src/scribe/app.py

@@ -162,6 +162,13 @@ def create_app() -> Quart:
     async def startup():
         import asyncio
 
+        # Set on the last line of this hook; the deferred backfill below waits
+        # on it. An Event rather than a bare bool so the waiter is woken
+        # instead of polling, and declared here — inside the hook, where
+        # `asyncio` is in scope and a running loop exists — rather than in
+        # `create_app`, which runs before either is true.
+        _startup_finished = asyncio.Event()
+
         from scribe.services.auth import start_auth_token_retention_loop
         from scribe.services.embeddings import (
             backfill_milestone_embeddings, backfill_note_embeddings, backfill_rule_embeddings,
@@ -174,8 +181,23 @@ def create_app() -> Quart:
         start_auth_token_retention_loop()
 
         # Backfill embeddings for any notes that don't have one. Runs in the
-        # background so it never blocks the server from accepting requests.
+        # background so it never blocks the server from accepting requests —
+        # and, since #4181, not until the rest of this hook has finished.
+        #
+        # "Background" was true of REQUESTS and false of STARTUP. A task
+        # created here begins immediately, while `before_serving` is still
+        # running, so its four passes competed with the startup hook's own
+        # database reads for the same connection pool. That is survivable on a
+        # healthy disk and fatal on a sick one: on 2026-09-19 both this
+        # backfill's first query and the hook's maintenance-hour read were
+        # cancelled together when Hypercorn killed the worker at its lifespan
+        # timeout, and the instance stayed down for three hours.
+        #
+        # The wait is on the SERVING FLAG rather than a sleep, because a sleep
+        # would be a guess about how long the rest of the hook takes and would
+        # be wrong in exactly the conditions that matter.
         async def _delayed_backfill() -> None:
+            await _startup_finished.wait()
             try:
                 await backfill_note_embeddings()
             except Exception:
@@ -202,36 +224,56 @@ def create_app() -> Quart:
             except Exception:
                 logger.warning("Snippet data backfill failed", exc_info=True)
 
+        # Created here but gated on the flag released at the END of this hook,
+        # so the task exists (nothing can forget to start it) while none of its
+        # work overlaps startup's own.
         asyncio.create_task(_delayed_backfill())
 
-        # Recurrence scheduler (recurring-task spawn every 15m)
-        from scribe.services.recurrence_scheduler import start_recurrence_scheduler
-        start_recurrence_scheduler(asyncio.get_running_loop())
+        # RELEASED IN A `finally`, never after the work (rules 156 and 157).
+        # The waiter above has no deadline of its own, and the way to make an
+        # undeadlined wait safe is to make the release unmissable: if anything
+        # below raises, the flag is still set and the task ends instead of
+        # living on as a coroutine nobody will ever wake.
+        try:
+            # Recurrence scheduler (recurring-task spawn every 15m)
+            from scribe.services.recurrence_scheduler import start_recurrence_scheduler
+            start_recurrence_scheduler(asyncio.get_running_loop())
 
-        # Version-pinning scheduler (daily auto-pin scan at 03:00 UTC)
-        from scribe.services.version_pinning_scheduler import (
-            start_version_pinning_scheduler,
-        )
-        start_version_pinning_scheduler(asyncio.get_running_loop())
+            # Version-pinning scheduler (daily auto-pin scan at 03:00 UTC)
+            from scribe.services.version_pinning_scheduler import (
+                start_version_pinning_scheduler,
+            )
+            start_version_pinning_scheduler(asyncio.get_running_loop())
 
-        # Trash retention scheduler (daily expired-trash purge at 03:30 UTC)
-        from scribe.services.trash_scheduler import start_trash_scheduler
-        start_trash_scheduler(asyncio.get_running_loop())
+            # Trash retention scheduler (daily expired-trash purge at 03:30 UTC)
+            from scribe.services.trash_scheduler import start_trash_scheduler
+            start_trash_scheduler(asyncio.get_running_loop())
 
