
+    def test_use_oauth_saved_as_lowercase_string(self, mock_save, mock_notify, mock_settings, client):
+        """Test that use_oauth is saved as 'true' or 'false' string."""
+        mock_save.return_value = True
+
+        client.post(
+            "/api/google-drive/update-settings",
+            data={"refresh_token": "tok", "use_oauth": "true"},
+            follow_redirects=False,
+        )
+
+        use_oauth_calls = [call for call in mock_save.call_args_list if call[0][1] == "google_drive_use_oauth"]
+        assert len(use_oauth_calls) == 1
+        assert use_oauth_calls[0][0][2] in ("true", "false")
+
+    @patch("app.api.google_drive.settings")
+    @patch("app.api.google_drive.notify_settings_updated")
+    @patch("app.api.google_drive.save_setting_to_db")
+    def test_notify_called(self, mock_save, mock_notify, mock_settings, client):
+        """Test that notify_settings_updated is called."""
+        mock_save.return_value = True
+
+        client.post(
+            "/api/google-drive/update-settings",
+            data={"refresh_token": "tok"},
+            follow_redirects=False,
+        )
+
+        mock_notify.assert_called_once()
+
+
+# ---------------------------------------------------------------------------
+# TestOneDriveSaveSettingsDbPersist
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestOneDriveSaveSettingsDbPersist:
+    """Unit tests for save_onedrive_settings DB persistence."""
+
+    @patch("app.api.onedrive.settings")
+    @patch("app.api.onedrive.notify_settings_updated")
+    @patch("app.api.onedrive.save_setting_to_db")
+    def test_db_written_even_without_env_file(self, mock_save, mock_notify, mock_settings, client):
+        """Test that DB is written even when .env file does not exist."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            response = client.post(
+                "/api/onedrive/save-settings",
+                data={"refresh_token": "od-refresh", "tenant_id": "common"},
+                follow_redirects=False,
+            )
+
+        assert response.status_code == 200
+        data = response.json()
+        assert data["status"] == "success"
+        mock_save.assert_called()
+
+    @patch("app.api.onedrive.settings")
+    @patch("app.api.onedrive.notify_settings_updated")
+    @patch("app.api.onedrive.save_setting_to_db")
+    def test_all_fields_persisted(self, mock_save, mock_notify, mock_settings, client):
+        """Test that all provided fields are persisted to DB."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            client.post(
+                "/api/onedrive/save-settings",
+                data={
+                    "refresh_token": "tok",
+                    "client_id": "cid",
+                    "client_secret": "csec",
+                    "tenant_id": "my-tenant",
+                    "folder_path": "/docs",
+                },
+                follow_redirects=False,
+            )
+
+        keys_saved = [call[0][1] for call in mock_save.call_args_list]
+        assert "onedrive_refresh_token" in keys_saved
+        assert "onedrive_client_id" in keys_saved
+        assert "onedrive_client_secret" in keys_saved
+        assert "onedrive_tenant_id" in keys_saved
+        assert "onedrive_folder_path" in keys_saved
+
+    @patch("app.api.onedrive.settings")
+    @patch("app.api.onedrive.notify_settings_updated")
+    @patch("app.api.onedrive.save_setting_to_db")
+    def test_notify_called(self, mock_save, mock_notify, mock_settings, client):
+        """Test that notify_settings_updated is called."""
+        mock_save.return_value = True
+
+        with patch("os.path.exists", return_value=False):
+            client.post(
+                "/api/onedrive/save-settings",
+                data={"refresh_token": "tok"},
+                follow_redirects=False,
+            )
+
+        mock_notify.assert_called_once()
+
+
+# ---------------------------------------------------------------------------
+# TestGetSettingsForExport
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestGetSettingsForExport:
+    """Unit tests for the get_settings_for_export service function."""
+
+    def test_source_db_returns_only_db_settings(self, db_session):
+        """Test that source=db returns only DB-persisted settings."""
