diff --git a/syft/internal/fileresolver/directory_indexer.go b/syft/internal/fileresolver/directory_indexer.go
index 47349a445..01f332a3d 100644
--- a/syft/internal/fileresolver/directory_indexer.go
+++ b/syft/internal/fileresolver/directory_indexer.go
@@ -332,7 +332,19 @@ func (r directoryIndexer) addFileToIndex(p string, info os.FileInfo) error {
 func (r directoryIndexer) addSymlinkToIndex(p string, info os.FileInfo) (string, error) {
 	linkTarget, err := os.Readlink(p)
 	if err != nil {
-		return "", fmt.Errorf("unable to readlink for path=%q: %w", p, err)
+		if runtime.GOOS == WindowsOS {
+			p = posixToWindows(p)
+		}
+
+		linkTarget, err = filepath.EvalSymlinks(p)
+
+		if runtime.GOOS == WindowsOS {
+			p = windowsToPosix(p)
+		}
+
+		if err != nil {
+			return "", fmt.Errorf("unable to readlink for path=%q: %w", p, err)
+		}
 	}
 
 	if filepath.IsAbs(linkTarget) {