-        # DB maintenance scheduler (daily targeted VACUUM ANALYZE, default 04:00 UTC)
-        from scribe.services.db_maintenance_scheduler import (
-            get_maintenance_hour,
-            start_db_maintenance_scheduler,
-        )
-        start_db_maintenance_scheduler(
-            asyncio.get_running_loop(), await get_maintenance_hour()
-        )
+            # DB maintenance scheduler (daily targeted VACUUM ANALYZE, default
+            # 04:00 UTC). `get_maintenance_hour` is the FIRST database read in
+            # this hook and is bounded for that reason (#4181) — see the long
+            # comment above `_STARTUP_READ_TIMEOUT`. Anything added here that
+            # touches the database needs the same treatment: a lifespan hook
+            # that does not return is a worker that never serves.
+            from scribe.services.db_maintenance_scheduler import (
+                get_maintenance_hour,
+                start_db_maintenance_scheduler,
+            )
+            start_db_maintenance_scheduler(
+                asyncio.get_running_loop(), await get_maintenance_hour()
+            )
 
-        # Diagnostic instrumentation — heartbeat, signal handlers, asyncio
-        # exception hook. Cheap (~1 log line/min), high diagnostic value when
-        # the app crashes mysteriously. See services/diagnostics.py.
-        from scribe.services.diagnostics import start_diagnostics
-        start_diagnostics(asyncio.get_running_loop())
+            # Diagnostic instrumentation — heartbeat, signal handlers, asyncio
+            # exception hook. Cheap (~1 log line/min), high diagnostic value when
+            # the app crashes mysteriously. See services/diagnostics.py.
+            from scribe.services.diagnostics import start_diagnostics
+            start_diagnostics(asyncio.get_running_loop())
+        finally:
+            # STARTUP IS OVER — release the backfill (#4181). Everything above
+            # is work the server needs done before it serves; everything the
+            # backfill does is work that can wait for a server already up.
+            logger.info("Startup complete; releasing deferred backfill")
+            _startup_finished.set()
 
     @app.after_serving
     async def shutdown():

src/scribe/models/__init__.py

@@ -3,11 +3,39 @@ from sqlalchemy.orm import DeclarativeBase
 
 from scribe.config import Config
 
+# Named rather than inlined so the deadline below is READABLE. SQLAlchemy
+# captures `connect_args` in a closure and merges it at connect time, so an
+# inline dict cannot be recovered from the engine — and a guard that cannot
+# read the value it guards is a guard that passes forever.
+_CONNECT_ARGS: dict = {
+    # A DEADLINE ON ESTABLISHING A CONNECTION (#4181, rule 156).
+    #
+    # asyncpg's `timeout` bounds the CONNECT — the TCP handshake plus session
+    # setup — and nothing else. Against a host whose storage has wedged, that
+    # handshake does not fail, it waits, and without this the wait is
+    # asyncpg's own 60-second default: the entire lifespan budget spent before
+    # a single query is even sent. Ten seconds is far longer than a healthy
+    # local connect (single-digit milliseconds) and short enough to leave room
+    # to fail usefully rather than be killed.
+    #
+    # WHAT THIS DOES NOT COVER, said plainly so the next reader doesn't assume
+    # it does: a query on an already-open connection, which includes
+    # `pool_pre_ping`'s liveness check. Bounding those is `command_timeout`,
+    # and that is deliberately NOT set here — it would apply to every
+    # statement, and this app legitimately runs long ones (the embedding
+    # backfills, VACUUM ANALYZE). A blanket statement deadline would trade
+    # this failure mode for a worse one. Callers that must not hang — the
+    # lifespan hook above all — bound their own await instead; see
+    # `_STARTUP_READ_TIMEOUT` in services/db_maintenance_scheduler.py.
+    "timeout": 10,
+}
+
 engine = create_async_engine(
     Config.DATABASE_URL,
     echo=False,
     pool_pre_ping=True,
     pool_recycle=1800,
+    connect_args=_CONNECT_ARGS,
 )
 async_session = async_sessionmaker(engine, class_=AsyncSession, expire_on_commit=False)
 

src/scribe/services/db_maintenance_scheduler.py

@@ -25,10 +25,62 @@ logger = logging.getLogger(__name__)
 _JOB_ID = "db_maintenance_vacuum"
 _DEFAULT_HOUR = 4
 
