diff --git a/README.md b/README.md
index 800ec34..e41e715 100644
--- a/README.md
+++ b/README.md
@@ -202,7 +202,11 @@ routewatch/
   batches for performance
 - **Backpressure**: Probabilistic message dropping when queues exceed 50%
   capacity
-- **Graceful Shutdown**: 60-second timeout, flushes all pending batches
+- **Graceful Shutdown**: on SIGTERM or SIGINT the streamer stops, the handlers
+  write the batches they hold, the HTTP server stops and the database is
+  checkpointed and closed. The daemon gives this 8 seconds and exits with status
+  0; "Running under upaas" says what a stop loses, logs and leaves undone when
+  the 8 seconds run out.
 - **Reconnection**: Any end of the stream other than shutdown, including RIS
   Live ending the response normally, marks the feed disconnected and reconnects
   with exponential backoff (5s-320s). The backoff resets after a stream that
@@ -369,6 +373,24 @@ What the [upaas](https://git.eeqj.de/sneak/upaas) app needs:
   `/.well-known/healthcheck.json` on the container port. upaas reads the
   container's health 60 seconds after a deploy and fails the deploy unless it is
   `healthy`.
+- Stop grace: the container needs 9 seconds between SIGTERM and SIGKILL. upaas
+  gives 10 (`stopTimeoutSeconds` in its `internal/docker/client.go`), as
+  `docker stop` does by default. The daemon allows 8 seconds for the handlers to
+  write what they hold and for the requests in progress to finish, then stops
+  the HTTP server, closes the database and exits with status 0. A longer grace
+  changes nothing. What is not written after 8 seconds is lost, and the streamer
+  and each handler log how much. When the prefix handler has fallen behind the
+  feed, a stop loses far more: its batch is full at 250,000 updates and the
+  streamer's worker for it waits for room, so the streamer's stop takes the
+  whole 8 seconds and every handler then skips its last write. Lost then are the
+  messages left on the four handlers' queues, what the AS, peer and peering
+  handlers hold, the prefix handler's batch, and the write it has in progress,
+  up to another 250,000 updates, which take about 20 seconds and are cut off by
+  the exit; withdrawals and peer downs are among them. A route withdrawn in them
+  stays in the live route table until its peer announces or withdraws the prefix
+  again or its session goes down. When the 8 seconds run out the database is not
+  closed, and SQLite rolls back a write the exit cut off when the database next
+  opens.
 
 ## Development
 
diff --git a/cmd/streamdumper/main.go b/cmd/streamdumper/main.go
index 95a0722..57ff529 100644
--- a/cmd/streamdumper/main.go
+++ b/cmd/streamdumper/main.go
@@ -35,7 +35,7 @@ func main() {
 	if err != nil {
 		log.Fatal("Failed to start streamer:", err)
 	}
-	defer s.Stop()
+	defer s.Stop(context.Background())
 
 	// Set up context with cancellation
 	ctx, cancel := context.WithCancel(context.Background())
diff --git a/internal/routewatch/app.go b/internal/routewatch/app.go
index 3aeb1e3..a4d1d5b 100644
--- a/internal/routewatch/app.go
+++ b/internal/routewatch/app.go
@@ -137,7 +137,12 @@ func (rw *RouteWatch) Run(ctx context.Context) error {
 	return nil
 }
 
-// Shutdown performs graceful shutdown of all services
+// Shutdown stops all services in order: the streamer, the handlers, which
+// write what they hold, the WHOIS fetcher, the database maintainer and the
+// HTTP server, and last the database, which it checkpoints and closes. Each
+// stage waits at most until ctx ends, so Shutdown returns soon after: a
+// handler logs what it could not write by then, and the HTTP server closes
+// the connections of requests still running.
 func (rw *RouteWatch) Shutdown(ctx context.Context) {
 	rw.mu.Lock()
 	if rw.shutdown {
@@ -150,51 +155,48 @@ func (rw *RouteWatch) Shutdown(ctx context.Context) {
 	rw.mu.Unlock()
 
 	// Stop the streamer first: it returns once the handlers have been handed
-	// every message it queued. Then each handler writes what it holds.
-	rw.streamer.Stop()
+	// every message it queued, or when ctx ends. Then each handler writes
+	// what it holds.
+	rw.streamer.Stop(ctx)
 
 	if rw.dbHandler != nil {
 		rw.logger.Info("Flushing database handler")
-		rw.dbHandler.Stop()
+		rw.dbHandler.Stop(ctx)
 	}
 
 	if rw.peerHandler != nil {
 		rw.logger.Info("Flushing peer handler")
-		rw.peerHandler.Stop()
+		rw.peerHandler.Stop(ctx)
 	}
 
 	if rw.prefixHandler != nil {
 		rw.logger.Info("Flushing prefix handler")
-		rw.prefixHandler.Stop()
+		rw.prefixHandler.Stop(ctx)
 	}
 
 	if rw.peeringHandler != nil {
 		rw.logger.Info("Flushing peering handler")
-		rw.peeringHandler.Stop()
+		rw.peeringHandler.Stop(ctx)
 	}
 
 	// Stop ASN WHOIS fetcher
 	if rw.asnFetcher != nil {
-		rw.asnFetcher.Stop()
+		rw.asnFetcher.Stop(ctx)
 	}
 
 	// Stop database maintainer
 	if rw.dbMaintainer != nil {
-		rw.dbMaintainer.Stop()
+		rw.dbMaintainer.Stop(ctx)
 	}
 
-	// Stop HTTP server with a timeout of its own, however much of ctx is left
-	const serverStopTimeout = 5 * time.Second
-
-	stopCtx, cancel := context.WithTimeout(
-		context.WithoutCancel(ctx), serverStopTimeout)
-	defer cancel()
-
-	err := rw.server.Stop(stopCtx)
+	err := rw.server.Stop(ctx)
 	if err != nil {
-		rw.logger.Error("Failed to stop HTTP server gracefully", "error", err)
+		rw.logger.Error("Stopped the HTTP server before every request finished",
+			"error", err)
 	}
 
+	rw.closeDatabase(ctx)
+
 	// Log final metrics
 	metrics := rw.streamer.GetMetrics()
 	rw.logger.Info("Final metrics",
@@ -206,6 +208,27 @@ func (rw *RouteWatch) Shutdown(ctx context.Context) {
 	)
 }
 
