diff --git a/TODO.md b/TODO.md
index 7431d94..da9276c 100644
--- a/TODO.md
+++ b/TODO.md
@@ -31,7 +31,9 @@ confirm make check still passes.
   `OnStop` context; on expiry the outstanding count is logged at warn
   level and parked retry backoffs are released instead of being dropped
   silently, and deliveries submitted after the drain begins are refused
-  so shutdown cannot be extended indefinitely
+  so shutdown cannot be extended indefinitely; an `OnStop` context that
+  is already expired on entry with nothing outstanding drains quietly
+  rather than warning about deliveries that were never abandoned
 - 2026-08-07: golangci-lint bumped to v2.12.2 (commit-pinned installs
   in `Dockerfile` and `script/bootstrap`); `.golangci.yml` set to the
   org-standard v2-schema config used across the org's repos
diff --git a/internal/notify/shutdown.go b/internal/notify/shutdown.go
index dd1c3c7..0269889 100644
--- a/internal/notify/shutdown.go
+++ b/internal/notify/shutdown.go
@@ -64,6 +64,11 @@ func (svc *Service) startDelivery(endpoint string, fn func()) {
 // closed, which releases any retry loop sleeping in backoff.
 // Deliveries already inside an HTTP round trip are bounded by
 // the existing httpClientTimeout instead.
+//
+// A ctx that is already expired on entry is not by itself cause
+// for alarm: if nothing is outstanding there is nothing to
+// abandon, and the drain says so at debug level rather than
+// warning about deliveries that do not exist.
 func (svc *Service) drain(ctx context.Context) {
 	svc.drainMu.Lock()
 	svc.draining = true
@@ -82,6 +87,22 @@ func (svc *Service) drain(ctx context.Context) {
 			"all in-flight notifications completed",
 		)
 	case <-ctx.Done():
+		// outstanding is decremented before the WaitGroup
+		// counter, and startDelivery can no longer add to it
+		// now that draining is set, so a zero here means every
+		// delivery really did finish.  ctx expiring in that
+		// state (an OnStop context that was already cancelled
+		// on entry is the usual way) abandons nothing, so it
+		// must not close abandon or warn about it.
+		abandoned := svc.outstanding.Load()
+		if abandoned == 0 {
+			svc.log.Debug(
+				"all in-flight notifications completed",
+			)
+
+			return
+		}
+
 		svc.abandonOnce.Do(func() {
 			if svc.abandon != nil {
 				close(svc.abandon)
@@ -91,7 +112,7 @@ func (svc *Service) drain(ctx context.Context) {
 		svc.log.Warn(
 			"shutdown deadline reached with notifications "+
 				"still in flight; abandoning them",
-			"abandoned", svc.outstanding.Load(),
+			"abandoned", abandoned,
 			"error", ctx.Err(),
 		)
 	}
diff --git a/internal/notify/shutdown_test.go b/internal/notify/shutdown_test.go
index e88224f..f938b64 100644
--- a/internal/notify/shutdown_test.go
+++ b/internal/notify/shutdown_test.go
@@ -41,6 +41,16 @@ const (
 	// settleDelay is how long to wait before asserting that
 	// something did *not* happen.
 	settleDelay = 50 * time.Millisecond
+
+	// idleDrainBound is the upper bound on a drain that has
+	// nothing in flight.  It is deliberately far above the cost
+	// of the goroutine hop through inFlight.Wait() — which
+	// reached 57ms on a loaded box under -race with the package's
+	// parallel tests — and far below drainSlack, the deadline
+	// such a drain is given.  A drain that blocked until its
+	// deadline instead of returning on the WaitGroup therefore
+	// still fails this bound, but scheduling delay alone cannot.
+	idleDrainBound = 500 * time.Millisecond
 )
 
 // syncBuffer is an io.Writer safe for concurrent use, so log
@@ -128,6 +138,13 @@ func TestDrainWaitsForInFlightDelivery(t *testing.T) {
 		t.Fatal("delivery never reached the endpoint")
 	}
 
+	// As in TestDrainBoundedByContextDeadline: start is captured
+	// before the clock it is compared against, here the timer
+	// holding the delivery open, so elapsed covers the whole hold
+	// and the lower bound cannot come out short from scheduling
+	// delay alone.
+	start := time.Now()
+
 	timer := time.AfterFunc(inFlightHold, func() {
 		close(release)
 	})
@@ -138,8 +155,6 @@ func TestDrainWaitsForInFlightDelivery(t *testing.T) {
 	)
 	defer cancel()
 