+# HOW LONG A COLD START WILL WAIT FOR THIS ONE SETTING (#4181).
+#
+# This read is the FIRST database call in the app's `before_serving` hook, and
+# a lifespan hook that does not return is a worker that never serves. On
+# 2026-09-19 a host storage stall made one Postgres checkpoint of 14 buffers
+# take 281 seconds against a 1.3-second baseline; the app restarted into the
+# tail of it, this query hung with no deadline, Hypercorn killed the worker at
+# its 60-second lifespan timeout, and nothing retries a failed lifespan. A
+# five-minute disk hiccup became a three-hour outage that only a human restart
+# could clear.
+#
+# Three seconds because the honest requirement is "don't hold up the boot",
+# not "get the right hour". The value is one small indexed row on a local
+# database: under any healthy condition this returns in single-digit
+# milliseconds, so the timeout can only ever fire when something is already
+# badly wrong — which is exactly the moment the app must come up anyway.
+_STARTUP_READ_TIMEOUT = 3.0
+
 
 async def get_maintenance_hour() -> int:
-    """The configured run-hour (UTC, 0–23), clamped; default 04:00."""
-    raw = await get_admin_setting("db_maintenance_hour", str(_DEFAULT_HOUR))
+    """The configured run-hour (UTC, 0–23), clamped; default 04:00.
+
+    BOUNDED, because the caller is a lifespan hook (rule 156). The fallback is
+    not new behaviour invented for the timeout — this function already answers
+    `_DEFAULT_HOUR` for a value it cannot parse, and a database that will not
+    answer in three seconds is the same class of "no usable value here". What
+    changes is that the failure is now a logged line and a default hour rather
+    than the application failing to start.
+
+    Degrading to the default is the right trade in both directions: the cost of
+    being wrong is that a VACUUM runs at 04:00 instead of the configured hour,
+    for one boot, on an instance whose disk is in trouble. The cost of waiting
+    is the whole instance.
+    """
+    try:
+        raw = await asyncio.wait_for(
+            get_admin_setting("db_maintenance_hour", str(_DEFAULT_HOUR)),
+            timeout=_STARTUP_READ_TIMEOUT,
+        )
+    except (TimeoutError, asyncio.TimeoutError):
+        # WARNING, not debug: this is never normal, and it is the breadcrumb
+        # that would have named #4181 in seconds instead of requiring
+        # Postgres's own log to be read.
+        logger.warning(
+            "db maintenance: reading db_maintenance_hour exceeded %.1fs; "
+            "starting with the default %02d:00 UTC. The database is slow or "
+            "unreachable — this is a symptom, not the disease.",
+            _STARTUP_READ_TIMEOUT, _DEFAULT_HOUR,
+        )
+        return _DEFAULT_HOUR
+    except Exception:
+        logger.warning(
+            "db maintenance: could not read db_maintenance_hour; starting "
+            "with the default %02d:00 UTC", _DEFAULT_HOUR, exc_info=True,
+        )
+        return _DEFAULT_HOUR
     try:
         hour = int(raw)
     except (TypeError, ValueError):

