diff --git a/cmd/kubeadm/app/phases/addons/dns/dns.go b/cmd/kubeadm/app/phases/addons/dns/dns.go
index 5e4355de025..179bc634ab0 100644
--- a/cmd/kubeadm/app/phases/addons/dns/dns.go
+++ b/cmd/kubeadm/app/phases/addons/dns/dns.go
@@ -273,12 +273,26 @@ func createCoreDNSAddon(deploymentBytes, serviceBytes, configBytes []byte, clien
 		return errors.Wrap(err, "unable to fetch CoreDNS current installed version and ConfigMap.")
 	}
 
-	var hasCoreDNSMigrationFailed bool
-	if IsCoreDNSConfigMapMigrationRequired(corefile) {
+	canMigrateCorefile, err := isCoreDNSVersionSupported(client)
+	if err != nil {
+		return err
+	}
+
+	corefileMigrationRequired, err := isCoreDNSConfigMapMigrationRequired(corefile, currentInstalledCoreDNSVersion)
+	if err != nil {
+		return err
+	}
+
+	if !canMigrateCorefile {
+		klog.Warningf("the CoreDNS Configuration will not be migrated due to unsupported version of CoreDNS. " +
+			"The existing CoreDNS Corefile configuration and deployment has been retained.")
+	}
+
+	if corefileMigrationRequired && canMigrateCorefile {
 		if err := migrateCoreDNSCorefile(client, coreDNSConfigMap, corefile, currentInstalledCoreDNSVersion); err != nil {
 			// Errors in Corefile Migration is verified during preflight checks. This part will be executed when a user has chosen
 			// to ignore preflight check errors.
-			hasCoreDNSMigrationFailed = true
+			canMigrateCorefile = false
 			klog.Warningf("the CoreDNS Configuration was not migrated: %v. The existing CoreDNS Corefile configuration has been retained.", err)
 			if err := apiclient.CreateOrRetainConfigMap(client, coreDNSConfigMap, kubeadmconstants.CoreDNSConfigMap); err != nil {
 				return err
@@ -326,7 +340,7 @@ func createCoreDNSAddon(deploymentBytes, serviceBytes, configBytes []byte, clien
 	}
 
 	// Create the deployment for CoreDNS or retain it in case the CoreDNS migration has failed during upgrade
-	if hasCoreDNSMigrationFailed {
+	if !canMigrateCorefile {
 		if err := apiclient.CreateOrRetainDeployment(client, coreDNSDeployment, kubeadmconstants.CoreDNSDeploymentName); err != nil {
 			return err
 		}
@@ -362,40 +376,57 @@ func createDNSService(dnsService *v1.Service, serviceBytes []byte, client client
 	return nil
 }
 
-// IsCoreDNSConfigMapMigrationRequired checks if a migration of the CoreDNS ConfigMap is required.
-func IsCoreDNSConfigMapMigrationRequired(corefile string) bool {
+// isCoreDNSConfigMapMigrationRequired checks if a migration of the CoreDNS ConfigMap is required.
+func isCoreDNSConfigMapMigrationRequired(corefile, currentInstalledCoreDNSVersion string) (bool, error) {
+	var isMigrationRequired bool
 	if corefile == "" || migration.Default("", corefile) {
-		return false
+		return isMigrationRequired, nil
 	}
-	return true
+	deprecated, err := migration.Deprecated(currentInstalledCoreDNSVersion, kubeadmconstants.CoreDNSVersion, corefile)
+	if err != nil {
+		return isMigrationRequired, errors.Wrap(err, "unable to get list of changes to the configuration.")
+	}
+
+	// Check if there are any plugins/options which needs to be removed or is a new default
+	for _, dep := range deprecated {
+		if dep.Severity == "removed" || dep.Severity == "newDefault" {
+			isMigrationRequired = true
+		}
+	}
+
+	return isMigrationRequired, nil
+}
+
+func isCoreDNSVersionSupported(client clientset.Interface) (bool, error) {
+	isValidVersion := true
+	coreDNSPodList, err := client.CoreV1().Pods(metav1.NamespaceSystem).List(
+		context.TODO(),
+		metav1.ListOptions{
+			LabelSelector: "k8s-app=kube-dns",
+		},
+	)
+	if err != nil {
+		return false, errors.Wrap(err, "unable to list CoreDNS pods")
+	}
+
+	for _, pod := range coreDNSPodList.Items {
+		imageID := strings.Split(pod.Status.ContainerStatuses[0].ImageID, ":")
+		if !migration.Released(imageID[2]) {
+			isValidVersion = false
+		}
+	}
+
+	return isValidVersion, nil
 }
 
