diff --git a/pkg/background/generate/generate.go b/pkg/background/generate/generate.go
index 6e2f65926f..42c586f7dc 100644
--- a/pkg/background/generate/generate.go
+++ b/pkg/background/generate/generate.go
@@ -101,7 +101,7 @@ func (c *GenerateController) ProcessUR(ur *urkyverno.UpdateRequest) error {
 	var resource *unstructured.Unstructured
 	var genResources []kyverno.ResourceSpec
 	var precreatedResource bool
-	logger.Info("start processing UR", "resourceVersion", ur.GetResourceVersion())
+	logger.Info("start processing UR", "ur", ur.Name, "resourceVersion", ur.GetResourceVersion())
 
 	// 1 - Check if the resource exists
 	resource, err = common.GetResource(c.client, ur.Spec, c.log)
diff --git a/pkg/background/request_process.go b/pkg/background/request_process.go
index 5d18797dd8..cb87af3194 100644
--- a/pkg/background/request_process.go
+++ b/pkg/background/request_process.go
@@ -2,11 +2,15 @@ package background
 
 import (
 	"context"
+	"strconv"
 
+	"github.com/go-logr/logr"
 	urkyverno "github.com/kyverno/kyverno/api/kyverno/v1beta1"
 	"github.com/kyverno/kyverno/pkg/background/generate"
 	"github.com/kyverno/kyverno/pkg/background/mutate"
 	"github.com/kyverno/kyverno/pkg/config"
+	dclient "github.com/kyverno/kyverno/pkg/dclient"
+	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 )
 
@@ -55,3 +59,64 @@ func (c *Controller) UnmarkUR(ur *urkyverno.UpdateRequest) error {
 	_, err = c.kyvernoClient.KyvernoV1beta1().UpdateRequests(config.KyvernoNamespace()).UpdateStatus(context.TODO(), newUR, metav1.UpdateOptions{})
 	return err
 }
+
+func (c *Controller) HandleDeleteUR(ur urkyverno.UpdateRequest) error {
+	logger := c.log.WithValues("kind", ur.Kind, "namespace", ur.Namespace, "name", ur.Name)
+	// 1- Corresponding policy has been deleted
+	// then we don't delete the generated resources
+
+	// 2- The trigger resource is deleted, then delete the generated resources
+	if !ownerResourceExists(logger, c.client, ur) {
+		deleteUR := false
+		// check retry count in annotaion
+		urAnnotations := ur.Annotations
+		if val, ok := urAnnotations["generate.kyverno.io/retry-count"]; ok {
+			retryCount, err := strconv.ParseUint(val, 10, 32)
+			if err != nil {
+				logger.Error(err, "unable to convert retry-count")
+				return err
+			}
+
+			if retryCount >= 5 {
+				deleteUR = true
+			}
+		}
+
+		if deleteUR {
+			if err := deleteGeneratedResources(logger, c.client, ur); err != nil {
+				return err
+			}
+			// - trigger-resource is deleted
+			// - generated-resources are deleted
+			// - > Now delete the UpdateRequest CR
+			return c.kyvernoClient.KyvernoV1beta1().UpdateRequests(config.KyvernoNamespace()).Delete(context.TODO(), ur.Name, metav1.DeleteOptions{})
+		}
+	}
+	return nil
+}
+
+func ownerResourceExists(log logr.Logger, client dclient.Interface, ur urkyverno.UpdateRequest) bool {
+	_, err := client.GetResource("", ur.Spec.Resource.Kind, ur.Spec.Resource.Namespace, ur.Spec.Resource.Name)
+	// trigger resources has been deleted
+	if apierrors.IsNotFound(err) {
+		return false
+	}
+	if err != nil {
+		log.Error(err, "failed to get resource", "genKind", ur.Spec.Resource.Kind, "genNamespace", ur.Spec.Resource.Namespace, "genName", ur.Spec.Resource.Name)
+	}
+	// if there was an error while querying the resources we don't delete the generated resources
+	// but expect the deletion in next reconciliation loop
+	return true
+}
+
+func deleteGeneratedResources(log logr.Logger, client dclient.Interface, ur urkyverno.UpdateRequest) error {
+	for _, genResource := range ur.Status.GeneratedResources {
+		err := client.DeleteResource("", genResource.Kind, genResource.Namespace, genResource.Name, false)
+		if err != nil && !apierrors.IsNotFound(err) {
+			return err
+		}
+
+		log.V(3).Info("generated resource deleted", "genKind", ur.Spec.Resource.Kind, "genNamespace", ur.Spec.Resource.Namespace, "genName", ur.Spec.Resource.Name)
+	}
+	return nil
+}
diff --git a/pkg/background/update_request_controller.go b/pkg/background/update_request_controller.go
index e012909f21..642f404cd3 100644
--- a/pkg/background/update_request_controller.go
+++ b/pkg/background/update_request_controller.go
@@ -204,7 +204,9 @@ func (c *Controller) syncUpdateRequest(key string) error {
 
 	logger.V(3).Info("UR is marked successfully", "ur", ur.GetName(), "resourceVersion", ur.GetResourceVersion())
 	if err := c.ProcessUR(ur); err != nil {
-		return fmt.Errorf("failed to process UR %s: %v", key, err)
+		logger.Info("failed to process the UR, triggering handle delete operation", "handler", ur.Status.Handler, "ur", ur.GetName(), "err", err)
+		err = c.HandleDeleteUR(*ur)
+		return fmt.Errorf("failed to process delete UR %s: %v", key, err)
 	}
 
 	if err = c.UnmarkUR(ur); err != nil {