diff --git a/cmd/prometheus/main.go b/cmd/prometheus/main.go
index cd7f533d1..7544f276a 100644
--- a/cmd/prometheus/main.go
+++ b/cmd/prometheus/main.go
@@ -445,6 +445,9 @@ func main() {
 	serverOnlyFlag(a, "alertmanager.notification-queue-capacity", "The capacity of the queue for pending Alertmanager notifications.").
 		Default("10000").IntVar(&cfg.notifier.QueueCapacity)
 
+	serverOnlyFlag(a, "alertmanager.drain-notification-queue-on-shutdown", "Send any outstanding Alertmanager notifications when shutting down. If false, any outstanding Alertmanager notifications will be dropped when shutting down.").
+		Default("true").BoolVar(&cfg.notifier.DrainOnShutdown)
+
 	// TODO: Remove in Prometheus 3.0.
 	alertmanagerTimeout := a.Flag("alertmanager.timeout", "[DEPRECATED] This flag has no effect.").Hidden().String()
 
diff --git a/docs/command-line/prometheus.md b/docs/command-line/prometheus.md
index aa9bf3bfb..1fc032d09 100644
--- a/docs/command-line/prometheus.md
+++ b/docs/command-line/prometheus.md
@@ -50,6 +50,7 @@ The Prometheus monitoring server
 | <code class="text-nowrap">--rules.alert.resend-delay</code> | Minimum amount of time to wait before resending an alert to Alertmanager. Use with server mode only. | `1m` |
 | <code class="text-nowrap">--rules.max-concurrent-evals</code> | Global concurrency limit for independent rules that can run concurrently. When set, "query.max-concurrency" may need to be adjusted accordingly. Use with server mode only. | `4` |
 | <code class="text-nowrap">--alertmanager.notification-queue-capacity</code> | The capacity of the queue for pending Alertmanager notifications. Use with server mode only. | `10000` |
+| <code class="text-nowrap">--alertmanager.drain-notification-queue-on-shutdown</code> | Send any outstanding Alertmanager notifications when shutting down. If false, any outstanding Alertmanager notifications will be dropped when shutting down. Use with server mode only. | `true` |
 | <code class="text-nowrap">--query.lookback-delta</code> | The maximum lookback duration for retrieving metrics during expression evaluations and federation. Use with server mode only. | `5m` |
 | <code class="text-nowrap">--query.timeout</code> | Maximum time a query may take before being aborted. Use with server mode only. | `2m` |
 | <code class="text-nowrap">--query.max-concurrency</code> | Maximum number of queries executed concurrently. Use with server mode only. | `20` |
diff --git a/notifier/notifier.go b/notifier/notifier.go
index cd00a4507..68b0d4961 100644
--- a/notifier/notifier.go
+++ b/notifier/notifier.go
@@ -110,10 +110,11 @@ type Manager struct {
 
 	metrics *alertMetrics
 
-	more   chan struct{}
-	mtx    sync.RWMutex
-	ctx    context.Context
-	cancel func()
+	more chan struct{}
+	mtx  sync.RWMutex
+
+	stopOnce      *sync.Once
+	stopRequested chan struct{}
 
 	alertmanagers map[string]*alertmanagerSet
 	logger        log.Logger
@@ -121,9 +122,10 @@ type Manager struct {
 
 // Options are the configurable parameters of a Handler.
 type Options struct {
-	QueueCapacity  int
-	ExternalLabels labels.Labels
-	RelabelConfigs []*relabel.Config
+	QueueCapacity   int
+	DrainOnShutdown bool
+	ExternalLabels  labels.Labels
+	RelabelConfigs  []*relabel.Config
 	// Used for sending HTTP requests to the Alertmanager.
 	Do func(ctx context.Context, client *http.Client, req *http.Request) (*http.Response, error)
 
@@ -217,8 +219,6 @@ func do(ctx context.Context, client *http.Client, req *http.Request) (*http.Resp
 
 // NewManager is the manager constructor.
 func NewManager(o *Options, logger log.Logger) *Manager {
-	ctx, cancel := context.WithCancel(context.Background())
-
 	if o.Do == nil {
 		o.Do = do
 	}
@@ -227,12 +227,12 @@ func NewManager(o *Options, logger log.Logger) *Manager {
 	}
 
 	n := &Manager{
-		queue:  make([]*Alert, 0, o.QueueCapacity),
-		ctx:    ctx,
-		cancel: cancel,
-		more:   make(chan struct{}, 1),
-		opts:   o,
-		logger: logger,
+		queue:         make([]*Alert, 0, o.QueueCapacity),
+		more:          make(chan struct{}, 1),
+		stopRequested: make(chan struct{}),
+		stopOnce:      &sync.Once{},
+		opts:          o,
+		logger:        logger,
 	}
 
 	queueLenFunc := func() float64 { return float64(n.queueLen()) }
@@ -298,42 +298,100 @@ func (n *Manager) nextBatch() []*Alert {
 	return alerts
 }
 
