diff --git a/internal/handlers/api.go b/internal/handlers/api.go
index b9bf7e2..e46a6a8 100644
--- a/internal/handlers/api.go
+++ b/internal/handlers/api.go
@@ -813,7 +813,14 @@ func (hdlr *Handlers) HandleGetMessages() http.HandlerFunc {
 			timeout = maxLongPollTimeout
 		}
 
-		msgs, lastQID, err := hdlr.params.Database.PollMessages(
+		// Register with the broker before reading the queue.
+		// Notify wakes only the channels registered at that
+		// moment, so a message queued after the read below
+		// must find this one there already.
+		waitCh := hdlr.broker.Wait(sessionID)
+		defer hdlr.broker.Remove(sessionID, waitCh)
+
+		msgs, lastQID, err := hdlr.pollMessages(
 			request.Context(), clientID,
 			afterID, pollMessageLimit,
 		)
@@ -841,19 +848,21 @@ func (hdlr *Handlers) HandleGetMessages() http.HandlerFunc {
 
 		hdlr.longPoll(
 			writer, request,
-			sessionID, clientID, afterID, timeout,
+			waitCh, clientID, afterID, timeout,
 		)
 	}
 }
 
+// longPoll waits up to timeout seconds for the broker to
+// signal waitCh, then answers with the messages queued for
+// clientID after afterID.
 func (hdlr *Handlers) longPoll(
 	writer http.ResponseWriter,
 	request *http.Request,
-	sessionID, clientID, afterID int64,
+	waitCh <-chan struct{},
+	clientID, afterID int64,
 	timeout int,
 ) {
-	waitCh := hdlr.broker.Wait(sessionID)
-
 	timer := time.NewTimer(
 		time.Duration(timeout) * time.Second,
 	)
@@ -864,14 +873,10 @@ func (hdlr *Handlers) longPoll(
 	case <-waitCh:
 	case <-timer.C:
 	case <-request.Context().Done():
-		hdlr.broker.Remove(sessionID, waitCh)
-
 		return
 	}
 
-	hdlr.broker.Remove(sessionID, waitCh)
-
-	msgs, lastQID, err := hdlr.params.Database.PollMessages(
+	msgs, lastQID, err := hdlr.pollMessages(
 		request.Context(), clientID,
 		afterID, pollMessageLimit,
 	)
diff --git a/internal/handlers/api_test.go b/internal/handlers/api_test.go
index 05b8603..9395e63 100644
--- a/internal/handlers/api_test.go
+++ b/internal/handlers/api_test.go
@@ -140,6 +140,7 @@ type testServer struct {
 	fxApp      *fxtest.App
 	broker     *broker.Broker
 	database   *db.Database
+	handlers   *handlers.Handlers
 }
 
 func newTestServer(
@@ -170,6 +171,7 @@ func newTestServerWith(
 		srv      *server.Server
 		brk      *broker.Broker
 		database *db.Database
+		hdlr     *handlers.Handlers
 	)
 
 	app := fxtest.New(t,
@@ -210,7 +212,7 @@ func newTestServerWith(
 			newTestHandlers,
 			newTestServerFx,
 		),
-		fx.Populate(&srv, &brk, &database),
+		fx.Populate(&srv, &brk, &database, &hdlr),
 	)
 
 	app.RequireStart()
@@ -228,6 +230,7 @@ func newTestServerWith(
 		fxApp:      app,
 		broker:     brk,
 		database:   database,
+		handlers:   hdlr,
 	}
 }
 
