diff --git a/templates/addons/windows/kube-proxy-windows.yaml b/templates/addons/windows/kube-proxy-windows.yaml
index bd087b992d7..6c16dc7e02f 100644
--- a/templates/addons/windows/kube-proxy-windows.yaml
+++ b/templates/addons/windows/kube-proxy-windows.yaml
@@ -5,6 +5,11 @@ data:
     mkdir -force /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount
     mkdir -force /host/k/kube-proxy
 
+    if($env:USE_CI_VERSION && Test-Path -Path "/host/k/kube-proxy.exe")
+    {
+      cp -force /host/k/kube-proxy.exe /k/kube-proxy/kube-proxy.exe
+    }
+
     cp -force /k/kube-proxy/* /host/k/kube-proxy
     cp -force /var/lib/kube-proxy/* /host/var/lib/kube-proxy
     cp -force /var/run/secrets/kubernetes.io/serviceaccount/* /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount #FIXME?
@@ -57,7 +62,9 @@ spec:
           valueFrom:
             fieldRef:
               fieldPath: status.podIP
-        image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION}-nanoserver
+        - name: USE_CI_VERSION
+          value: "${USE_CI_VERSION:false}"
+        image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION/+/_}-nanoserver
         name: kube-proxy
         volumeMounts:
         - name: wins
diff --git a/templates/test/ci/cluster-template-prow-ci-version-windows.yaml b/templates/test/ci/cluster-template-prow-ci-version-windows.yaml
index ae402d2c66a..ff0322a9334 100644
--- a/templates/test/ci/cluster-template-prow-ci-version-windows.yaml
+++ b/templates/test/ci/cluster-template-prow-ci-version-windows.yaml
@@ -412,8 +412,8 @@ spec:
         marketplace:
           offer: capi-windows
           publisher: cncf-upstream
-          sku: k8s-1dot18dot13-windows-2019
-          version: 2020.12.11
+          sku: k8s-1dot18dot19-windows-2019
+          version: 2021.05.17
       osDisk:
         diskSizeGB: 128
         managedDisk:
@@ -466,10 +466,14 @@ spec:
             }
           }
 
+          # We are using a VHD that maps to v1.18.19 so the kubeproxy image is already pulled. (pull it just in case)
+          # Tag it to the ci version.  The image knows how to use the copy locally.
+          docker pull sigwindowstools/kube-proxy:v1.18.19-nanoserver
+          docker tag sigwindowstools/kube-proxy:v1.18.19-nanoserver "sigwindowstools/kube-proxy:${CI_VERSION/+/_}-nanoserver"
+
           kubeadm.exe version -o=short
           kubectl.exe version --client=true --short=true
           kubelet.exe --version
-          #kubeproxy.exe --version
         path: C:/replace-k8s-binaries.ps1
         permissions: "0744"
       joinConfiguration:
@@ -1284,6 +1288,11 @@ data:
         mkdir -force /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount
         mkdir -force /host/k/kube-proxy
 
+        if($env:USE_CI_VERSION && Test-Path -Path "/host/k/kube-proxy.exe")
+        {
+          cp -force /host/k/kube-proxy.exe /k/kube-proxy/kube-proxy.exe
+        }
+
         cp -force /k/kube-proxy/* /host/k/kube-proxy
         cp -force /var/lib/kube-proxy/* /host/var/lib/kube-proxy
         cp -force /var/run/secrets/kubernetes.io/serviceaccount/* /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount #FIXME?
@@ -1336,7 +1345,9 @@ data:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
-            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION}-nanoserver
+            - name: USE_CI_VERSION
+              value: "${USE_CI_VERSION:false}"
+            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION/+/_}-nanoserver
             name: kube-proxy
             volumeMounts:
             - name: wins
diff --git a/templates/test/ci/cluster-template-prow-machine-pool-windows.yaml b/templates/test/ci/cluster-template-prow-machine-pool-windows.yaml
index 8a8498ad416..50be005ab61 100644
--- a/templates/test/ci/cluster-template-prow-machine-pool-windows.yaml
+++ b/templates/test/ci/cluster-template-prow-machine-pool-windows.yaml
@@ -1106,6 +1106,11 @@ data:
         mkdir -force /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount
         mkdir -force /host/k/kube-proxy
 
