Squash Odysseus development history

routes/auth_routes.py

@@ -3,17 +3,27 @@
 from fastapi import APIRouter, Request, Response, HTTPException
 from pydantic import BaseModel
 from typing import Optional
+import asyncio
 import logging
 import os
 
-from core.auth import AuthManager
+import json
+import re
+from pathlib import Path
+
+from core.atomic_io import atomic_write_json, atomic_write_text
+from core.auth import AuthManager, RESERVED_USERNAMES, SetAdminResult, TOKEN_TTL
+from src.constants import DEEP_RESEARCH_DIR, MEMORY_FILE, PASSWORD_MIN_LENGTH, SKILLS_DIR
 from src.rate_limiter import RateLimiter
+from src.settings_scrub import scrub_settings
 from src.settings import (
     load_settings as _load_settings,
     save_settings as _save_settings,
     load_features as _load_features,
     save_features as _save_features,
     DEFAULT_SETTINGS,
+    RETIRED_SETTING_KEYS,
+    without_retired_settings,
 )
 from src.integrations import (
     load_integrations,
@@ -21,6 +31,7 @@ from src.integrations import (
     update_integration,
     delete_integration,
     get_integration,
+    mask_integration_secret,
     execute_api_call,
     INTEGRATION_PRESETS,
     migrate_from_settings,
@@ -61,9 +72,47 @@ class DeleteUserRequest(BaseModel):
     username: str
 
 
+class RenameUserRequest(BaseModel):
+    username: str
+
+
+class SetAdminRequest(BaseModel):
+    is_admin: bool
+
+
+class SetOpenRegistrationRequest(BaseModel):
+    enabled: bool
+
 SESSION_COOKIE = "odysseus_session"
 
 
+def _secure_cookie(request: Request) -> bool:
+    """Decide the ``Secure`` attribute of the session cookie.
+
+    ``SECURE_COOKIES`` stays authoritative when it holds an explicit value:
+    ``true`` always marks the cookie Secure (the documented knob for a TLS
+    proxy), ``false`` never does, which is the escape hatch for an install
+    that still answers on plain HTTP alongside HTTPS. Anything else —
+    unset, or the present-but-empty value docker-compose injects for a
+    variable the host has not defined — derives it from the request, so an
+    HTTPS login gets a Secure cookie without any configuration.
+
+    Either the connection scheme or ``X-Forwarded-Proto`` saying https is
+    enough, which is the same test ``core/middleware.py`` applies before it
+    sends HSTS. Uvicorn's proxy-headers middleware already folds that header
+    into the scheme for the proxies it trusts, so reading it here only adds
+    the case of a terminator that is not on a trusted address; the cost is
+    that a client talking to the app directly can set the header and lock
+    its own session out over plain HTTP.
+    """
+    configured = os.getenv("SECURE_COOKIES", "").strip().lower()
+    if configured in ("true", "false"):
+        return configured == "true"
+    # A chained proxy sends a list — the client-facing hop comes first.
+    forwarded_proto = request.headers.get("x-forwarded-proto", "").split(",")[0]
+    return request.url.scheme == "https" or forwarded_proto.strip().lower() == "https"
+
+
 def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
     router = APIRouter(prefix="/api/auth", tags=["auth"])
 