+// closeDatabase checkpoints and closes the database, unless ctx has ended: a
+// write may then still be running, and both would wait for it. SQLite rolls
+// back a write cut off by the exit when the database next opens.
+func (rw *RouteWatch) closeDatabase(ctx context.Context) {
+	if ctx.Err() != nil {
+		rw.logger.Error("Stop deadline passed; the database is not closed")
+
+		return
+	}
+
+	err := rw.db.Checkpoint(ctx)
+	if err != nil {
+		rw.logger.Error("Failed to checkpoint the database", "error", err)
+	}
+
+	err = rw.db.Close()
+	if err != nil {
+		rw.logger.Error("Failed to close the database", "error", err)
+	}
+}
+
 // getModule provides all fx dependencies
 func getModule() []fx.Option {
 	return []fx.Option{
diff --git a/internal/routewatch/app_integration_internal_test.go b/internal/routewatch/app_integration_internal_test.go
index 8f094ca..8cb2474 100644
--- a/internal/routewatch/app_integration_internal_test.go
+++ b/internal/routewatch/app_integration_internal_test.go
@@ -4,8 +4,11 @@ import (
 	"context"
 	"fmt"
 	"io"
+	"net"
 	"net/http"
 	"net/http/httptest"
+	"slices"
+	"strconv"
 	"strings"
 	"sync"
 	"testing"
@@ -643,3 +646,187 @@ func TestShutdownWritesTheUpdatesQueuedInTheStreamer(t *testing.T) {
 		}
 	}
 }
+
+// freePort returns a TCP port that was free a moment ago, for a server the
+// test starts.
+func freePort(t *testing.T) int {
+	t.Helper()
+
+	var listenConfig net.ListenConfig
+
+	listener, err := listenConfig.Listen(t.Context(), "tcp", ":0")
+	if err != nil {
+		t.Fatalf("failed to find a free port: %v", err)
+	}
+	defer func() { _ = listener.Close() }()
+
+	addr, ok := listener.Addr().(*net.TCPAddr)
+	if !ok {
+		t.Fatalf("listener address %v is not a TCP address", listener.Addr())
+	}
+
+	return addr.Port
+}
+
+// TestShutdownReturnsByItsDeadlineWhileAWriteIsBlocked starts the HTTP server
+// and has the AS handler start a write that the store holds until the test
+// ends, past Shutdown's deadline. Shutdown must return within its deadline
+// plus a small margin, with the HTTP server stopped, and must neither
+// checkpoint nor close the database: the real one would wait for the write.
+// Before the fix Shutdown waited for the write.
+func TestShutdownReturnsByItsDeadlineWhileAWriteIsBlocked(t *testing.T) {
+	t.Parallel()
+
+	const (
+		deadline = 100 * time.Millisecond
+		// margin is how long Shutdown may take after its deadline, to stop
+		// the HTTP server.
+		margin = 2 * time.Second
+	)
+
+	blocking := newBlockingStore()
+	defer blocking.releaseWrites()
+
+	store := &closeOrderStore{Store: blocking}
+	log := logger.New()
+	port := freePort(t)
+	cfg := &config.Config{Port: port}
+	s := streamer.New(log, metrics.New())
+
+	rw := New(Dependencies{
+		DB:       store,
+		Streamer: s,
+		Server:   server.New(store, s, log, cfg),
+		Logger:   log,
+		Config:   cfg,
+	})
+
+	err := rw.server.Start(t.Context())
+	if err != nil {
+		t.Fatalf("failed to start the HTTP server: %v", err)
+	}
+
+	rw.dbHandler = NewASHandler(store, log)
+	fill := ristypes.ASPath{Sequence: slices.Repeat([]int{testASNA}, asnBatchSize)}
+	startBlockedWrite(t, blocking, rw.dbHandler,
+		[]*ristypes.RISMessage{{Path: fill}})
+
+	ctx, cancel := context.WithTimeout(t.Context(), deadline)
+	defer cancel()
+
+	shutDown := make(chan struct{})
+
+	go func() {
+		rw.Shutdown(ctx)
+		close(shutDown)
+	}()
+
+	select {
+	case <-shutDown:
+	case <-time.After(deadline + margin):
+		t.Fatalf("Shutdown did not return within %s of its deadline while "+
+			"a write was blocked", margin)
+	}
+
+	var dialer net.Dialer
+
+	addr := net.JoinHostPort("127.0.0.1", strconv.Itoa(port))
+
+	conn, err := dialer.DialContext(t.Context(), "tcp", addr)
+	if err == nil {
+		_ = conn.Close()
+
+		t.Errorf("the HTTP server still accepts connections on %s after "+
+			"Shutdown returned", addr)
+	}
+
+	store.callsMu.Lock()
+	defer store.callsMu.Unlock()
+
+	if slices.Contains(store.calls, callCheckpoint) ||
+		slices.Contains(store.calls, callClose) {
+		t.Errorf("Shutdown made the calls %q past its deadline, want no %s "+
+			"and no %s", store.calls, callCheckpoint, callClose)
+	}
+}
+
+// closeOrderStore is a store that records, in order, the AS writes,
+// checkpoints and closes it is given. It passes the AS writes on to Store.
+type closeOrderStore struct {
+	database.Store
+
+	callsMu sync.Mutex
+	calls   []string
+}
+
+// The calls closeOrderStore records.
+const (
+	callWrite      = "AS write"
+	callCheckpoint = "checkpoint"
+	callClose      = "close"
+)
+
+func (s *closeOrderStore) GetOrCreateASNBatch(asns map[int]time.Time) error {
+	s.record(callWrite)
+
+	return s.Store.GetOrCreateASNBatch(asns)
+}
+
+func (s *closeOrderStore) Checkpoint(_ context.Context) error {
+	s.record(callCheckpoint)
+
+	return nil
+}
+
+func (s *closeOrderStore) Close() error {
+	s.record(callClose)
+
+	return nil
+}
+
+func (s *closeOrderStore) record(call string) {
+	s.callsMu.Lock()
+	defer s.callsMu.Unlock()
+
+	s.calls = append(s.calls, call)
+}
+
+// TestShutdownCheckpointsAndClosesTheDatabaseLast hands the AS handler one
+// message and shuts down with time to spare. The handler's last write must
+// come first, then a checkpoint, then the close. Before the fix Shutdown
+// neither checkpointed nor closed the database.
+func TestShutdownCheckpointsAndClosesTheDatabaseLast(t *testing.T) {
+	t.Parallel()
+
+	const deadline = 10 * time.Second
+
+	store := &closeOrderStore{Store: newMockStore()}
+	log := logger.New()
+	cfg := &config.Config{}
+	s := streamer.New(log, metrics.New())
+
+	rw := New(Dependencies{
+		DB:       store,
+		Streamer: s,
+		Server:   server.New(store, s, log, cfg),
+		Logger:   log,
+		Config:   cfg,
+	})
+	rw.dbHandler = NewASHandler(store, log)
+	rw.dbHandler.HandleMessage(&ristypes.RISMessage{
+		Path: ristypes.ASPath{Sequence: []int{testASNA}},
+	})
+
+	ctx, cancel := context.WithTimeout(t.Context(), deadline)
+	defer cancel()
+
+	rw.Shutdown(ctx)
+
+	store.callsMu.Lock()
+	defer store.callsMu.Unlock()
+
+	want := []string{callWrite, callCheckpoint, callClose}
+	if !slices.Equal(store.calls, want) {
+		t.Errorf("Shutdown made the calls %q, want %q", store.calls, want)
+	}
+}
diff --git a/internal/routewatch/ashandler.go b/internal/routewatch/ashandler.go
index 1484165..3991c80 100644
--- a/internal/routewatch/ashandler.go
+++ b/internal/routewatch/ashandler.go
@@ -1,6 +1,7 @@
 package routewatch
 
 import (
+	"context"
 	"slices"
 	"sync"
 	"time"
@@ -39,18 +40,23 @@ type ASHandler struct {
 	db     database.Store
 	logger *logger.Logger
 
-	// Batching. mu guards batch only: the flush goroutine takes the batch
-	// under mu and writes it after releasing mu, so HandleMessage waits for
-	// a database write only while batch is at asnBatchMaxSize.
+	// Batching. mu guards batch and writing only: the flush goroutine takes
+	// the batch under mu and writes it after releasing mu, so HandleMessage
+	// waits for a database write only while batch is at asnBatchMaxSize.
 	mu    sync.Mutex
 	batch []asnOp
+	// writing is how many operations the flush goroutine took from batch
+	// and has not finished writing.
+	writing int
 	// batchTaken is signalled when the flush goroutine takes batch; its L is
 	// &mu.
 	batchTaken  sync.Cond
 	batchFullCh chan struct{} // wakes the flush goroutine when batch is full
 	lastFlush   time.Time     // used only by the flush goroutine
-	stopCh      chan struct{}
-	wg          sync.WaitGroup
+	// stopCh hands Stop's context to the flush goroutine. It holds one, so
+	// Stop does not wait for a write in progress to hand it over.
+	stopCh chan context.Context
+	done   chan struct{} // closed when the flush goroutine returns
 }
 
 type asnOp struct {
@@ -70,12 +76,12 @@ func NewASHandler(db database.Store, logger *logger.Logger) *ASHandler {
 		batch:       make([]asnOp, 0, asnBatchSize),
 		batchFullCh: make(chan struct{}, 1),
 		lastFlush:   time.Now(),
-		stopCh:      make(chan struct{}),
+		stopCh:      make(chan context.Context, 1),
+		done:        make(chan struct{}),
 	}
 	h.batchTaken.L = &h.mu
 
 	// Start the flush timer goroutine
-	h.wg.Add(1)
 	go h.flushLoop()
 
 	return h
@@ -147,20 +153,32 @@ func (h *ASHandler) HandleMessage(msg *ristypes.RISMessage) {
 	}
 }
 
-// Stop gracefully shuts down the ASHandler by signaling the background flush
-// goroutine to terminate and waiting for it to complete. Any pending ASN
-// operations in the current batch are flushed to the database before Stop
-// returns. This method should be called during application shutdown to ensure
-// no data is lost.
-func (h *ASHandler) Stop() {
-	close(h.stopCh)
-	h.wg.Wait()
+// Stop stops the flush goroutine, which writes the operations the handler holds
+// before it returns, and waits for it until ctx ends. Once ctx has ended the
+// flush goroutine skips that last write, and a write still running is lost
+// when the process exits, so Stop logs how many operations are not written.
+func (h *ASHandler) Stop(ctx context.Context) {
+	h.stopCh <- ctx
+
+	select {
+	case <-h.done:
+	case <-ctx.Done():
+	}
+
+	h.mu.Lock()
+	unwritten := h.writing + len(h.batch)
+	h.mu.Unlock()
+
+	if unwritten > 0 {
+		h.logger.Error("Stop deadline passed before the AS handler wrote "+
+			"its updates", "updates", unwritten)
+	}
 }
 
 // flushLoop runs in a goroutine, the only one that writes the batch: it
 // flushes when the batch is full, periodically, and once more on Stop.
 func (h *ASHandler) flushLoop() {
-	defer h.wg.Done()
+	defer close(h.done)
 
 	ticker := time.NewTicker(asnBatchTimeout)
 	defer ticker.Stop()
@@ -173,9 +191,11 @@ func (h *ASHandler) flushLoop() {
 			}
 		case <-h.batchFullCh:
 			h.flushBatch()
-		case <-h.stopCh:
-			// Final flush
-			h.flushBatch()
+		case ctx := <-h.stopCh:
+			// Final flush, unless the stop deadline has passed
+			if ctx.Err() == nil {
+				h.flushBatch()
+			}
 
 			return
 		}
@@ -183,7 +203,8 @@ func (h *ASHandler) flushLoop() {
 }
 
 // takeBatch returns the pending operations and leaves an empty batch in their
-// place for HandleMessage to fill.
+// place for HandleMessage to fill. They count in writing until flushBatch has
+// written them.
 func (h *ASHandler) takeBatch() []asnOp {
 	h.mu.Lock()
 	defer h.mu.Unlock()
@@ -193,6 +214,7 @@ func (h *ASHandler) takeBatch() []asnOp {
 	}
 
 	batch := h.batch
+	h.writing = len(batch)
 	h.batch = make([]asnOp, 0, asnBatchSize)
 	h.batchTaken.Broadcast()
 
