diff --git a/chart/templates/mutating-webhook.yaml b/chart/templates/mutating-webhook.yaml
index 1e6890b5..7b407f1c 100644
--- a/chart/templates/mutating-webhook.yaml
+++ b/chart/templates/mutating-webhook.yaml
@@ -7,7 +7,6 @@ webhooks:
 - admissionReviewVersions:
   - v1
   clientConfig:
-    caBundle: ""
     service:
       name: skyhook-operator-webhook-service
       namespace: {{ .Release.Namespace }}
@@ -35,7 +34,6 @@ webhooks:
 - admissionReviewVersions:
   - v1
   clientConfig:
-    caBundle: ""
     service:
       name: skyhook-operator-webhook-service
       namespace: {{ .Release.Namespace }}
diff --git a/chart/templates/validating-webhook.yaml b/chart/templates/validating-webhook.yaml
index 6081dcfb..bdd45d16 100644
--- a/chart/templates/validating-webhook.yaml
+++ b/chart/templates/validating-webhook.yaml
@@ -7,7 +7,6 @@ webhooks:
 - admissionReviewVersions:
   - v1
   clientConfig:
-    caBundle: ""
     service:
       name: skyhook-operator-webhook-service
       namespace: {{ .Release.Namespace }}
@@ -34,7 +33,6 @@ webhooks:
 - admissionReviewVersions:
   - v1
   clientConfig:
-    caBundle: ""
     service:
       name: skyhook-operator-webhook-service
       namespace: {{ .Release.Namespace }}
diff --git a/operator/internal/controller/webhook_controller.go b/operator/internal/controller/webhook_controller.go
index 140c1f24..ffecff31 100644
--- a/operator/internal/controller/webhook_controller.go
+++ b/operator/internal/controller/webhook_controller.go
@@ -27,6 +27,7 @@ import (
 	"time"
 
 	"sigs.k8s.io/controller-runtime/pkg/builder"
+	"sigs.k8s.io/controller-runtime/pkg/handler"
 	"sigs.k8s.io/controller-runtime/pkg/predicate"
 
 	"github.com/NVIDIA/skyhook/operator/api/v1alpha1"
@@ -127,9 +128,29 @@ func (r *WebhookController) SetupWithManager(mgr ctrl.Manager) error {
 		For(&corev1.Secret{}, builder.WithPredicates(predicate.NewPredicateFuncs(func(obj client.Object) bool {
 			return obj.GetNamespace() == r.namespace && obj.GetName() == r.opts.SecretName
 		}))).
+		// Watch webhook configurations so the leader detects external changes (e.g. Helm upgrade
+		// resetting caBundle) and fixes them immediately instead of waiting for the 24h requeue.
+		Watches(&admissionregistrationv1.ValidatingWebhookConfiguration{},
+			handler.EnqueueRequestsFromMapFunc(r.webhookConfigToSecret),
+			builder.WithPredicates(predicate.NewPredicateFuncs(func(obj client.Object) bool {
+				return obj.GetName() == validatingWebhookConfigName
+			}))).
+		Watches(&admissionregistrationv1.MutatingWebhookConfiguration{},
+			handler.EnqueueRequestsFromMapFunc(r.webhookConfigToSecret),
+			builder.WithPredicates(predicate.NewPredicateFuncs(func(obj client.Object) bool {
+				return obj.GetName() == mutatingWebhookConfigName
+			}))).
 		Complete(r)
 }
 
+// webhookConfigToSecret maps webhook config change events back to the cert Secret,
+// so the existing Reconcile() can verify and fix the caBundle.
+func (r *WebhookController) webhookConfigToSecret(_ context.Context, _ client.Object) []reconcile.Request {
+	return []reconcile.Request{{
+		NamespacedName: types.NamespacedName{Name: r.opts.SecretName, Namespace: r.namespace},
+	}}
+}
+
 // permissions
 //+kubebuilder:rbac:groups=admissionregistration.k8s.io,resources=validatingwebhookconfigurations;mutatingwebhookconfigurations,verbs=get;list;watch;create;update;patch;delete
 //+kubebuilder:rbac:groups=core,resources=secrets,verbs=get;list;watch;create;update;patch;delete
@@ -480,8 +501,8 @@ func deploymentPolicyMutatingRules() []admissionregistrationv1.RuleWithOperation
 func validatingWebhookNeedsUpdate(webhook *admissionregistrationv1.ValidatingWebhook, caBundle []byte, expectedRules []admissionregistrationv1.RuleWithOperations) bool {
 	needUpdate := false
 
-	// Check if CABundle needs to be set
-	if len(webhook.ClientConfig.CABundle) == 0 {
+	// Check if CABundle needs to be set or updated (catches both empty and stale values)
+	if !bytes.Equal(webhook.ClientConfig.CABundle, caBundle) {
 		webhook.ClientConfig.CABundle = caBundle
 		needUpdate = true
 	}
@@ -499,8 +520,8 @@ func validatingWebhookNeedsUpdate(webhook *admissionregistrationv1.ValidatingWeb
 func mutatingWebhookNeedsUpdate(webhook *admissionregistrationv1.MutatingWebhook, caBundle []byte, expectedRules []admissionregistrationv1.RuleWithOperations) bool {
 	needUpdate := false
 
-	// Check if CABundle needs to be set
-	if len(webhook.ClientConfig.CABundle) == 0 {
+	// Check if CABundle needs to be set or updated (catches both empty and stale values)
+	if !bytes.Equal(webhook.ClientConfig.CABundle, caBundle) {
 		webhook.ClientConfig.CABundle = caBundle
 		needUpdate = true
 	}
diff --git a/operator/internal/controller/webhook_controller_test.go b/operator/internal/controller/webhook_controller_test.go
index 370924a2..0747ff09 100644
--- a/operator/internal/controller/webhook_controller_test.go
+++ b/operator/internal/controller/webhook_controller_test.go
@@ -293,6 +293,32 @@ var _ = Describe("WebhookController", Ordered, func() {
 			Expect(needsUpdate).To(BeTrue(), "should detect empty CABundle")
 			Expect(webhook.ClientConfig.CABundle).To(Equal(caBundle), "CABundle should be updated")
 		})
+
+		It("should update CABundle when stale (non-empty but wrong)", func() {
+			expectedRules := skyhookRules()
+			correctCA := []byte("correct-ca")
+			staleCA := []byte("stale-ca-from-previous-cert")
+
+			validatingWebhook := admissionregistrationv1.ValidatingWebhook{
+				ClientConfig: admissionregistrationv1.WebhookClientConfig{
+					CABundle: staleCA,
+				},
+				Rules: expectedRules,
+			}
+			needsUpdate := validatingWebhookNeedsUpdate(&validatingWebhook, correctCA, expectedRules)
+			Expect(needsUpdate).To(BeTrue(), "should detect stale validating CABundle")
+			Expect(validatingWebhook.ClientConfig.CABundle).To(Equal(correctCA))
+
+			mutatingWebhook := admissionregistrationv1.MutatingWebhook{
+				ClientConfig: admissionregistrationv1.WebhookClientConfig{
+					CABundle: staleCA,
+				},
+				Rules: expectedRules,
+			}
+			needsUpdate = mutatingWebhookNeedsUpdate(&mutatingWebhook, correctCA, expectedRules)
+			Expect(needsUpdate).To(BeTrue(), "should detect stale mutating CABundle")
+			Expect(mutatingWebhook.ClientConfig.CABundle).To(Equal(correctCA))
+		})
 	})
 
 	Describe("Disk and Secret-to-Disk Sync Logic", func() {