diff --git a/test/e2e/clusterctl_upgrade_test.go b/test/e2e/clusterctl_upgrade_test.go
index 652d35b07510..ec7823c50a29 100644
--- a/test/e2e/clusterctl_upgrade_test.go
+++ b/test/e2e/clusterctl_upgrade_test.go
@@ -26,35 +26,37 @@ import (
 	"sigs.k8s.io/cluster-api/test/framework"
 )
 
-var _ = Describe("When testing clusterctl upgrades (v0.4=>current)", func() {
-	ClusterctlUpgradeSpec(ctx, func() ClusterctlUpgradeSpecInput {
-		return ClusterctlUpgradeSpecInput{
-			E2EConfig:                 e2eConfig,
-			ClusterctlConfigPath:      clusterctlConfigPath,
-			BootstrapClusterProxy:     bootstrapClusterProxy,
-			ArtifactFolder:            artifactFolder,
-			SkipCleanup:               skipCleanup,
-			InfrastructureProvider:    pointer.String("docker"),
-			InitWithBinary:            "https://github.com/kubernetes-sigs/cluster-api/releases/download/v0.4.8/clusterctl-{OS}-{ARCH}",
-			InitWithProvidersContract: "v1alpha4",
-			// NOTE: If this version is changed here the image and SHA must also be updated in all DockerMachineTemplates in `test/data/infrastructure-docker/v0.4/bases.
-			InitWithKubernetesVersion: "v1.23.17",
-			WorkloadKubernetesVersion: "v1.23.17",
-			MgmtFlavor:                "topology",
-			WorkloadFlavor:            "",
-			// This check ensures that ownerReference apiVersions are updated for all types after the upgrade.
-			PostUpgrade: func(proxy framework.ClusterProxy, namespace, clusterName string) {
-				framework.AssertOwnerReferences(namespace, proxy.GetKubeconfigPath(),
-					framework.CoreOwnerReferenceAssertion,
-					framework.ExpOwnerReferenceAssertions,
-					framework.DockerInfraOwnerReferenceAssertions,
-					framework.KubeadmBootstrapOwnerReferenceAssertions,
-					framework.KubeadmControlPlaneOwnerReferenceAssertions,
-					framework.KubernetesReferenceAssertions,
-				)
-			},
-		}
-	})
+var _ = FDescribe("When testing clusterctl upgrades (v0.4=>current)", func() {
+	for i := 0; i < 10; i++ {
+		ClusterctlUpgradeSpec(ctx, func() ClusterctlUpgradeSpecInput {
+			return ClusterctlUpgradeSpecInput{
+				E2EConfig:                 e2eConfig,
+				ClusterctlConfigPath:      clusterctlConfigPath,
+				BootstrapClusterProxy:     bootstrapClusterProxy,
+				ArtifactFolder:            artifactFolder,
+				SkipCleanup:               skipCleanup,
+				InfrastructureProvider:    pointer.String("docker"),
+				InitWithBinary:            "https://github.com/kubernetes-sigs/cluster-api/releases/download/v0.4.8/clusterctl-{OS}-{ARCH}",
+				InitWithProvidersContract: "v1alpha4",
+				// NOTE: If this version is changed here the image and SHA must also be updated in all DockerMachineTemplates in `test/data/infrastructure-docker/v0.4/bases.
+				InitWithKubernetesVersion: "v1.23.17",
+				WorkloadKubernetesVersion: "v1.23.17",
+				MgmtFlavor:                "topology",
+				WorkloadFlavor:            "",
+				// This check ensures that ownerReference apiVersions are updated for all types after the upgrade.
+				PostUpgrade: func(proxy framework.ClusterProxy, namespace, clusterName string) {
+					framework.AssertOwnerReferences(namespace, proxy.GetKubeconfigPath(),
+						framework.CoreOwnerReferenceAssertion,
+						framework.ExpOwnerReferenceAssertions,
+						framework.DockerInfraOwnerReferenceAssertions,
+						framework.KubeadmBootstrapOwnerReferenceAssertions,
+						framework.KubeadmControlPlaneOwnerReferenceAssertions,
+						framework.KubernetesReferenceAssertions,
+					)
+				},
+			}
+		})
+	}
 })
 
 var _ = Describe("When testing clusterctl upgrades (v1.0=>current)", func() {
diff --git a/test/framework/alltypes_helpers.go b/test/framework/alltypes_helpers.go
index d5ce38bb5f5c..681271b5922e 100644
--- a/test/framework/alltypes_helpers.go
+++ b/test/framework/alltypes_helpers.go
@@ -88,8 +88,12 @@ func getClusterAPITypes(ctx context.Context, lister Lister) []metav1.TypeMeta {
 	Eventually(func() error {
 		return lister.List(ctx, crdList, capiProviderOptions()...)
 	}, retryableOperationTimeout, retryableOperationInterval).Should(Succeed(), "failed to list CRDs for CAPI providers")
+	crdListCertManager := &apiextensionsv1.CustomResourceDefinitionList{}
+	Eventually(func() error {
+		return lister.List(ctx, crdListCertManager, client.MatchingLabels{"app": "cert-manager"})
+	}, retryableOperationTimeout, retryableOperationInterval).Should(Succeed(), "failed to list CRDs for CAPI providers")
 
