diff --git a/.github/workflows/packer.yml b/.github/workflows/packer.yml
index 28d9517ce..00fb61621 100644
--- a/.github/workflows/packer.yml
+++ b/.github/workflows/packer.yml
@@ -624,4 +624,5 @@ jobs:
             image_builder/deploy/00controller.yaml
             image_builder/deploy/01ui.yaml
             image_builder/deploy/version-config.yaml
+            image_builder/deploy/version-checker.yaml
             image_builder/deploy/vjailbreak-settings.yaml
\ No newline at end of file
diff --git a/Makefile b/Makefile
index c0002a673..a3eed5e77 100644
--- a/Makefile
+++ b/Makefile
@@ -55,6 +55,7 @@ generate-manifests: vjail-controller ui
 	rm -rf image_builder/deploy && mkdir -p image_builder/deploy && chmod 755 image_builder/deploy
 	envsubst < ui/deploy/ui.yaml > image_builder/deploy/01ui.yaml
 	envsubst < image_builder/configs/version-config.yaml > image_builder/deploy/version-config.yaml
+	cp image_builder/cronjob/version-checker.yaml image_builder/deploy/version-checker.yaml
 	cp image_builder/configs/vjailbreak-settings.yaml image_builder/deploy/vjailbreak-settings.yaml
 	make -C k8s/migration/ build-installer && cp k8s/migration/dist/install.yaml image_builder/deploy/00controller.yaml
 	
@@ -81,4 +82,4 @@ build-image: generate-manifests
 	docker build --platform linux/amd64 --output=artifacts/ -t vjailbreak-image:local image_builder/ 
 
 run-local:
-	cd k8s/migration/cmd/ && go run main.go --kubeconfig ${KUBECONFIG} --local true
+	cd k8s/migration/cmd/ && go run main.go --kubeconfig ${KUBECONFIG} --local true
\ No newline at end of file
diff --git a/image_builder/cronjob/version-checker.yaml b/image_builder/cronjob/version-checker.yaml
new file mode 100644
index 000000000..587d18bd5
--- /dev/null
+++ b/image_builder/cronjob/version-checker.yaml
@@ -0,0 +1,92 @@
+apiVersion: v1
+kind: ServiceAccount
+metadata:
+  name: version-checker-sa
+  namespace: migration-system
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: Role
+metadata:
+  name: configmap-editor-role
+  namespace: migration-system
+rules:
+  - apiGroups: [""]
+    resources: ["configmaps"]
+    resourceNames: ["version-config"]
+    verbs: ["get", "patch"]
+---
+apiVersion: rbac.authorization.k8s.io/v1
+kind: RoleBinding
+metadata:
+  name: version-checker-binding
+  namespace: migration-system
+subjects:
+  - kind: ServiceAccount
+    name: version-checker-sa
+    namespace: migration-system
+roleRef:
+  kind: Role
+  name: configmap-editor-role
+  apiGroup: rbac.authorization.k8s.io
+---
+apiVersion: batch/v1
+kind: CronJob
+metadata:
+  name: vjailbreak-version-checker
+  namespace: migration-system
+spec:
+  schedule: "0 0 * * *"
+  concurrencyPolicy: Forbid
+  jobTemplate:
+    spec:
+      ttlSecondsAfterFinished: 300
+      template:
+        spec:
+          serviceAccountName: version-checker-sa
+          restartPolicy: OnFailure
+          containers:
+            - name: version-checker
+              image: alpine:3.18
+              command:
+                - /bin/sh
+                - -c
+                - |
+                  set -e
+                  apk add --no-cache curl jq
+
+                  curl -LO "https://dl.k8s.io/release/v1.34.0/bin/linux/amd64/kubectl"
+
+                  chmod +x kubectl
+                  mv kubectl /usr/local/bin/
+
+                  echo "Checking for latest version"
+                  CURRENT_VERSION=$(kubectl get configmap version-config -n migration-system -o jsonpath='{.data.version}')
+                  echo "Current version: $CURRENT_VERSION"
+
+                  if [ -z "$CURRENT_VERSION" ]; then
+                    echo "Error: 'version' key not found in ConfigMap. Exiting."
+                    exit 1
+                  fi
+
+                  LATEST_TAG=$(curl -s "https://api.github.com/repos/platform9/vjailbreak/tags" | jq -r '.[0].name')
+
+                  if [ -z "$LATEST_TAG" ] || [ "$LATEST_TAG" == "null" ]; then
+                    echo "Error: Could not fetch latest tag from GitHub. Exiting."
+                    exit 1
+                  fi
+                  echo "Latest tag on GitHub: $LATEST_TAG"
+
+                  CURRENT_SEMVER=${CURRENT_VERSION#v}
+                  LATEST_SEMVER=${LATEST_TAG#v}
+                  HIGHEST_VERSION=$(printf "%s\n%s" "$CURRENT_SEMVER" "$LATEST_SEMVER" | sort -V | tail -n1)
+
+                  if [ "$LATEST_SEMVER" != "$CURRENT_SEMVER" ] && [ "$HIGHEST_VERSION" == "$LATEST_SEMVER" ]; then
+                    echo "New version found! Updating ConfigMap..."
+                    PATCH_DATA="{\"data\":{\"upgradeAvailable\":\"true\",\"upgradeVersion\":\"$LATEST_TAG\"}}"
+                    kubectl patch configmap version-config -n migration-system --type='merge' -p="$PATCH_DATA"
+                    echo "ConfigMap 'version-config' updated successfully."
+                  else
+                    echo "You are on the latest version. No update needed."
+                  fi
+
+                  echo "Version Check Complete"
\ No newline at end of file
diff --git a/image_builder/vjailbreak-image.pkr.hcl b/image_builder/vjailbreak-image.pkr.hcl
index afe892ea1..8a6fd1113 100644
--- a/image_builder/vjailbreak-image.pkr.hcl
+++ b/image_builder/vjailbreak-image.pkr.hcl
@@ -73,6 +73,11 @@ build {
     destination = "/tmp/vjailbreak-settings.yaml"
   }
 
+  provisioner "file" {
+    source      = "${path.root}/cronjob/version-checker.yaml"
+    destination = "/tmp/version-checker.yaml"
+  }
+
   provisioner "file" {
     source      = "${path.root}/images"
     destination = "/home/ubuntu"
@@ -97,6 +102,7 @@ build {
     "sudo mv /tmp/daemonset.yaml /etc/pf9/yamls/daemonset.yaml",
     "sudo mv /tmp/env /etc/pf9/env",
     "sudo mv /tmp/vjailbreak-settings.yaml /etc/pf9/yamls/vjailbreak-settings.yaml",
+    "sudo mv /tmp/version-checker.yaml /etc/pf9/yamls/version-checker.yaml",
     "sudo mv /tmp/opensource.txt /home/ubuntu/opensource.txt",
     "sudo chmod +x /etc/pf9/install.sh",
     "sudo chown root:root /etc/pf9/k3s.env",