@@ -222,5 +244,9 @@ func (h *ASHandler) flushBatch() {
 			"error", err, "count", len(asnMap))
 	}
 
+	h.mu.Lock()
+	h.writing = 0
+	h.mu.Unlock()
+
 	h.lastFlush = time.Now()
 }
diff --git a/internal/routewatch/asnfetcher.go b/internal/routewatch/asnfetcher.go
index 5dbf1eb..46a1765 100644
--- a/internal/routewatch/asnfetcher.go
+++ b/internal/routewatch/asnfetcher.go
@@ -43,7 +43,7 @@ type ASNFetcher struct {
 	logger         *slog.Logger
 	immediateQueue chan int
 	stopCh         chan struct{}
-	wg             sync.WaitGroup
+	done           chan struct{} // closed when the fetcher goroutine returns
 
 	// fetchMu ensures only one fetch runs at a time
 	fetchMu sync.Mutex
@@ -67,6 +67,7 @@ func NewASNFetcher(db database.Store, logger *slog.Logger) *ASNFetcher {
 		logger:          logger.With("component", "asn_fetcher"),
 		immediateQueue:  make(chan int, immediateQueueSize),
 		stopCh:          make(chan struct{}),
+		done:            make(chan struct{}),
 		currentInterval: baseInterval,
 		successTimes:    make([]time.Time, 0),
 		errorTimes:      make([]time.Time, 0),
@@ -76,8 +77,6 @@ func NewASNFetcher(db database.Store, logger *slog.Logger) *ASNFetcher {
 // Start begins the background ASN fetcher goroutine. It runs until Stop:
 // the end of ctx does not stop it.
 func (f *ASNFetcher) Start(ctx context.Context) {
-	f.wg.Add(1)
-
 	go f.run(context.WithoutCancel(ctx))
 
 	f.logger.Info("ASN fetcher started",
@@ -87,11 +86,17 @@ func (f *ASNFetcher) Start(ctx context.Context) {
 	)
 }
 
-// Stop gracefully shuts down the fetcher.
-func (f *ASNFetcher) Stop() {
+// Stop stops the fetcher and waits, until ctx ends, for a lookup in progress to
+// finish.
+func (f *ASNFetcher) Stop(ctx context.Context) {
 	close(f.stopCh)
-	f.wg.Wait()
-	f.logger.Info("ASN fetcher stopped")
+
+	select {
+	case <-f.done:
+		f.logger.Info("ASN fetcher stopped")
+	case <-ctx.Done():
+		f.logger.Warn("Stop deadline passed before the ASN fetcher stopped")
+	}
 }
 
 // QueueImmediate queues an ASN for immediate WHOIS lookup.
@@ -197,7 +202,7 @@ func (f *ASNFetcher) recordFailure() {
 
 // run is the main background loop.
 func (f *ASNFetcher) run(ctx context.Context) {
-	defer f.wg.Done()
+	defer close(f.done)
 
 	timer := time.NewTimer(f.getInterval())
 	defer timer.Stop()
diff --git a/internal/routewatch/asnfetcher_internal_test.go b/internal/routewatch/asnfetcher_internal_test.go
index d929068..7c0486b 100644
--- a/internal/routewatch/asnfetcher_internal_test.go
+++ b/internal/routewatch/asnfetcher_internal_test.go
@@ -155,3 +155,51 @@ func TestFetchAndUpdateMarksAnASWithoutReferral(t *testing.T) {
 			baseInterval)
 	}
 }
+
+// TestASNFetcherStopReturnsByItsDeadline starts a fetcher, has it look up an
+// AS whose WHOIS server does not answer until the test ends, and stops it with
+// a short deadline while that lookup is in progress. Stop must return all the
+// same instead of waiting for the lookup.
+func TestASNFetcherStopReturnsByItsDeadline(t *testing.T) {
+	t.Parallel()
+
+	const stopDeadline = 100 * time.Millisecond
+
+	lookupStarted := make(chan struct{})
+	release := make(chan struct{})
+
+	f := NewASNFetcher(newMockStore(), logger.New().Logger)
+	f.whoisClient.DialContext = func(
+		context.Context, string, string,
+	) (net.Conn, error) {
+		close(lookupStarted)
+		<-release
+
+		return nil, syscall.ECONNREFUSED
+	}
+
+	f.Start(t.Context())
+	f.QueueImmediate(testASNA)
+
+	select {
+	case <-lookupStarted:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the fetcher did not start the lookup")
+	}
+
+	ctx, cancel := context.WithTimeout(t.Context(), stopDeadline)
+	defer cancel()
+
+	if !returnsInTime(func() { f.Stop(ctx) }) {
+		t.Fatalf("Stop with a deadline of %s did not return while a lookup "+
+			"was in progress", stopDeadline)
+	}
+
+	close(release)
+
+	select {
+	case <-f.done:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the fetcher goroutine did not return after the lookup ended")
+	}
+}
diff --git a/internal/routewatch/batchwrite_internal_test.go b/internal/routewatch/batchwrite_internal_test.go
index 82ebeb0..605a8d9 100644
--- a/internal/routewatch/batchwrite_internal_test.go
+++ b/internal/routewatch/batchwrite_internal_test.go
@@ -1,6 +1,10 @@
 package routewatch
 
 import (
+	"bytes"
+	"context"
+	"encoding/json"
+	"log/slog"
 	"slices"
 	"sync"
 	"testing"
@@ -22,8 +26,9 @@ const (
 )
 
 // blockingStore is a mockStore whose batch writes for the AS, peer and prefix
-// handlers wait until the test calls releaseWrites. writeStarted is closed when
-// the first of them starts. It records what each write was given.
+// handlers, delete of a peer's routes and peering write wait until the test
+// calls releaseWrites. writeStarted is closed when the first of them starts. It
+// records what each batch write was given.
 type blockingStore struct {
 	*mockStore
 
@@ -85,6 +90,18 @@ func (s *blockingStore) UpdatePeerBatch(peers map[string]database.PeerUpdate) er
 	return nil
 }
 
+func (s *blockingStore) DeleteLiveRoutesOfPeer(peerIP string) (int, error) {
+	s.waitForRelease()
+
+	return s.mockStore.DeleteLiveRoutesOfPeer(peerIP)
+}
+
+func (s *blockingStore) RecordPeering(asA, asB int, ts time.Time) error {
+	s.waitForRelease()
+
+	return s.mockStore.RecordPeering(asA, asB, ts)
+}
+
 func (s *blockingStore) waitForRelease() {
 	s.startOnce.Do(func() { close(s.writeStarted) })
 	<-s.release
@@ -96,6 +113,40 @@ func (s *blockingStore) releaseWrites() {
 	s.releaseOnce.Do(func() { close(s.release) })
 }
 
+// stopLog holds what a handler's Stop logs it did not write.
+//
+//nolint:tagliatelle // field names are the keys the handlers log
+type stopLog struct {
+	Msg       string `json:"msg"`
+	Updates   int    `json:"updates"`
+	PeersDown int    `json:"peers_down"`
+	Paths     int    `json:"paths"`
+}
+
+// newErrorLogger returns a logger that writes only errors, as JSON lines, to
+// logs.
+func newErrorLogger(logs *bytes.Buffer) *logger.Logger {
+	return &logger.Logger{Logger: slog.New(slog.NewJSONHandler(logs,
+		&slog.HandlerOptions{Level: slog.LevelError}))}
+}
+
+// lastLogged decodes the last line in logs, which is the one Stop logs: a
+// handler logs nothing after it.
+func lastLogged(t *testing.T, logs *bytes.Buffer) stopLog {
+	t.Helper()
+
+	lines := bytes.Split(bytes.TrimSpace(logs.Bytes()), []byte("\n"))
+
+	var logged stopLog
+
+	err := json.Unmarshal(lines[len(lines)-1], &logged)
+	if err != nil {
+		t.Fatalf("want the error Stop logs, got %q: %v", logs.String(), err)
+	}
+
+	return logged
+}
+
 // returnsInTime reports whether f returns within handleMessageTimeout.
 func returnsInTime(f func()) bool {
 	done := make(chan struct{})
@@ -151,14 +202,14 @@ func handleWhileAWriteIsBlocked(
 	store *blockingStore,
 	h interface {
 		HandleMessage(msg *ristypes.RISMessage)
-		Stop()
+		Stop(ctx context.Context)
 	},
 	fill []*ristypes.RISMessage,
 	extra *ristypes.RISMessage,
 ) {
 	t.Helper()
 
