diff --git a/ci-operator/config/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12.yaml b/ci-operator/config/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12.yaml
index 347b21a11b392..4431a210288d5 100644
--- a/ci-operator/config/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12.yaml
+++ b/ci-operator/config/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12.yaml
@@ -4,7 +4,7 @@ base_images:
     namespace: openshift
     tag: rhel-8-release-golang-1.19-openshift-4.12
   operator-sdk:
-    name: "4.12"
+    name: "4.14"
     namespace: origin
     tag: operator-sdk
 binary_build_commands: make build
@@ -148,6 +148,106 @@ tests:
           cpu: 1000m
           memory: 400Mi
     workflow: ipi-aws-ovn-hybrid
+- always_run: false
+  as: azure-e2e-upgrade
+  steps:
+    cluster_profile: azure4
+    test:
+    - as: install
+      cli: latest
+      commands: |-
+        export WMCO_NS=openshift-windows-machine-config-operator
+        oc create namespace $WMCO_NS
+        oc label --overwrite=true ns $WMCO_NS openshift.io/cluster-monitoring=true \
+        pod-security.kubernetes.io/enforce=privileged
+        # deploy og
+        oc create -f - <<EOF
+        apiVersion: operators.coreos.com/v1
+        kind: OperatorGroup
+        metadata:
+          name: windows-machine-config-operator
+          namespace: ${WMCO_NS}
+        spec:
+          targetNamespaces:
+            - ${WMCO_NS}
+        EOF
+
+        # install operator via subscription
+        oc create -f - <<EOF
+        apiVersion: operators.coreos.com/v1alpha1
+        kind: Subscription
+        metadata:
+          name: windows-machine-config-operator
+          namespace: ${WMCO_NS}
+        spec:
+          channel: stable
+          installPlanApproval: Automatic
+          name: windows-machine-config-operator
+          source: redhat-operators
+          sourceNamespace: openshift-marketplace
+        EOF
+
+        # oc wait will immediately fail if the deployment does not exist yet, first retry until the deployment is
+        # created by the subscription controller
+        retries=0
+        while ! oc get -n $WMCO_NS deployment windows-machine-config-operator; do
+          if [[ $retries -eq 10 ]]; then
+            echo "max retries hit"
+            exit 1
+          fi
+          sleep 1m
+          retries=$((retries+1))
+        done
+        oc wait --timeout=10m --for condition=Available -n $WMCO_NS deployment windows-machine-config-operator
+      from: cli
+      resources:
+        requests:
+          cpu: 1000m
+          memory: 400Mi
+    - as: test-setup
+      cli: latest
+      commands: |-
+        #!/bin/bash
+        set -euo pipefail
+        export KUBE_SSH_KEY_PATH=${CLUSTER_PROFILE_DIR}/ssh-privatekey
+        oc create secret generic cloud-private-key --from-file=private-key.pem="${KUBE_SSH_KEY_PATH}" -n openshift-windows-machine-config-operator
+        make upgrade-test-setup
+      from: windows-machine-config-operator-test
+      resources:
+        requests:
+          cpu: 1000m
+          memory: 400Mi
+    - as: upgrade
+      cli: latest
+      commands: |
+        export WMCO_NS=openshift-windows-machine-config-operator
+        operator-sdk cleanup --timeout 1m windows-machine-config-operator -n $WMCO_NS || {
+          echo "operator-sdk cleanup timed out"
+        }
+        operator-sdk run bundle --timeout=10m --security-context-config restricted -n $WMCO_NS "$OO_BUNDLE"
+        sleep 5m
+        oc wait --timeout=5m --for condition=Available -n $WMCO_NS deployment windows-machine-config-operator
+      dependencies:
+      - env: OO_BUNDLE
+        name: wmco-bundle
+      from: operator-sdk
+      resources:
+        requests:
+          cpu: 1000m
+          memory: 400Mi
+    - as: test
+      cli: latest