@@ -82,9 +131,13 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(429, "Too many requests — try again later")
         if auth_manager.is_configured:
             raise HTTPException(400, "Already configured")
-        if len(body.password) < 8:
-            raise HTTPException(400, "Password must be at least 8 characters")
-        ok = auth_manager.setup(body.username, body.password)
+        if len(body.password) < PASSWORD_MIN_LENGTH:
+            raise HTTPException(400, f"Password must be at least {PASSWORD_MIN_LENGTH} characters")
+        if len(body.username.strip()) < 1:
+            raise HTTPException(400, "Username is required")
+        if body.username.lower() in RESERVED_USERNAMES:
+            raise HTTPException(403, "Username is reserved")
+        ok = await asyncio.to_thread(auth_manager.setup, body.username, body.password)
         if not ok:
             raise HTTPException(500, "Setup failed")
         return {"ok": True, "message": "Admin account created"}
@@ -98,11 +151,13 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(400, "Run setup first")
         if not auth_manager.signup_enabled:
             raise HTTPException(403, "Registration is disabled. Ask an admin for an account.")
-        if len(body.password) < 8:
-            raise HTTPException(400, "Password must be at least 8 characters")
+        if len(body.password) < PASSWORD_MIN_LENGTH:
+            raise HTTPException(400, f"Password must be at least {PASSWORD_MIN_LENGTH} characters")
         if len(body.username.strip()) < 1:
             raise HTTPException(400, "Username is required")
-        ok = auth_manager.create_user(body.username, body.password, is_admin=False)
+        if body.username.lower() in RESERVED_USERNAMES:
+            raise HTTPException(403, "Username is reserved")
+        ok = await asyncio.to_thread(auth_manager.create_user, body.username, body.password, is_admin=False)
         if not ok:
             raise HTTPException(409, "Username already taken")
         return {"ok": True, "message": "Account created"}
@@ -113,7 +168,7 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(429, "Too many requests — try again later")
         # Verify password first
         username = body.username.strip().lower()
-        if not auth_manager.verify_password(username, body.password):
+        if not await asyncio.to_thread(auth_manager.verify_password, username, body.password):
             raise HTTPException(401, "Invalid credentials")
         # Check 2FA if enabled
         if auth_manager.totp_enabled(username):
@@ -122,8 +177,8 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
                 return {"ok": False, "requires_totp": True, "username": username}
             if not auth_manager.totp_verify(username, body.totp_code):
                 raise HTTPException(401, "Invalid 2FA code")
-        # All checks passed — create session
-        token = auth_manager.create_session(username, body.password)
+        # All checks passed — create session (password already verified above)
+        token = await asyncio.to_thread(auth_manager.create_session_trusted, username)
         if not token:
             raise HTTPException(401, "Invalid credentials")
         cookie_kwargs = dict(
@@ -131,11 +186,11 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             value=token,
             httponly=True,
             samesite="lax",
-            secure=os.getenv("SECURE_COOKIES", "false").lower() == "true",
+            secure=_secure_cookie(request),
             path="/",
         )
         if body.remember:
-            cookie_kwargs["max_age"] = 60 * 60 * 24 * 7  # 7 days
+            cookie_kwargs["max_age"] = TOKEN_TTL
         response.set_cookie(**cookie_kwargs)
         return {"ok": True, "username": username}
 
@@ -164,16 +219,23 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             pass
         return result
 
+    @router.get("/policy")
+    async def auth_policy():
+        """Return public auth policy constants for the frontend."""
+        return auth_manager.policy()
+
     @router.post("/change-password")
     async def change_password(body: ChangePasswordRequest, request: Request):
         user = _get_current_user(request)
         if not user:
             raise HTTPException(401, "Not authenticated")
-        if len(body.new_password) < 8:
-            raise HTTPException(400, "Password must be at least 8 characters")
-        ok = auth_manager.change_password(user, body.current_password, body.new_password)
+        if len(body.new_password) < PASSWORD_MIN_LENGTH:
+            raise HTTPException(400, f"Password must be at least {PASSWORD_MIN_LENGTH} characters")
+        current_token = request.cookies.get(SESSION_COOKIE)
+        ok = await asyncio.to_thread(auth_manager.change_password, user, body.current_password, body.new_password)
         if not ok:
             raise HTTPException(400, "Current password is incorrect")
+        await asyncio.to_thread(auth_manager.revoke_user_sessions, user, current_token)
         return {"ok": True}
 
     # ------------------------------------------------------------------
@@ -248,8 +310,12 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
         user = _get_current_user(request)
         if not user or not auth_manager.is_admin(user):
             raise HTTPException(403, "Admin only")
-        if len(body.password) < 8:
-            raise HTTPException(400, "Password must be at least 8 characters")
+        if len(body.password) < PASSWORD_MIN_LENGTH:
+            raise HTTPException(400, f"Password must be at least {PASSWORD_MIN_LENGTH} characters")
+        if len(body.username.strip()) < 1:
+            raise HTTPException(400, "Username is required")
+        if body.username.lower() in RESERVED_USERNAMES:
+            raise HTTPException(403, "Username is reserved")
         ok = auth_manager.create_user(body.username, body.password, body.is_admin)
         if not ok:
             raise HTTPException(409, "Username already taken")
@@ -266,23 +332,361 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(404, "User not found or is admin")
         return {"ok": True, "privileges": auth_manager.get_privileges(username)}
 