-	defer h.Stop()
+	defer h.Stop(t.Context())
 	defer store.releaseWrites()
 
 	startBlockedWrite(t, store, h, fill)
@@ -178,14 +229,14 @@ func handleAtMaxBatchSize(
 	store *blockingStore,
 	h interface {
 		HandleMessage(msg *ristypes.RISMessage)
-		Stop()
+		Stop(ctx context.Context)
 	},
 	fill, toMax []*ristypes.RISMessage,
 	extra *ristypes.RISMessage,
 ) {
 	t.Helper()
 
-	defer h.Stop()
+	defer h.Stop(t.Context())
 	defer store.releaseWrites()
 
 	startBlockedWrite(t, store, h, fill)
@@ -217,6 +268,173 @@ func handleAtMaxBatchSize(
 	}
 }
 
+// stopWhileAWriteIsBlocked starts a blocked write with the messages in fill,
+// hands h the message extra, and stops h with a deadline that passes while
+// store holds the write. Stop must return all the same. Then it lets the write
+// finish and waits until done, closed when h's flush goroutine returns. Past
+// the deadline that goroutine skips its last write, so extra is not written,
+// and Stop logs as not written both extra and what the held write took.
+func stopWhileAWriteIsBlocked(
+	t *testing.T,
+	store *blockingStore,
+	h interface {
+		HandleMessage(msg *ristypes.RISMessage)
+		Stop(ctx context.Context)
+	},
+	done <-chan struct{},
+	fill []*ristypes.RISMessage,
+	extra *ristypes.RISMessage,
+) {
+	t.Helper()
+
+	const stopDeadline = 100 * time.Millisecond
+
+	defer store.releaseWrites()
+
+	startBlockedWrite(t, store, h, fill)
+	h.HandleMessage(extra)
+
+	ctx, cancel := context.WithTimeout(t.Context(), stopDeadline)
+	defer cancel()
+
+	if !returnsInTime(func() { h.Stop(ctx) }) {
+		t.Fatalf("Stop with a deadline of %s did not return while a write "+
+			"was blocked", stopDeadline)
+	}
+
+	store.releaseWrites()
+
+	select {
+	case <-done:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the flush goroutine did not return after the write finished")
+	}
+}
+
+func TestPrefixHandlerSkipsItsLastWriteAfterTheStopDeadline(t *testing.T) {
+	t.Parallel()
+
+	const extraPrefix = "198.51.100.0/24"
+
+	var logs bytes.Buffer
+
+	store := newBlockingStore()
+	h := NewPrefixHandler(store, newErrorLogger(&logs))
+	fill := slices.Repeat([]string{testV4Prefix}, prefixBatchSize)
+	// The peer's session goes down first, so the write held is the delete of
+	// its routes, and Stop must log that peer down too.
+	stopWhileAWriteIsBlocked(t, store, h, h.done,
+		[]*ristypes.RISMessage{sessionDown(), prefixAnnouncement(fill)},
+		prefixAnnouncement([]string{extraPrefix}))
+
+	store.mu.Lock()
+	defer store.mu.Unlock()
+
+	if store.prefixes[extraPrefix] {
+		t.Errorf("%s was written after the stop deadline", extraPrefix)
+	}
+
+	logged := lastLogged(t, &logs)
+	if logged.Updates != prefixBatchSize+1 || logged.PeersDown != 1 {
+		t.Errorf("Stop logged %d updates and %d peer downs not written, "+
+			"want %d and 1", logged.Updates, logged.PeersDown, prefixBatchSize+1)
+	}
+}
+
+func TestASHandlerSkipsItsLastWriteAfterTheStopDeadline(t *testing.T) {
+	t.Parallel()
+
+	// Each message gives an update for its origin AS and one for each AS
+	// in its path: fill asnBatchSize+1, extra 2.
+	const wantUpdates = asnBatchSize + 1 + 2
+
+	var logs bytes.Buffer
+
+	store := newBlockingStore()
+	h := NewASHandler(store, newErrorLogger(&logs))
+	fill := ristypes.ASPath{Sequence: slices.Repeat([]int{testASNA}, asnBatchSize)}
+	stopWhileAWriteIsBlocked(t, store, h, h.done,
+		[]*ristypes.RISMessage{{Path: fill}},
+		&ristypes.RISMessage{Path: ristypes.ASPath{Sequence: []int{testASNB}}})
+
+	store.mu.Lock()
+	defer store.mu.Unlock()
+
+	if store.asns[testASNB] {
+		t.Errorf("AS%d was written after the stop deadline", testASNB)
+	}
+
+	if logged := lastLogged(t, &logs); logged.Updates != wantUpdates {
+		t.Errorf("Stop logged %d updates not written, want %d",
+			logged.Updates, wantUpdates)
+	}
+}
+
+func TestPeerHandlerSkipsItsLastWriteAfterTheStopDeadline(t *testing.T) {
+	t.Parallel()
+
+	const otherPeerIP = "2001:db8:ffff::2"
+
+	var logs bytes.Buffer
+
+	store := newBlockingStore()
+	h := NewPeerHandler(store, newErrorLogger(&logs))
+	stopWhileAWriteIsBlocked(t, store, h, h.done,
+		slices.Repeat([]*ristypes.RISMessage{{Peer: testPeerIP}}, peerBatchSize),
+		&ristypes.RISMessage{Peer: otherPeerIP})
+
+	store.mu.Lock()
+	defer store.mu.Unlock()
+
+	if store.peers[otherPeerIP] {
+		t.Errorf("peer %s was written after the stop deadline", otherPeerIP)
+	}
+
+	if logged := lastLogged(t, &logs); logged.Updates != peerBatchSize+1 {
+		t.Errorf("Stop logged %d updates not written, want %d",
+			logged.Updates, peerBatchSize+1)
+	}
+}
+
+// TestPeeringHandlerStopCountsTheWriteInProgress hands a running peering
+// handler one AS path and stops it with a deadline that passes while store
+// holds Stop's last write, of that path's peering. Stop must log that path as
+// not written.
+func TestPeeringHandlerStopCountsTheWriteInProgress(t *testing.T) {
+	t.Parallel()
+
+	const stopDeadline = 100 * time.Millisecond
+
+	var logs bytes.Buffer
+
+	store := newBlockingStore()
+	defer store.releaseWrites()
+
+	h := NewPeeringHandler(store, newErrorLogger(&logs))
+	handle(h, time.Now().UTC(), testASNA, testASNB)
+
+	ctx, cancel := context.WithTimeout(t.Context(), stopDeadline)
+	defer cancel()
+
+	if !returnsInTime(func() { h.Stop(ctx) }) {
+		t.Fatalf("Stop with a deadline of %s did not return while a write "+
+			"was blocked", stopDeadline)
+	}
+
+	store.releaseWrites()
+
+	select {
+	case <-h.done:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the processing goroutine did not return after the write " +
+			"finished")
+	}
+
+	if logged := lastLogged(t, &logs); logged.Paths != 1 {
+		t.Errorf("Stop logged %d paths not written, want 1", logged.Paths)
+	}
+}
+
 // prefixAnnouncement returns a message in which testPeerIP announces prefixes
 // with origin AS testASNA.
 func prefixAnnouncement(prefixes []string) *ristypes.RISMessage {
diff --git a/internal/routewatch/cli.go b/internal/routewatch/cli.go
index ea7d475..1bf6907 100644
--- a/internal/routewatch/cli.go
+++ b/internal/routewatch/cli.go
@@ -14,8 +14,14 @@ import (
 )
 
 const (
-	// shutdownTimeout is the maximum time allowed for graceful shutdown
-	shutdownTimeout = 60 * time.Second
+	// shutdownTimeout is how long Shutdown has after a stop signal. upaas,
+	// like docker stop by default, kills the container 10 seconds after the
+	// stop signal (README "Running under upaas").
+	shutdownTimeout = 8 * time.Second
+	// stopTimeout is fx's limit on the stop hook, past which fx exits with
+	// status 1: shutdownTimeout and time for Shutdown to close the HTTP
+	// server after its deadline.
+	stopTimeout = 9 * time.Second
 	// debugInterval is how often to log debug stats
 	debugInterval = 60 * time.Second
 	// bytesPerMB is bytes per megabyte
@@ -63,7 +69,7 @@ func logDebugStats(logger *logger.Logger) {
 func CLIEntry() {
 	app := fx.New(
 		fx.Options(getModule()...),
-		fx.StopTimeout(shutdownTimeout), // Allow 60 seconds for graceful shutdown
+		fx.StopTimeout(stopTimeout),
 		fx.Invoke(func(
 			lc fx.Lifecycle,
 			rw *RouteWatch,
@@ -106,6 +112,10 @@ func CLIEntry() {
 				},
 				OnStop: func(ctx context.Context) error {
 					logger.Info("Shutting down RouteWatch")
+
+					ctx, cancel := context.WithTimeout(ctx, shutdownTimeout)
+					defer cancel()
+
 					rw.Shutdown(ctx)
 
 					return nil
diff --git a/internal/routewatch/dbmaintainer.go b/internal/routewatch/dbmaintainer.go
index 6ecdf0b..abd075c 100644
--- a/internal/routewatch/dbmaintainer.go
+++ b/internal/routewatch/dbmaintainer.go
@@ -46,7 +46,7 @@ type DBMaintainer struct {
 	db     database.Store
 	logger *slog.Logger
 	stopCh chan struct{}
-	wg     sync.WaitGroup
+	done   chan struct{} // closed when the maintenance goroutine returns
 
