diff --git a/pkg/controller/operators/olm/apiservices.go b/pkg/controller/operators/olm/apiservices.go
index d3524cd8e7..c71b5594f3 100644
--- a/pkg/controller/operators/olm/apiservices.go
+++ b/pkg/controller/operators/olm/apiservices.go
@@ -295,7 +295,7 @@ func (a *Operator) getWebhookCABundle(csv *v1alpha1.ClusterServiceVersion, desc
 			if err != nil {
 				continue
 			}
-			if crd.Spec.Conversion == nil || crd.Spec.Conversion.Webhook == nil || crd.Spec.Conversion.Webhook.ClientConfig == nil && crd.Spec.Conversion.Webhook.ClientConfig.CABundle == nil {
+			if crd.Spec.Conversion == nil || crd.Spec.Conversion.Webhook == nil || crd.Spec.Conversion.Webhook.ClientConfig == nil || crd.Spec.Conversion.Webhook.ClientConfig.CABundle == nil {
 				continue
 			}
 
@@ -472,7 +472,7 @@ func (a *Operator) areWebhooksAvailable(csv *v1alpha1.ClusterServiceVersion) (bo
 					return false, err
 				}
 
-				if crd.Spec.Conversion == nil || crd.Spec.Conversion.Strategy != "Webhook" || crd.Spec.Conversion.Webhook == nil || crd.Spec.Conversion.Webhook.ClientConfig == nil && crd.Spec.Conversion.Webhook.ClientConfig.CABundle == nil {
+				if crd.Spec.Conversion == nil || crd.Spec.Conversion.Strategy != "Webhook" || crd.Spec.Conversion.Webhook == nil || crd.Spec.Conversion.Webhook.ClientConfig == nil || crd.Spec.Conversion.Webhook.ClientConfig.CABundle == nil {
 					return false, fmt.Errorf("conversionWebhook not ready")
 				}
 				webhookCount++
diff --git a/pkg/controller/operators/olm/operator.go b/pkg/controller/operators/olm/operator.go
index 539fa99ad9..efd5e33b37 100644
--- a/pkg/controller/operators/olm/operator.go
+++ b/pkg/controller/operators/olm/operator.go
@@ -2359,7 +2359,12 @@ func (a *Operator) updateInstallStatus(csv *v1alpha1.ClusterServiceVersion, inst
 		return fmt.Errorf(msg)
 	}
 
-	if !webhooksInstalled || webhookErr != nil {
+	if webhookErr != nil {
+		csv.SetPhaseWithEventIfChanged(v1alpha1.CSVPhaseInstallReady, requeueConditionReason, fmt.Sprintf("Webhook install failed: %s", webhookErr), now, a.recorder)
+		return webhookErr
+	}
+
+	if !webhooksInstalled {
 		msg := "webhooks not installed"
 		csv.SetPhaseWithEventIfChanged(requeuePhase, requeueConditionReason, msg, now, a.recorder)
 		if err := a.csvQueueSet.Requeue(csv.GetNamespace(), csv.GetName()); err != nil {
diff --git a/pkg/controller/operators/olm/operator_test.go b/pkg/controller/operators/olm/operator_test.go
index f2d4b3842c..8377073c23 100644
--- a/pkg/controller/operators/olm/operator_test.go
+++ b/pkg/controller/operators/olm/operator_test.go
@@ -3513,7 +3513,7 @@ func TestWebhookCABundleRetrieval(t *testing.T) {
 					), "csv1-dep1", []string{"c1.g1"}),
 				},
 				crds: []runtime.Object{
-					crd("c1", "v1", "g1"),
+					crdWithConversionWebhook(crd("c1", "v1", "g1"), nil),
 				},
 				desc: v1alpha1.WebhookDescription{
 					GenerateName:   "webhook",