@@ -34,6 +34,8 @@ func TestCopyFromContainerPathDoesNotExist(t *testing.T) {

 	assert.Check(t, is.ErrorContains(err, "Could not find the file /dne in container "+cid))

 }

+// TestCopyFromContainerPathIsNotDir tests that an error is returned when

+// trying to create a directory on a path that's a file.

 func TestCopyFromContainerPathIsNotDir(t *testing.T) {

 	skip.If(t, testEnv.UsingSnapshotter(), "FIXME: https://github.com/moby/moby/issues/47107")

 	ctx := setupTest(t)

@@ -41,14 +43,29 @@ func TestCopyFromContainerPathIsNotDir(t *testing.T) {

 	apiClient := testEnv.APIClient()

 	cid := container.Create(ctx, t, apiClient)

-	path := "/etc/passwd/"

-	expected := "not a directory"

+	// Pick a path that already exists as a file; on Linux "/etc/passwd"

+	// is expected to be there, so we pick that for convenience.

+	existingFile := "/etc/passwd/"

+	expected := []string{"not a directory"}

 	if testEnv.DaemonInfo.OSType == "windows" {

-		path = "c:/windows/system32/drivers/etc/hosts/"

-		expected = "The filename, directory name, or volume label syntax is incorrect."

+		existingFile = "c:/windows/system32/drivers/etc/hosts/"

+

+		// Depending on the version of Windows, this produces a "ERROR_INVALID_NAME" (Windows < 2025),

+		// or a "ERROR_DIRECTORY" (Windows 2025); https://learn.microsoft.com/en-us/windows/win32/debug/system-error-codes--0-499-

+		expected = []string{

+			"The directory name is invalid.",                                     // ERROR_DIRECTORY

+			"The filename, directory name, or volume label syntax is incorrect.", // ERROR_INVALID_NAME

+		}

+	}

+	_, _, err := apiClient.CopyFromContainer(ctx, cid, existingFile)

+	var found bool

+	for _, expErr := range expected {

+		if err != nil && strings.Contains(err.Error(), expErr) {

+			found = true

+			break

+		}

 	}

-	_, _, err := apiClient.CopyFromContainer(ctx, cid, path)

-	assert.ErrorContains(t, err, expected)

+	assert.Check(t, found, "Expected error to be one of %v, but got %v", expected, err)

 }

 func TestCopyToContainerPathDoesNotExist(t *testing.T) {