 	// Stats tracking
 	statsMu             sync.Mutex
@@ -67,14 +67,13 @@ func NewDBMaintainer(db database.Store, logger *slog.Logger) *DBMaintainer {
 		db:     db,
 		logger: logger.With("component", "db_maintainer"),
 		stopCh: make(chan struct{}),
+		done:   make(chan struct{}),
 	}
 }
 
 // Start begins the background maintenance goroutine. It runs until Stop:
 // the end of ctx does not stop it.
 func (m *DBMaintainer) Start(ctx context.Context) {
-	m.wg.Add(1)
-
 	go m.run(context.WithoutCancel(ctx))
 
 	m.logger.Info("Database maintainer started",
@@ -84,16 +83,23 @@ func (m *DBMaintainer) Start(ctx context.Context) {
 	)
 }
 
-// Stop gracefully shuts down the maintainer.
-func (m *DBMaintainer) Stop() {
+// Stop stops the maintainer and waits, until ctx ends, for a maintenance task
+// in progress to finish.
+func (m *DBMaintainer) Stop(ctx context.Context) {
 	close(m.stopCh)
-	m.wg.Wait()
-	m.logger.Info("Database maintainer stopped")
+
+	select {
+	case <-m.done:
+		m.logger.Info("Database maintainer stopped")
+	case <-ctx.Done():
+		m.logger.Warn("Stop deadline passed before the database maintainer " +
+			"stopped")
+	}
 }
 
 // run is the main background loop.
 func (m *DBMaintainer) run(ctx context.Context) {
-	defer m.wg.Done()
+	defer close(m.done)
 
 	// Use different timers for each task
 	checkpointTimer := time.NewTimer(checkpointInterval)
diff --git a/internal/routewatch/dbmaintainer_internal_test.go b/internal/routewatch/dbmaintainer_internal_test.go
index 94d258a..6889580 100644
--- a/internal/routewatch/dbmaintainer_internal_test.go
+++ b/internal/routewatch/dbmaintainer_internal_test.go
@@ -6,6 +6,7 @@ import (
 	"encoding/json"
 	"log/slog"
 	"testing"
+	"time"
 
 	"git.eeqj.de/sneak/routewatch/internal/database"
 )
@@ -52,3 +53,68 @@ func TestIncompleteCheckpointNotLoggedAsCompleted(t *testing.T) {
 			m.checkpointCount)
 	}
 }
+
+// heldCheckpointStore is a store whose checkpoint closes started and then
+// waits until release is closed.
+type heldCheckpointStore struct {
+	*mockStore
+
+	started chan struct{}
+	release chan struct{}
+}
+
+// Checkpoint waits until release is closed.
+func (s heldCheckpointStore) Checkpoint(context.Context) error {
+	close(s.started)
+	<-s.release
+
+	return nil
+}
+
+// TestDBMaintainerStopReturnsByItsDeadline stops the maintainer with a short
+// deadline while its goroutine runs a checkpoint that the store holds until
+// the test ends. Stop must return all the same instead of waiting for the
+// checkpoint.
+func TestDBMaintainerStopReturnsByItsDeadline(t *testing.T) {
+	t.Parallel()
+
+	const stopDeadline = 100 * time.Millisecond
+
+	store := heldCheckpointStore{
+		mockStore: newMockStore(),
+		started:   make(chan struct{}),
+		release:   make(chan struct{}),
+	}
+	m := NewDBMaintainer(store, slog.Default())
+
+	// Start would run the first checkpoint only after checkpointInterval.
+	// This goroutine stands for the one Start runs and checkpoints at once.
+	go func() {
+		defer close(m.done)
+
+		m.runCheckpoint(t.Context())
+	}()
+
+	select {
+	case <-store.started:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the maintainer did not start the checkpoint")
+	}
+
+	ctx, cancel := context.WithTimeout(t.Context(), stopDeadline)
+	defer cancel()
+
+	if !returnsInTime(func() { m.Stop(ctx) }) {
+		t.Fatalf("Stop with a deadline of %s did not return while a "+
+			"checkpoint was in progress", stopDeadline)
+	}
+
+	close(store.release)
+
+	select {
+	case <-m.done:
+	case <-time.After(handleMessageTimeout):
+		t.Fatal("the maintenance goroutine did not return after the " +
+			"checkpoint ended")
+	}
+}
diff --git a/internal/routewatch/peerhandler.go b/internal/routewatch/peerhandler.go
index dcb1bc4..7854695 100644
--- a/internal/routewatch/peerhandler.go
+++ b/internal/routewatch/peerhandler.go
@@ -5,6 +5,7 @@ package routewatch
 // peer state in the database.
 
 import (
+	"context"
 	"strconv"
 	"sync"
 	"time"
@@ -42,18 +43,24 @@ type PeerHandler struct {
 	db     database.Store
 	logger *logger.Logger
 
-	// Batching. mu guards peerBatch only: the flush goroutine takes the batch
-	// under mu and writes it after releasing mu, so HandleMessage waits for
-	// a database write only while peerBatch is at peerBatchMaxSize.
+	// Batching. mu guards peerBatch and writing only: the flush goroutine
+	// takes the batch under mu and writes it after releasing mu, so
+	// HandleMessage waits for a database write only while peerBatch is at
+	// peerBatchMaxSize.
 	mu        sync.Mutex
 	peerBatch []peerUpdate
+	// writing is how many updates the flush goroutine took from peerBatch
+	// and has not finished writing.
+	writing int
 	// batchTaken is signalled when the flush goroutine takes peerBatch; its L
 	// is &mu.
 	batchTaken  sync.Cond
 	batchFullCh chan struct{} // wakes the flush goroutine when peerBatch is full
 	lastFlush   time.Time     // used only by the flush goroutine
-	stopCh      chan struct{}
-	wg          sync.WaitGroup
+	// stopCh hands Stop's context to the flush goroutine. It holds one, so
+	// Stop does not wait for a write in progress to hand it over.
+	stopCh chan context.Context
+	done   chan struct{} // closed when the flush goroutine returns
 }
 
 type peerUpdate struct {
@@ -74,12 +81,12 @@ func NewPeerHandler(db database.Store, logger *logger.Logger) *PeerHandler {
 		peerBatch:   make([]peerUpdate, 0, peerBatchSize),
 		batchFullCh: make(chan struct{}, 1),
 		lastFlush:   time.Now(),
-		stopCh:      make(chan struct{}),
+		stopCh:      make(chan context.Context, 1),
+		done:        make(chan struct{}),
 	}
 	h.batchTaken.L = &h.mu
 
 	// Start the flush timer goroutine
-	h.wg.Add(1)
 	go h.flushLoop()
 
 	return h
@@ -144,16 +151,32 @@ func (h *PeerHandler) HandleMessage(msg *ristypes.RISMessage) {
 	}
 }
 
-// Stop gracefully stops the handler and flushes remaining batches
-func (h *PeerHandler) Stop() {
-	close(h.stopCh)
-	h.wg.Wait()
+// Stop stops the flush goroutine, which writes the updates the handler holds
+// before it returns, and waits for it until ctx ends. Once ctx has ended the
+// flush goroutine skips that last write, and a write still running is lost
+// when the process exits, so Stop logs how many updates are not written.
+func (h *PeerHandler) Stop(ctx context.Context) {
+	h.stopCh <- ctx
+
+	select {
+	case <-h.done:
+	case <-ctx.Done():
+	}
+
+	h.mu.Lock()
+	unwritten := h.writing + len(h.peerBatch)
+	h.mu.Unlock()
+
+	if unwritten > 0 {
+		h.logger.Error("Stop deadline passed before the peer handler wrote "+
+			"its updates", "updates", unwritten)
+	}
 }
 
 // flushLoop runs in a goroutine, the only one that writes the batch: it
 // flushes when the batch is full, periodically, and once more on Stop.
 func (h *PeerHandler) flushLoop() {
-	defer h.wg.Done()
+	defer close(h.done)
 
 	ticker := time.NewTicker(peerBatchTimeout)
 	defer ticker.Stop()
@@ -166,9 +189,11 @@ func (h *PeerHandler) flushLoop() {
 			}
 		case <-h.batchFullCh:
 			h.flushBatch()
-		case <-h.stopCh:
-			// Final flush
-			h.flushBatch()
+		case ctx := <-h.stopCh:
+			// Final flush, unless the stop deadline has passed
+			if ctx.Err() == nil {
+				h.flushBatch()
+			}
 
 			return
 		}
@@ -176,7 +201,8 @@ func (h *PeerHandler) flushLoop() {
 }
 
 // takeBatch returns the pending updates and leaves an empty batch in their
-// place for HandleMessage to fill.
+// place for HandleMessage to fill. They count in writing until flushBatch has
+// written them.
 func (h *PeerHandler) takeBatch() []peerUpdate {
 	h.mu.Lock()
 	defer h.mu.Unlock()
@@ -186,6 +212,7 @@ func (h *PeerHandler) takeBatch() []peerUpdate {
 	}
 
 	batch := h.peerBatch
+	h.writing = len(batch)
 	h.peerBatch = make([]peerUpdate, 0, peerBatchSize)
 	h.batchTaken.Broadcast()
 
