diff --git a/packages/backend/src/services/backgroundJobService.ts b/packages/backend/src/services/backgroundJobService.ts
index 35023f2..4bc8ccd 100644
--- a/packages/backend/src/services/backgroundJobService.ts
+++ b/packages/backend/src/services/backgroundJobService.ts
@@ -222,13 +222,15 @@ class BackgroundJobService {
           });
           
           // Quick filename matching logic
-          const normalizedS3Filename = filename.replace(/\.[^/.]+$/, '').toLowerCase();
+          // Decode URL-encoded sequences so %20, %27 etc. are compared correctly
+          const safeDecode = (s: string): string => { try { return decodeURIComponent(s); } catch { return s; } };
+          const normalizedS3Filename = safeDecode(filename).replace(/\.[^/.]+$/, '').toLowerCase();
           let matchedSong = null;
           
           for (const song of allSongs) {
             if (song.location) {
               const rekordboxFilename = song.location.split(/[/\\]/).pop() || song.location;
-              const normalizedRekordboxFilename = rekordboxFilename.replace(/\.[^/.]+$/, '').toLowerCase();
+              const normalizedRekordboxFilename = safeDecode(rekordboxFilename).replace(/\.[^/.]+$/, '').toLowerCase();
               
               if (normalizedS3Filename === normalizedRekordboxFilename) {
                 matchedSong = song;
diff --git a/packages/backend/src/services/songMatchingService.ts b/packages/backend/src/services/songMatchingService.ts
index 5e581d3..d072a16 100644
--- a/packages/backend/src/services/songMatchingService.ts
+++ b/packages/backend/src/services/songMatchingService.ts
@@ -487,8 +487,10 @@ export class SongMatchingService {
   private matchLocation(filename: string, location: string): { score: number; reason: string } {
     if (!filename || !location) return { score: 0, reason: '' };
 
-    const cleanFilename = this.cleanString(filename);
-    const cleanLocation = this.cleanString(location);
+    // Decode URL-encoded sequences so Rekordbox paths with %20 etc. match S3 keys correctly
+    const safeDecode = (s: string): string => { try { return decodeURIComponent(s); } catch { return s; } };
+    const cleanFilename = this.cleanString(safeDecode(filename));
+    const cleanLocation = this.cleanString(safeDecode(location));
 
     // Extract filename from location path (handle different path separators)
     const pathParts = cleanLocation.split(/[\/\\]/);