diff --git a/integration/volume_copy_up_test.go b/integration/volume_copy_up_test.go
index b04a9be37..07023c3b0 100644
--- a/integration/volume_copy_up_test.go
+++ b/integration/volume_copy_up_test.go
@@ -27,6 +27,13 @@ import (
 	exec "golang.org/x/sys/execabs"
 )
 
+const (
+	containerUserName = "ContainerUser"
+	// containerUserSID is a well known SID that is set on the
+	// ContainerUser username inside a Windows container.
+	containerUserSID = "S-1-5-93-2-2"
+)
+
 func TestVolumeCopyUp(t *testing.T) {
 	var (
 		testImage   = GetImage(VolumeCopyUp)
@@ -84,9 +91,6 @@ func TestVolumeCopyUp(t *testing.T) {
 }
 
 func TestVolumeOwnership(t *testing.T) {
-	if goruntime.GOOS == "windows" {
-		t.Skip("Skipped on Windows.")
-	}
 	var (
 		testImage   = GetImage(VolumeOwnership)
 		execTimeout = time.Minute
@@ -101,7 +105,7 @@ func TestVolumeOwnership(t *testing.T) {
 	cnConfig := ContainerConfig(
 		"container",
 		testImage,
-		WithCommand("tail", "-f", "/dev/null"),
+		WithCommand("sleep", "150"),
 	)
 	cn, err := runtimeService.CreateContainer(sb, cnConfig, sbConfig)
 	require.NoError(t, err)
@@ -111,17 +115,32 @@ func TestVolumeOwnership(t *testing.T) {
 
 	// ghcr.io/containerd/volume-ownership:2.1 contains a test_dir
 	// volume, which is owned by nobody:nogroup.
+	// On Windows, the folder is situated in C:\volumes\test_dir and is owned
+	// by ContainerUser (SID: S-1-5-93-2-2). A helper tool get_owner.exe should
+	// exist inside the container that returns the owner in the form of USERNAME:SID.
 	t.Logf("Check ownership of test directory inside container")
-	stdout, stderr, err := runtimeService.ExecSync(cn, []string{
+
+	cmd := []string{
 		"stat", "-c", "%U:%G", "/test_dir",
-	}, execTimeout)
+	}
+	expectedContainerOutput := "nobody:nogroup\n"
+	expectedHostOutput := "nobody:nogroup\n"
+	if goruntime.GOOS == "windows" {
+		cmd = []string{
+			"C:\\bin\\get_owner.exe",
+			"C:\\volumes\\test_dir",
+		}
+		expectedContainerOutput = fmt.Sprintf("%s:%s", containerUserName, containerUserSID)
+		// The username is unknown on the host, but we can still get the SID.
+		expectedHostOutput = containerUserSID
+	}
+	stdout, stderr, err := runtimeService.ExecSync(cn, cmd, execTimeout)
 	require.NoError(t, err)
 	assert.Empty(t, stderr)
-	assert.Equal(t, "nobody:nogroup\n", string(stdout))
+	assert.Equal(t, expectedContainerOutput, string(stdout))
 
 	t.Logf("Check ownership of test directory on the host")
-	hostCmd := fmt.Sprintf("find %s/containers/%s/volumes/* | xargs stat -c %%U:%%G", *criRoot, cn)
-	output, err := exec.Command("sh", "-c", hostCmd).CombinedOutput()
+	output, err := getVolumeHostPathOwnership(*criRoot, cn)
 	require.NoError(t, err)
-	assert.Equal(t, "nobody:nogroup\n", string(output))
+	assert.Equal(t, expectedHostOutput, output)
 }
diff --git a/integration/volume_copy_up_unix_test.go b/integration/volume_copy_up_unix_test.go
new file mode 100644
index 000000000..e191aaa2d
--- /dev/null
+++ b/integration/volume_copy_up_unix_test.go
@@ -0,0 +1,35 @@
+//go:build !windows
+// +build !windows
+
+/*
+   Copyright The containerd 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 integration
+
+import (
+	"fmt"
+
+	exec "golang.org/x/sys/execabs"
+)
+
+func getVolumeHostPathOwnership(criRoot, containerID string) (string, error) {
+	hostCmd := fmt.Sprintf("find %s/containers/%s/volumes/* | xargs stat -c %%U:%%G", criRoot, containerID)
+	output, err := exec.Command("sh", "-c", hostCmd).CombinedOutput()
+	if err != nil {
+		return "", err
+	}
+	return string(output), nil
+}
diff --git a/integration/volume_copy_up_windows_test.go b/integration/volume_copy_up_windows_test.go
new file mode 100644
index 000000000..f879b53aa
--- /dev/null
+++ b/integration/volume_copy_up_windows_test.go
@@ -0,0 +1,59 @@
+//go:build windows
+// +build windows
+
+/*
+   Copyright The containerd 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 integration
+
+import (
+	"fmt"
+	"io/ioutil"
+	"os"
+	"path/filepath"
+
+	"golang.org/x/sys/windows"
+)
+
+func getVolumeHostPathOwnership(criRoot, containerID string) (string, error) {
+	hostPath := fmt.Sprintf("%s/containers/%s/volumes/", criRoot, containerID)
+	if _, err := os.Stat(hostPath); err != nil {
+		return "", err
+	}
+
+	volumes, err := ioutil.ReadDir(hostPath)
+	if err != nil {
+		return "", err
+	}
+
+	if len(volumes) != 1 {
+		return "", fmt.Errorf("expected to find exactly 1 volume (got %d)", len(volumes))
+	}
+
+	secInfo, err := windows.GetNamedSecurityInfo(
+		filepath.Join(hostPath, volumes[0].Name()), windows.SE_FILE_OBJECT,
+		windows.OWNER_SECURITY_INFORMATION|windows.DACL_SECURITY_INFORMATION)
+
+	if err != nil {
+		return "", err
+	}
+
+	sid, _, err := secInfo.Owner()
+	if err != nil {
+		return "", err
+	}
+	return sid.String(), nil
+}