diff --git a/cache/contenthash/checksum.go b/cache/contenthash/checksum.go
index ef129cc7..3fe5c658 100644
--- a/cache/contenthash/checksum.go
+++ b/cache/contenthash/checksum.go
@@ -736,26 +736,33 @@ func getFollowLinksWalk(root *iradix.Node, k []byte, follow bool, linksWalked *i
 
 	dir, file := splitKey(k)
 
-	_, parent, err := getFollowLinksWalk(root, dir, follow, linksWalked)
+	k, parent, err := getFollowLinksWalk(root, dir, follow, linksWalked)
 	if err != nil {
 		return nil, nil, err
 	}
-	if parent != nil && parent.Type == CacheRecordTypeSymlink {
-		*linksWalked++
-		if *linksWalked > 255 {
-			return nil, nil, errors.Errorf("too many links")
+	if parent != nil {
+		if parent.Type == CacheRecordTypeSymlink {
+			*linksWalked++
+			if *linksWalked > 255 {
+				return nil, nil, errors.Errorf("too many links")
+			}
+			dirPath := path.Clean(string(convertKeyToPath(dir)))
+			if dirPath == "." || dirPath == "/" {
+				dirPath = ""
+			}
+			link := path.Clean(parent.Linkname)
+			if !path.IsAbs(link) {
+				link = path.Join("/", path.Join(path.Dir(dirPath), link))
+			}
+			return getFollowLinksWalk(root, append(convertPathToKey([]byte(link)), file...), follow, linksWalked)
 		}
-		dirPath := path.Clean(string(convertKeyToPath(dir)))
-		if dirPath == "." || dirPath == "/" {
-			dirPath = ""
-		}
-		link := path.Clean(parent.Linkname)
-		if !path.IsAbs(link) {
-			link = path.Join("/", path.Join(path.Dir(dirPath), link))
-		}
-		return getFollowLinksWalk(root, append(convertPathToKey([]byte(link)), file...), follow, linksWalked)
-	}
 
+		k = append(k, file...)
+		v, ok = root.Get(k)
+		if ok {
+			return k, v.(*CacheRecord), nil
+		}
+	}
 	return nil, nil, nil
 }
 
diff --git a/cache/contenthash/checksum_test.go b/cache/contenthash/checksum_test.go
index 05d4f868..bc81f170 100644
--- a/cache/contenthash/checksum_test.go
+++ b/cache/contenthash/checksum_test.go
@@ -564,6 +564,61 @@ func TestSymlinkAbsDirSuffix(t *testing.T) {
 	require.NoError(t, err)
 }
 
+func TestSymlinkThroughParent(t *testing.T) {
+	t.Parallel()
+	tmpdir, err := ioutil.TempDir("", "buildkit-state")
+	require.NoError(t, err)
+	defer os.RemoveAll(tmpdir)
+
+	snapshotter, err := native.NewSnapshotter(filepath.Join(tmpdir, "snapshots"))
+	require.NoError(t, err)
+	cm := setupCacheManager(t, tmpdir, snapshotter)
+	defer cm.Close()
+
+	ch := []string{
+		"ADD lib dir",
+		"ADD lib/sub dir",
+		"ADD lib/sub/foo file data0",
+		"ADD lib/sub/link symlink ../../lib2",
+		"ADD lib2 dir",
+		"ADD lib2/sub dir",
+		"ADD lib2/sub/foo file data0",
+		"ADD link1 symlink /lib",
+		"ADD link2 symlink /lib/",
+		"ADD link3 symlink /lib/.",
+		"ADD link4 symlink /lib/../lib",
+		"ADD link5 symlink ../lib",
+	}
+	ref := createRef(t, cm, ch)
+
+	dgst, err := Checksum(context.TODO(), ref, "link1/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	dgst, err = Checksum(context.TODO(), ref, "link2/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	dgst, err = Checksum(context.TODO(), ref, "link3/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	dgst, err = Checksum(context.TODO(), ref, "link4/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	dgst, err = Checksum(context.TODO(), ref, "link5/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	dgst, err = Checksum(context.TODO(), ref, "link1/sub/link/sub/foo", true)
+	require.NoError(t, err)
+	require.Equal(t, dgstFileData0, dgst)
+
+	err = ref.Release(context.TODO())
+	require.NoError(t, err)
+}
+
 func TestSymlinkInPathHandleChange(t *testing.T) {
 	t.Parallel()
 	tmpdir, err := ioutil.TempDir("", "buildkit-state")