-    @router.post("/signup-toggle")
+    @router.put("/users/{username}/rename")
+    async def rename_user(username: str, body: RenameUserRequest, request: Request):
+        user = _get_current_user(request)
+        if not user or not auth_manager.is_admin(user):
+            raise HTTPException(403, "Admin only")
+        old_username = (username or "").strip().lower()
+        new_username = (body.username or "").strip().lower()
+        if not new_username:
+            raise HTTPException(400, "Username required")
+        if old_username == new_username:
+            return {"ok": True, "username": new_username, "renamed_self": old_username == user}
+        if old_username not in auth_manager.users:
+            raise HTTPException(404, "User not found")
+        if new_username in auth_manager.users:
+            raise HTTPException(409, "Username already taken")
+
+        # Gate on auth first. Every mutation below is contingent on this
+        # succeeding — doing it last meant a rejected rename (e.g. reserved
+        # username) left file-backed owner fields already rewritten with no
+        # way to roll them back.
+        ok = auth_manager.rename_user(old_username, new_username, user)
+        if not ok:
+            raise HTTPException(400, "Cannot rename user")
+
+        def _rollback_auth_rename() -> bool:
+            # On self-rename the admin session has already moved to the new
+            # username, so the rollback must authenticate as the new user.
+            rollback_user = new_username if user == old_username else user
+            try:
+                return bool(auth_manager.rename_user(new_username, old_username, rollback_user))
+            except Exception as rollback_err:
+                logger.error(
+                    "Failed to roll back auth rename %s -> %s after owner migration failure: %s",
+                    new_username, old_username, rollback_err,
+                )
+                return False
+
+        # Usernames are ownership keys for user data. Rename the common
+        # owner-scoped DB rows so the account keeps access to its sessions,
+        # docs, email accounts, tasks, etc.
+        try:
+            from sqlalchemy import func
+            from core.database import (
+                Base,
+                EmailAccount,
+                SessionLocal,
+                lock_email_account_owner_mutations,
+            )
+            db = SessionLocal()
+            try:
+                # Email-account defaults are protected by per-owner mutex rows.
+                # A rename crosses two owner partitions, so lock both in the
+                # shared helper's canonical order before inspecting either.
+                lock_email_account_owner_mutations(
+                    db, old_username, new_username
+                )
+
+                source_default_ids = [
+                    row[0]
+                    for row in (
+                        db.query(EmailAccount.id)
+                        .filter(
+                            func.lower(EmailAccount.owner) == old_username,
+                            EmailAccount.is_default == True,  # noqa: E712
+                        )
+                        .order_by(EmailAccount.created_at.asc(), EmailAccount.id.asc())
+                        .all()
+                    )
+                ]
+                destination_default_ids = [
+                    row[0]
+                    for row in (
+                        db.query(EmailAccount.id)
+                        .filter(
+                            func.lower(EmailAccount.owner) == new_username,
+                            EmailAccount.is_default == True,  # noqa: E712
+                        )
+                        .order_by(EmailAccount.created_at.asc(), EmailAccount.id.asc())
+                        .all()
+                    )
+                ]
+                if destination_default_ids:
+                    clear_default_ids = (
+                        destination_default_ids[1:] + source_default_ids
+                    )
+                else:
+                    clear_default_ids = source_default_ids[1:]
+                if clear_default_ids:
+                    (
+                        db.query(EmailAccount)
+                        .filter(EmailAccount.id.in_(clear_default_ids))
+                        .update(
+                            {EmailAccount.is_default: False},
+                            synchronize_session=False,
+                        )
+                    )
+
+                for mapper in Base.registry.mappers:
+                    model = mapper.class_
+                    if not hasattr(model, "owner"):
+                        continue
+                    (
+                        db.query(model)
+                        .filter(func.lower(model.owner) == old_username)
+                        .update({"owner": new_username}, synchronize_session=False)
+                    )
+                db.commit()
+            except Exception:
+                db.rollback()
+                raise
+            finally:
+                db.close()
+        except Exception as e:
+            logger.error("Failed to rename owner references %s -> %s: %s", old_username, new_username, e)
+            if not _rollback_auth_rename():
+                logger.error(
+                    "Auth rename %s -> %s could not be rolled back after owner migration failure",
+                    old_username, new_username,
+                )
+            raise HTTPException(500, "Failed to rename user data")
+
+        # Per-user prefs are JSON-backed, not SQL-backed.
+        try:
+            from routes.prefs_routes import _load as _load_prefs, _save as _save_prefs
+            prefs = _load_prefs()
+            users = prefs.get("_users") if isinstance(prefs, dict) else None
+            if isinstance(users, dict):
+                prefs_key = next(
+                    (k for k in users if str(k).strip().lower() == old_username),
+                    None,
+                )
+                new_taken = any(str(k).strip().lower() == new_username for k in users)
+                if prefs_key is not None and not new_taken:
+                    users[new_username] = users.pop(prefs_key)
+                    _save_prefs(prefs)
+        except Exception as e:
+            logger.warning("Failed to rename user prefs %s -> %s: %s", old_username, new_username, e)
+
+        # In-flight deep-research tasks live in the process-local
+        # ResearchHandler registry. They are not covered by the persisted JSON
+        # migration above, but the research routes filter and cancel by this
+        # owner field while the job is running. Do this before sweeping
+        # completed JSON files so a job that finishes during the rename saves
+        # with the new owner or is caught by the disk sweep below.
+        try:
+            rh = getattr(request.app.state, "research_handler", None)
+            rename_owner = getattr(rh, "rename_owner", None)
+            if callable(rename_owner):
+                rename_owner(old_username, new_username)
+        except Exception as e:
+            logger.warning("Failed to rename active research tasks %s -> %s: %s", old_username, new_username, e)
+
+        # deep_research: each completed report is a standalone JSON file with
+        # an `owner` field. research_routes filters by d.get("owner") == user,
+        # so a stale owner makes every report invisible to the renamed user.
+        try:
+            dr_dir = Path(DEEP_RESEARCH_DIR)
+            if dr_dir.is_dir():
+                for p in dr_dir.glob("*.json"):
+                    try:
+                        d = json.loads(p.read_text(encoding="utf-8"))
+                        if str(d.get("owner", "")).strip().lower() == old_username:
+                            d["owner"] = new_username
+                            atomic_write_json(str(p), d)
+                    except Exception as err:
+                        logger.warning("Failed to update research owner in %s: %s", p.name, err)
+        except Exception as e:
