The email auto-calendar pass (settings.email_auto_calendar / the
extract_email_events task) scans recently received mail and lets an LLM
create / update / cancel calendar events. Two problems made it a cross-tenant,
remotely triggerable hole:
1. No owner scoping. _auto_summarize_pass(account_id=None) fans out over EVERY
enabled account of EVERY user. For each message it fetched an upcoming-events
snapshot with NO owner filter (all tenants' events) and handed those uids +
titles to the extraction LLM, then executed the model's ops via
do_manage_calendar(...) with owner=None. do_manage_calendar only filters by
owner when owner is not None, so create/update/delete ran across ALL users'
calendars. Net: every user's event titles/times were disclosed to the model,
and the model could cancel/move/duplicate any tenant's events by uid.
2. No prompt-injection wrapping. The raw email From/Subject/body were
interpolated straight into an instruction-shaped extraction prompt (unlike
the chat path, which wraps external text via src/prompt_security). Anyone
who can email a user whose instance has auto-calendar enabled could inject
operations: create attacker-controlled "meeting" events (the path even
auto-harvests URLs from the body into the event location/description — a
phishing primitive) or cancel/modify the victim's real events, with zero
human in the loop.
Fix:
- Add core.database.get_upcoming_events(owner) and use it for the snapshot, so
the LLM only ever sees the processed account owner's events.
- Look up the EmailAccount owner in _auto_summarize_pass_single and pass owner=
to every do_manage_calendar call, so create/update/delete are scoped to that
user (owner=None stays the single-user / legacy escape hatch).
- Tell the extraction model the email is untrusted data and not to follow
instructions inside it (defense-in-depth against injection).
Add tests/test_calendar_owner_scope.py: get_upcoming_events returns only the
given owner's events (and everything when owner is None). Fails against the old
unscoped query.
Hardens issues found in a security review of the current tree (separate from
the cookbook SSH PR):
- Email thread rendering (static/js/emailLibrary.js): the flat read path runs
inbound HTML through the allowlist sanitizer, but the two threaded paths
(_renderTurnsAsBubbles / _renderTurnsFromServer — the default view) injected
server-parsed `body_html` raw into the DOM. A crafted inbound email could
inject arbitrary markup (phishing/form/credential-capture/tracking; full XSS
if a deployment relaxes the script CSP). Now sanitized on all paths.
- Attachment extraction (routes/email_routes.py, routes/email_helpers.py): the
on-disk extraction dir was `ATTACHMENTS_DIR / f"{folder}_{uid}"` with
user-controlled folder/uid and no containment, so a folder like `../../tmp`
could escape ATTACHMENTS_DIR. New attachment_extract_dir() flattens both to a
single safe segment and asserts containment.
- Diagnostics routes (routes/diagnostics_routes.py): /api/db/stats,
/api/rag/stats, /api/test/youtube, /api/test-research relied only on the
global session check (any logged-in user). Now require_admin-gated.
- Defense-in-depth HTML escaping: session HTML export escapes the session name
(routes/session_routes.py); the MCP OAuth page escapes the reflected Host
header / server_id (routes/mcp_routes.py).
- Internal-tool token now compared with secrets.compare_digest (constant time)
in core/middleware.py and app.py.
Adds regression tests in tests/test_security_regressions.py.
chat_routes.py persisted a session's "mode" in three best-effort spots —
reading the current mode, writing the effective mode, and setting
research_pending on the stream path. Each opened a session with SessionLocal()
and called .close() as the LAST statement inside a try/except, so if anything
before close() raised (e.g. a SQLite "database is locked" under concurrent chat
streams) the except only logged and the connection was never returned to the
pool.
DATABASE_URL defaults to file-backed SQLite, whose engine uses SQLAlchemy's
default QueuePool (5 connections + 10 overflow). Repeated leaks on these hot
paths exhaust the pool; later requests then block for pool_timeout and fail
with "QueuePool limit ... reached", taking the app down until restart.
Move the logic into two best-effort helpers in core.database, next to the
existing session helpers (update_session_last_accessed, get_session_by_id):
- get_session_mode(session_id) -> Optional[str]
- set_session_mode(session_id, mode) -> bool
Both route through the existing get_db_session() context manager, which commits
on success, rolls back on error, and always closes in a finally, so the
connection is returned to the pool on every path. chat_routes.py now calls
these instead of hand-rolling sessions, also removing three copies of the same
try/except.
Add tests/test_session_mode_helpers.py: the helpers commit+close on success
and, on a mid-operation DB error, swallow + roll back + close (no leak). The
error-path tests fail against the old close()-inside-try pattern.