@@ -227,5 +254,9 @@ func (h *PeerHandler) flushBatch() {
 			"error", err, "count", len(dbPeerMap))
 	}
 
+	h.mu.Lock()
+	h.writing = 0
+	h.mu.Unlock()
+
 	h.lastFlush = time.Now()
 }
diff --git a/internal/routewatch/peeringhandler.go b/internal/routewatch/peeringhandler.go
index d30d06b..f304082 100644
--- a/internal/routewatch/peeringhandler.go
+++ b/internal/routewatch/peeringhandler.go
@@ -1,6 +1,7 @@
 package routewatch
 
 import (
+	"context"
 	"encoding/json"
 	"sync"
 	"time"
@@ -45,9 +46,14 @@ type PeeringHandler struct {
 	mu           sync.Mutex
 	asPaths      map[string]time.Time // key is JSON-encoded AS path
 	droppedPaths int                  // paths dropped because the map was full
+	// writing is how many paths processPeerings took from asPaths and has
+	// not finished writing the peerings of.
+	writing int
 
-	stopCh chan struct{}
-	wg     sync.WaitGroup
+	// stopCh hands Stop's context to the processing goroutine. It holds one,
+	// so Stop does not wait for a write in progress to hand it over.
+	stopCh chan context.Context
+	done   chan struct{} // closed when the processing goroutine returns
 }
 
 // NewPeeringHandler creates and initializes a new PeeringHandler with the
@@ -59,12 +65,11 @@ func NewPeeringHandler(db database.Store, logger *logger.Logger) *PeeringHandler
 		db:      db,
 		logger:  logger,
 		asPaths: make(map[string]time.Time),
-		stopCh:  make(chan struct{}),
+		stopCh:  make(chan context.Context, 1),
+		done:    make(chan struct{}),
 	}
 
 	// Start the periodic processing goroutine
-	h.wg.Add(1)
-
 	go h.processLoop()
 
 	return h
@@ -132,18 +137,33 @@ func (h *PeeringHandler) ProcessPeeringsNow() {
 	h.processPeerings()
 }
 
-// Stop gracefully shuts down the handler by signaling the background
-// goroutine to stop and waiting while it processes the remaining AS paths,
-// so no peering data is lost during shutdown.
-func (h *PeeringHandler) Stop() {
-	close(h.stopCh)
-	h.wg.Wait()
+// Stop stops the processing goroutine, which writes the peerings of the AS
+// paths the handler holds before it returns, and waits for it until ctx ends.
+// Once ctx has ended the processing goroutine skips that last write, and a
+// write still running is lost when the process exits, so Stop logs how many
+// paths' peerings are not written.
+func (h *PeeringHandler) Stop(ctx context.Context) {
+	h.stopCh <- ctx
+
+	select {
+	case <-h.done:
+	case <-ctx.Done():
+	}
+
+	h.mu.Lock()
+	unwritten := h.writing + len(h.asPaths)
+	h.mu.Unlock()
+
+	if unwritten > 0 {
+		h.logger.Error("Stop deadline passed before the peering handler wrote "+
+			"its peerings", "paths", unwritten)
+	}
 }
 
 // processLoop runs periodically to process AS paths into peerings, and once
 // more on Stop.
 func (h *PeeringHandler) processLoop() {
-	defer h.wg.Done()
+	defer close(h.done)
 
 	ticker := time.NewTicker(peeringProcessInterval)
 	defer ticker.Stop()
@@ -152,9 +172,11 @@ func (h *PeeringHandler) processLoop() {
 		select {
 		case <-ticker.C:
 			h.processPeerings()
-		case <-h.stopCh:
-			// Final processing
-			h.processPeerings()
+		case ctx := <-h.stopCh:
+			// Final processing, unless the stop deadline has passed
+			if ctx.Err() == nil {
+				h.processPeerings()
+			}
 
 			return
 		}
@@ -169,6 +191,7 @@ func (h *PeeringHandler) processPeerings() {
 	h.mu.Lock()
 	paths := h.asPaths
 	h.asPaths = make(map[string]time.Time)
+	h.writing = len(paths)
 	dropped := h.droppedPaths
 	h.mu.Unlock()
 
@@ -234,6 +257,10 @@ func (h *PeeringHandler) processPeerings() {
 		}
 	}
 
+	h.mu.Lock()
+	h.writing = 0
+	h.mu.Unlock()
+
 	h.logger.Info("Processed AS peerings",
 		"paths", len(paths),
 		"unique_peerings", len(peerings),
diff --git a/internal/routewatch/peeringhandler_internal_test.go b/internal/routewatch/peeringhandler_internal_test.go
index 13c5d66..b11737a 100644
--- a/internal/routewatch/peeringhandler_internal_test.go
+++ b/internal/routewatch/peeringhandler_internal_test.go
@@ -53,7 +53,6 @@ func newTestHandler(db database.Store) *PeeringHandler {
 		db:      db,
 		logger:  logger.New(),
 		asPaths: make(map[string]time.Time),
-		stopCh:  make(chan struct{}),
 	}
 }
 
@@ -197,7 +196,7 @@ func TestPeeringHandlerStopWritesTheRemainingPaths(t *testing.T) {
 	h := NewPeeringHandler(store, logger.New())
 
 	handle(h, time.Now().UTC(), testASNA, testASNB)
-	h.Stop()
+	h.Stop(t.Context())
 
 	if got := store.callCount(); got != 1 {
 		t.Errorf("want 1 RecordPeering call when Stop returns, got %d", got)
diff --git a/internal/routewatch/prefixhandler.go b/internal/routewatch/prefixhandler.go
index 4467e2a..329651e 100644
--- a/internal/routewatch/prefixhandler.go
+++ b/internal/routewatch/prefixhandler.go
@@ -1,6 +1,7 @@
 package routewatch
 
 import (
+	"context"
 	"net"
 	"net/netip"
 	"slices"
@@ -50,9 +51,9 @@ type PrefixHandler struct {
 	logger  *logger.Logger
 	metrics *metrics.Tracker
 
-	// Batching. mu guards batch, held and peersDown only: the flush goroutine
-	// takes them under mu and writes them after releasing mu, so
-	// HandleMessage waits for a database write only while batch is at
+	// Batching. mu guards batch, held, peersDown, writing and deleting only:
+	// the flush goroutine takes them under mu and writes them after releasing
+	// mu, so HandleMessage waits for a database write only while batch is at
 	// prefixBatchMaxSize.
 	mu    sync.Mutex
 	batch []prefixUpdate
@@ -66,13 +67,21 @@ type PrefixHandler struct {
 	// since the batch was taken, and those whose route delete failed in the
 	// last flush.
 	peersDown []string
+	// writing is how many updates the flush goroutine took and has not
+	// finished writing.
+	writing int
+	// deleting is how many peers from peersDown the flush goroutine took and
+	// has not yet deleted the routes of.
+	deleting int
 	// batchTaken is signalled when the flush goroutine takes batch; its L is
 	// &mu.
 	batchTaken  sync.Cond
 	batchFullCh chan struct{} // wakes the flush goroutine when batch is full
 	lastFlush   time.Time     // used only by the flush goroutine
-	stopCh      chan struct{}
-	wg          sync.WaitGroup
+	// stopCh hands Stop's context to the flush goroutine. It holds one, so
+	// Stop does not wait for a write in progress to hand it over.
+	stopCh chan context.Context
+	done   chan struct{} // closed when the flush goroutine returns
 }
 
 type prefixUpdate struct {
@@ -95,12 +104,12 @@ func NewPrefixHandler(db database.Store, logger *logger.Logger) *PrefixHandler {
 		batch:       make([]prefixUpdate, 0, prefixBatchSize),
 		batchFullCh: make(chan struct{}, 1),
 		lastFlush:   time.Now(),
-		stopCh:      make(chan struct{}),
+		stopCh:      make(chan context.Context, 1),
+		done:        make(chan struct{}),
 	}
 	h.batchTaken.L = &h.mu
 
 	// Start the flush timer goroutine
-	h.wg.Add(1)
 	go h.flushLoop()
 
 	return h
@@ -202,10 +211,39 @@ func (h *PrefixHandler) HandleMessage(msg *ristypes.RISMessage) {
 	}
 }
 
-// Stop gracefully stops the handler and flushes remaining batches
-func (h *PrefixHandler) Stop() {
-	close(h.stopCh)
-	h.wg.Wait()
+// Stop stops the flush goroutine, which writes the updates and peer downs the
+// handler holds before it returns, and waits for it until ctx ends. Once ctx
+// has ended the flush goroutine skips that last write, and a write still
+// running is lost when the process exits. A peer whose route delete fails in
+// the last write is not retried either. Stop logs how many updates are not
+// written and how many peer downs have not had their routes deleted.
+func (h *PrefixHandler) Stop(ctx context.Context) {
+	h.stopCh <- ctx
+
+	select {
+	case <-h.done:
+	case <-ctx.Done():
+	}
+
+	h.mu.Lock()
+	unwritten := h.writing + len(h.batch) + len(h.held)
+	peersDown := h.deleting + len(h.peersDown)
+	h.mu.Unlock()
+
+	if unwritten == 0 && peersDown == 0 {
+		return
+	}
+
+	if ctx.Err() != nil {
+		h.logger.Error("Stop deadline passed before the prefix handler wrote "+
+			"its updates", "updates", unwritten, "peers_down", peersDown)
+
+		return
+	}
+
+	h.logger.Error("The prefix handler stopped without deleting the routes "+
+		"of peers whose session went down", "updates", unwritten,
+		"peers_down", peersDown)
 }
 