+            logger.warning("Failed to rename research owner references %s -> %s: %s", old_username, new_username, e)
+
+        # memory.json: a flat JSON array where each entry carries an `owner`
+        # field. memory_manager.load(owner=user) filters on it, so stale
+        # entries disappear from the memory panel.
+        try:
+            if os.path.isfile(MEMORY_FILE):
+                with open(MEMORY_FILE, encoding="utf-8") as fh:
+                    entries = json.loads(fh.read())
+                if isinstance(entries, list):
+                    changed = False
+                    for entry in entries:
+                        if isinstance(entry, dict) and str(entry.get("owner", "")).strip().lower() == old_username:
+                            entry["owner"] = new_username
+                            changed = True
+                    if changed:
+                        atomic_write_json(MEMORY_FILE, entries)
+        except Exception as e:
+            logger.warning("Failed to rename memory.json owner references %s -> %s: %s", old_username, new_username, e)
+
+        # uploads.json: upload rows use owner metadata for access checks and
+        # owner-prefixed index keys for dedupe. Rename both so attachments keep
+        # resolving after the account username changes.
+        try:
+            upload_handler = getattr(request.app.state, "upload_handler", None)
+            rename_owner = getattr(upload_handler, "rename_owner", None)
+            if callable(rename_owner):
+                rename_owner(old_username, new_username)
+        except Exception as e:
+            logger.warning("Failed to rename upload owner references %s -> %s: %s", old_username, new_username, e)
+
+        # direct personal RAG uploads live in per-owner directories and the
+        # vector metadata also carries the username used for owner-filtered
+        # search. Keep both in sync with the auth rename.
+        try:
+            from routes.personal_routes import rename_personal_upload_owner
+            personal_docs_manager = getattr(request.app.state, "personal_docs_manager", None)
+            if personal_docs_manager is not None:
+                rag_manager = getattr(personal_docs_manager, "rag_manager", None)
+                rename_personal_upload_owner(
+                    old_username,
+                    new_username,
+                    personal_docs_manager=personal_docs_manager,
+                    rag_manager=rag_manager,
+                )
+        except Exception as e:
+            logger.warning("Failed to rename personal RAG upload owner references %s -> %s: %s", old_username, new_username, e)
+
+        # skills: SKILL.md frontmatter carries owner: <username>; the usage
+        # sidecar (_usage.json) keys entries as owner::skill-name. Both must
+        # be updated or the renamed user's Skills panel goes empty.
+        try:
+            skills_root = Path(SKILLS_DIR)
+            if skills_root.is_dir():
+                _owner_re = re.compile(
+                    r'(?m)^(owner:\s*)' + re.escape(old_username) + r'\s*$',
+                    re.IGNORECASE,
+                )
+                for p in skills_root.rglob("SKILL.md"):
+                    try:
+                        text = p.read_text(encoding="utf-8")
+                        new_text = _owner_re.sub(r'\g<1>' + new_username, text)
+                        if new_text != text:
+                            atomic_write_text(str(p), new_text)
+                    except Exception as err:
+                        logger.warning("Failed to update skill owner in %s: %s", p, err)
+                usage_path = skills_root / "_usage.json"
+                if usage_path.is_file():
+                    try:
+                        usage = json.loads(usage_path.read_text(encoding="utf-8"))
+                        if isinstance(usage, dict):
+                            new_usage = {}
+                            changed = False
+                            for k, v in usage.items():
+                                owner_part, sep, skill_part = k.partition("::")
+                                if sep and owner_part.lower() == old_username:
+                                    new_usage[new_username + "::" + skill_part] = v
+                                    changed = True
+                                else:
+                                    new_usage[k] = v
+                            if changed:
+                                atomic_write_json(str(usage_path), new_usage)
+                    except Exception as err:
+                        logger.warning("Failed to update skills usage keys %s -> %s: %s", old_username, new_username, err)
+        except Exception as e:
+            logger.warning("Failed to rename skills owner references %s -> %s: %s", old_username, new_username, e)
+
+        # The in-memory session cache (session_manager.sessions) stores each
+        # session's owner at load time. Without this patch the renamed user's
+        # sessions are invisible on the next /api/sessions call because
+        # get_sessions_for_user does an exact `s.owner == username` comparison
+        # against stale in-memory values.
+        sm = getattr(request.app.state, "session_manager", None)
+        if sm is not None:
+            for sess in list(getattr(sm, "sessions", {}).values()):
+                if str(getattr(sess, "owner", None) or "").strip().lower() == old_username:
+                    sess.owner = new_username
+
+        # The owner-rename loop above updated ApiToken.owner in the DB, but the
+        # bearer-token cache still maps each token to the OLD owner. Without
+        # refreshing it, the renamed user's API tokens resolve to the old (now
+        # non-existent) owner and stop reaching their data until the cache next
+        # goes dirty. Invalidate it now, like the token CRUD routes do.
+        invalidator = getattr(request.app.state, "invalidate_token_cache", None)
+        if callable(invalidator):
+            invalidator()
+        return {"ok": True, "username": new_username, "renamed_self": old_username == user}
+
+    @router.put("/users/{username}/admin")
+    async def set_user_admin(username: str, body: SetAdminRequest, request: Request):
+        """Promote/demote a user to/from admin. Admin only.
+
+        The last remaining admin can't be demoted (no lockout). Self-demotion
+        is allowed while another admin exists; the `self` flag tells the UI to
+        reload the acting user into the normal-user view.
+        """
+        user = _get_current_user(request)
+        if not user or not auth_manager.is_admin(user):
+            raise HTTPException(403, "Admin only")
+        result = auth_manager.set_admin(username, body.is_admin, user)
+        if result is SetAdminResult.USER_NOT_FOUND:
+            raise HTTPException(404, "User not found")
+        if result is SetAdminResult.NOT_AUTHORIZED:
+            raise HTTPException(403, "Admin only")
+        if result is SetAdminResult.LAST_ADMIN:
+            raise HTTPException(400, "Cannot demote the last admin")
+        target = (username or "").strip().lower()
+        return {
+            "ok": True,
+            "is_admin": body.is_admin,
+            "self": target == (user or "").strip().lower(),
+        }
+
+    @router.post("/signup-toggle", deprecated=True)
     async def toggle_signup(request: Request):
-        """Toggle open registration on/off. Admin only."""
+        """
+        Toggle open registration on/off. Admin only.
+
+        DEPRECATED: This endpoint uses toggle semantics which can lead to unsafe state changes.
+        Use PUT /open-signup instead.
+
+        This endpoint is kept for backward compatibility and may be removed in future versions.
+        """
         user = _get_current_user(request)
         if not user or not auth_manager.is_admin(user):
             raise HTTPException(403, "Admin only")
         auth_manager.signup_enabled = not auth_manager.signup_enabled
         return {"ok": True, "signup_enabled": auth_manager.signup_enabled}
 