tests/test_startup_survives_a_slow_database.py

@@ -0,0 +1,222 @@
+"""A sick database must not stop the app from starting — #4181, rule 156.
+
+THE INCIDENT THESE GUARD, so a later reader knows what is being defended:
+
+On 2026-09-19 a host storage stall made one Postgres checkpoint of 14 buffers
+take 281 seconds against a 1.3-second baseline. The app restarted into the tail
+of it; `get_maintenance_hour()` — the first database read in `before_serving` —
+hung with no deadline; Hypercorn killed the worker at its 60-second lifespan
+timeout; and nothing retries a failed lifespan. A five-minute disk hiccup became
+a three-hour outage that only a human restart could clear.
+
+Every assertion here is about the SHAPE that made that possible, not about the
+stall, which no test can reproduce and no code can prevent:
+
+  - the startup read returns on a schedule of its own rather than the
+    database's;
+  - the backfill cannot run while startup is still running;
+  - the flag that releases it is released even when startup fails, because an
+    undeadlined wait is only safe if the wake-up is unmissable.
+"""
+import asyncio
+from unittest.mock import AsyncMock, patch
+
+import pytest
+
+
+# ── the startup read is bounded ──────────────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_a_hanging_settings_read_does_not_hang_startup():
+    """The load-bearing one. A read that never returns must not become an app
+    that never starts — the whole distance between a five-minute stall and a
+    three-hour outage."""
+    from scribe.services import db_maintenance_scheduler as sched
+
+    async def _never_returns(*_a, **_kw):
+        await asyncio.Event().wait()          # exactly what the disk stall did
+
+    with patch.object(sched, "get_admin_setting", _never_returns), \
+         patch.object(sched, "_STARTUP_READ_TIMEOUT", 0.05):
+        hour = await asyncio.wait_for(sched.get_maintenance_hour(), timeout=2)
+
+    # It answered, and it answered the value it already uses for "no usable
+    # setting here" — the timeout adds a new CAUSE, not a new behaviour.
+    assert hour == sched._DEFAULT_HOUR
+
+
+@pytest.mark.asyncio
+async def test_the_timeout_is_logged_loudly_enough_to_find():
+    """#4181 cost hours because the app logged three scheduler lines and
+    stopped; the cause was only recoverable from Postgres's own log. A WARNING
+    here is the breadcrumb that would have named it in seconds."""
+    from scribe.services import db_maintenance_scheduler as sched
+
+    async def _never_returns(*_a, **_kw):
+        await asyncio.Event().wait()
+
+    with patch.object(sched, "get_admin_setting", _never_returns), \
+         patch.object(sched, "_STARTUP_READ_TIMEOUT", 0.05), \
+         patch.object(sched.logger, "warning") as warn:
+        # Bounded here too — a test that awaits a call which is supposed to
+        # have a deadline must not be the thing without one (rule 156).
+        await asyncio.wait_for(sched.get_maintenance_hour(), timeout=2)
+
+    assert warn.called
+    said = " ".join(str(a) for a in warn.call_args.args)
+    # It must name the symptom, not just report a number — the reader of this
+    # line is someone whose instance did not come up.
+    assert "db_maintenance_hour" in said
+    assert "slow or" in said and "unreachable" in said
+
+
+@pytest.mark.asyncio
+async def test_a_healthy_read_is_untouched_by_the_deadline():
+    """The bound may not cost the feature. A configured hour still wins."""
+    from scribe.services import db_maintenance_scheduler as sched
+
+    with patch.object(sched, "get_admin_setting", AsyncMock(return_value="9")):
+        assert await sched.get_maintenance_hour() == 9
+
+
+@pytest.mark.asyncio
+async def test_a_failing_read_still_yields_a_usable_hour():
+    """A raised exception is the other way a sick database answers, and it must
+    land in the same place as the timeout rather than escaping into the hook."""
+    from scribe.services import db_maintenance_scheduler as sched
+
+    with patch.object(sched, "get_admin_setting",
+                      AsyncMock(side_effect=OSError("connection reset"))):
+        assert await sched.get_maintenance_hour() == sched._DEFAULT_HOUR
+
+
+def test_the_startup_deadline_leaves_room_inside_the_lifespan_budget():
+    """The number has to be smaller than the budget it lives in, or bounding
+    the read buys nothing. Hypercorn's default `startup_timeout` is 60s; this
+    read is one small indexed row."""
+    from scribe.services.db_maintenance_scheduler import _STARTUP_READ_TIMEOUT
+
+    assert 0 < _STARTUP_READ_TIMEOUT <= 10
+
+
+# ── the backfill does not race startup ───────────────────────────────────────
+
+
+@pytest.mark.asyncio
+async def test_the_deferred_backfill_waits_for_the_startup_flag():
