diff --git a/hack/util.sh b/hack/util.sh
index 2daf8a4f2eb..37197bcbbeb 100755
--- a/hack/util.sh
+++ b/hack/util.sh
@@ -38,3 +38,42 @@ capz::util::should_build_kubernetes() {
     fi
     echo "false"
 }
+
+capz::util::resolve_k8s_versions() {
+    if [ -n "${KUBERNETES_VERSION:-}" ]; then
+        k8s::resolveVersion "KUBERNETES_VERSION" "$KUBERNETES_VERSION"
+        export KUBERNETES_VERSION=$resolveVersion
+    fi
+
+    if [ -n "${KUBERNETES_VERSION_UPGRADE_TO:-}" ]; then
+        k8s::resolveVersion "KUBERNETES_VERSION_UPGRADE_TO" "$KUBERNETES_VERSION_UPGRADE_TO"
+        export KUBERNETES_VERSION_UPGRADE_TO=$resolveVersion
+    fi
+
+    if [ -n "${KUBERNETES_VERSION_UPGRADE_FROM:-}" ]; then
+        k8s::resolveVersion "KUBERNETES_VERSION_UPGRADE_FROM" "$KUBERNETES_VERSION_UPGRADE_FROM"
+        export KUBERNETES_VERSION_UPGRADE_FROM=$resolveVersion
+    fi
+}
+
+# k8s::resolveVersion resolves kubernetes version labels (e.g. latest) to the corresponding version numbers.
+# The result will be available in the resolveVersion variable which is accessible from the caller.
+#
+# NOTE: this doesn't guarantee a reference VM image will be available for this version.
+# TODO: check the capi offer for the image.
+k8s::resolveVersion() {
+    local variableName=$1
+    local version=$2
+
+    resolveVersion=$version
+    if [[ "$version" =~ ^v ]]; then
+        return
+    fi
+
+    if [[ "$version" =~ ^ci/ ]]; then
+        resolveVersion=$(curl -LsS "http://dl.k8s.io/ci/${version#ci/}.txt")
+    else
+        resolveVersion=$(curl -LsS "http://dl.k8s.io/release/${version}.txt")
+    fi
+    echo "+ $variableName=\"$version\" resolved to \"$resolveVersion\""
+}
\ No newline at end of file
diff --git a/scripts/ci-e2e.sh b/scripts/ci-e2e.sh
index 95dc20b8d99..3096c26667a 100755
--- a/scripts/ci-e2e.sh
+++ b/scripts/ci-e2e.sh
@@ -72,6 +72,8 @@ export AZURE_CONTROL_PLANE_MACHINE_TYPE="${AZURE_CONTROL_PLANE_MACHINE_TYPE:-"St
 export AZURE_NODE_MACHINE_TYPE="${AZURE_NODE_MACHINE_TYPE:-"Standard_D2s_v3"}"
 export KIND_EXPERIMENTAL_DOCKER_NETWORK="bridge"
 
+capz::util::resolve_k8s_versions
+
 # Generate SSH key.
 AZURE_SSH_PUBLIC_KEY_FILE=${AZURE_SSH_PUBLIC_KEY_FILE:-""}
 if [ -z "${AZURE_SSH_PUBLIC_KEY_FILE}" ]; then
diff --git a/test/e2e/capi_test.go b/test/e2e/capi_test.go
index 1f9334c758a..c377894e222 100644
--- a/test/e2e/capi_test.go
+++ b/test/e2e/capi_test.go
@@ -23,6 +23,7 @@ import (
 	"fmt"
 	"os"
 
+	"github.com/blang/semver"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
 	corev1 "k8s.io/api/core/v1"
@@ -228,6 +229,12 @@ var _ = Describe("Running the Cluster API E2E tests", func() {
 })
 
 var _ = Describe("When upgrading a workload cluster and testing K8S conformance [Conformance] [K8s-Upgrade]", func() {
+	// Opt into Windows for versions greater than or equal to 1.22
+	if semver.MustParse(e2eConfig.Variables[capi_e2e.KubernetesVersionUpgradeFrom]).GTE(semver.MustParse("v1.22.0")) {
+		Expect(os.Setenv("WINDOWS_WORKER_MACHINE_COUNT", "2")).To(Succeed())
+		Expect(os.Setenv("K8S_FEATURE_GATES", "WindowsHostProcessContainers=true")).To(Succeed())
+	}
+
 	capi_e2e.ClusterUpgradeConformanceSpec(context.TODO(), func() capi_e2e.ClusterUpgradeConformanceSpecInput {
 		return capi_e2e.ClusterUpgradeConformanceSpecInput{
 			E2EConfig:             e2eConfig,