diff --git a/internal/serving/disk/symlink/path_test.go b/internal/serving/disk/symlink/path_test.go
index 6b0a41f3f8b3ea6e78e54c0a48c6acd8c4311623..23978037d9737d2d26c87a2e1d689192bc864b6b 100644
--- a/internal/serving/disk/symlink/path_test.go
+++ b/internal/serving/disk/symlink/path_test.go
@@ -26,6 +26,10 @@ func tmpDir(t *testing.T) (vfs.Root, string, func()) {
 	tmpDir, err := ioutil.TempDir("", "symlink_tests")
 	require.NoError(t, err)
 
+	// On some systems `/tmp` can be a symlink
+	tmpDir, err = filepath.EvalSymlinks(tmpDir)
+	require.NoError(t, err)
+
 	root, err := fs.Root(context.Background(), tmpDir)
 	require.NoError(t, err)
 
@@ -70,7 +74,7 @@ var EvalSymlinksTests = []EvalSymlinksTest{
 	{"test/link2/..", "test"},
 	{"test/dir/link3", "."},
 	{"test/link2/link3/test", "test"},
-	{"test/linkabs", "../.."},
+	{"test/linkabs", "/"},
 	{"test/link4/..", "test"},
 	{"src/versions/current/modules/test", "src/pool/test"},
 }
diff --git a/internal/vfs/local/root.go b/internal/vfs/local/root.go
index 0ed2206df03cbd32af8739302f653d66f8d7b415..9cd67a9f05d24266dd32a5949b5ce01b4fc7d5df 100644
--- a/internal/vfs/local/root.go
+++ b/internal/vfs/local/root.go
@@ -65,10 +65,18 @@ func (r *Root) Readlink(ctx context.Context, name string) (string, error) {
 		return "", err
 	}
 
-	if filepath.IsAbs(target) {
+	// If `target` is local to `rootPath` return relative
+	if strings.HasPrefix(target, r.rootPath+"/") {
 		return filepath.Rel(filepath.Dir(fullPath), target)
 	}
 
+	// If `target` is absolute return as-is making `EvalSymlinks`
+	// to discover misuse of a root path
+	if filepath.IsAbs(target) {
+		return target, nil
+	}
+
+	// If `target` is relative, return as-is
 	return target, nil
 }
 
diff --git a/internal/vfs/local/root_test.go b/internal/vfs/local/root_test.go
index c8ee6616ebf9e1a3bda57464080aa80e0ed6761d..f89e7736d25e34bb551be43996a4279c055ebc33 100644
--- a/internal/vfs/local/root_test.go
+++ b/internal/vfs/local/root_test.go
@@ -119,7 +119,8 @@ func TestReadlink(t *testing.T) {
 func TestReadlinkAbsolutePath(t *testing.T) {
 	// create structure as:
 	// /tmp/dir: directory
-	// /tmp/dir/symlink: points to `/tmp/file`
+	// /tmp/dir/symlink: points to `/tmp/file` outside of the `/tmp/dir`
+	// /tmp/dir/symlink2: points to `/tmp/dir/file`
 	tmpDir, cleanup := tmpDir(t)
 	defer cleanup()
 
@@ -132,13 +133,36 @@ func TestReadlinkAbsolutePath(t *testing.T) {
 	err = os.Symlink(filePath, symlinkPath)
 	require.NoError(t, err)
 
-	root, err := localVFS.Root(context.Background(), dirPath)
+	symlinkPath = filepath.Join(dirPath, "symlink2")
+	dirFilePath := filepath.Join(dirPath, "file")
+	err = os.Symlink(dirFilePath, symlinkPath)
 	require.NoError(t, err)
 
-	targetPath, err := root.Readlink(context.Background(), "symlink")
+	root, err := localVFS.Root(context.Background(), dirPath)
 	require.NoError(t, err)
 
-	assert.Equal(t, "../file", targetPath, "the relative path is returned")
+	tests := map[string]struct {
+		path           string
+		expectedTarget string
+	}{
+		"the absolute path is returned for file outside of `/tmp/dir": {
+			path:           "symlink",
+			expectedTarget: filePath,
+		},
+		"the relative path is returned for file inside the `/tmp/dir": {
+			path:           "symlink2",
+			expectedTarget: "file",
+		},
+	}
+
+	for name, test := range tests {
+		t.Run(name, func(t *testing.T) {
+			targetPath, err := root.Readlink(context.Background(), test.path)
+			require.NoError(t, err)
+
+			assert.Equal(t, test.expectedTarget, targetPath)
+		})
+	}
 }
 
 func TestLstat(t *testing.T) {