diff --git a/apps/api/internal/httpapi/callback_http.go b/apps/api/internal/httpapi/callback_http.go
index 4bb8ef6b..2c072499 100644
--- a/apps/api/internal/httpapi/callback_http.go
+++ b/apps/api/internal/httpapi/callback_http.go
@@ -17,6 +17,9 @@ const callbackTimeout = 3 * time.Second
 var blockedCallbackPrefixes = []netip.Prefix{
 	netip.MustParsePrefix("0.0.0.0/8"),
 	netip.MustParsePrefix("100.64.0.0/10"),
+	// Azure reserves this public-looking virtual IP for platform services
+	// inside every virtual network, including health and DHCP endpoints.
+	netip.MustParsePrefix("168.63.129.16/32"),
 	netip.MustParsePrefix("192.0.0.0/24"),
 	netip.MustParsePrefix("192.0.2.0/24"),
 	netip.MustParsePrefix("192.31.196.0/24"),
diff --git a/apps/api/internal/httpapi/integration_security_test.go b/apps/api/internal/httpapi/integration_security_test.go
index a51f3250..7b6f84d9 100644
--- a/apps/api/internal/httpapi/integration_security_test.go
+++ b/apps/api/internal/httpapi/integration_security_test.go
@@ -159,6 +159,7 @@ func TestCallbackAddressPolicy(t *testing.T) {
 		"127.0.0.1":            false,
 		"10.0.0.1":             false,
 		"169.254.169.254":      false,
+		"168.63.129.16":        false,
 		"100.64.0.1":           false,
 		"198.18.0.1":           false,
 		"192.0.2.1":            false,
@@ -186,6 +187,27 @@ func TestCallbackAddressPolicy(t *testing.T) {
 	}
 }
 
+func TestCallbackDialerRejectsAzurePlatformVIPBeforeDial(t *testing.T) {
+	t.Parallel()
+	var dialed atomic.Bool
+	dialer := &callbackDialer{
+		lookupNetIP: func(context.Context, string, string) ([]netip.Addr, error) {
+			t.Fatal("literal callback address unexpectedly triggered DNS resolution")
+			return nil, nil
+		},
+		dialContext: func(context.Context, string, string) (net.Conn, error) {
+			dialed.Store(true)
+			return nil, errors.New("unexpected dial")
+		},
+	}
+	if _, err := dialer.DialContext(context.Background(), "tcp", "168.63.129.16:80"); err == nil {
+		t.Fatal("expected Azure platform virtual IP to be rejected")
+	}
+	if dialed.Load() {
+		t.Fatal("callback dialer connected to the Azure platform virtual IP")
+	}
+}
+
 func TestCallbackDialerRejectsMixedDNSAnswersBeforeDial(t *testing.T) {
 	t.Parallel()
 	var dialed atomic.Bool
@@ -271,6 +293,37 @@ func TestCallbackDeliveryBlocksLoopbackForBothCallbackTypes(t *testing.T) {
 	}
 }
 
+func TestCallbackDeliveryBlocksAzurePlatformVIPForBothCallbackTypes(t *testing.T) {
+	t.Parallel()
+	var dialed atomic.Bool
+	policyDialer := &callbackDialer{
+		lookupNetIP: net.DefaultResolver.LookupNetIP,
+		dialContext: func(context.Context, string, string) (net.Conn, error) {
+			dialed.Store(true)
+			return nil, errors.New("unexpected dial")
+		},
+	}
+	server := &Server{callbackClient: &http.Client{
+		Transport: &http.Transport{DialContext: policyDialer.DialContext},
+		Timeout:   callbackTimeout,
+	}}
+	if _, _, err := server.postSlashCallback(context.Background(), store.SlashCommand{
+		CallbackURL:   "http://168.63.129.16/slash",
+		SigningSecret: "slash-secret",
+	}, []byte(`{"command":"/probe"}`)); err == nil {
+		t.Fatal("slash callback accepted the Azure platform virtual IP")
+	}
+	if _, _, err := server.postEventCallback(context.Background(), store.EventSubscription{
+		CallbackURL:   "http://168.63.129.16/event",
+		SigningSecret: "event-secret",
+	}, store.Event{ID: "evt_probe"}, []byte(`{"event":"probe"}`)); err == nil {
+		t.Fatal("event callback accepted the Azure platform virtual IP")
+	}
+	if dialed.Load() {
+		t.Fatal("callback delivery connected to the Azure platform virtual IP")
+	}
+}
+
 func expectSlashStatusAsUser(t *testing.T, userID, endpoint string, status int) {
 	t.Helper()
 	body := url.Values{"command": {"/deploy"}, "text": {"prod"}}.Encode()