diff --git a/test/e2e/windows/BUILD b/test/e2e/windows/BUILD
index 349816bbbb0..24852689975 100644
--- a/test/e2e/windows/BUILD
+++ b/test/e2e/windows/BUILD
@@ -11,6 +11,7 @@ go_library(
         "hybrid_network.go",
         "memory_limits.go",
         "networking.go",
+        "security_context.go",
         "service.go",
         "volumes.go",
     ],
@@ -37,6 +38,7 @@ go_library(
         "//test/e2e/framework/node:go_default_library",
         "//test/e2e/framework/pod:go_default_library",
         "//test/e2e/framework/service:go_default_library",
+        "//test/utils:go_default_library",
         "//test/utils/image:go_default_library",
         "//vendor/github.com/onsi/ginkgo:go_default_library",
         "//vendor/github.com/onsi/gomega:go_default_library",
diff --git a/test/e2e/windows/security_context.go b/test/e2e/windows/security_context.go
new file mode 100644
index 00000000000..c27da490e55
--- /dev/null
+++ b/test/e2e/windows/security_context.go
@@ -0,0 +1,106 @@
+/*
+Copyright 2019 The Kubernetes Authors.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+package windows
+
+import (
+	v1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/util/uuid"
+	"k8s.io/kubernetes/test/e2e/framework"
+	e2elog "k8s.io/kubernetes/test/e2e/framework/log"
+	testutils "k8s.io/kubernetes/test/utils"
+	imageutils "k8s.io/kubernetes/test/utils/image"
+
+	"github.com/onsi/ginkgo"
+)
+
+const runAsUserNameContainerName = "run-as-username-container"
+
+var _ = SIGDescribe("[Feature:Windows] SecurityContext RunAsUserName", func() {
+	f := framework.NewDefaultFramework("windows-run-as-username")
+
+	ginkgo.It("should be able create pods and run containers with a given username", func() {
+		ginkgo.By("Creating 2 pods: 1 with the default user, and one with a custom one.")
+		podDefault := runAsUserNamePod(nil)
+		f.TestContainerOutput("check default user", podDefault, 0, []string{"ContainerUser"})
+
+		podUserName := runAsUserNamePod(toPtr("ContainerAdministrator"))
+		f.TestContainerOutput("check set user", podUserName, 0, []string{"ContainerAdministrator"})
+	})
+
+	ginkgo.It("should not be able to create pods with unknown usernames", func() {
+		ginkgo.By("Creating a pod with an invalid username")
+		podInvalid := f.PodClient().Create(runAsUserNamePod(toPtr("FooLish")))
+
+		e2elog.Logf("Waiting for pod %s to enter the error state.", podInvalid.Name)
+		framework.ExpectNoError(f.WaitForPodTerminated(podInvalid.Name, ""))
+
+		podInvalid, _ = f.PodClient().Get(podInvalid.Name, metav1.GetOptions{})
+		podTerminatedReason := testutils.TerminatedContainers(podInvalid)[runAsUserNameContainerName]
+		if "ContainerCannotRun" != podTerminatedReason {
+			e2elog.Failf("The container terminated reason was supposed to be: 'ContainerCannotRun', not: '%q'", podTerminatedReason)
+		}
+	})
+
+	ginkgo.It("should override SecurityContext username if set", func() {
+		ginkgo.By("Creating a pod with 2 containers with different username configurations.")
+
+		pod := runAsUserNamePod(toPtr("ContainerAdministrator"))
+		pod.Spec.Containers[0].SecurityContext.WindowsOptions.RunAsUserName = toPtr("ContainerUser")
+		pod.Spec.Containers = append(pod.Spec.Containers, v1.Container{
+			Name:    "run-as-username-new-container",
+			Image:   imageutils.GetE2EImage(imageutils.NonRoot),
+			Command: []string{"cmd", "/S", "/C", "echo %username%"},
+		})
+
+		f.TestContainerOutput("check overridden username", pod, 0, []string{"ContainerUser"})
+		f.TestContainerOutput("check pod SecurityContext username", pod, 1, []string{"ContainerAdministrator"})
+	})
+})
+
+func runAsUserNamePod(username *string) *v1.Pod {
+	podName := "run-as-username-" + string(uuid.NewUUID())
+	return &v1.Pod{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: podName,
+		},
+		Spec: v1.PodSpec{
+			Containers: []v1.Container{
+				{
+					Name:    runAsUserNameContainerName,
+					Image:   imageutils.GetE2EImage(imageutils.NonRoot),
+					Command: []string{"cmd", "/S", "/C", "echo %username%"},
+					SecurityContext: &v1.SecurityContext{
+						WindowsOptions: &v1.WindowsSecurityContextOptions{
+							RunAsUserName: username,
+						},
+					},
+				},
+			},
+			SecurityContext: &v1.PodSecurityContext{
+				WindowsOptions: &v1.WindowsSecurityContextOptions{
+					RunAsUserName: username,
+				},
+			},
+			RestartPolicy: v1.RestartPolicyNever,
+		},
+	}
+}
+
+func toPtr(s string) *string {
+	return &s
+}