diff --git a/test/e2e/data/e2e_conf.yaml b/test/e2e/data/e2e_conf.yaml
index c0a3f68efa..ec208285d0 100644
--- a/test/e2e/data/e2e_conf.yaml
+++ b/test/e2e/data/e2e_conf.yaml
@@ -27,6 +27,15 @@ providers:
     files:
     - sourcePath: "../data/shared/capi/metadata.yaml"
   # For clusterctl upgrade test
+  - name: v1.11.0
+    value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.11.0/core-components.yaml"
+    type: "url"
+    contract: v1beta2
+    replacements:
+    - old: --metrics-addr=127.0.0.1:8080
+      new: --metrics-addr=:8080
+    files:
+    - sourcePath: "../data/shared/capi/metadata.yaml"
   - name: "{go://sigs.k8s.io/cluster-api@v1.10}"
     value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/{go://sigs.k8s.io/cluster-api@v1.10}/core-components.yaml"
     type: url
@@ -51,6 +60,15 @@ providers:
     files:
     - sourcePath: "../data/shared/capi/metadata.yaml"
   # For clusterctl upgrade test
+  - name: v1.11.0
+    value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.11.0/bootstrap-components.yaml"
+    type: "url"
+    contract: v1beta2
+    replacements:
+    - old: --metrics-addr=127.0.0.1:8080
+      new: --metrics-addr=:8080
+    files:
+    - sourcePath: "../data/shared/capi/metadata.yaml"
   - name: "{go://sigs.k8s.io/cluster-api@v1.10}"
     value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/{go://sigs.k8s.io/cluster-api@v1.10}/bootstrap-components.yaml"
     type: url
@@ -75,6 +93,15 @@ providers:
     files:
     - sourcePath: "../data/shared/capi/metadata.yaml"
   # For clusterctl upgrade test
+  - name: v1.11.0
+    value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/v1.11.0/control-plane-components.yaml"
+    type: "url"
+    contract: v1beta2
+    replacements:
+    - old: --metrics-addr=127.0.0.1:8080
+      new: --metrics-addr=:8080
+    files:
+    - sourcePath: "../data/shared/capi/metadata.yaml"
   - name: "{go://sigs.k8s.io/cluster-api@v1.10}"
     value: "https://github.com/kubernetes-sigs/cluster-api/releases/download/{go://sigs.k8s.io/cluster-api@v1.10}/control-plane-components.yaml"
     type: url
@@ -119,6 +146,21 @@ providers:
       new: "--v=4"
     - old: "--leader-elect"
       new: "--leader-elect=false\n        - --sync-period=1m"
+  # This is only for clusterctl upgrade tests
+  - name: "{go://github.com/kubernetes-sigs/cluster-api-provider-openstack@v0.13}"
+    value: "https://github.com/kubernetes-sigs/cluster-api-provider-openstack/releases/download/{go://github.com/kubernetes-sigs/cluster-api-provider-openstack@v0.13}/infrastructure-components.yaml"
+    type: url
+    contract: v1beta2
+    files:
+    - sourcePath: "../data/shared/provider/metadata.yaml"
+    - sourcePath: "./infrastructure-openstack-no-artifact/cluster-template.yaml"
+    replacements:
+    - old: "imagePullPolicy: Always"
+      new: "imagePullPolicy: IfNotPresent"
+    - old: "--v=2"
+      new: "--v=4"
+    - old: "--leader-elect"
+      new: "--leader-elect=false\n        - --sync-period=1m"
   - name: v0.13.99
     value: ../../../config/default
     # This is the upcoming version.
diff --git a/test/e2e/suites/e2e/clusterctl_upgrade_test.go b/test/e2e/suites/e2e/clusterctl_upgrade_test.go
index 6e1b0ba7e7..2b32fa8385 100644
--- a/test/e2e/suites/e2e/clusterctl_upgrade_test.go
+++ b/test/e2e/suites/e2e/clusterctl_upgrade_test.go
@@ -33,7 +33,9 @@ import (
 var (
 	capoRelease011 string
 	capoRelease012 string
+	capoRelease013 string
 	capiRelease110 string
+	capiRelease111 string
 )
 
 var _ = Describe("When testing clusterctl upgrades for CAPO (v0.11=>current) and ORC (v1.0.2=>current) [clusterctl-upgrade]", func() {
@@ -103,3 +105,37 @@ var _ = Describe("When testing clusterctl upgrades for CAPO (v0.12=>current) and
 		}
 	})
 })
+
+var _ = Describe("When testing clusterctl upgrades for CAPO (v0.13=>current) and ORC (v1.0.2=>current)[clusterctl-upgrade]", func() {
+	BeforeEach(func(ctx context.Context) {
+		setDownloadE2EImageEnvVar()
+		// Note: This gives the version without the 'v' prefix, so we need to add it below.
+		capoRelease013, err = clusterctl.ResolveRelease(ctx, "go://github.com/kubernetes-sigs/cluster-api-provider-openstack@v0.13")
+		Expect(err).ToNot(HaveOccurred(), "failed to get stable release of CAPO")
+		capoRelease013 = "v" + capoRelease013
+		// We need CAPI v1.11 here for clusterctl init with the v1beta2 contract.
+		// This is hard-coded to the .0 release because the test will fail if there are no
+		// newer patch releases to upgrade to.
+		capiRelease111 = "v1.11.0"
+	})
+
+	capi_e2e.ClusterctlUpgradeSpec(context.TODO(), func() capi_e2e.ClusterctlUpgradeSpecInput {
+		return capi_e2e.ClusterctlUpgradeSpecInput{
+			E2EConfig:                         e2eCtx.E2EConfig,
+			ClusterctlConfigPath:              e2eCtx.Environment.ClusterctlConfigPath,
+			BootstrapClusterProxy:             e2eCtx.Environment.BootstrapClusterProxy,
+			ArtifactFolder:                    e2eCtx.Settings.ArtifactFolder,
+			SkipCleanup:                       false,
+			InitWithBinary:                    "https://github.com/kubernetes-sigs/cluster-api/releases/download/" + capiRelease111 + "/clusterctl-{OS}-{ARCH}",
+			InitWithProvidersContract:         "v1beta1",
+			InitWithInfrastructureProviders:   []string{"openstack:" + capoRelease013},
+			InitWithCoreProvider:              "cluster-api:" + capiRelease111,
+			InitWithBootstrapProviders:        []string{"kubeadm:" + capiRelease111},
+			InitWithControlPlaneProviders:     []string{"kubeadm:" + capiRelease111},
+			MgmtFlavor:                        shared.FlavorDefault,
+			WorkloadFlavor:                    shared.FlavorDefault,
+			InitWithKubernetesVersion:         e2eCtx.E2EConfig.MustGetVariable(shared.KubernetesVersion),
+			InitWithRuntimeExtensionProviders: []string{"openstack-resource-controller:v1.0.2"},
+		}
+	})
+})