diff --git a/pkg/fileutils/fileutils.go b/pkg/fileutils/fileutils.go
index fd4fb7f08f..31c5f78ec6 100644
--- a/pkg/fileutils/fileutils.go
+++ b/pkg/fileutils/fileutils.go
@@ -77,8 +77,11 @@ func (pm *PatternMatcher) Matches(file string) (bool, error) {
 
 		if !match && parentPath != "." {
 			// Check to see if the pattern matches one of our parent dirs.
-			if len(pattern.dirs) <= len(parentPathDirs) {
-				match, _ = pattern.match(strings.Join(parentPathDirs[:len(pattern.dirs)], string(os.PathSeparator)))
+			for i := range parentPathDirs {
+				match, _ = pattern.match(strings.Join(parentPathDirs[:i+1], string(os.PathSeparator)))
+				if match {
+					break
+				}
 			}
 		}
 
diff --git a/pkg/fileutils/fileutils_test.go b/pkg/fileutils/fileutils_test.go
index 36064b6f5f..e11711b653 100644
--- a/pkg/fileutils/fileutils_test.go
+++ b/pkg/fileutils/fileutils_test.go
@@ -328,6 +328,8 @@ func TestMatches(t *testing.T) {
 		{"dir/**", "dir/file/", true},
 		{"dir/**", "dir/dir2/file", true},
 		{"dir/**", "dir/dir2/file/", true},
+		{"**/dir", "dir", true},
+		{"**/dir", "dir/file", true},
 		{"**/dir2/*", "dir/dir2/file", true},
 		{"**/dir2/*", "dir/dir2/file/", true},
 		{"**/dir2/**", "dir/dir2/dir3/file", true},