diff --git a/ci-operator/config/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master.yaml b/ci-operator/config/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master.yaml
index d13dd88ed80ab..22646fafc3415 100644
--- a/ci-operator/config/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master.yaml
+++ b/ci-operator/config/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master.yaml
@@ -73,6 +73,10 @@ tests:
   openshift_installer_custom_test_image:
     cluster_profile: azure4
     from: stable:cluster-api-actuator-pkg
+- as: e2e-upgrade
+  steps:
+    cluster_profile: azure4
+    workflow: openshift-upgrade-azure-loki
 - as: git-history
   commands: ./hack/verify_history.sh
   container:
diff --git a/ci-operator/jobs/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master-presubmits.yaml b/ci-operator/jobs/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master-presubmits.yaml
index 35d5ab96e692c..17eacb7d00469 100644
--- a/ci-operator/jobs/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master-presubmits.yaml
+++ b/ci-operator/jobs/openshift/cluster-api-provider-azure/openshift-cluster-api-provider-azure-master-presubmits.yaml
@@ -145,6 +145,71 @@ presubmits:
         secret:
           secretName: result-aggregator
     trigger: (?m)^/test( | .* )e2e-azure-operator,?($|\s.*)
+  - agent: kubernetes
+    always_run: false
+    branches:
+    - master
+    cluster: build01
+    context: ci/prow/e2e-upgrade
+    decorate: true
+    decoration_config:
+      skip_cloning: true
+    labels:
+      ci-operator.openshift.io/prowgen-controlled: "true"
+      pj-rehearse.openshift.io/can-be-rehearsed: "true"
+    name: pull-ci-openshift-cluster-api-provider-azure-master-e2e-upgrade
+    optional: true
+    path_alias: sigs.k8s.io/cluster-api-provider-azure
+    rerun_command: /test e2e-upgrade
+    spec:
+      containers:
+      - args:
+        - --image-import-pull-secret=/etc/pull-secret/.dockerconfigjson
+        - --lease-server-password-file=/etc/boskos/password
+        - --report-password-file=/etc/report/password.txt
+        - --report-username=ci
+        - --secret-dir=/usr/local/e2e-upgrade-cluster-profile
+        - --target=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: /usr/local/e2e-upgrade-cluster-profile
+          name: cluster-profile
+        - 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: password
+            path: password
+          secretName: boskos-credentials
+      - name: cluster-profile
+        projected:
+          sources:
+          - secret:
+              name: cluster-secrets-azure4
+      - name: pull-secret
+        secret:
+          secretName: registry-pull-credentials
+      - name: result-aggregator
+        secret:
+          secretName: result-aggregator
+    trigger: (?m)^/test( | .* )e2e-upgrade,?($|\s.*)
   - agent: kubernetes
     always_run: true
     branches:
diff --git a/ci-operator/step-registry/ipi/azure/pre/stableinitial/OWNERS b/ci-operator/step-registry/ipi/azure/pre/stableinitial/OWNERS
new file mode 120000
index 0000000000000..ec405d65a79df
--- /dev/null
+++ b/ci-operator/step-registry/ipi/azure/pre/stableinitial/OWNERS
@@ -0,0 +1 @@
+../OWNERS
\ No newline at end of file
diff --git a/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.metadata.json b/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.metadata.json
new file mode 100644
index 0000000000000..4d2940996f252
--- /dev/null
+++ b/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.metadata.json
@@ -0,0 +1,8 @@
+{
+	"path": "ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.yaml",
+	"owners": {
+		"approvers": [
+			"abhinavdahiya"
+		]
+	}
+}
\ No newline at end of file
diff --git a/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.yaml b/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.yaml
new file mode 100644
index 0000000000000..62cac557d1a5d
--- /dev/null
+++ b/ci-operator/step-registry/ipi/azure/pre/stableinitial/ipi-azure-pre-stableinitial-chain.yaml
@@ -0,0 +1,8 @@
+chain:
+  as: ipi-azure-pre-stableinitial
+  steps:
+  - chain: ipi-conf-azure
+  - chain: ipi-install-stableinitial
+  documentation: |-
+    The IPI setup step contains all steps that provision an OpenShift cluster
+    from stable-initial imagestream with a default configuration on Azure.
