fix: Don't report a non-entitled wildcard as Pending

internal/controller/gateway_controller.go

@@ -329,16 +329,6 @@ func (r *GatewayReconciler) ensureDownstreamGateway(
 		listenerCertHealth,
 	)
 
-	// A listener the user asked for that never reaches the downstream gateway
-	// makes the gateway dishonest about being programmed, whatever held it back.
-	// Derived from the listener set actually built, so a new reason to withhold
-	// one is covered without being enumerated here.
-	droppedListeners := summarizeDroppedListeners(
-		upstreamGateway,
-		desiredDownstreamGateway,
-		listenerCertHealth,
-	)
-
 	if err := writeDownstreamGateway(ctx, downstreamStrategy, upstreamGateway, downstreamGateway,
 		desiredDownstreamGateway.Spec, awaitsHostnameClaim(hostnameRefusals)); err != nil {
 		result.Err = err
@@ -388,6 +378,17 @@ func (r *GatewayReconciler) ensureDownstreamGateway(
 		clearCertificateServiceFailing(upstreamClusterName, upstreamGateway)
 	}
 
+	// A listener the user asked for that never reaches the downstream gateway
+	// makes the gateway dishonest about being programmed, whatever held it back.
+	// Derived from the listener set actually built, so a new reason to withhold
+	// one is covered without being enumerated here. Summarized after the
+	// certificate service so an entitlement block is known.
+	droppedListeners := summarizeDroppedListeners(
+		upstreamGateway,
+		desiredDownstreamGateway,
+		listenerCertHealth,
+	)
+
 	certResult := r.ensureListenerCertificates(
 		ctx,
 		upstreamGateway,
@@ -955,8 +956,8 @@ func (r *GatewayReconciler) getDesiredDownstreamGateway(
 }
 
 // listenerDropReport names the spec listeners that never reached the downstream
-// gateway, and records whether an unusable certificate held back every one of
-// them.
+// gateway, and records whether a certificate still on its way held back every
+// one of them.
 type listenerDropReport struct {
 	names           []gatewayv1.SectionName
 	allCertWithheld bool
@@ -1030,7 +1031,8 @@ func summarizeDroppedListeners(
 
 		report.names = append(report.names, l.Name)
 
-		if status, gated := listenerCertHealth[l.Name]; !gated || status.healthy {
+		if status, gated := listenerCertHealth[l.Name]; !gated || status.healthy ||
+			status.issuanceReason == certificateServiceReasonWildcardNotEntitled {
 			report.allCertWithheld = false
 		}
 	}

internal/controller/gateway_controller_test.go

@@ -2161,6 +2161,21 @@ func TestReconcileGatewayStatus_DroppedListenerIsNotProgrammed(t *testing.T) {
 			expectStatus: metav1.ConditionFalse,
 			expectReason: string(gatewayv1.GatewayReasonPending),
 		},
+		{
+			name:             "listener withheld by a wildcard the project is not entitled to",
+			listeners:        []gatewayv1.Listener{customListener("custom-https", "*.claimed.example.com")},
+			claimedHostnames: []string{"*.claimed.example.com"},
+			certHealth: map[gatewayv1.SectionName]listenerCertStatus{
+				"custom-https": {
+					reason:          gatewayv1.ListenerReasonInvalidCertificateRef,
+					message:         "wildcard hostnames are not enabled",
+					issuanceBlocked: true,
+					issuanceReason:  certificateServiceReasonWildcardNotEntitled,
+				},
+			},
+			expectStatus: metav1.ConditionFalse,
+			expectReason: string(gatewayv1.GatewayReasonListenersNotValid),
+		},
 		{
 			name: "certificate and hostname drops report the hostname",
 			listeners: []gatewayv1.Listener{

internal/controller/wildcard_entitlement_test.go

@@ -492,3 +492,26 @@ func seriesMatching(t *testing.T, vec prometheus.Collector, want prometheus.Labe
 	}
 	return count
 }
+
+func TestWildcardNotEntitledIsNotReportedPending(t *testing.T) {
+	f := newEntitlementFixture(t, "*.shop.example.com", false, fakeWildcardEntitlements{entitled: false})
+
+	_, created, _ := f.h.reconcile()
+	require.NotNil(t, created, "downstream gateway")
+	downstream := &gatewayv1.Gateway{}
+	require.NoError(t, f.h.downstream.Get(f.h.ctx, client.ObjectKeyFromObject(created), downstream))
+	apimeta.SetStatusCondition(&downstream.Status.Conditions, metav1.Condition{
+		Type:   string(gatewayv1.GatewayConditionProgrammed),
+		Status: metav1.ConditionTrue,
+		Reason: string(gatewayv1.GatewayReasonProgrammed),
+	})
+	require.NoError(t, f.h.downstream.Status().Update(f.h.ctx, downstream))
+
+	upstream, _, _ := f.h.reconcile()
+
+	programmed := apimeta.FindStatusCondition(upstream.Status.Conditions, string(gatewayv1.GatewayConditionProgrammed))
+	require.NotNil(t, programmed, "upstream Programmed condition")
+	assert.Equal(t, metav1.ConditionFalse, programmed.Status)
+	assert.Equal(t, string(gatewayv1.GatewayReasonListenersNotValid), programmed.Reason,
+		"a wildcard the project is not entitled to never gets a certificate, so it is not Pending")
+}