@@ -24,19 +24,21 @@
 func hashFile(filename string) (string, error) {
 	f, err := os.Open(filename)
 	if err != nil {
-		return "", err
+		return "", errors.Wrapf(err, "could not open file %s for hashing", filename)
 	}
 	defer f.Close()
 	hash := fnv.New64a()
 	if _, err := io.Copy(hash, f); err != nil {
-		return "", err
+		return "", errors.Wrapf(err, "could not hash file %s", filename)
 	}
+
 	return fmt.Sprintf(`W/"%x"`, hash.Sum(nil)), nil
 }
 
 func registerFile(urlpath string, filepath string) error {
 	if files[urlpath] != (File{}) {
 		log.Info("registerFile called with duplicate file", "url_path", urlpath)
+
 		return nil
 	}
 	hash, err := hashFile(filepath)
@@ -47,6 +49,7 @@ files[urlpath] = File{
 		filename: filepath,
 		etag:     hash,
 	}
+
 	return nil
 }
 
@@ -62,13 +65,16 @@ }
 		urlPath, _ := strings.CutSuffix(relPath, "index.html")
 		if !f.IsDir() {
 			log.Debug("registering file", "urlpath", "/"+urlPath)
+
 			return registerFile("/"+urlPath, filePath)
 		}
+
 		return nil
 	})
 	if err != nil {
-		return err
+		return errors.Wrap(err, "could not walk directory")
 	}
+
 	return nil
 }