+      commands: |-
+        #!/bin/bash
+        set -euo pipefail
+        export KUBE_SSH_KEY_PATH=${CLUSTER_PROFILE_DIR}/ssh-privatekey
+        make upgrade-test
+      from: windows-machine-config-operator-test
+      resources:
+        requests:
+          cpu: 1000m
+          memory: 400Mi
+    workflow: ipi-azure-ovn-hybrid
 - always_run: false
   as: platform-none-vsphere-e2e-operator
   steps:
diff --git a/ci-operator/jobs/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12-presubmits.yaml b/ci-operator/jobs/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12-presubmits.yaml
index 793c69ed0a05c..52176e0f872e7 100644
--- a/ci-operator/jobs/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12-presubmits.yaml
+++ b/ci-operator/jobs/openshift/windows-machine-config-operator/openshift-windows-machine-config-operator-release-4.12-presubmits.yaml
@@ -234,6 +234,84 @@ presubmits:
         secret:
           secretName: result-aggregator
     trigger: (?m)^/test( | .* )(azure-e2e-operator|remaining-required),?($|\s.*)
+  - agent: kubernetes
+    always_run: false
+    branches:
+    - ^release-4\.12$
+    - ^release-4\.12-
+    cluster: build03
+    context: ci/prow/azure-e2e-upgrade
+    decorate: true
+    labels:
+      ci-operator.openshift.io/cloud: azure4
+      ci-operator.openshift.io/cloud-cluster-profile: azure4
+      ci.openshift.io/generator: prowgen
+      pj-rehearse.openshift.io/can-be-rehearsed: "true"
+    name: pull-ci-openshift-windows-machine-config-operator-release-4.12-azure-e2e-upgrade
+    rerun_command: /test azure-e2e-upgrade
+    spec:
+      containers:
+      - args:
+        - --gcs-upload-secret=/secrets/gcs/service-account.json
+        - --image-import-pull-secret=/etc/pull-secret/.dockerconfigjson
+        - --lease-server-credentials-file=/etc/boskos/credentials
+        - --report-credentials-file=/etc/report/credentials
+        - --secret-dir=/secrets/ci-pull-credentials
+        - --secret-dir=/usr/local/azure-e2e-upgrade-cluster-profile
+        - --target=azure-e2e-upgrade
+        command:
+        - ci-operator
+        image: ci-operator:latest
+        imagePullPolicy: Always
+        name: ""
+        resources:
+          requests:
+            cpu: 10m
+        volumeMounts:
+        - mountPath: /etc/boskos
+          name: boskos
+          readOnly: true
+        - mountPath: /secrets/ci-pull-credentials
+          name: ci-pull-credentials
+          readOnly: true
+        - mountPath: /usr/local/azure-e2e-upgrade-cluster-profile
+          name: cluster-profile
+        - mountPath: /secrets/gcs
+          name: gcs-credentials
+          readOnly: true
+        - mountPath: /secrets/manifest-tool
+          name: manifest-tool-local-pusher
+          readOnly: true
+        - mountPath: /etc/pull-secret
+          name: pull-secret
+          readOnly: true
+        - mountPath: /etc/report
+          name: result-aggregator
+          readOnly: true
+      serviceAccountName: ci-operator
+      volumes:
+      - name: boskos
+        secret:
+          items:
+          - key: credentials
+            path: credentials
+          secretName: boskos-credentials
+      - name: ci-pull-credentials
+        secret:
+          secretName: ci-pull-credentials
+      - name: cluster-profile
+        secret:
+          secretName: cluster-secrets-azure4
+      - name: manifest-tool-local-pusher
+        secret:
+          secretName: manifest-tool-local-pusher
+      - name: pull-secret
+        secret:
+          secretName: registry-pull-credentials
+      - name: result-aggregator
+        secret:
+          secretName: result-aggregator
+    trigger: (?m)^/test( | .* )(azure-e2e-upgrade|remaining-required),?($|\s.*)
   - agent: kubernetes
     always_run: false
     branches: