diff --git a/core/playlists.go b/core/playlists.go
index a29dfa247..81393bc94 100644
--- a/core/playlists.go
+++ b/core/playlists.go
@@ -9,6 +9,7 @@ import (
 	"net/url"
 	"os"
 	"path/filepath"
+	"regexp"
 	"strings"
 	"time"
 
@@ -228,31 +229,39 @@ func (s *playlists) normalizePaths(ctx context.Context, pls *model.Playlist, fol
 	if err != nil {
 		return nil, err
 	}
-	// Normalize paths to be relative to the library root. Search for roots in any library
-	var res []string
+
+	// Create regex patterns for each library path
+	patterns := make([]string, len(libs))
+	for i, lib := range libs {
+		cleanPath := filepath.Clean(lib.Path)
+		escapedPath := regexp.QuoteMeta(cleanPath)
+		patterns[i] = fmt.Sprintf("^%s(?:/|$)", escapedPath)
+	}
+	// Combine all patterns into a single regex
+	combinedPattern := strings.Join(patterns, "|")
+	libRegex := regexp.MustCompile(combinedPattern)
+
+	res := make([]string, 0, len(lines))
 	for idx, line := range lines {
 		var libPath string
 		var filePath string
+
 		if folder != nil && !filepath.IsAbs(line) {
 			libPath = folder.LibraryPath
 			filePath = filepath.Join(folder.AbsolutePath(), line)
 		} else {
-			for _, lib := range libs {
-				if strings.HasPrefix(line, lib.Path) {
-					libPath = lib.Path
-					filePath = line
-					break
-				}
+			cleanLine := filepath.Clean(line)
+			if libPath = libRegex.FindString(cleanLine); libPath != "" {
+				filePath = cleanLine
 			}
 		}
+
 		if libPath != "" {
-			var err error
-			filePath, err = filepath.Rel(libPath, filePath)
-			if err != nil {
+			if rel, err := filepath.Rel(libPath, filePath); err == nil {
+				res = append(res, rel)
+			} else {
 				log.Trace(ctx, "Error getting relative path", "playlist", pls.Name, "path", line, "folder", folder, err)
-				continue
 			}
-			res = append(res, filePath)
 		} else {
 			log.Warn(ctx, "Path in playlist not found in any library", "path", line, "line", idx)
 		}
diff --git a/core/playlists_test.go b/core/playlists_test.go
index 7241dd1b5..7a85c6c70 100644
--- a/core/playlists_test.go
+++ b/core/playlists_test.go
@@ -56,10 +56,9 @@ var _ = Describe("Playlists", func() {
 				pls, err := ps.ImportFile(ctx, folder, "pls1.m3u")
 				Expect(err).ToNot(HaveOccurred())
 				Expect(pls.OwnerID).To(Equal("123"))
-				Expect(pls.Tracks).To(HaveLen(3))
+				Expect(pls.Tracks).To(HaveLen(2))
 				Expect(pls.Tracks[0].Path).To(Equal("tests/fixtures/playlists/test.mp3"))
 				Expect(pls.Tracks[1].Path).To(Equal("tests/fixtures/playlists/test.ogg"))
-				Expect(pls.Tracks[2].Path).To(Equal("tests/fixtures/01 Invisible (RED) Edit Version.mp3"))
 				Expect(mockPlsRepo.last).To(Equal(pls))
 			})
 
diff --git a/tests/fixtures/playlists/pls1.m3u b/tests/fixtures/playlists/pls1.m3u
index d8f30e943..98e6d9675 100644
--- a/tests/fixtures/playlists/pls1.m3u
+++ b/tests/fixtures/playlists/pls1.m3u
@@ -1,3 +1,2 @@
 test.mp3
-test.ogg
-file:///tests/fixtures/01%20Invisible%20(RED)%20Edit%20Version.mp3
\ No newline at end of file
+test.ogg
\ No newline at end of file
diff --git a/tests/test_helpers.go b/tests/test_helpers.go
index e1d29622a..1251c90cd 100644
--- a/tests/test_helpers.go
+++ b/tests/test_helpers.go
@@ -2,7 +2,6 @@ package tests
 
 import (
 	"context"
-	"io/fs"
 	"os"
 	"path/filepath"
 
@@ -18,7 +17,7 @@ func TempFileName(t testingT, prefix, suffix string) string {
 	return filepath.Join(t.TempDir(), prefix+id.NewRandom()+suffix)
 }
 
-func TempFile(t testingT, prefix, suffix string) (fs.File, string, error) {
+func TempFile(t testingT, prefix, suffix string) (*os.File, string, error) {
 	name := TempFileName(t, prefix, suffix)
 	f, err := os.Create(name)
 	return f, name, err
diff --git a/utils/slice/slice_test.go b/utils/slice/slice_test.go
index 40569c07b..c6d4be1e0 100644
--- a/utils/slice/slice_test.go
+++ b/utils/slice/slice_test.go
@@ -140,7 +140,7 @@ var _ = Describe("Slice Utils", func() {
 			Expect(count).To(Equal(expected))
 		},
 		Entry("returns empty slice for an empty input", "tests/fixtures/empty.txt", 0),
-		Entry("returns the lines of a file", "tests/fixtures/playlists/pls1.m3u", 3),
+		Entry("returns the lines of a file", "tests/fixtures/playlists/pls1.m3u", 2),
 		Entry("returns empty if file does not exist", "tests/fixtures/NON-EXISTENT", 0),
 	)