diff --git a/lib/utils/file_uploader.dart b/lib/utils/file_uploader.dart
index 41385fe64..85150cc7e 100644
--- a/lib/utils/file_uploader.dart
+++ b/lib/utils/file_uploader.dart
@@ -194,12 +194,13 @@ class FileUploader {
         _logger.severe("Could not generate thumbnail for " + file.toString());
         throw InvalidFileError();
       }
-      final thumbnailSize = thumbnailData.length;
-      if (thumbnailSize > THUMBNAIL_DATA_LIMIT) {
+      var thumbnailSize = thumbnailData.length;
+      while (thumbnailSize > THUMBNAIL_DATA_LIMIT) {
         thumbnailData = await compressThumbnail(thumbnailData);
         _logger.info("Thumbnail size " + thumbnailSize.toString());
         _logger.info(
             "Compressed thumbnail size " + thumbnailData.length.toString());
+        thumbnailSize = thumbnailData.length;
       }
 
       final encryptedThumbnailData =