diff --git a/validation/linux_masked_paths.go b/validation/linux_masked_paths.go
index 0c6460446..673dab4a1 100644
--- a/validation/linux_masked_paths.go
+++ b/validation/linux_masked_paths.go
@@ -1,22 +1,39 @@
 package main
 
 import (
+	"fmt"
 	"io/ioutil"
 	"os"
 	"path/filepath"
 
 	"github.com/opencontainers/runtime-tools/validation/util"
+	"golang.org/x/sys/unix"
 )
 
-func main() {
+func checkMaskedPaths() error {
 	g, err := util.GetDefaultGenerator()
 	if err != nil {
-		util.Fatal(err)
+		return err
 	}
-	g.AddLinuxMaskedPaths("/masked-dir")
-	g.AddLinuxMaskedPaths("/masked-file")
+
+	maskedDir := "masked-dir"
+	maskedSubDir := "masked-subdir"
+	maskedFile := "masked-file"
+
+	maskedDirTop := filepath.Join("/", maskedDir)
+	maskedFileTop := filepath.Join("/", maskedFile)
+
+	maskedDirSub := filepath.Join(maskedDirTop, maskedSubDir)
+	maskedFileSub := filepath.Join(maskedDirTop, maskedFile)
+	maskedFileSubSub := filepath.Join(maskedDirSub, maskedFile)
+
+	g.AddLinuxMaskedPaths(maskedDirTop)
+	g.AddLinuxMaskedPaths(maskedFileTop)
+	g.AddLinuxMaskedPaths(maskedDirSub)
+	g.AddLinuxMaskedPaths(maskedFileSub)
+	g.AddLinuxMaskedPaths(maskedFileSubSub)
 	err = util.RuntimeInsideValidate(g, func(path string) error {
-		testDir := filepath.Join(path, "masked-dir")
+		testDir := filepath.Join(path, maskedDirSub)
 		err = os.MkdirAll(testDir, 0777)
 		if err != nil {
 			return err
@@ -28,13 +45,130 @@ func main() {
 		}
 		defer os.Remove(tmpfile.Name())
 
-		testFile := filepath.Join(path, "masked-file")
-
 		// runtimetest cannot check the readability of empty files, so
 		// write something.
+		testSubSubFile := filepath.Join(path, maskedFileSubSub)
+		if err := ioutil.WriteFile(testSubSubFile, []byte("secrets"), 0777); err != nil {
+			return err
+		}
+
+		testSubFile := filepath.Join(path, maskedFileSub)
+		if err := ioutil.WriteFile(testSubFile, []byte("secrets"), 0777); err != nil {
+			return err
+		}
+
+		testFile := filepath.Join(path, maskedFile)
 		return ioutil.WriteFile(testFile, []byte("secrets"), 0777)
 	})
+	return err
+}
+
+func checkMaskedRelPaths() error {
+	g, err := util.GetDefaultGenerator()
+	if err != nil {
+		return err
+	}
+
+	// Deliberately set a relative path to be masked, and expect an error
+	maskedRelPath := "masked-relpath"
+
+	g.AddLinuxMaskedPaths(maskedRelPath)
+	err = util.RuntimeInsideValidate(g, func(path string) error {
+		testFile := filepath.Join(path, maskedRelPath)
+		if _, err := os.Stat(testFile); err != nil && os.IsNotExist(err) {
+			return err
+		}
+
+		return nil
+	})
+	if err != nil {
+		return nil
+	}
+	return fmt.Errorf("expected: err != nil, actual: err == nil")
+}
+
+func checkMaskedSymlinks() error {
+	g, err := util.GetDefaultGenerator()
 	if err != nil {
+		return err
+	}
+
+	// Deliberately create a masked symlink that points an invalid file,
+	// and expect an error.
+	maskedSymlink := "/masked-symlink"
+
+	g.AddLinuxMaskedPaths(maskedSymlink)
+	err = util.RuntimeInsideValidate(g, func(path string) error {
+		testFile := filepath.Join(path, maskedSymlink)
+		// ln -s .. /masked-symlink ; readlink -f /masked-symlink; ls -L /masked-symlink
+		if err := os.Symlink("../masked-symlink", testFile); err != nil {
+			return err
+		}
+		rPath, errR := os.Readlink(testFile)
+		if errR != nil {
+			return errR
+		}
+		_, errS := os.Stat(rPath)
+		if errS != nil && os.IsNotExist(errS) {
+			return errS
+		}
+
+		return nil
+	})
+	if err != nil {
+		return nil
+	}
+	return fmt.Errorf("expected: err != nil, actual: err == nil")
+}
+
+func checkMaskedDeviceNodes(mode uint32) error {
+	g, err := util.GetDefaultGenerator()
+	if err != nil {
+		return err
+	}
+
+	maskedDevice := "/masked-device"
+
+	g.AddLinuxMaskedPaths(maskedDevice)
+	return util.RuntimeInsideValidate(g, func(path string) error {
+		testFile := filepath.Join(path, maskedDevice)
+
+		if err := unix.Mknod(testFile, mode, 0); err != nil {
+			return err
+		}
+
+		if _, err := os.Stat(testFile); err != nil && os.IsNotExist(err) {
+			return err
+		}
+
+		return nil
+	})
+}
+
+func main() {
+	if err := checkMaskedPaths(); err != nil {
+		util.Fatal(err)
+	}
+
+	if err := checkMaskedRelPaths(); err != nil {
 		util.Fatal(err)
 	}
+
+	if err := checkMaskedSymlinks(); err != nil {
+		util.Fatal(err)
+	}
+
+	// test creation of different type of devices, i.e. block device,
+	// character device, and FIFO.
+	modes := []uint32{
+		unix.S_IFBLK | 0666,
+		unix.S_IFCHR | 0666,
+		unix.S_IFIFO | 0666,
+	}
+
+	for _, m := range modes {
+		if err := checkMaskedDeviceNodes(m); err != nil {
+			util.Fatal(err)
+		}
+	}
 }