+    @router.put("/open-signup")
+    async def set_signup_enabled(body: SetOpenRegistrationRequest, request: Request):
+        """Set open signup enabled state. Admin only."""
+        user = _get_current_user(request)
+        if not user or not auth_manager.is_admin(user):
+            raise HTTPException(403, "Admin only")
+        auth_manager.signup_enabled = body.enabled
+        return {"ok": True,"signup_enabled": auth_manager.signup_enabled}
+
     @router.delete("/users")
     async def admin_delete_user(body: DeleteUserRequest, request: Request):
         user = _get_current_user(request)
         if not user or not auth_manager.is_admin(user):
             raise HTTPException(403, "Admin only")
-        ok = auth_manager.delete_user(body.username, user)
+
+        def _invalidate_api_token_cache():
+            try:
+                invalidator = getattr(request.app.state, "invalidate_token_cache", None)
+                if invalidator:
+                    invalidator()
+            except Exception:
+                pass
+
+        try:
+            ok = auth_manager.delete_user(body.username, user)
+        except Exception:
+            # delete_user can touch ApiToken rows before a later auth-store write
+            # fails. Dirty the bearer cache anyway so a partial token purge does
+            # not leave already-cached tokens authenticating until restart.
+            _invalidate_api_token_cache()
+            raise
         if not ok:
             raise HTTPException(400, "Cannot delete user")
+        # delete_user removes the user's ApiToken rows, but the bearer-auth
+        # middleware serves from an in-memory prefix->token cache that only
+        # rebuilds when flagged dirty. Without this, a deleted user's already
+        # cached token keeps authenticating until some other token op or a
+        # restart clears the cache. Mirror what the token routes do.
+        _invalidate_api_token_cache()
         return {"ok": True}
 
