diff --git a/boilerplate/_data/last-boilerplate-commit b/boilerplate/_data/last-boilerplate-commit
index 01f9820c..65923da3 100644
--- a/boilerplate/_data/last-boilerplate-commit
+++ b/boilerplate/_data/last-boilerplate-commit
@@ -1 +1 @@
-03d10f359a4a9d3b38c4f5e1494f771ef603fc3f
+8ca4e1dfcab3443c52acf52b3912b6cf1c5f79a4
diff --git a/test/e2e/certman_operator_tests.go b/test/e2e/certman_operator_tests.go
index 11a53108..28840d2b 100644
--- a/test/e2e/certman_operator_tests.go
+++ b/test/e2e/certman_operator_tests.go
@@ -529,7 +529,7 @@ var _ = ginkgo.Describe("Certman Operator", ginkgo.Ordered, ginkgo.ContinueOnFai
 
 		gomega.Expect(certRequestsCount).To(gomega.Equal(1), "Should have exactly 1 certificate request")
 
-		ginkgo.GinkgoLogr.Info("✅ Metrics verification successful",
+		ginkgo.GinkgoLogr.Info(" Metrics verification successful",
 			"certificateRequestsCount", certRequestsCount)
 	})
 
@@ -812,6 +812,100 @@ var _ = ginkgo.Describe("Certman Operator", ginkgo.Ordered, ginkgo.ContinueOnFai
 		}, pollingDuration, 30*time.Second).Should(gomega.BeTrue(), "ClusterDeployment should be automatically added as owner of CertificateRequest by operator")
 	})
 
+	ginkgo.It("Delete a CertificateRequest and ensures it is recreated", func(ctx context.Context) {
+
+		crGVR := schema.GroupVersionResource{
+			Group:    "certman.managed.openshift.io",
+			Version:  "v1alpha1",
+			Resource: "certificaterequests",
+		}
+
+		log.Log.Info("STEP 1: Fetching CertificateRequest owned by our ClusterDeployment", "clusterDeployment", clusterDeploymentName, "namespace", certConfig.TestNamespace)
+		originalCR, err := utils.FindCertificateRequestForClusterDeployment(ctx, dynamicClient, crGVR, certConfig.TestNamespace, clusterDeploymentName)
+		if err != nil {
+			log.Log.Info("No CertificateRequest found for our ClusterDeployment, skipping test", "error", err)
+			ginkgo.Skip("SKIPPED: No CertificateRequest found for ClusterDeployment. This test runs after \"should create ClusterDeployment and CertificateRequest\" and requires that CR to exist.")
+		}
+
+		originalCRName := originalCR.GetName()
+		originalCRUID := originalCR.GetUID()
+		crList, err := dynamicClient.Resource(crGVR).Namespace(certConfig.TestNamespace).List(ctx, metav1.ListOptions{})
+		gomega.Expect(err).ToNot(gomega.HaveOccurred(), "Failed to list CertificateRequests for count")
+		initialIssuedCertCount := len(crList.Items)
+
+		// Step 2: Delete the CertificateRequest owned by our ClusterDeployment
+		log.Log.Info("STEP 2: Deleting the CertificateRequest owned by our ClusterDeployment", "name", originalCRName)
+		err = dynamicClient.Resource(crGVR).Namespace(certConfig.TestNamespace).Delete(ctx, originalCRName, metav1.DeleteOptions{})
+		gomega.Expect(err).ToNot(gomega.HaveOccurred(), "Failed to delete CertificateRequest")
+
+		// Step 3: Handle deletion blocked by finalizer
+		gomega.Eventually(func() bool {
+			cr, err := dynamicClient.Resource(crGVR).Namespace(certConfig.TestNamespace).Get(ctx, originalCRName, metav1.GetOptions{})
+			if err != nil {
+				log.Log.Info("CR appears to be deleted already", "name", originalCRName)
+				return true
+			}
+			if cr.GetDeletionTimestamp() == nil {
+				log.Log.Info("CR not marked for deletion yet", "name", cr.GetName())
+				return false
+			}
+
+			finalizers, found, err := unstructured.NestedStringSlice(cr.Object, "metadata", "finalizers")
+			if err != nil {
+				log.Log.Error(err, "Error retrieving finalizers")
+				return false
+			}
+			if !found || len(finalizers) == 0 {
+				log.Log.Info("No finalizers present", "name", cr.GetName())
+				return false
+			}
+
+			crCopy := cr.DeepCopy()
+			_ = unstructured.SetNestedStringSlice(crCopy.Object, []string{}, "metadata", "finalizers")
+
+			_, err = dynamicClient.Resource(crGVR).Namespace(certConfig.TestNamespace).Update(ctx, crCopy, metav1.UpdateOptions{})
+			if err != nil {
+				log.Log.Error(err, "Failed to remove finalizer")
+				return false
+			}
+			return true
+		}, 1*time.Minute, 5*time.Second).Should(gomega.BeTrue(), "Finalizer should be removed")
+
+		// Step 4: Wait for new CertificateRequest with new UID (operator recreates it for our ClusterDeployment)
+		var newCRName string
+		gomega.Eventually(func() bool {
+			newList, err := dynamicClient.Resource(crGVR).Namespace(certConfig.TestNamespace).List(ctx, metav1.ListOptions{})
+			if err != nil {
+				log.Log.Error(err, "Failed to list new CertificateRequests")
+				return false
+			}
+			if len(newList.Items) == 0 {
+				log.Log.Info("Still waiting for new CertificateRequest (none found)")
+				return false
+			}
+
+			newCount := len(newList.Items)
+			logger.Info("CertificateRequest count after reconciliation", "count", newCount)
+			if newCount != initialIssuedCertCount {
+				logger.Info("CertificateRequest count mismatch", "expected", initialIssuedCertCount, "got", newCount)
+				return false
+			}
+
+			for _, cr := range newList.Items {
+				log.Log.Info("Found CR candidate", "name", cr.GetName(), "uid", cr.GetUID())
+				if cr.GetUID() != originalCRUID {
+					newCRName = cr.GetName()
+					log.Log.Info("New CertificateRequest detected", "name", newCRName, "uid", cr.GetUID())
+					return true
+				}
+			}
+			return false
+		}, 2*time.Minute, 10*time.Second).Should(gomega.BeTrue(), "New CertificateRequest should appear")
+
+		secretNameFromCR, _ := utils.GetCertificateSecretNameFromCR(originalCR)
+		log.Log.Info("Test completed: CertificateRequest recreated by operator", "newCR", newCRName, "certificateSecret", secretNameFromCR)
+	})
+
 	ginkgo.AfterAll(func(ctx context.Context) {
 
 		logger.Info("Cleanup: Running AfterAll cleanup")