+        if($env:USE_CI_VERSION && Test-Path -Path "/host/k/kube-proxy.exe")
+        {
+          cp -force /host/k/kube-proxy.exe /k/kube-proxy/kube-proxy.exe
+        }
+
         cp -force /k/kube-proxy/* /host/k/kube-proxy
         cp -force /var/lib/kube-proxy/* /host/var/lib/kube-proxy
         cp -force /var/run/secrets/kubernetes.io/serviceaccount/* /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount #FIXME?
@@ -1158,7 +1163,9 @@ data:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
-            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION}-nanoserver
+            - name: USE_CI_VERSION
+              value: "${USE_CI_VERSION:false}"
+            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION/+/_}-nanoserver
             name: kube-proxy
             volumeMounts:
             - name: wins
diff --git a/templates/test/ci/cluster-template-prow-windows.yaml b/templates/test/ci/cluster-template-prow-windows.yaml
index 8b643e43d66..64af2f31b79 100644
--- a/templates/test/ci/cluster-template-prow-windows.yaml
+++ b/templates/test/ci/cluster-template-prow-windows.yaml
@@ -1114,6 +1114,11 @@ data:
         mkdir -force /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount
         mkdir -force /host/k/kube-proxy
 
+        if($env:USE_CI_VERSION && Test-Path -Path "/host/k/kube-proxy.exe")
+        {
+          cp -force /host/k/kube-proxy.exe /k/kube-proxy/kube-proxy.exe
+        }
+
         cp -force /k/kube-proxy/* /host/k/kube-proxy
         cp -force /var/lib/kube-proxy/* /host/var/lib/kube-proxy
         cp -force /var/run/secrets/kubernetes.io/serviceaccount/* /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount #FIXME?
@@ -1166,7 +1171,9 @@ data:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
-            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION}-nanoserver
+            - name: USE_CI_VERSION
+              value: "${USE_CI_VERSION:false}"
+            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION/+/_}-nanoserver
             name: kube-proxy
             volumeMounts:
             - name: wins
diff --git a/templates/test/ci/prow-ci-version-windows/patches/machine-deployment-ci-version.yaml b/templates/test/ci/prow-ci-version-windows/patches/machine-deployment-ci-version.yaml
index a449435b640..7b6010dc8dc 100644
--- a/templates/test/ci/prow-ci-version-windows/patches/machine-deployment-ci-version.yaml
+++ b/templates/test/ci/prow-ci-version-windows/patches/machine-deployment-ci-version.yaml
@@ -15,11 +15,15 @@
           curl.exe --retry 10 --retry-delay 5 "$$ci_url/$$binary.exe" --output "c:/k/$$binary.exe"
         }
       }
-      
+
+      # We are using a VHD that maps to v1.18.19 so the kubeproxy image is already pulled. (pull it just in case)
+      # Tag it to the ci version.  The image knows how to use the copy locally.
+      docker pull sigwindowstools/kube-proxy:v1.18.19-nanoserver
+      docker tag sigwindowstools/kube-proxy:v1.18.19-nanoserver "sigwindowstools/kube-proxy:${CI_VERSION/+/_}-nanoserver"
+
       kubeadm.exe version -o=short
       kubectl.exe version --client=true --short=true
       kubelet.exe --version
-      #kubeproxy.exe --version
     path: C:/replace-k8s-binaries.ps1
     permissions: "0744"
 - op: add
diff --git a/templates/test/ci/prow-ci-version-windows/patches/windows-image-update.yaml b/templates/test/ci/prow-ci-version-windows/patches/windows-image-update.yaml
index 559f80512b9..79d7502076f 100644
--- a/templates/test/ci/prow-ci-version-windows/patches/windows-image-update.yaml
+++ b/templates/test/ci/prow-ci-version-windows/patches/windows-image-update.yaml
@@ -12,5 +12,5 @@ spec:
         marketplace:
           publisher: cncf-upstream
           offer: capi-windows
-          sku: k8s-1dot18dot13-windows-2019
-          version: "2020.12.11"
\ No newline at end of file
+          sku: k8s-1dot18dot19-windows-2019
+          version: "2021.05.17"
\ No newline at end of file
diff --git a/templates/test/dev/cluster-template-custom-builds-windows.yaml b/templates/test/dev/cluster-template-custom-builds-windows.yaml
index a27440bec42..f2efdd69870 100644
--- a/templates/test/dev/cluster-template-custom-builds-windows.yaml
+++ b/templates/test/dev/cluster-template-custom-builds-windows.yaml
@@ -334,8 +334,8 @@ spec:
         marketplace:
           offer: capi-windows
           publisher: cncf-upstream
-          sku: k8s-1dot18dot13-windows-2019
-          version: 2020.12.11
+          sku: k8s-1dot18dot19-windows-2019
+          version: 2021.05.17
       osDisk:
         diskSizeGB: 128
         managedDisk:
@@ -384,10 +384,14 @@ spec:
             curl.exe --retry 10 --retry-delay 5 "$$ci_url/$$binary.exe" --output "c:/k/$$binary.exe"
           }
 