+        from app.utils.settings_service import get_settings_for_export
+
+        save_setting_to_db(db_session, "workdir", "/tmp/test", changed_by="test")
+        result = get_settings_for_export(db_session, source="db")
+
+        assert "WORKDIR" in result
+        assert result["WORKDIR"] == "/tmp/test"
+
+    def test_source_effective_includes_metadata_keys(self, db_session):
+        """Test that source=effective includes keys from SETTING_METADATA."""
+        from app.utils.settings_service import get_settings_for_export
+
+        result = get_settings_for_export(db_session, source="effective")
+
+        # The effective export should include keys from SETTING_METADATA that have values
+        # At a minimum check it returns a dict
+        assert isinstance(result, dict)
+        # Keys should be uppercase
+        for k in result:
+            assert k == k.upper()
+
+    def test_keys_are_uppercase(self, db_session):
+        """Test that all keys are returned in uppercase."""
+        from app.utils.settings_service import get_settings_for_export
+
+        save_setting_to_db(db_session, "workdir", "/tmp", changed_by="test")
+        result = get_settings_for_export(db_session, source="db")
+
+        for k in result:
+            assert k == k.upper(), f"Key {k!r} is not uppercase"
+
+    def test_none_values_excluded(self, db_session):
+        """Test that None values are excluded from the export."""
+        from app.utils.settings_service import get_settings_for_export
+
+        result = get_settings_for_export(db_session, source="db")
+
+        for v in result.values():
+            assert v is not None
+
+    def test_db_only_excludes_env_only_values(self, db_session):
+        """Test that source=db does NOT include ENV-only values (only DB rows)."""
+        from app.utils.settings_service import get_settings_for_export
+
+        # Ensure no settings in DB
+        result = get_settings_for_export(db_session, source="db")
+        # DB is empty so result should be empty
+        assert len(result) == 0
+
+
+# ---------------------------------------------------------------------------
+# TestExportEnvEndpoint
+# ---------------------------------------------------------------------------
+
+
+@pytest.mark.unit
+class TestExportEnvEndpoint:
+    """Unit tests for export_env_settings endpoint function."""
+
+    def test_requires_admin(self, client):
+        """Test that the endpoint requires admin access (no session)."""
+        response = client.get("/api/settings/export-env")
+        assert response.status_code in (302, 401, 403)
+
+    def test_returns_text_plain(self, db_session):
+        """Test that the endpoint returns text/plain response."""
+        import asyncio
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        result = asyncio.run(export_env_settings(mock_request, db_session, mock_admin, source="db"))
+        assert result.media_type == "text/plain"
+
+    def test_content_disposition_header(self, db_session):
+        """Test that the response includes a content-disposition attachment header."""
+        import asyncio
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        result = asyncio.run(export_env_settings(mock_request, db_session, mock_admin, source="db"))
+        cd = result.headers.get("content-disposition", "")
+        assert "attachment" in cd
+        assert ".env" in cd
+
+    def test_invalid_source_returns_400(self, db_session):
+        """Test that an invalid source parameter raises HTTPException 400."""
+        import asyncio
+
+        from fastapi import HTTPException
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        with pytest.raises(HTTPException) as exc_info:
+            asyncio.run(export_env_settings(mock_request, db_session, mock_admin, source="invalid"))
+        assert exc_info.value.status_code == 400
+
+    def test_default_source_is_db(self, db_session):
+        """Test that default source is db (filename contains 'db')."""
+        import asyncio
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        result = asyncio.run(export_env_settings(mock_request, db_session, mock_admin))
+        cd = result.headers.get("content-disposition", "")
+        assert "db" in cd
+
+    def test_effective_source_returns_response(self, db_session):
+        """Test that source=effective returns a valid response."""
+        import asyncio
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        result = asyncio.run(export_env_settings(mock_request, db_session, mock_admin, source="effective"))
+        assert result.media_type == "text/plain"
+
+    def test_output_contains_docuelevate_header(self, db_session):
+        """Test that the export output contains a DocuElevate header comment."""
+        import asyncio
+
+        from app.api.settings import export_env_settings
+
+        mock_request = MagicMock()
+        mock_admin = {"id": "admin", "is_admin": True}
+
+        result = asyncio.run(export_env_settings(mock_request, db_session, mock_admin, source="db"))
+        assert b"DocuElevate" in result.body