diff --git a/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-master0.yml b/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-master0.yml
index 2c32b4768b..480ccf7c46 100644
--- a/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-master0.yml
+++ b/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-master0.yml
@@ -44,6 +44,11 @@
     - name: k8s/master0 | Add k8s annotation for containerd
       command: >-
         kubectl annotate node {{ inventory_hostname }} --overwrite kubeadm.alpha.kubernetes.io/cri-socket=unix:///run/containerd/containerd.sock
+      register: result
+      until:
+        - result is succeeded
+      retries: 5
+      delay: 1
 
     # Note: Usage of the --config flag for reconfiguring the cluster during upgrade is not recommended since v1.16
     - name: k8s/master0 | Upgrade K8s cluster to v{{ version }}
diff --git a/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-masterN.yml b/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-masterN.yml
index c615ecc858..eea8bb0693 100644
--- a/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-masterN.yml
+++ b/ansible/playbooks/roles/upgrade/tasks/kubernetes/upgrade-masterN.yml
@@ -10,6 +10,11 @@
     - name: k8s/masterN | Add k8s annotation for containerd
       command: >-
         kubectl annotate node {{ inventory_hostname }} --overwrite kubeadm.alpha.kubernetes.io/cri-socket=unix:///run/containerd/containerd.sock
+      register: result
+      until:
+        - result is succeeded
+      retries: 5
+      delay: 1
 
     - name: k8s/masterN | Upgrade master {{ inventory_hostname }}
       command: >-