     # ---- Feature visibility (admin-managed) ----
@@ -308,39 +712,16 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
 
     # ---- App settings (admin-managed) ----
 
-    _SECRET_KEY_PATTERNS = ("_api_key", "_password", "_secret", "_token", "_key")
-
-    def _is_secret_key(name: str) -> bool:
-        n = (name or "").lower()
-        if n in ("google_pse_cx",):  # public identifier, not a secret
-            return False
-        return any(n.endswith(p) or n == p.lstrip("_") for p in _SECRET_KEY_PATTERNS)
-
-    def _scrub_settings(settings: dict) -> dict:
-        """Return a copy of settings with secret-shaped values masked.
-
-        Frontend reads /settings without auth for things like keybinds + TTS
-        prefs. Secrets (search-provider keys, IMAP/SMTP passwords) must NOT
-        be exposed to non-admin callers.
-        """
-        scrubbed = {}
-        for k, v in (settings or {}).items():
-            if _is_secret_key(k) and isinstance(v, str) and v:
-                scrubbed[k] = ""  # presence preserved, value blanked
-            else:
-                scrubbed[k] = v
-        return scrubbed
-
     @router.get("/settings")
     async def get_settings(request: Request):
         """Returns app settings. Admins get the full set; non-admins get
         a scrubbed copy with secret keys blanked. The frontend uses this
         for keybinds + TTS prefs, so it stays callable without admin."""
         user = _get_current_user(request)
-        settings = _load_settings()
+        settings = without_retired_settings(_load_settings())
         if user and auth_manager.is_admin(user):
             return settings
-        return _scrub_settings(settings)
+        return scrub_settings(settings)
 