+// Run dispatches notifications continuously, returning once Stop has been called and all
+// pending notifications have been drained from the queue (if draining is enabled).
+//
+// Dispatching of notifications occurs in parallel to processing target updates to avoid one starving the other.
+// Refer to https://github.com/prometheus/prometheus/issues/13676 for more details.
+func (n *Manager) Run(tsets <-chan map[string][]*targetgroup.Group) {
+	wg := sync.WaitGroup{}
+	wg.Add(2)
+
+	go func() {
+		defer wg.Done()
+		n.targetUpdateLoop(tsets)
+	}()
+
+	go func() {
+		defer wg.Done()
+		n.sendLoop()
+		n.drainQueue()
+	}()
+
+	wg.Wait()
+	level.Info(n.logger).Log("msg", "Notification manager stopped")
+}
+
 // sendLoop continuously consumes the notifications queue and sends alerts to
 // the configured Alertmanagers.
 func (n *Manager) sendLoop() {
 	for {
+		// If we've been asked to stop, that takes priority over sending any further notifications.
 		select {
-		case <-n.ctx.Done():
+		case <-n.stopRequested:
 			return
-		case <-n.more:
-		}
-		alerts := n.nextBatch()
+		default:
+			select {
+			case <-n.stopRequested:
+				return
 
-		if !n.sendAll(alerts...) {
-			n.metrics.dropped.Add(float64(len(alerts)))
-		}
-		// If the queue still has items left, kick off the next iteration.
-		if n.queueLen() > 0 {
-			n.setMore()
+			case <-n.more:
+				n.sendOneBatch()
+
+				// If the queue still has items left, kick off the next iteration.
+				if n.queueLen() > 0 {
+					n.setMore()
+				}
+			}
 		}
 	}
 }
 
-// Run receives updates of target groups and triggers a reload.
-// The dispatching of notifications occurs in the background to prevent blocking the receipt of target updates.
-// Refer to https://github.com/prometheus/prometheus/issues/13676 for more details.
-func (n *Manager) Run(tsets <-chan map[string][]*targetgroup.Group) {
-	go n.sendLoop()
+// targetUpdateLoop receives updates of target groups and triggers a reload.
+func (n *Manager) targetUpdateLoop(tsets <-chan map[string][]*targetgroup.Group) {
 	for {
+		// If we've been asked to stop, that takes priority over processing any further target group updates.
 		select {
-		case <-n.ctx.Done():
+		case <-n.stopRequested:
 			return
-		case ts := <-tsets:
-			n.reload(ts)
+		default:
+			select {
+			case <-n.stopRequested:
+				return
+			case ts := <-tsets:
+				n.reload(ts)
+			}
 		}
 	}
 }
 
+func (n *Manager) sendOneBatch() {
+	alerts := n.nextBatch()
+
+	if !n.sendAll(alerts...) {
+		n.metrics.dropped.Add(float64(len(alerts)))
+	}
+}
+
+func (n *Manager) drainQueue() {
+	if !n.opts.DrainOnShutdown {
+		if n.queueLen() > 0 {
+			level.Warn(n.logger).Log("msg", "Draining remaining notifications on shutdown is disabled, and some notifications have been dropped", "count", n.queueLen())
+			n.metrics.dropped.Add(float64(n.queueLen()))
+		}
+
+		return
+	}
+
+	level.Info(n.logger).Log("msg", "Draining any remaining notifications...")
+
+	for n.queueLen() > 0 {
+		n.sendOneBatch()
+	}
+
+	level.Info(n.logger).Log("msg", "Remaining notifications drained")
+}
+
 func (n *Manager) reload(tgs map[string][]*targetgroup.Group) {
 	n.mtx.Lock()
 	defer n.mtx.Unlock()
@@ -546,7 +604,7 @@ func (n *Manager) sendAll(alerts ...*Alert) bool {
 		for _, am := range ams.ams {
 			wg.Add(1)
 
-			ctx, cancel := context.WithTimeout(n.ctx, time.Duration(ams.cfg.Timeout))
+			ctx, cancel := context.WithTimeout(context.Background(), time.Duration(ams.cfg.Timeout))
 			defer cancel()
 
 			go func(ctx context.Context, client *http.Client, url string, payload []byte, count int) {
@@ -624,10 +682,19 @@ func (n *Manager) sendOne(ctx context.Context, c *http.Client, url string, b []b
 	return nil
 }
 
-// Stop shuts down the notification handler.
+// Stop signals the notification manager to shut down and immediately returns.
+//
+// Run will return once the notification manager has successfully shut down.
+//
+// The manager will optionally drain any queued notifications before shutting down.
+//
+// Stop is safe to call multiple times.
 func (n *Manager) Stop() {
 	level.Info(n.logger).Log("msg", "Stopping notification manager...")
-	n.cancel()
+
+	n.stopOnce.Do(func() {
+		close(n.stopRequested)
+	})
 }
 
