diff --git a/ci-operator/config/openshift/cert-manager-operator/openshift-cert-manager-operator-master.yaml b/ci-operator/config/openshift/cert-manager-operator/openshift-cert-manager-operator-master.yaml
index 773fa8bae41ce..19a8538976d17 100644
--- a/ci-operator/config/openshift/cert-manager-operator/openshift-cert-manager-operator-master.yaml
+++ b/ci-operator/config/openshift/cert-manager-operator/openshift-cert-manager-operator-master.yaml
@@ -113,6 +113,54 @@ tests:
         requests:
           cpu: 100m
     workflow: optional-operators-ci-operator-sdk-aws
+- as: e2e-operator-upgrade
+  steps:
+    cluster_profile: aws
+    test:
+    - as: install
+      cli: latest
+      commands: |
+        export REGISTRY_AUTH_FILE=/tmp/import-secret/.dockerconfigjson
+        export DOCKER_CONFIG=/tmp/.docker
+        mkdir -p $DOCKER_CONFIG
+        cp $REGISTRY_AUTH_FILE $DOCKER_CONFIG/config.json
+        cd /tmp
+        oc create namespace cert-manager-operator
+        operator-sdk run bundle --security-context-config restricted -n cert-manager-operator registry.redhat.io/cert-manager/cert-manager-operator-bundle:v1.14.1
+        oc wait --timeout=10m --for condition=Available -n cert-manager-operator deployment cert-manager-operator-controller-manager
+        oc get deployment -n cert-manager
+      credentials:
+      - mount_path: /tmp/pull-secret
+        name: registry-pull-credentials
+        namespace: test-credentials
+      - mount_path: /tmp/import-secret
+        name: ci-pull-credentials
+        namespace: test-credentials
+      from: cli-operator-sdk
+      resources:
+        requests:
+          cpu: 100m
+    - as: upgrade
+      cli: latest
+      commands: |
+        operator-sdk run bundle-upgrade --security-context-config restricted -n cert-manager-operator "$OO_BUNDLE"
+        oc wait --timeout=10m --for condition=Available -n cert-manager-operator deployment cert-manager-operator-controller-manager
+        oc get deployment -n cert-manager
+      dependencies:
+      - env: OO_BUNDLE
+        name: cert-manager-operator-bundle
+      from: cli-operator-sdk
+      resources:
+        requests:
+          cpu: 100m
+    - as: test
+      cli: latest
+      commands: make test-e2e
+      from: src
+      resources:
+        requests:
+          cpu: 100m
+    workflow: ipi-aws
 zz_generated_metadata:
   branch: master
   org: openshift
diff --git a/ci-operator/jobs/openshift/cert-manager-operator/openshift-cert-manager-operator-master-presubmits.yaml b/ci-operator/jobs/openshift/cert-manager-operator/openshift-cert-manager-operator-master-presubmits.yaml
index 9481d2c8202f7..c9b0b684015f2 100644
--- a/ci-operator/jobs/openshift/cert-manager-operator/openshift-cert-manager-operator-master-presubmits.yaml
+++ b/ci-operator/jobs/openshift/cert-manager-operator/openshift-cert-manager-operator-master-presubmits.yaml
@@ -125,6 +125,78 @@ presubmits:
         secret:
           secretName: result-aggregator
     trigger: (?m)^/test( | .* )e2e-operator,?($|\s.*)
+  - agent: kubernetes
+    always_run: true
+    branches:
+    - ^master$
+    - ^master-
+    cluster: build01
+    context: ci/prow/e2e-operator-upgrade
+    decorate: true
+    labels:
+      ci-operator.openshift.io/cloud: aws
+      ci-operator.openshift.io/cloud-cluster-profile: aws
+      ci.openshift.io/generator: prowgen
+      pj-rehearse.openshift.io/can-be-rehearsed: "true"
+    name: pull-ci-openshift-cert-manager-operator-master-e2e-operator-upgrade
+    rerun_command: /test e2e-operator-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
+        - --target=e2e-operator-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: /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: 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( | .* )e2e-operator-upgrade,?($|\s.*)
   - agent: kubernetes
     always_run: true
     branches: