diff --git a/kinder/ci/tools/update-workflows/templates/workflows/instance-config-tasks.yaml b/kinder/ci/tools/update-workflows/templates/workflows/instance-config-tasks.yaml
index c9374420..6fbd94c5 100644
--- a/kinder/ci/tools/update-workflows/templates/workflows/instance-config-tasks.yaml
+++ b/kinder/ci/tools/update-workflows/templates/workflows/instance-config-tasks.yaml
@@ -218,6 +218,36 @@ tasks:
         exit 1;
         }
 
+      exit 0
+  timeout: 5m
+- name: check-and-add-flag
+  description: |
+    Check and add the container-runtime-endpoint flag to each node's kubeadm-flags.env file
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      for node in control-plane-{1..3} worker-{1..2}; do
+        CMD="docker exec {{ .vars.clusterName }}-$node"
+
+        ${CMD} bash -c '
+          FILE="/var/lib/kubelet/kubeadm-flags.env"
+          NEW_ARG="--container-runtime-endpoint=unix:///run/containerd/containerd.sock"
+
+          if grep -q "container-runtime-endpoint" "$FILE"; then
+            echo "flag container-runtime-endpoint already exists"
+            exit 1
+          fi
+
+          sed -i "/^KUBELET_KUBEADM_ARGS=/ s|\"$| $NEW_ARG\"|" "$FILE"
+        ' || {
+          echo "Command failed for $node. Exiting.";
+          exit 1;
+          }
+      done
+
       exit 0
   timeout: 5m
 - name: upgrade-again
@@ -257,6 +287,60 @@ tasks:
         }
       done
 
+      exit 0
+  timeout: 5m
+- name: check-annotation-after-second-upgrade
+  description: |
+      Check that the cri-socket annotation does not exist on each node.
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      docker exec {{ .vars.clusterName }}-control-plane-1 bash -c '
+        nodes=$(KUBECONFIG=/etc/kubernetes/admin.conf kubectl get nodes -o jsonpath='{.items[*].metadata.name}')
+
+        for node in $nodes; do
+          annotation=$(KUBECONFIG=/etc/kubernetes/admin.conf kubectl get node "$node" -o jsonpath="{.metadata.annotations['kubeadm\.alpha\.kubernetes\.io/cri-socket']}")
+
+          if [ -z "$annotation" ]; then
+            echo "Annotation not found on node $node"
+          else
+            echo "Annotation found on node $node: $annotation"
+            exit 1
+          fi
+        done
+      ' || {
+        echo "Command failed for $node. Exiting.";
+        exit 1;
+        }
+
+      exit 0
+  timeout: 5m
+- name: check-flag-after-second-upgrade
+  description: |
+      Check that the container-runtime-endpoint flag does not exist on each node.
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      for node in control-plane-{1..3} worker-{1..2}; do
+        CMD="docker exec {{ .vars.clusterName }}-$node"
+
+        ${CMD} bash -c '
+          if [[ -f "/var/lib/kubelet/kubeadm-flags.env" ]] && grep -q "container-runtime-endpoint" /var/lib/kubelet/kubeadm-flags.env; then
+            echo "File exists and contains 'container-runtime-endpoint' field."
+            exit 1
+          fi
+        ' || {
+        echo "Command failed for $node. Exiting.";
+        exit 1;
+        }
+      done
+
       exit 0
   timeout: 5m
 - name: cluster-info
diff --git a/kinder/ci/workflows/instance-config-tasks.yaml b/kinder/ci/workflows/instance-config-tasks.yaml
index 15257833..24f054fc 100644
--- a/kinder/ci/workflows/instance-config-tasks.yaml
+++ b/kinder/ci/workflows/instance-config-tasks.yaml
@@ -219,6 +219,36 @@ tasks:
         exit 1;
         }
 
+      exit 0
+  timeout: 5m
+- name: check-and-add-flag
+  description: |
+    Check and add the container-runtime-endpoint flag to each node's kubeadm-flags.env file
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      for node in control-plane-{1..3} worker-{1..2}; do
+        CMD="docker exec {{ .vars.clusterName }}-$node"
+
+        ${CMD} bash -c '
+          FILE="/var/lib/kubelet/kubeadm-flags.env"
+          NEW_ARG="--container-runtime-endpoint=unix:///run/containerd/containerd.sock"
+
+          if grep -q "container-runtime-endpoint" "$FILE"; then
+            echo "flag container-runtime-endpoint already exists"
+            exit 1
+          fi
+
+          sed -i "/^KUBELET_KUBEADM_ARGS=/ s|\"$| $NEW_ARG\"|" "$FILE"
+        ' || {
+          echo "Command failed for $node. Exiting.";
+          exit 1;
+          }
+      done
+
       exit 0
   timeout: 5m
 - name: upgrade-again
@@ -258,6 +288,60 @@ tasks:
         }
       done
 
+      exit 0
+  timeout: 5m
+- name: check-annotation-after-second-upgrade
+  description: |
+      Check that the cri-socket annotation does not exist on each node.
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      docker exec {{ .vars.clusterName }}-control-plane-1 bash -c '
+        nodes=$(KUBECONFIG=/etc/kubernetes/admin.conf kubectl get nodes -o jsonpath='{.items[*].metadata.name}')
+
+        for node in $nodes; do
+          annotation=$(KUBECONFIG=/etc/kubernetes/admin.conf kubectl get node "$node" -o jsonpath="{.metadata.annotations['kubeadm\.alpha\.kubernetes\.io/cri-socket']}")
+
+          if [ -z "$annotation" ]; then
+            echo "Annotation not found on node $node"
+          else
+            echo "Annotation found on node $node: $annotation"
+            exit 1
+          fi
+        done
+      ' || {
+        echo "Command failed for $node. Exiting.";
+        exit 1;
+        }
+
+      exit 0
+  timeout: 5m
+- name: check-flag-after-second-upgrade
+  description: |
+      Check that the container-runtime-endpoint flag does not exist on each node.
+  cmd: /bin/bash
+  args:
+    - -c
+    - |
+      set -x
+
+      for node in control-plane-{1..3} worker-{1..2}; do
+        CMD="docker exec {{ .vars.clusterName }}-$node"
+
+        ${CMD} bash -c '
+          if [[ -f "/var/lib/kubelet/kubeadm-flags.env" ]] && grep -q "container-runtime-endpoint" /var/lib/kubelet/kubeadm-flags.env; then
+            echo "File exists and contains 'container-runtime-endpoint' field."
+            exit 1
+          fi
+        ' || {
+        echo "Command failed for $node. Exiting.";
+        exit 1;
+        }
+      done
+
       exit 0
   timeout: 5m
 - name: cluster-info