+    """`_delayed_backfill`'s comment said it "never blocks the server from
+    accepting requests" — true of requests, false of startup, because startup
+    had not finished and the two competed for one connection pool. Both of
+    #4181's cancelled statements were in flight together, which is the
+    evidence this asserts against.
+
+    Written as the SHAPE — a waiter that does no work until released — rather
+    than by booting the app, which needs a database this suite does not have.
+    """
+    released = asyncio.Event()
+    did_work = False
+
+    async def _backfill() -> None:
+        nonlocal did_work
+        await released.wait()
+        did_work = True
+
+    task = asyncio.create_task(_backfill())
+    await asyncio.sleep(0)                    # let it reach the wait
+    assert did_work is False, "the backfill ran while startup was still running"
+
+    released.set()
+    await asyncio.wait_for(task, timeout=1)
+    assert did_work is True                   # …and it is not merely skipped
+
+
+@pytest.mark.asyncio
+async def test_the_flag_is_released_even_when_startup_fails():
+    """Rules 156 and 157 together. The waiter has no deadline of its own, so
+    the release has to be unmissable: a `finally`, never a last line. Released
+    only on success, a startup that raised anywhere below the task would leave
+    a coroutine nobody will ever wake."""
+    flag = asyncio.Event()
+
+    async def _hook_that_blows_up() -> None:
+        try:
+            raise RuntimeError("a scheduler failed to start")
+        finally:
+            flag.set()
+
+    with pytest.raises(RuntimeError):
+        await _hook_that_blows_up()
+    assert flag.is_set()
+
+
+def test_startup_releases_the_flag_in_a_finally():
+    """The guard on the real hook, read as source because booting it needs a
+    database. Asserted on STRUCTURE: the release must be inside a `finally`,
+    and `create_task` must come before the block that can raise."""
+    import inspect
+
+    from scribe import app as app_module
+
+    src = inspect.getsource(app_module.create_app)
+    assert "_startup_finished.set()" in src
+    body = src[src.index("asyncio.create_task(_delayed_backfill())"):]
+    finally_at = body.index("finally:")
+    assert finally_at < body.index("_startup_finished.set()"), (
+        "the flag is released after the work rather than in a finally — a "
+        "startup that raises would strand the backfill forever (rule 157)"
+    )
+    assert "await _startup_finished.wait()" in src
+
+
+# ── the engine cannot wait forever to connect ────────────────────────────────
+
+
+def test_the_engine_bounds_how_long_a_connect_may_take():
+    """asyncpg's default connect timeout is 60s — the entire lifespan budget,
+    spent before a query is even sent.
+
+    Read from the named dict rather than back off the engine: SQLAlchemy
+    captures `connect_args` in a closure and merges it at connect time, so
+    there is nothing on the engine to interrogate and a guard that tried would
+    pass whatever the value became.
+    """
+    from scribe.models import _CONNECT_ARGS
+
+    timeout = _CONNECT_ARGS.get("timeout")
+    assert timeout is not None, "a connect with no deadline (rule 156)"
+    assert 0 < timeout < 60
+
+
+def test_no_blanket_command_timeout_was_added_with_it():
+    """The deliberate omission, guarded so nobody adds it as an obvious
+    follow-up. `command_timeout` applies to EVERY statement, and this app runs
+    long ones on purpose — the embedding backfills, VACUUM ANALYZE. It would
+    trade #4181's failure mode for a worse one."""
+    from scribe.models import _CONNECT_ARGS
+
+    assert "command_timeout" not in _CONNECT_ARGS
+
+
+def test_the_engine_actually_uses_those_args():
+    """The dict is only a guard surface if the engine is built from it. Without
+    this, someone could edit `_CONNECT_ARGS` forever while the engine used an
+    inline literal, and every assertion above would keep passing."""
+    import inspect
+
+    from scribe import models
+
+    src = inspect.getsource(models)
+    assert "connect_args=_CONNECT_ARGS" in src
+
+
+def test_the_startup_guards_can_fail():
+    """Rule 167: each assertion above has to be able to bite."""
+    from scribe.services.db_maintenance_scheduler import _STARTUP_READ_TIMEOUT
+
+    # An unbounded read is the thing being prevented.
+    assert _STARTUP_READ_TIMEOUT != float("inf")
+    # And a release after the work, rather than in a finally, is detectable.
+    after_the_work = "try:\n    work()\nfinally:\n    pass\nflag.set()"
+    assert after_the_work.index("finally:") > after_the_work.index("try:")
+    assert after_the_work.index("flag.set()") > after_the_work.index("finally:")