 func migrateCoreDNSCorefile(client clientset.Interface, cm *v1.ConfigMap, corefile, currentInstalledCoreDNSVersion string) error {
-	// Take a copy of the Corefile data as `Corefile-backup` and update the ConfigMap
-	// Also point the CoreDNS deployment to the `Corefile-backup` data.
-
-	if _, err := client.CoreV1().ConfigMaps(cm.ObjectMeta.Namespace).Update(context.TODO(), &v1.ConfigMap{
-		ObjectMeta: metav1.ObjectMeta{
-			Name:      kubeadmconstants.CoreDNSConfigMap,
-			Namespace: metav1.NamespaceSystem,
-		},
-		Data: map[string]string{
-			"Corefile":        corefile,
-			"Corefile-backup": corefile,
-		},
-	}, metav1.UpdateOptions{}); err != nil {
-		return errors.Wrap(err, "unable to update the CoreDNS ConfigMap with backup Corefile")
-	}
-	if err := patchCoreDNSDeployment(client, "Corefile-backup"); err != nil {
-		return err
-	}
-
 	// Since the current configuration present is not the default version, try and migrate it.
 	updatedCorefile, err := migration.Migrate(currentInstalledCoreDNSVersion, kubeadmconstants.CoreDNSVersion, corefile, false)
 	if err != nil {
 		return errors.Wrap(err, "unable to migrate CoreDNS ConfigMap")
 	}
 
+	// Take a copy of the existing Corefile data as `Corefile-backup` and update the ConfigMap
 	if _, err := client.CoreV1().ConfigMaps(cm.ObjectMeta.Namespace).Update(context.TODO(), &v1.ConfigMap{
 		ObjectMeta: metav1.ObjectMeta{
 			Name:      kubeadmconstants.CoreDNSConfigMap,
@@ -408,6 +439,12 @@ func migrateCoreDNSCorefile(client clientset.Interface, cm *v1.ConfigMap, corefi
 	}, metav1.UpdateOptions{}); err != nil {
 		return errors.Wrap(err, "unable to update the CoreDNS ConfigMap")
 	}
+
+	// Point the CoreDNS deployment to the `Corefile-backup` data.
+	if err := setCorefile(client, "Corefile-backup"); err != nil {
+		return err
+	}
+
 	fmt.Println("[addons] Migrating CoreDNS Corefile")
 	changes, err := migration.Deprecated(currentInstalledCoreDNSVersion, kubeadmconstants.CoreDNSVersion, corefile)
 	if err != nil {
@@ -445,12 +482,12 @@ func GetCoreDNSInfo(client clientset.Interface) (*v1.ConfigMap, string, string,
 	return coreDNSConfigMap, corefile, currentCoreDNSversion, nil
 }
 
-func patchCoreDNSDeployment(client clientset.Interface, coreDNSCorefileName string) error {
+func setCorefile(client clientset.Interface, coreDNSCorefileName string) error {
 	dnsDeployment, err := client.AppsV1().Deployments(metav1.NamespaceSystem).Get(context.TODO(), kubeadmconstants.CoreDNSDeploymentName, metav1.GetOptions{})
 	if err != nil {
 		return err
 	}
-	patch := fmt.Sprintf(`{"spec":{"template":{"spec":{"volumes":[{"name": "config-volume", "configMap":{"name": "coredns", "items":[{"key": "%s", "path": "%s"}]}}]}}}}`, coreDNSCorefileName, coreDNSCorefileName)
+	patch := fmt.Sprintf(`{"spec":{"template":{"spec":{"volumes":[{"name": "config-volume", "configMap":{"name": "coredns", "items":[{"key": "%s", "path": "Corefile"}]}}]}}}}`, coreDNSCorefileName)
 
 	if _, err := client.AppsV1().Deployments(dnsDeployment.ObjectMeta.Namespace).Patch(context.TODO(), dnsDeployment.Name, types.StrategicMergePatchType, []byte(patch), metav1.PatchOptions{}); err != nil {
 		return errors.Wrap(err, "unable to patch the CoreDNS deployment")