 // peerSessionDown notes that the peer's BGP session went down, so that the next
@@ -230,7 +268,7 @@ func (h *PrefixHandler) peerSessionDown(peer string) {
 // flushLoop runs in a goroutine, the only one that writes the batch: it
 // flushes when the batch is full, periodically, and once more on Stop.
 func (h *PrefixHandler) flushLoop() {
-	defer h.wg.Done()
+	defer close(h.done)
 
 	ticker := time.NewTicker(prefixBatchTimeout)
 	defer ticker.Stop()
@@ -243,9 +281,11 @@ func (h *PrefixHandler) flushLoop() {
 			}
 		case <-h.batchFullCh:
 			h.flushBatch()
-		case <-h.stopCh:
-			// Final flush
-			h.flushBatch()
+		case ctx := <-h.stopCh:
+			// Final flush, unless the stop deadline has passed
+			if ctx.Err() == nil {
+				h.flushBatch()
+			}
 
 			return
 		}
@@ -254,7 +294,9 @@ func (h *PrefixHandler) flushLoop() {
 
 // takeBatch returns the pending updates, the held ones first, and the peers in
 // peersDown, and leaves an empty batch, no held updates and no peers in their
-// place for HandleMessage to fill.
+// place for HandleMessage to fill. The updates count in writing until
+// flushBatch has written them, and the peers in deleting until their routes
+// are deleted.
 func (h *PrefixHandler) takeBatch() ([]prefixUpdate, []string) {
 	h.mu.Lock()
 	defer h.mu.Unlock()
@@ -268,6 +310,8 @@ func (h *PrefixHandler) takeBatch() ([]prefixUpdate, []string) {
 		batch = slices.Concat(h.held, h.batch)
 	}
 
+	h.writing = len(batch)
+	h.deleting = len(peersDown)
 	h.held = nil
 	h.batch = make([]prefixUpdate, 0, prefixBatchSize)
 	h.peersDown = nil
@@ -354,6 +398,10 @@ func (h *PrefixHandler) flushBatch() {
 
 	successCount := h.writeBatch(routesToUpsert, routesToDelete, prefixesToUpdate)
 
+	h.mu.Lock()
+	h.writing = 0
+	h.mu.Unlock()
+
 	elapsed := time.Since(startTime)
 	h.logger.Debug("Flushed prefix batch",
 		"batch_size", batchSize,
@@ -369,7 +417,8 @@ func (h *PrefixHandler) flushBatch() {
 // deleteLiveRoutesOfPeers deletes all live routes of each of peers, the peers
 // whose BGP session went down, and returns those whose delete failed. Most
 // downs come from peers that have no routes, so only a delete that removed
-// routes is logged.
+// routes is logged. A peer whose delete succeeded no longer counts in deleting;
+// a failed one counts until keepForNextFlush puts it back in peersDown.
 func (h *PrefixHandler) deleteLiveRoutesOfPeers(peers []string) []string {
 	var failed []string
 
@@ -386,6 +435,10 @@ func (h *PrefixHandler) deleteLiveRoutesOfPeers(peers []string) []string {
 			continue
 		}
 
+		h.mu.Lock()
+		h.deleting--
+		h.mu.Unlock()
+
 		if deleted > 0 {
 			h.logger.Info(
 				"Deleted the live routes of a peer whose session went down",
@@ -439,8 +492,12 @@ func (h *PrefixHandler) keepForNextFlush(
 		kept = slices.Clone(kept[len(kept)-prefixBatchSize:])
 	}
 
-	// takeBatch left held empty, and only this flush fills it.
+	// takeBatch left held empty, and only this flush fills it. The kept
+	// updates now count in held, not in writing, and the failed peers in
+	// peersDown, not in deleting.
 	h.held = kept
+	h.writing = len(toWrite)
+	h.deleting = 0
 
 	for _, peer := range failedPeers {
 		if !slices.Contains(h.peersDown, peer) {
diff --git a/internal/routewatch/prefixhandler_internal_test.go b/internal/routewatch/prefixhandler_internal_test.go
index 0fb851a..12aeb9d 100644
--- a/internal/routewatch/prefixhandler_internal_test.go
+++ b/internal/routewatch/prefixhandler_internal_test.go
@@ -1,11 +1,13 @@
 package routewatch
 
 import (
+	"bytes"
 	"context"
 	"errors"
 	"fmt"
 	"net/netip"
 	"slices"
+	"strings"
 	"sync"
 	"testing"
 	"time"
@@ -766,6 +768,53 @@ func TestPrefixHandlerKeepsAtMostABatchOfUpdatesWhileADeleteKeepsFailing(
 	}
 }
 
+// TestPrefixHandlerStopLogsAFailedDeleteWithoutTheDeadline stops a prefix
+// handler, with no deadline, after a peer's session went down and the peer
+// announced a prefix, into a database whose every delete of a peer's routes
+// fails. Stop must log the peer down and the announcement as not written, and
+// must not say that the stop deadline passed.
+func TestPrefixHandlerStopLogsAFailedDeleteWithoutTheDeadline(t *testing.T) {
+	t.Parallel()
+
+	var logs bytes.Buffer
+
+	h := NewPrefixHandler(peerDeleteAlwaysFailsStore{Database: newTestDatabase(t)},
+		newErrorLogger(&logs))
+	h.HandleMessage(sessionDown())
+	h.HandleMessage(peerAnnouncement(testPeerIP, testV4Prefix))
+	h.Stop(t.Context())
+
+	logged := lastLogged(t, &logs)
+	if strings.Contains(logged.Msg, "deadline") {
+		t.Errorf("Stop logged %q although its deadline had not passed",
+			logged.Msg)
+	}
+
+	if logged.Updates != 1 || logged.PeersDown != 1 {
+		t.Errorf("Stop logged %d updates and %d peer downs not written, "+
+			"want 1 and 1", logged.Updates, logged.PeersDown)
+	}
+}
+
+// TestPrefixHandlerStopLogsNothingAfterADeleteThatSucceeds stops a prefix
+// handler, with no deadline, after a peer's session went down, into a database
+// whose delete of the peer's routes succeeds. Stop must log nothing: a peer
+// whose routes are deleted no longer counts as a peer down left undone.
+func TestPrefixHandlerStopLogsNothingAfterADeleteThatSucceeds(t *testing.T) {
+	t.Parallel()
+
+	var logs bytes.Buffer
+
+	h := NewPrefixHandler(newTestDatabase(t), newErrorLogger(&logs))
+	h.HandleMessage(sessionDown())
+	h.Stop(t.Context())
+
+	if logs.Len() != 0 {
+		t.Errorf("Stop logged %q after the routes of the peer whose session "+
+			"went down were deleted", logs.String())
+	}
+}
+
 // newTestDatabase opens a database in a new temporary directory. It is closed
 // when the test ends.
 func newTestDatabase(t *testing.T) *database.Database {
diff --git a/internal/server/server.go b/internal/server/server.go
index 8d8b88c..a6cf203 100644
--- a/internal/server/server.go
+++ b/internal/server/server.go
@@ -109,7 +109,9 @@ func (s *Server) Start(ctx context.Context) error {
 	return nil
 }
 
-// Stop gracefully stops the HTTP server
+// Stop stops the HTTP server. It waits, until ctx ends, for the requests in
+// progress to finish, and then closes the connections of those still running
+// and returns ctx's error.
 func (s *Server) Stop(ctx context.Context) error {
 	if s.srv == nil {
 		return nil
@@ -117,7 +119,12 @@ func (s *Server) Stop(ctx context.Context) error {
 
 	s.logger.Info("Stopping HTTP server")
 
-	return s.srv.Shutdown(ctx)
+	err := s.srv.Shutdown(ctx)
+	if err != nil {
+		return errors.Join(err, s.srv.Close())
+	}
+
+	return nil
 }
 
