diff --git a/daemon/oci_windows.go b/daemon/oci_windows.go
index be560e5c98..a3ba893827 100644
--- a/daemon/oci_windows.go
+++ b/daemon/oci_windows.go
@@ -56,6 +56,16 @@ func (daemon *Daemon) createSpec(c *container.Container) (*libcontainerd.Spec, e
 		s.Process.Args = escapeArgs(s.Process.Args)
 	}
 	s.Process.Cwd = c.Config.WorkingDir
+	if len(s.Process.Cwd) == 0 {
+		// We default to C:\ to workaround the oddity of the case that the
+		// default directory for cmd running as LocalSystem (or
+		// ContainerAdministrator) is c:\windows\system32. Hence docker run
+		// <image> cmd will by default end in c:\windows\system32, rather
+		// than 'root' (/) on Linux. The oddity is that if you have a dockerfile
+		// which has no WORKDIR and has a COPY file ., . will be interpreted
+		// as c:\. Hence, setting it to default of c:\ makes for consistency.
+		s.Process.Cwd = `C:\`
+	}
 	s.Process.Env = c.CreateDaemonEnvironment(linkedEnv)
 	s.Process.InitialConsoleSize = c.HostConfig.ConsoleSize
 	s.Process.Terminal = c.Config.Tty
diff --git a/integration-cli/docker_cli_build_test.go b/integration-cli/docker_cli_build_test.go
index 137f42f83a..b1347284d6 100644
--- a/integration-cli/docker_cli_build_test.go
+++ b/integration-cli/docker_cli_build_test.go
@@ -2074,8 +2074,18 @@ func (s *DockerSuite) TestBuildRelativeWorkdir(c *check.C) {
 		expected4     string
 		expectedFinal string
 	)
+	// TODO Windows: The expectedFinal needs fixing to match Windows
+	// filepath semantics. However, this is a non-trivial change. @jhowardmsft
+	// Short story - need to make the configuration file platform semantically
+	// consistent, so even if `WORKDIR /test2/test3` is specified in a Dockerfile,
+	// the configuration should be stored as C:\test2\test3. Something similar to
+	// 	if runtime.GOOS == "windows" && len(workdir) > 2 && string(workdir[0]) == `\` {
+	//		workdir = "C:" + workdir
+	//  }
+	// in builder\dockerfile\dispatchers.go, function workdir(), but also
+	// ironing out all other cases where this causes other failures.
 	if daemonPlatform == "windows" {
-		expected1 = `C:/Windows/system32`
+		expected1 = `C:/`
 		expected2 = `C:/test1`
 		expected3 = `C:/test2`
 		expected4 = `C:/test2/test3`
@@ -2090,13 +2100,13 @@ func (s *DockerSuite) TestBuildRelativeWorkdir(c *check.C) {
 
 	_, err := buildImage(name,
 		`FROM busybox
-		RUN sh -c "[ "$PWD" = '`+expected1+`' ]"
+		RUN sh -c "[ "$PWD" = "`+expected1+`" ]"
 		WORKDIR test1
-		RUN sh -c "[ "$PWD" = '`+expected2+`' ]"
+		RUN sh -c "[ "$PWD" = "`+expected2+`" ]"
 		WORKDIR /test2
-		RUN sh -c "[ "$PWD" = '`+expected3+`' ]"
+		RUN sh -c "[ "$PWD" = "`+expected3+`" ]"
 		WORKDIR test3
-		RUN sh -c "[ "$PWD" = '`+expected4+`' ]"`,
+		RUN sh -c "[ "$PWD" = "`+expected4+`" ]"`,
 		true)
 	if err != nil {
 		c.Fatal(err)