+          # We are using a VHD that maps to v1.18.19 so the kubeproxy image is already pulled. (pull it just in case)
+          # Tag it to the ci version.  The image knows how to use the copy locally.
+          docker pull sigwindowstools/kube-proxy:v1.18.19-nanoserver
+          docker tag sigwindowstools/kube-proxy:v1.18.19-nanoserver "sigwindowstools/kube-proxy:${KUBE_GIT_VERSION/+/_}-nanoserver"
+
           kubeadm.exe version -o=short
           kubectl.exe version --client=true --short=true
           kubelet.exe --version
-          #kubeproxy.exe --version
         path: C:/replace-k8s-binaries.ps1
         permissions: "0744"
       joinConfiguration:
@@ -1202,6 +1206,11 @@ data:
         mkdir -force /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount
         mkdir -force /host/k/kube-proxy
 
+        if($env:USE_CI_VERSION && Test-Path -Path "/host/k/kube-proxy.exe")
+        {
+          cp -force /host/k/kube-proxy.exe /k/kube-proxy/kube-proxy.exe
+        }
+
         cp -force /k/kube-proxy/* /host/k/kube-proxy
         cp -force /var/lib/kube-proxy/* /host/var/lib/kube-proxy
         cp -force /var/run/secrets/kubernetes.io/serviceaccount/* /host/var/lib/kube-proxy/var/run/secrets/kubernetes.io/serviceaccount #FIXME?
@@ -1254,7 +1263,9 @@ data:
               valueFrom:
                 fieldRef:
                   fieldPath: status.podIP
-            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION}-nanoserver
+            - name: USE_CI_VERSION
+              value: "${USE_CI_VERSION:false}"
+            image: sigwindowstools/kube-proxy:${KUBERNETES_VERSION/+/_}-nanoserver
             name: kube-proxy
             volumeMounts:
             - name: wins
diff --git a/templates/test/dev/custom-builds-windows/patches/custom-builds-windows.yaml b/templates/test/dev/custom-builds-windows/patches/custom-builds-windows.yaml
index 03e7d0c4f41..27a5a634eee 100644
--- a/templates/test/dev/custom-builds-windows/patches/custom-builds-windows.yaml
+++ b/templates/test/dev/custom-builds-windows/patches/custom-builds-windows.yaml
@@ -12,10 +12,14 @@
         curl.exe --retry 10 --retry-delay 5 "$$ci_url/$$binary.exe" --output "c:/k/$$binary.exe"
       }
 
+      # We are using a VHD that maps to v1.18.19 so the kubeproxy image is already pulled. (pull it just in case)
+      # Tag it to the ci version.  The image knows how to use the copy locally.
+      docker pull sigwindowstools/kube-proxy:v1.18.19-nanoserver
+      docker tag sigwindowstools/kube-proxy:v1.18.19-nanoserver "sigwindowstools/kube-proxy:${KUBE_GIT_VERSION/+/_}-nanoserver"
+
       kubeadm.exe version -o=short
       kubectl.exe version --client=true --short=true
       kubelet.exe --version
-      #kubeproxy.exe --version
     path: C:/replace-k8s-binaries.ps1
     permissions: "0744"
 - op: add
diff --git a/templates/test/dev/custom-builds-windows/patches/windows-image-update.yaml b/templates/test/dev/custom-builds-windows/patches/windows-image-update.yaml
index 559f80512b9..79d7502076f 100644
--- a/templates/test/dev/custom-builds-windows/patches/windows-image-update.yaml
+++ b/templates/test/dev/custom-builds-windows/patches/windows-image-update.yaml
@@ -12,5 +12,5 @@ spec:
         marketplace:
           publisher: cncf-upstream
           offer: capi-windows
-          sku: k8s-1dot18dot13-windows-2019
-          version: "2020.12.11"
\ No newline at end of file
+          sku: k8s-1dot18dot19-windows-2019
+          version: "2021.05.17"
\ No newline at end of file
diff --git a/test/e2e/conformance_test.go b/test/e2e/conformance_test.go
index 40bebeb74a7..b88cf87a2b8 100644
--- a/test/e2e/conformance_test.go
+++ b/test/e2e/conformance_test.go
@@ -99,6 +99,8 @@ var _ = Describe("Conformance Tests", func() {
 
 			if isWindows(kubetestConfigFilePath) {
 				flavor = flavor + "-windows"
+				// tell windows kube-proxy to use the version supplied via CI
+				Expect(os.Setenv("USE_CI_VERSION", "true")).To(Succeed())
 			}
 		}