-	start := time.Now()
-
 	svc.Drain(ctx)
 
 	elapsed := time.Since(start)
@@ -211,28 +226,53 @@ func TestDrainBoundedByContextDeadline(t *testing.T) {
 			svc.OutstandingDeliveries() == 1
 	})
 
+	// start must be captured *before* the deadline clock starts,
+	// so that the measured interval is a superset of the deadline
+	// interval.  Capturing it after context.WithTimeout would
+	// make elapsed structurally smaller than drainDeadline and
+	// the lower bound below unfalsifiable-by-luck: it would fail
+	// whenever the two statements were separated by any
+	// scheduling delay, and pass otherwise, regardless of what
+	// the drain did.
+	start := time.Now()
+
 	ctx, cancel := context.WithTimeout(
 		context.Background(), drainDeadline,
 	)
 	defer cancel()
 
-	start := time.Now()
+	// The upper bound is enforced by a watchdog rather than by
+	// measuring after the fact: a drain that is not bounded at
+	// all never returns here (the delivery is parked in a backoff
+	// that never fires), so an unbounded drain must fail this
+	// test promptly instead of hanging the package until the test
+	// binary's 30s timeout.
+	returned := make(chan struct{})
 
-	svc.Drain(ctx)
+	go func() {
+		defer close(returned)
 
-	elapsed := time.Since(start)
+		svc.Drain(ctx)
+	}()
 
-	if elapsed < drainDeadline {
-		t.Errorf(
-			"drain returned after %v, before its %v deadline",
-			elapsed, drainDeadline,
+	select {
+	case <-returned:
+	case <-time.After(drainSlack):
+		t.Fatalf(
+			"drain did not return within %v; its %v deadline "+
+				"did not bound it",
+			drainSlack, drainDeadline,
 		)
 	}
 
-	if elapsed > drainSlack {
+	// The lower bound is the real assertion: the drain must have
+	// waited for its whole deadline rather than giving up on the
+	// outstanding delivery early.  With start captured above, an
+	// early return is the only thing that can make it fail.
+	if elapsed := time.Since(start); elapsed < drainDeadline {
 		t.Errorf(
-			"drain took %v, want it bounded well under %v",
-			elapsed, drainSlack,
+			"drain returned after %v, before its %v deadline",
+			elapsed, drainDeadline,
 		)
 	}
 
@@ -440,19 +480,52 @@ func TestDrainWithoutDeliveriesReturnsImmediately(t *testing.T) {
 
 	svc := notify.NewTestService(http.DefaultTransport)
 
+	// Captured before the deadline clock, as elsewhere in this
+	// file; for an upper bound that is the conservative
+	// direction, since the measured interval can then only be
+	// longer than the drain itself.
+	start := time.Now()
+
 	ctx, cancel := context.WithTimeout(
 		context.Background(), drainSlack,
 	)
 	defer cancel()
 
-	start := time.Now()
-
 	svc.Drain(ctx)
 
-	if elapsed := time.Since(start); elapsed > settleDelay {
+	if elapsed := time.Since(start); elapsed > idleDrainBound {
 		t.Errorf(
-			"drain of an idle service took %v, want ~0",
-			elapsed,
+			"drain of an idle service took %v, want well "+
+				"under its %v deadline",
+			elapsed, drainSlack,
+		)
+	}
+}
+
+// TestDrainWithCancelledContextDoesNotWarn verifies that an
+// OnStop context that is already dead on entry does not produce
+// an "abandoning them" warning when there was nothing in flight
+// to abandon.  The expired context wins the select immediately,
+// so only the outstanding count can tell the difference between
+// a genuine timeout and a shutdown that had simply already run
+// out of time with no work left.
+func TestDrainWithCancelledContextDoesNotWarn(t *testing.T) {
+	t.Parallel()
+
+	svc, logs := newLoggingService(http.DefaultTransport)
+
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	svc.Drain(ctx)
+
+	if output := logs.String(); strings.Contains(
+		output, `"level":"WARN"`,
+	) {
+		t.Errorf(
+			"drain with nothing in flight warned about "+
+				"abandoned deliveries; log output: %s",
+			output,
 		)
 	}
 }