diff --git a/API/Extensions/FileInfoExtensions.cs b/API/Extensions/FileInfoExtensions.cs
index d96b06de6..82f6e663f 100644
--- a/API/Extensions/FileInfoExtensions.cs
+++ b/API/Extensions/FileInfoExtensions.cs
@@ -10,9 +10,9 @@ namespace API.Extensions
             return comparison.Equals(fileInfo.LastWriteTime);
         }
         
-        public static bool IsLastWriteOlder(this FileInfo fileInfo, DateTime comparison)
+        public static bool IsLastWriteLessThan(this FileInfo fileInfo, DateTime comparison)
         {
-            return comparison > fileInfo.LastWriteTime;
+            return fileInfo.LastWriteTime < comparison;
         }
     }
 }
\ No newline at end of file
diff --git a/API/Services/MetadataService.cs b/API/Services/MetadataService.cs
index 405e4c7e1..889bde5f9 100644
--- a/API/Services/MetadataService.cs
+++ b/API/Services/MetadataService.cs
@@ -33,7 +33,7 @@ namespace API.Services
        public void UpdateMetadata(Chapter chapter, bool forceUpdate)
        {
           var firstFile = chapter.Files.OrderBy(x => x.Chapter).FirstOrDefault();
-          if (ShouldFindCoverImage(chapter.CoverImage, forceUpdate) && firstFile != null && new FileInfo(firstFile.FilePath).IsLastWriteOlder(firstFile.LastModified))
+          if (ShouldFindCoverImage(chapter.CoverImage, forceUpdate) && firstFile != null && !new FileInfo(firstFile.FilePath).IsLastWriteLessThan(firstFile.LastModified))
           {
              chapter.Files ??= new List<MangaFile>();
              chapter.CoverImage = _archiveService.GetCoverImage(firstFile.FilePath, true);
@@ -53,7 +53,7 @@ namespace API.Services
              // Skip calculating Cover Image (I/O) if the chapter already has it set
              if (firstChapter == null || ShouldFindCoverImage(firstChapter.CoverImage))
              {
-                if (firstFile != null && !new FileInfo(firstFile.FilePath).IsLastWriteOlder(firstFile.LastModified))
+                if (firstFile != null && !new FileInfo(firstFile.FilePath).IsLastWriteLessThan(firstFile.LastModified))
                 {
                    volume.CoverImage = _archiveService.GetCoverImage(firstFile.FilePath, true);
                 }