diff --git a/config/notifiers.go b/config/notifiers.go
index fe28ca05c4..74c74a92a0 100644
--- a/config/notifiers.go
+++ b/config/notifiers.go
@@ -535,6 +535,10 @@ type WebhookConfig struct {
 	// Alerts exceeding this threshold will be truncated. Setting this to 0
 	// allows an unlimited number of alerts.
 	MaxAlerts uint64 `yaml:"max_alerts" json:"max_alerts"`
+
+	// Timeout is the maximum time allowed to invoke the webhook. Setting this to 0
+	// does not impose a timeout.
+	Timeout time.Duration `yaml:"timeout" json:"timeout"`
 }
 
 // UnmarshalYAML implements the yaml.Unmarshaler interface.
diff --git a/docs/configuration.md b/docs/configuration.md
index 89403ca8f9..f2a4f6b197 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -1594,6 +1594,13 @@ url_file: <filepath>
 # above this threshold are truncated. When leaving this at its default value of
 # 0, all alerts are included.
 [ max_alerts: <int> | default = 0 ]
+
+# The maximum time to wait for a webhook request to complete, before failing the
+# request and allowing it to be retried. The default value of 0s indicates that
+# no timeout should be applied.
+# NOTE: This will have no effect if set higher than the group_interval.
+[ timeout: <duration> | default = 0s ]
+
 ```
 
 The Alertmanager
diff --git a/notify/webhook/webhook.go b/notify/webhook/webhook.go
index 1b5546ddbe..41b9f497dc 100644
--- a/notify/webhook/webhook.go
+++ b/notify/webhook/webhook.go
@@ -112,8 +112,17 @@ func (n *Notifier) Notify(ctx context.Context, alerts ...*types.Alert) (bool, er
 		url = strings.TrimSpace(string(content))
 	}
 
+	if n.conf.Timeout > 0 {
+		postCtx, cancel := context.WithTimeoutCause(ctx, n.conf.Timeout, fmt.Errorf("configured webhook timeout reached (%s)", n.conf.Timeout))
+		defer cancel()
+		ctx = postCtx
+	}
+
 	resp, err := notify.PostJSON(ctx, n.client, url, &buf)
 	if err != nil {
+		if ctx.Err() != nil {
+			err = fmt.Errorf("%w: %w", err, context.Cause(ctx))
+		}
 		return true, notify.RedactURL(err)
 	}
 	defer notify.Drain(resp)
diff --git a/test/with_api_v2/acceptance/send_test.go b/test/with_api_v2/acceptance/send_test.go
index 4e13d37ca5..fa190f44c1 100644
--- a/test/with_api_v2/acceptance/send_test.go
+++ b/test/with_api_v2/acceptance/send_test.go
@@ -464,3 +464,52 @@ receivers:
 
 	t.Log(co.Check())
 }
+
+func TestWebhookTimeout(t *testing.T) {
+	t.Parallel()
+
+	// This integration test uses an extended group_interval to check that
+	// the webhook level timeout has the desired effect, and that notification
+	// sending is retried in this case.
+	conf := `
+route:
+  receiver: "default"
+  group_by: [alertname]
+  group_wait:      1s
+  group_interval:  1m
+  repeat_interval: 1m
+
+receivers:
+- name: "default"
+  webhook_configs:
+  - url: 'http://%s'
+    timeout: 500ms
+`
+
+	at := NewAcceptanceTest(t, &AcceptanceOpts{
+		Tolerance: 150 * time.Millisecond,
+	})
+
+	co := at.Collector("webhook")
+	wh := NewWebhook(t, co)
+
+	wh.Func = func(ts float64) bool {
+		// Make some webhook requests slow enough to hit the webhook
+		// timeout, but not so slow as to hit the dispatcher timeout.
+		if ts < 3 {
+			time.Sleep(time.Second)
+			return true
+		}
+		return false
+	}
+
+	am := at.AlertmanagerCluster(fmt.Sprintf(conf, wh.Address()), 1)
+
+	am.Push(At(1), Alert("alertname", "test1"))
+
+	co.Want(Between(3, 4), Alert("alertname", "test1").Active(1))
+
+	at.Run()
+
+	t.Log(co.Check())
+}