 // SetASNFetcher sets the ASN WHOIS fetcher for on-demand lookups.
diff --git a/internal/server/server_internal_test.go b/internal/server/server_internal_test.go
new file mode 100644
index 0000000..a5f89bb
--- /dev/null
+++ b/internal/server/server_internal_test.go
@@ -0,0 +1,92 @@
+package server
+
+import (
+	"context"
+	"net"
+	"net/http"
+	"testing"
+	"time"
+
+	"git.eeqj.de/sneak/routewatch/internal/logger"
+)
+
+// TestStopClosesTheConnectionOfARequestStillRunning serves a request whose
+// handler does not return until the test ends, and stops the server with a
+// deadline that passes while the request runs. The client must then see its
+// connection closed. Before the fix Stop returned at the deadline and left the
+// connection open until the handler returned.
+func TestStopClosesTheConnectionOfARequestStillRunning(t *testing.T) {
+	t.Parallel()
+
+	const (
+		stopDeadline = 100 * time.Millisecond
+		// waitTimeout is how long the test waits for the request to reach
+		// the handler, and then for the client to see its connection closed.
+		waitTimeout = 2 * time.Second
+		// readHeaderTimeout bounds the test server's read of the request
+		// header, as every http.Server must.
+		readHeaderTimeout = time.Second
+	)
+
+	release := make(chan struct{})
+	defer close(release)
+
+	started := make(chan struct{})
+
+	var listenConfig net.ListenConfig
+
+	listener, err := listenConfig.Listen(t.Context(), "tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("failed to open the test listener: %v", err)
+	}
+
+	s := &Server{logger: logger.New(), srv: &http.Server{
+		Handler: http.HandlerFunc(func(http.ResponseWriter, *http.Request) {
+			close(started)
+			<-release
+		}),
+		ReadHeaderTimeout: readHeaderTimeout,
+	}}
+
+	go func() { _ = s.srv.Serve(listener) }()
+
+	answered := make(chan error, 1)
+
+	go func() {
+		req, err := http.NewRequestWithContext(t.Context(), http.MethodGet,
+			"http://"+listener.Addr().String()+"/", nil)
+		if err != nil {
+			answered <- err
+
+			return
+		}
+
+		resp, err := http.DefaultClient.Do(req)
+		if err == nil {
+			_ = resp.Body.Close()
+		}
+
+		answered <- err
+	}()
+
+	select {
+	case <-started:
+	case <-time.After(waitTimeout):
+		t.Fatal("the request did not reach the handler")
+	}
+
+	ctx, cancel := context.WithTimeout(t.Context(), stopDeadline)
+	defer cancel()
+
+	_ = s.Stop(ctx)
+
+	select {
+	case err := <-answered:
+		if err == nil {
+			t.Error("the request still running at the deadline was answered")
+		}
+	case <-time.After(waitTimeout):
+		t.Fatal("the connection of the request still running at the " +
+			"deadline was open after Stop returned")
+	}
+}
diff --git a/internal/streamer/streamer.go b/internal/streamer/streamer.go
index 698768f..2df25f5 100644
--- a/internal/streamer/streamer.go
+++ b/internal/streamer/streamer.go
@@ -253,9 +253,10 @@ func (s *Streamer) Start(ctx context.Context) error {
 
 // Stop ends the stream and stops the handler workers. It returns once each
 // worker has handed its handler every message left on its queue and then the
-// STATE messages held for it (see queueMessage). This method is safe to call
+// STATE messages held for it (see queueMessage), or once ctx ends, and then
+// logs how many messages were not handed over. This method is safe to call
 // multiple times.
-func (s *Streamer) Stop() {
+func (s *Streamer) Stop(ctx context.Context) {
 	s.mu.Lock()
 	if s.cancel == nil {
 		// Not started, or already stopped: closing the queues again would panic.
@@ -264,28 +265,56 @@ func (s *Streamer) Stop() {
 		return
 	}
 
-	// Once ctx is cancelled the read loop queues and holds nothing more (see
-	// dispatchMessage).
+	// Once the stream's context is cancelled the read loop queues and holds
+	// nothing more (see dispatchMessage).
 	s.cancel()
 	s.cancel = nil
 
+	notHandedOver := 0
+
 	for _, info := range s.handlers {
 		// The held messages came after everything on the queue. Each waits
-		// for the worker, which does not take s.mu, to make room.
-		for _, msg := range info.heldState {
-			info.queue <- msg
+		// for the worker, which does not take s.mu, to make room, until ctx
+		// ends.
+		for len(info.heldState) > 0 && ctx.Err() == nil {
+			select {
+			case info.queue <- info.heldState[0]:
+				info.heldState = info.heldState[1:]
+			case <-ctx.Done():
+			}
 		}
 
+		notHandedOver += len(info.heldState)
 		info.heldState = nil
 
 		// The worker returns once it has emptied the closed queue.
 		close(info.queue)
 	}
 
+	handlers := s.handlers
 	s.running = false
 	s.mu.Unlock()
 	s.metrics.SetConnected(false)
-	s.workers.Wait()
+
+	workersDone := make(chan struct{})
+
+	go func() {
+		s.workers.Wait()
+		close(workersDone)
+	}()
+
+	select {
+	case <-workersDone:
+	case <-ctx.Done():
+		for _, info := range handlers {
+			notHandedOver += len(info.queue)
+		}
+	}
+
+	if notHandedOver > 0 {
+		s.logger.Error("Stop deadline passed before the handlers took every "+
+			"message", "messages", notHandedOver)
+	}
 }
 
 // IsRunning reports whether the streamer is currently connected and processing
diff --git a/internal/streamer/streamer_internal_test.go b/internal/streamer/streamer_internal_test.go
index 308044a..20f33a5 100644
--- a/internal/streamer/streamer_internal_test.go
+++ b/internal/streamer/streamer_internal_test.go
@@ -1,9 +1,12 @@
 package streamer
 
 import (
+	"bytes"
 	"context"
+	"encoding/json"
 	"errors"
 	"io"
+	"log/slog"
 	"net/http"
 	"net/http/httptest"
 	"runtime"
@@ -377,7 +380,7 @@ func TestStopQueuesTheHeldStateMessages(t *testing.T) {
 	stopped := make(chan struct{})
 
 	go func() {
-		s.Stop()
+		s.Stop(t.Context())
 		close(stopped)
 	}()
 
@@ -412,6 +415,68 @@ func TestStopQueuesTheHeldStateMessages(t *testing.T) {
 	}
 }
 
+// TestStopReturnsByItsDeadline stops a streamer whose handler has a full queue
+// and a STATE message held for it, and a worker that stays busy until the test
+// ends, as one does whose handler waits for a database write. Stop must return
+// within its deadline plus a small margin instead of waiting for room on the
+// queue and for the worker, and log as not handed over the held message and
+// every message on the queue.
+func TestStopReturnsByItsDeadline(t *testing.T) {
+	t.Parallel()
+
+	const (
+		deadline = 100 * time.Millisecond
+		margin   = 2 * time.Second
+	)
+
+	var logs bytes.Buffer
+
+	s := newStreamerWithFullStateQueue("")
+	s.logger = &logger.Logger{Logger: slog.New(slog.NewJSONHandler(&logs,
+		&slog.HandlerOptions{Level: slog.LevelError}))}
+	s.handlers[0].heldState = []*ristypes.RISMessage{
+		{Type: ristypes.MessageTypeState},
+	}
+	wantNotHandedOver := 1 + len(s.handlers[0].queue)
+	// Stop cancels the stream Start would have started; there is none here.
+	s.cancel = func() {}
+
+	release := make(chan struct{})
+	defer close(release)
+
+	s.workers.Go(func() { <-release })
+
+	ctx, cancel := context.WithTimeout(t.Context(), deadline)
+	defer cancel()
+
+	stopped := make(chan struct{})
+
+	go func() {
+		s.Stop(ctx)
+		close(stopped)
+	}()
+
+	select {
+	case <-stopped:
+	case <-time.After(deadline + margin):
+		t.Fatalf("Stop did not return within %s of its deadline", margin)
+	}
+
+	var logged struct {
+		Messages int `json:"messages"`
+	}
+
+	err := json.Unmarshal(logs.Bytes(), &logged)
+	if err != nil {
+		t.Fatalf("want the error Stop logs, got %q: %v", logs.String(), err)
+	}
+
+	if logged.Messages != wantNotHandedOver {
+		t.Errorf("Stop logged %d messages not handed over, want %d",
+			logged.Messages, wantNotHandedOver)
+	}
+}
+
 // TestStopBeforeMessageReachesQueues stops the streamer after the read loop
 // has checked for cancellation but before it hands the message to the handler
 // queues. That is the gap a stop from another goroutine can land in, and it
@@ -429,7 +494,7 @@ func TestStopBeforeMessageReachesQueues(t *testing.T) {
 	s := New(logger.New(), metrics.New())
 	s.url = srv.URL
 	s.RegisterHandler(updateHandler{})
-	s.RegisterRawHandler(func(string) { s.Stop() })
+	s.RegisterRawHandler(func(string) { s.Stop(t.Context()) })
 
 	// Start would run the stream in the background, where the test cannot
 	// wait for it. Setting cancel as Start does lets Stop cancel the stream
@@ -443,7 +508,7 @@ func TestStopBeforeMessageReachesQueues(t *testing.T) {
 	}
 
 	// A second Stop must not close the queues again.
-	s.Stop()
+	s.Stop(t.Context())
 }
 
 // TestReconnectWhenStreamEnds has the server end the first response
@@ -676,7 +741,7 @@ func checkReconnect(
 	if err != nil {
 		t.Fatalf("Start returned error: %v", err)
 	}
-	defer s.Stop()
+	defer s.Stop(t.Context())
 
 	select {
 	case <-handler.handled: