diff --git a/test/docker/devconfig_test.go b/test/docker/devconfig_test.go
index 1501dbe..3c0aa59 100644
--- a/test/docker/devconfig_test.go
+++ b/test/docker/devconfig_test.go
@@ -78,7 +78,7 @@ func TestDevSecure(t *testing.T) {
 	hostConfig := container.HostConfig{
 		Binds: []string{
 			coverageBind(t),
-			tlsDir(t) + ":/var/tls",
+			tlsDir(t, false) + ":/var/tls",
 		},
 		// Assign a random port for the web server on the host
 		// TODO: Don't do this for all tests
@@ -98,7 +98,7 @@ func TestDevSecure(t *testing.T) {
 	defer cleanContainer(t, cli, ctr.ID)
 	startContainer(t, cli, ctr.ID)
 	waitForReady(t, cli, ctr.ID)
-	cert := filepath.Join(tlsDir(t), "server.crt")
+	cert := filepath.Join(tlsDir(t, true), "server.crt")
 	waitForWebReady(t, cli, ctr.ID, createTLSConfig(t, cert, tlsPassPhrase))
 	runJMSTests(t, cli, ctr.ID, true, "app", devAppPassword)
 	// Stop the container cleanly
diff --git a/test/docker/devconfig_test_util.go b/test/docker/devconfig_test_util.go
index 9bc7b3a..9042cd5 100644
--- a/test/docker/devconfig_test_util.go
+++ b/test/docker/devconfig_test_util.go
@@ -73,11 +73,21 @@ func waitForWebReady(t *testing.T, cli *client.Client, ID string, tlsConfig *tls
 }
 
 // tlsDir returns the host directory where the test certificate(s) are located
-func tlsDir(t *testing.T) string {
+func tlsDir(t *testing.T, unixPath bool) string {
 	dir, err := os.Getwd()
 	if err != nil {
 		t.Fatal(err)
 	}
+	if isWSL(t) {
+		// Check if the cwd is a symlink
+		dir, err = filepath.EvalSymlinks(dir)
+		if err != nil {
+			t.Fatal(err)
+		}
+		if !unixPath {
+			dir = strings.Replace(dir, getWindowsRoot(true), getWindowsRoot(false), 1)
+		}
+	}
 	return filepath.Join(dir, "../tls")
 }
 
@@ -106,7 +116,7 @@ func runJMSTests(t *testing.T, cli *client.Client, ID string, tls bool, user, pa
 	hostConfig := container.HostConfig{
 		Binds: []string{
 			coverageBind(t),
-			tlsDir(t) + ":/var/tls",
+			tlsDir(t, false) + ":/var/tls",
 		},
 	}
 	networkingConfig := network.NetworkingConfig{}
diff --git a/test/docker/docker_api_test_util.go b/test/docker/docker_api_test_util.go
index 8fff146..e891ba7 100644
--- a/test/docker/docker_api_test_util.go
+++ b/test/docker/docker_api_test_util.go
@@ -85,27 +85,29 @@ func coverageBind(t *testing.T) string {
 // isWSL return whether we are running in the Windows Subsystem for Linux
 func isWSL(t *testing.T) bool {
 	if runtime.GOOS == "linux" {
-
 		uname, err := exec.Command("uname", "-r").Output()
 		if (err != nil) {
 			t.Fatal(err)
 		}
-
 		return strings.Contains(string(uname), "Microsoft")
-
 	} else {
 		return false
 	}
 }
 
+// getWindowsRoot get the path of the root directory on Windows, in UNIX or OS-specific style
+func getWindowsRoot(unixStylePath bool) string {
+	if unixStylePath {
+		return "/mnt/c/"
+	} else {
+		return "C:/"
+	}
+}
+
 // getTempDir get the path of the tmp directory, in UNIX or OS-specific style
 func getTempDir(t *testing.T, unixStylePath bool) string {
 	if isWSL(t) {
-		if unixStylePath {
-			return "/mnt/c/Temp/"
-		} else {
-			return "C:/Temp/"
-		}
+		return getWindowsRoot(unixStylePath) + "Temp/"
 	} else {
 		return "/tmp/"
 	}