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/OWNERS b/ci-operator/step-registry/openshift/upgrade/azure/OWNERS
new file mode 100644
index 0000000000000..f14198cff70e7
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/OWNERS
@@ -0,0 +1,11 @@
+approvers:
+- smarterclayton
+- wking
+- stevekuznetsov
+- vrutkovs
+- abhinavdahiya
+- deads2k
+- crawford
+- ewolinetz
+- csrwng
+- staebler
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/loki/OWNERS b/ci-operator/step-registry/openshift/upgrade/azure/loki/OWNERS
new file mode 120000
index 0000000000000..ec405d65a79df
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/loki/OWNERS
@@ -0,0 +1 @@
+../OWNERS
\ No newline at end of file
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.metadata.json b/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.metadata.json
new file mode 100644
index 0000000000000..e12d4c3f55e25
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.metadata.json
@@ -0,0 +1,17 @@
+{
+	"path": "openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.yaml",
+	"owners": {
+		"approvers": [
+			"smarterclayton",
+			"wking",
+			"stevekuznetsov",
+			"vrutkovs",
+			"abhinavdahiya",
+			"deads2k",
+			"crawford",
+			"ewolinetz",
+			"csrwng",
+			"staebler"
+		]
+	}
+}
\ No newline at end of file
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.yaml b/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.yaml
new file mode 100644
index 0000000000000..171a03dde2082
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/loki/openshift-upgrade-azure-loki-workflow.yaml
@@ -0,0 +1,23 @@
+workflow:
+  as: openshift-upgrade-azure-loki
+  steps:
+    pre:
+    - ref: ipi-install-monitoringpvc
+    - ref: ipi-install-loki
+    - chain: ipi-azure-pre-stableinitial
+    test:
+    - ref: openshift-e2e-test
+    post:
+    - ref: gather-loki
+    - chain: ipi-azure-post
+    dependencies:
+      OPENSHIFT_INSTALL_RELEASE_IMAGE_OVERRIDE: "release:initial"
+      OPENSHIFT_UPGRADE_RELEASE_IMAGE_OVERRIDE: "release:latest"
+    env:
+      TEST_COMMAND: "run-upgrade"
+      TEST_SUITE: "all"
+      TEST_OPTIONS: ""
+  documentation: |-
+    The Openshift E2E Azure workflow executes the upgrade end-to-end test suite on Azure from 
+    stable-initial imagestream with a default cluster configuration, exercising an upgrade 
+    during the process.
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.metadata.json b/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.metadata.json
new file mode 100644
index 0000000000000..5d880dfb8571a
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.metadata.json
@@ -0,0 +1,17 @@
+{
+	"path": "openshift/upgrade/azure/openshift-upgrade-azure-workflow.yaml",
+	"owners": {
+		"approvers": [
+			"smarterclayton",
+			"wking",
+			"stevekuznetsov",
+			"vrutkovs",
+			"abhinavdahiya",
+			"deads2k",
+			"crawford",
+			"ewolinetz",
+			"csrwng",
+			"staebler"
+		]
+	}
+}
\ No newline at end of file
diff --git a/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.yaml b/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.yaml
new file mode 100644
index 0000000000000..f4e2abae1a30d
--- /dev/null
+++ b/ci-operator/step-registry/openshift/upgrade/azure/openshift-upgrade-azure-workflow.yaml
@@ -0,0 +1,16 @@
+workflow:
+  as: openshift-upgrade-azure
+  steps:
+    pre:
+    - chain: ipi-azure-pre
+    test:
+    - ref: openshift-e2e-test
+    post:
+    - chain: ipi-azure-post
+    dependencies:
+      OPENSHIFT_INSTALL_RELEASE_IMAGE_OVERRIDE: "release:initial"
+    env:
+      TEST_COMMAND: "run-upgrade"
+      TEST_SUITE: "all"
+  documentation: |-
+    The Openshift E2E Azure workflow executes the upgrade end-to-end test suite on Azure with a default cluster configuration, exercising an upgrade during the process.