@@ -2554,6 +2557,110 @@ func TestLongPollTimeout(t *testing.T) {
 	}
 }
 
+// TestLongPollReturnsMessageQueuedAfterFirstRead checks that
+// a message queued, and the broker notified, after the long
+// poll's first read of the queue found nothing but before the
+// poll waits, is returned at once and not when the poll times
+// out.
+func TestLongPollReturnsMessageQueuedAfterFirstRead(t *testing.T) {
+	const (
+		nick   = "lp_late"
+		sender = "lp_late_sender"
+
+		// pollTimeout is the long poll's timeout, in seconds.
+		pollTimeout = 10
+
+		// atOnce is the longest the long poll may take to
+		// return the message.
+		atOnce = 5 * time.Second
+	)
+
+	tserver := newTestServer(t)
+	token := tserver.createSession(nick)
+
+	_, lastID := tserver.pollMessages(token, 0)
+
+	sessionID, err := tserver.database.GetSessionByNick(t.Context(), nick)
+	if err != nil {
+		t.Fatalf("get session of %s: %v", nick, err)
+	}
+
+	queued := make(chan error, 1)
+
+	var once sync.Once
+
+	tserver.handlers.SetPollMessages(func(
+		ctx context.Context,
+		clientID, afterQueueID int64,
+		limit int,
+	) ([]db.IRCMessage, int64, error) {
+		msgs, lastQID, pollErr := tserver.database.PollMessages(
+			ctx, clientID, afterQueueID, limit,
+		)
+
+		once.Do(func() {
+			queued <- tserver.queueMessage(ctx, sessionID, sender, nick)
+		})
+
+		return msgs, lastQID, pollErr
+	})
+
+	start := time.Now()
+
+	msgs, err := tserver.longPoll(token, lastID, pollTimeout)
+	if err != nil {
+		t.Fatalf("long poll: %v", err)
+	}
+
+	elapsed := time.Since(start)
+
+	select {
+	case queueErr := <-queued:
+		if queueErr != nil {
+			t.Fatalf("queue message: %v", queueErr)
+		}
+	default:
+		t.Fatal("the long poll did not read the queue")
+	}
+
+	if elapsed > atOnce {
+		t.Fatalf("the long poll returned after %v, want within %v",
+			elapsed, atOnce)
+	}
+
+	if !findMessage(msgs, privmsgCmd, sender) {
+		t.Fatalf("long poll: got %v, want the PRIVMSG from %s",
+			msgs, sender)
+	}
+}
+
+// queueMessage stores a PRIVMSG from sender to nick, queues
+// it to the session sessionID and notifies the broker, as the
+// server does for a DM. It returns errors instead of failing
+// the test, so a handler's goroutine can call it.
+func (tserver *testServer) queueMessage(
+	ctx context.Context,
+	sessionID int64,
+	sender, nick string,
+) error {
+	msgID, _, err := tserver.database.InsertMessage(
+		ctx, privmsgCmd, sender, nick, sessionID, 0,
+		nil, json.RawMessage(`["hello"]`), nil,
+	)
+	if err != nil {
+		return fmt.Errorf("insert message: %w", err)
+	}
+
+	err = tserver.database.EnqueueToSession(ctx, sessionID, msgID)
+	if err != nil {
+		return fmt.Errorf("enqueue: %w", err)
+	}
+
+	tserver.broker.Notify(sessionID)
+
+	return nil
+}
+
 func TestEphemeralChannelCleanup(t *testing.T) {
 	const channel = "#ephemeral"
 
diff --git a/internal/handlers/export_test.go b/internal/handlers/export_test.go
new file mode 100644
index 0000000..67d1b65
--- /dev/null
+++ b/internal/handlers/export_test.go
@@ -0,0 +1,19 @@
+package handlers
+
+import (
+	"context"
+
+	"sneak.berlin/go/neoirc/internal/db"
+)
+
+// SetPollMessages makes HandleGetMessages read the client
+// output queue with poll in place of Database.PollMessages.
+func (hdlr *Handlers) SetPollMessages(
+	poll func(
+		ctx context.Context,
+		clientID, afterQueueID int64,
+		limit int,
+	) ([]db.IRCMessage, int64, error),
+) {
+	hdlr.pollMessages = poll
+}
diff --git a/internal/handlers/handlers.go b/internal/handlers/handlers.go
index 690b045..9a61699 100644
--- a/internal/handlers/handlers.go
+++ b/internal/handlers/handlers.go
@@ -64,6 +64,15 @@ type Handlers struct {
 	loginLimiter  *ratelimit.Limiter
 	stats         *stats.Tracker
 	cancelCleanup context.CancelFunc
+
+	// pollMessages is Database.PollMessages, with which
+	// HandleGetMessages reads the client output queue. Tests
+	// replace it to queue a message just after a read.
+	pollMessages func(
+		ctx context.Context,
+		clientID, afterQueueID int64,
+		limit int,
+	) ([]db.IRCMessage, int64, error)
 }
 
 // New creates a new Handlers instance.
@@ -95,6 +104,7 @@ func New(
 		hashcashVal:  hashcash.NewValidator(resource),
 		loginLimiter: ratelimit.New(loginRate, loginBurst),
 		stats:        params.Stats,
+		pollMessages: params.Database.PollMessages,
 	}
 
 	lifecycle.Append(fx.Hook{
diff --git a/internal/ircserver/relay.go b/internal/ircserver/relay.go
index bbb5309..c568133 100644
--- a/internal/ircserver/relay.go
+++ b/internal/ircserver/relay.go
@@ -27,17 +27,22 @@ func (c *Conn) relayMessages(ctx context.Context) {
 		default:
 		}
 
+		// Register with the broker before draining, so that a
+		// message queued after the drain has read the queue
+		// still signals waitCh.
+		waitCh := c.brk.Wait(c.sessionID)
+
 		// Drain any available messages.
 		delivered := c.drainQueue(ctx)
 
 		if delivered {
+			c.brk.Remove(c.sessionID, waitCh)
+
 			// Tight loop while there are messages.
 			continue
 		}
 
 		// Wait for notification or timeout.
-		waitCh := c.brk.Wait(c.sessionID)
-
 		select {
 		case <-waitCh:
 			// New message notification — loop back.