diff --git a/generate/generate.go b/generate/generate.go
index 84762c3c..bc92df66 100644
--- a/generate/generate.go
+++ b/generate/generate.go
@@ -1089,11 +1089,7 @@ func (g *Generator) DropProcessCapability(c string) error {
 		}
 	}
 
-	if err := validate.CapValid(cp, false); err != nil {
-		return err
-	}
-
-	return nil
+	return validate.CapValid(cp, false)
 }
 
 func mapStrToNamespace(ns string, path string) (rspec.LinuxNamespace, error) {
diff --git a/validate/validate.go b/validate/validate.go
index 9a4c0fea..11032ac3 100644
--- a/validate/validate.go
+++ b/validate/validate.go
@@ -178,6 +178,23 @@ func (v *Validator) CheckRoot() (errs error) {
 		return
 	}
 
+	if v.platform == "windows" {
+		matched, err := regexp.MatchString(`\\\\[?]\\Volume[{][a-fA-F0-9]{8}-[a-fA-F0-9]{4}-[a-fA-F0-9]{4}-[a-fA-F0-9]{4}-[a-fA-F0-9]{12}[}]\\`, v.spec.Root.Path)
+		if err != nil {
+			errs = multierror.Append(errs, err)
+		} else if !matched {
+			errs = multierror.Append(errs,
+				specerror.NewError(specerror.PathFormatOnWindows, fmt.Errorf("root.path is %q, but it MUST be a volume GUID path when target platform is windows", v.spec.Root.Path), rspec.Version))
+		}
+
+		if v.spec.Root.Readonly {
+			errs = multierror.Append(errs,
+				specerror.NewError(specerror.ReadonlyOnWindows, fmt.Errorf("root.readonly field MUST be omitted or false when target platform is windows"), rspec.Version))
+		}
+
+		return
+	}
+
 	absBundlePath, err := filepath.Abs(v.bundlePath)
 	if err != nil {
 		errs = multierror.Append(errs, fmt.Errorf("unable to convert %q to an absolute path", v.bundlePath))
@@ -218,13 +235,6 @@ func (v *Validator) CheckRoot() (errs error) {
 			specerror.NewError(specerror.ArtifactsInSingleDir, fmt.Errorf("root.path is %q, but it MUST be a child of %q", v.spec.Root.Path, absBundlePath), rspec.Version))
 	}
 
-	if v.platform == "windows" {
-		if v.spec.Root.Readonly {
-			errs = multierror.Append(errs,
-				specerror.NewError(specerror.ReadonlyOnWindows, fmt.Errorf("root.readonly field MUST be omitted or false when target platform is windows"), rspec.Version))
-		}
-	}
-
 	return
 }
 
diff --git a/validate/validate_test.go b/validate/validate_test.go
index 9c3e3ea2..e7e3f605 100644
--- a/validate/validate_test.go
+++ b/validate/validate_test.go
@@ -114,6 +114,8 @@ func TestCheckRoot(t *testing.T) {
 	}{
 		{rspec.Spec{Windows: &rspec.Windows{HyperV: &rspec.WindowsHyperV{}}, Root: &rspec.Root{}}, "windows", specerror.RootOnHyperV},
 		{rspec.Spec{Windows: &rspec.Windows{HyperV: &rspec.WindowsHyperV{}}, Root: nil}, "windows", specerror.NonError},
+		{rspec.Spec{Windows: &rspec.Windows{}, Root: &rspec.Root{Path: filepath.Join(tmpBundle, "rootfs")}}, "windows", specerror.PathFormatOnWindows},
+		{rspec.Spec{Windows: &rspec.Windows{}, Root: &rspec.Root{Path: "\\\\?\\Volume{ec84d99e-3f02-11e7-ac6c-00155d7682cf}\\"}}, "windows", specerror.NonError},
 		{rspec.Spec{Root: nil}, "linux", specerror.RootOnNonHyperV},
 		{rspec.Spec{Root: &rspec.Root{Path: "maverick-rootfs"}}, "linux", specerror.PathName},
 		{rspec.Spec{Root: &rspec.Root{Path: "rootfs"}}, "linux", specerror.NonError},