 // Alertmanager holds Alertmanager endpoint information.
diff --git a/notifier/notifier_test.go b/notifier/notifier_test.go
index 03290a58c..2cdaa9e06 100644
--- a/notifier/notifier_test.go
+++ b/notifier/notifier_test.go
@@ -847,3 +847,173 @@ loop2:
 		}
 	}
 }
+
+func TestStop_DrainingDisabled(t *testing.T) {
+	releaseReceiver := make(chan struct{})
+	receiverReceivedRequest := make(chan struct{}, 2)
+	alertsReceived := atomic.NewInt64(0)
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Let the test know we've received a request.
+		receiverReceivedRequest <- struct{}{}
+
+		var alerts []*Alert
+
+		b, err := io.ReadAll(r.Body)
+		require.NoError(t, err)
+
+		err = json.Unmarshal(b, &alerts)
+		require.NoError(t, err)
+
+		alertsReceived.Add(int64(len(alerts)))
+
+		// Wait for the test to release us.
+		<-releaseReceiver
+
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer func() {
+		server.Close()
+	}()
+
+	m := NewManager(
+		&Options{
+			QueueCapacity:   10,
+			DrainOnShutdown: false,
+		},
+		nil,
+	)
+
+	m.alertmanagers = make(map[string]*alertmanagerSet)
+
+	am1Cfg := config.DefaultAlertmanagerConfig
+	am1Cfg.Timeout = model.Duration(time.Second)
+
+	m.alertmanagers["1"] = &alertmanagerSet{
+		ams: []alertmanager{
+			alertmanagerMock{
+				urlf: func() string { return server.URL },
+			},
+		},
+		cfg: &am1Cfg,
+	}
+
+	notificationManagerStopped := make(chan struct{})
+
+	go func() {
+		defer close(notificationManagerStopped)
+		m.Run(nil)
+	}()
+
+	// Queue two alerts. The first should be immediately sent to the receiver, which should block until we release it later.
+	m.Send(&Alert{Labels: labels.FromStrings(labels.AlertName, "alert-1")})
+
+	select {
+	case <-receiverReceivedRequest:
+		// Nothing more to do.
+	case <-time.After(time.Second):
+		require.FailNow(t, "gave up waiting for receiver to receive notification of first alert")
+	}
+
+	m.Send(&Alert{Labels: labels.FromStrings(labels.AlertName, "alert-2")})
+
+	// Stop the notification manager, pause to allow the shutdown to be observed, and then allow the receiver to proceed.
+	m.Stop()
+	time.Sleep(time.Second)
+	close(releaseReceiver)
+
+	// Wait for the notification manager to stop and confirm only the first notification was sent.
+	// The second notification should be dropped.
+	select {
+	case <-notificationManagerStopped:
+		// Nothing more to do.
+	case <-time.After(time.Second):
+		require.FailNow(t, "gave up waiting for notification manager to stop")
+	}
+
+	require.Equal(t, int64(1), alertsReceived.Load())
+}
+
+func TestStop_DrainingEnabled(t *testing.T) {
+	releaseReceiver := make(chan struct{})
+	receiverReceivedRequest := make(chan struct{}, 2)
+	alertsReceived := atomic.NewInt64(0)
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Let the test know we've received a request.
+		receiverReceivedRequest <- struct{}{}
+
+		var alerts []*Alert
+
+		b, err := io.ReadAll(r.Body)
+		require.NoError(t, err)
+
+		err = json.Unmarshal(b, &alerts)
+		require.NoError(t, err)
+
+		alertsReceived.Add(int64(len(alerts)))
+
+		// Wait for the test to release us.
+		<-releaseReceiver
+
+		w.WriteHeader(http.StatusOK)
+	}))
+	defer func() {
+		server.Close()
+	}()
+
+	m := NewManager(
+		&Options{
+			QueueCapacity:   10,
+			DrainOnShutdown: true,
+		},
+		nil,
+	)
+
+	m.alertmanagers = make(map[string]*alertmanagerSet)
+
+	am1Cfg := config.DefaultAlertmanagerConfig
+	am1Cfg.Timeout = model.Duration(time.Second)
+
+	m.alertmanagers["1"] = &alertmanagerSet{
+		ams: []alertmanager{
+			alertmanagerMock{
+				urlf: func() string { return server.URL },
+			},
+		},
+		cfg: &am1Cfg,
+	}
+
+	notificationManagerStopped := make(chan struct{})
+
+	go func() {
+		defer close(notificationManagerStopped)
+		m.Run(nil)
+	}()
+
+	// Queue two alerts. The first should be immediately sent to the receiver, which should block until we release it later.
+	m.Send(&Alert{Labels: labels.FromStrings(labels.AlertName, "alert-1")})
+
+	select {
+	case <-receiverReceivedRequest:
+		// Nothing more to do.
+	case <-time.After(time.Second):
+		require.FailNow(t, "gave up waiting for receiver to receive notification of first alert")
+	}
+
+	m.Send(&Alert{Labels: labels.FromStrings(labels.AlertName, "alert-2")})
+
+	// Stop the notification manager and allow the receiver to proceed.
+	m.Stop()
+	close(releaseReceiver)
+
+	// Wait for the notification manager to stop and confirm both notifications were sent.
+	select {
+	case <-notificationManagerStopped:
+		// Nothing more to do.
+	case <-time.After(200 * time.Millisecond):
+		require.FailNow(t, "gave up waiting for notification manager to stop")
+	}
+
+	require.Equal(t, int64(2), alertsReceived.Load())
+}