diff --git a/data/images/paintings/thumbs/Domenico_Ghirlandaio_The_Last_Supper_Ghirlandaio_thumb.jpg b/data/images/paintings/thumbs/Domenico_Ghirlandaio_The_Last_Supper_Ghirlandaio_thumb.jpg
new file mode 100644
index 0000000..af2f693
Binary files /dev/null and b/data/images/paintings/thumbs/Domenico_Ghirlandaio_The_Last_Supper_Ghirlandaio_thumb.jpg differ
diff --git a/scripts/regenerate-thumbnails.js b/scripts/regenerate-thumbnails.js
index 9a6a083..3c78e48 100644
--- a/scripts/regenerate-thumbnails.js
+++ b/scripts/regenerate-thumbnails.js
@@ -19,6 +19,37 @@ function localPath(rel) {
   return path.join(IMAGE_DIR, rel);
 }
 
+function sleep(ms) {
+  return new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+function isPaintingThumbRel(rel) {
+  if (!rel) return false;
+  return rel.replace(/\\/g, '/').startsWith('paintings/thumbs/');
+}
+
+async function unlinkWithRetry(absPath, attempts = 5) {
+  if (!absPath || !fs.existsSync(absPath)) return;
+
+  for (let attempt = 1; attempt <= attempts; attempt++) {
+    try {
+      fs.unlinkSync(absPath);
+      return;
+    } catch (err) {
+      if (err.code === 'EBUSY' && attempt < attempts) {
+        await sleep(200 * attempt);
+        continue;
+      }
+      throw err;
+    }
+  }
+}
+
+async function unlinkOldThumbRel(thumbRel, imageRel) {
+  if (!thumbRel || thumbRel === imageRel || !isPaintingThumbRel(thumbRel)) return;
+  await unlinkWithRetry(localPath(thumbRel));
+}
+
 async function aspectRatio(filePath) {
   const meta = await sharp(filePath).metadata();
   if (!meta.width || !meta.height) return null;
@@ -65,14 +96,8 @@ async function aspectRatio(filePath) {
     }
 
     try {
-      if (fs.existsSync(thumbPath)) fs.unlinkSync(thumbPath);
-      if (
-        row.thumbnail_path &&
-        row.thumbnail_path !== thumbRel &&
-        fs.existsSync(localPath(row.thumbnail_path))
-      ) {
-        fs.unlinkSync(localPath(row.thumbnail_path));
-      }
+      await unlinkWithRetry(thumbPath);
+      await unlinkOldThumbRel(row.thumbnail_path, row.image_path);
 
       await generateThumbnailFromFull(fullPath, thumbPath);
       await pool.query(`UPDATE paintings SET thumbnail_path = $1 WHERE id = $2`, [thumbRel, row.id]);