-	for _, crd := range crdList.Items {
+	for _, crd := range append(crdList.Items, crdListCertManager.Items...) {
 		for _, version := range crd.Spec.Versions {
 			if !version.Storage {
 				continue
@@ -104,6 +108,7 @@ func getClusterAPITypes(ctx context.Context, lister Lister) []metav1.TypeMeta {
 			})
 		}
 	}
+
 	return discoveredTypes
 }
 
diff --git a/test/framework/clusterctl/clusterctl_helpers.go b/test/framework/clusterctl/clusterctl_helpers.go
index d970a5e3f229..c9cbd8ff4628 100644
--- a/test/framework/clusterctl/clusterctl_helpers.go
+++ b/test/framework/clusterctl/clusterctl_helpers.go
@@ -18,6 +18,7 @@ package clusterctl
 
 import (
 	"context"
+	"fmt"
 	"os"
 	"path/filepath"
 	"time"
@@ -128,6 +129,36 @@ func InitManagementClusterAndWatchControllerLogs(ctx context.Context, input Init
 			})
 		}
 	}
+
+	certManagerDeployments := framework.GetCertManagerDeployments(ctx, framework.GetControllerDeploymentsInput{
+		Lister: client,
+	})
+	for _, deployment := range certManagerDeployments {
+		fmt.Printf("Pod status of %q:\n%++v\n", deployment.Namespace, deployment.Name, deployment.Status)
+		// framework.WaitForDeploymentsAvailable(ctx, framework.WaitForDeploymentsAvailableInput{
+		// 	Getter:     client,
+		// 	Deployment: deployment,
+		// }, intervals...)
+
+		// Start streaming logs from all controller providers
+		framework.WatchDeploymentLogsByName(ctx, framework.WatchDeploymentLogsByNameInput{
+			GetLister:  client,
+			Cache:      input.ClusterProxy.GetCache(ctx),
+			ClientSet:  input.ClusterProxy.GetClientSet(),
+			Deployment: deployment,
+			LogPath:    filepath.Join(input.LogFolder, "logs", deployment.GetNamespace()),
+		})
+
+		// if !input.DisableMetricsCollection {
+		// 	framework.WatchPodMetrics(ctx, framework.WatchPodMetricsInput{
+		// 		GetLister:   client,
+		// 		ClientSet:   input.ClusterProxy.GetClientSet(),
+		// 		Deployment:  deployment,
+		// 		MetricsPath: filepath.Join(input.LogFolder, "metrics", deployment.GetNamespace()),
+		// 	})
+		// }
+	}
+
 }
 
 // UpgradeManagementClusterAndWaitInput is the input type for UpgradeManagementClusterAndWait.
diff --git a/test/framework/controller_helpers.go b/test/framework/controller_helpers.go
index a4327a37264d..28558ddb5a87 100644
--- a/test/framework/controller_helpers.go
+++ b/test/framework/controller_helpers.go
@@ -21,6 +21,7 @@ import (
 
 	. "github.com/onsi/gomega"
 	appsv1 "k8s.io/api/apps/v1"
+	"sigs.k8s.io/controller-runtime/pkg/client"
 )
 
 // GetControllerDeploymentsInput is the input for GetControllerDeployments.
@@ -46,6 +47,23 @@ func GetControllerDeployments(ctx context.Context, input GetControllerDeployment
 	return deployments
 }
 
+// GetControllerDeployments returns all the deployment for the cluster API controllers existing in a management cluster.
+func GetCertManagerDeployments(ctx context.Context, input GetControllerDeploymentsInput) []*appsv1.Deployment {
+	deploymentList := &appsv1.DeploymentList{}
+	Eventually(func() error {
+		return input.Lister.List(ctx, deploymentList, client.InNamespace("cert-manager"))
+	}, retryableOperationTimeout, retryableOperationInterval).Should(Succeed(), "Failed to list deployments for the cluster API controllers")
+
+	deployments := make([]*appsv1.Deployment, 0, len(deploymentList.Items))
+	for i := range deploymentList.Items {
+		d := &deploymentList.Items[i]
+		if !skipDeployment(d, input.ExcludeNamespaces) {
+			deployments = append(deployments, d)
+		}
+	}
+	return deployments
+}
+
 func skipDeployment(d *appsv1.Deployment, excludeNamespaces []string) bool {
 	if !d.DeletionTimestamp.IsZero() {
 		return true