diff --git a/pkg/cluster/k8sres.go b/pkg/cluster/k8sres.go
index 3ce4196ad..23fafca74 100644
--- a/pkg/cluster/k8sres.go
+++ b/pkg/cluster/k8sres.go
@@ -1191,7 +1191,7 @@ func (c *Cluster) generateStatefulSet(spec *acidv1.PostgresSpec) (*appsv1.Statef
 			Name:        c.statefulSetName(),
 			Namespace:   c.Namespace,
 			Labels:      c.labelsSet(true),
-			Annotations: c.PropagateAnnotationsToStatefulsets(annotations),
+			Annotations: c.AnnotationsToPropagate(annotations),
 		},
 		Spec: appsv1.StatefulSetSpec{
 			Replicas:             &numberOfInstances,
diff --git a/pkg/cluster/resources.go b/pkg/cluster/resources.go
index b38458af8..ac1437540 100644
--- a/pkg/cluster/resources.go
+++ b/pkg/cluster/resources.go
@@ -853,3 +853,24 @@ func (c *Cluster) updateConnectionPoolerDeployment(oldDeploymentSpec, newDeploym
 
 	return deployment, nil
 }
+
+//updateConnectionPoolerAnnotations updates the annotations of connection pooler deployment
+func (c *Cluster) updateConnectionPoolerAnnotations(annotations map[string]string) (*appsv1.Deployment, error) {
+	c.logger.Debugf("updating connection pooler annotations")
+	patchData, err := metaAnnotationsPatch(annotations)
+	if err != nil {
+		return nil, fmt.Errorf("could not form patch for the deployment metadata: %v", err)
+	}
+	result, err := c.KubeClient.Deployments(c.ConnectionPooler.Deployment.Namespace).Patch(
+		context.TODO(),
+		c.ConnectionPooler.Deployment.Name,
+		types.MergePatchType,
+		[]byte(patchData),
+		metav1.PatchOptions{},
+		"")
+	if err != nil {
+		return nil, fmt.Errorf("could not patch conenction pooler annotations %q: %v", patchData, err)
+	}
+	return result, nil
+
+}
diff --git a/pkg/cluster/sync.go b/pkg/cluster/sync.go
index 07d4855d8..e9762af4c 100644
--- a/pkg/cluster/sync.go
+++ b/pkg/cluster/sync.go
@@ -353,8 +353,7 @@ func (c *Cluster) syncStatefulSet() error {
 				}
 			}
 		}
-
-		annotations := c.PropagateAnnotationsToStatefulsets(c.Statefulset.Annotations)
+		annotations := c.AnnotationsToPropagate(c.Statefulset.Annotations)
 		c.updateStatefulSetAnnotations(annotations)
 
 		if !podsRollingUpdateRequired && !c.OpConfig.EnableLazySpiloUpgrade {
@@ -395,9 +394,9 @@ func (c *Cluster) syncStatefulSet() error {
 	return nil
 }
 
-// PropagateAnnotationsToStatefulsets updates annotations to statefulsets if required
+// AnnotationsToPropagate get the annotations to update if required
 // based on the annotations in postgres CRD
-func (c *Cluster) PropagateAnnotationsToStatefulsets(annotations map[string]string) map[string]string {
+func (c *Cluster) AnnotationsToPropagate(annotations map[string]string) map[string]string {
 	ToPropagateAnnotations := c.OpConfig.StatefulsetPropagateAnnotations
 	PgCRDAnnotations := c.Postgresql.ObjectMeta.GetAnnotations()
 
@@ -405,14 +404,18 @@ func (c *Cluster) PropagateAnnotationsToStatefulsets(annotations map[string]stri
 		for _, anno := range ToPropagateAnnotations {
 			for k, v := range PgCRDAnnotations {
 				matched, err := regexp.MatchString(anno, k)
-				if err == nil && matched {
+				if err != nil {
+					c.logger.Errorf("annotations matching issue: %v", err)
+					return nil
+				}
+				if matched {
 					annotations[k] = v
 				}
 			}
 		}
 	}
-	return annotations
 
+	return annotations
 }
 
 // checkAndSetGlobalPostgreSQLConfiguration checks whether cluster-wide API parameters
@@ -841,6 +844,11 @@ func (c *Cluster) syncConnectionPoolerWorker(oldSpec, newSpec *acidv1.Postgresql
 		}
 	}
 
+	newAnnotations := c.AnnotationsToPropagate(c.ConnectionPooler.Deployment.Annotations)
+	if newAnnotations != nil {
+		c.updateConnectionPoolerAnnotations(newAnnotations)
+	}
+
 	service, err := c.KubeClient.
 		Services(c.Namespace).
 		Get(context.TODO(), c.connectionPoolerName(), metav1.GetOptions{})