     @router.post("/settings")
     async def set_settings(request: Request):
@@ -350,11 +731,29 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(403, "Admin only")
         body = await request.json()
         current = _load_settings()
+        # Per-key validation for numeric settings: coerce to int and clamp to a
+        # sane range so a bad value can't disable the agent or let it run away.
+        _INT_RANGES = {
+            "agent_max_rounds": (1, 200),
+            "agent_max_tool_calls": (0, 1000),  # 0 = unlimited
+            "auto_compact_threshold_percent": (50, 95),
+        }
         for key in DEFAULT_SETTINGS:
-            if key in body:
-                current[key] = body[key]
+            if key in RETIRED_SETTING_KEYS:
+                continue
+            if key not in body:
+                continue
+            val = body[key]
+            if key in _INT_RANGES:
+                lo, hi = _INT_RANGES[key]
+                try:
+                    val = int(val)
+                except (TypeError, ValueError):
+                    raise HTTPException(400, f"{key} must be an integer")
+                val = max(lo, min(val, hi))
+            current[key] = val
         _save_settings(current)
-        return current
+        return without_retired_settings(current)
 
     # ---- Integrations CRUD ----
 
@@ -369,12 +768,7 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(403, "Admin only")
         items = load_integrations()
         # Mask API keys for frontend display
-        safe = []
-        for item in items:
-            copy = dict(item)
-            if copy.get("api_key"):
-                copy["api_key"] = copy["api_key"][:4] + "****"
-            safe.append(copy)
+        safe = [mask_integration_secret(item) for item in items]
         return {"integrations": safe}
 
     @router.get("/integrations/presets")
@@ -390,7 +784,7 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
             raise HTTPException(403, "Admin only")
         body = await request.json()
         item = add_integration(body)
-        return {"ok": True, "integration": item}
+        return {"ok": True, "integration": mask_integration_secret(item)}
 
     @router.put("/integrations/{integration_id}")
     async def update_integration_route(integration_id: str, request: Request):
@@ -402,7 +796,7 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
         item = update_integration(integration_id, body)
         if not item:
             raise HTTPException(404, "Integration not found")
-        return {"ok": True, "integration": item}
+        return {"ok": True, "integration": mask_integration_secret(item)}
 
     @router.delete("/integrations/{integration_id}")
     async def delete_integration_route(integration_id: str, request: Request):
@@ -482,7 +876,31 @@ def setup_auth_routes(auth_manager: AuthManager) -> APIRouter:
                     }
                 return {"ok": False, "message": f"ntfy returned HTTP {r.status_code} from {full_url}: {r.text[:200]}"}
             except Exception as e:
-                return {"ok": False, "message": f"ntfy publish to {full_url} failed: {e}"[:300]}
+                hint = ""
+                if parsed.hostname not in ("127.0.0.1", "localhost"):
+                    hint = " If this is Docker Compose ntfy, set NTFY_BIND to that host/Tailscale IP and NTFY_BASE_URL to the same server URL in .env, then recreate ntfy."
+                return {"ok": False, "message": f"ntfy publish to {full_url} failed: {e}.{hint}"[:500]}
+
+        if preset == "discord_webhook":
+            import httpx
+            webhook_url = (integ.get("base_url") or "").strip()
+            if not webhook_url:
+                return {"ok": False, "message": "No webhook URL set — paste the full Discord webhook URL into the Base URL field."}
+            payload = {
+                "embeds": [{
+                    "title": "Odysseus connectivity test",
+                    "description": "If you see this, your Discord Webhook integration is wired up correctly.",
+                    "color": 5793266,
+                }]
+            }
+            try:
+                async with httpx.AsyncClient(timeout=8.0) as client:
+                    r = await client.post(webhook_url, json=payload)
+                if r.is_success:
+                    return {"ok": True, "message": "Test embed sent — check your Discord channel to confirm it arrived."}
+                return {"ok": False, "message": f"Discord returned HTTP {r.status_code}: {r.text[:200]}"}
+            except Exception as e:
+                return {"ok": False, "message": f"Request failed: {e}"[:400]}
 
         # All other presets: GET against a known health endpoint.
         # Fall back to detecting from name if preset is missing.