diff --git a/LightlessSync/WebAPI/Files/FileDownloadManager.cs b/LightlessSync/WebAPI/Files/FileDownloadManager.cs
index cc82d04..b8f81f2 100644
--- a/LightlessSync/WebAPI/Files/FileDownloadManager.cs
+++ b/LightlessSync/WebAPI/Files/FileDownloadManager.cs
@@ -215,6 +215,26 @@ public partial class FileDownloadManager : DisposableMediatorSubscriberBase
 
                 await Task.Delay(retryDelay, ct).ConfigureAwait(false);
             }
+            catch (TaskCanceledException ex) when (!ct.IsCancellationRequested)
+            {
+                response?.Dispose();
+                retryCount++;
+
+                Logger.LogWarning(ex, "Cancellation/timeout during download of {requestUrl}. Attempt {attempt} of {maxRetries}", requestUrl, retryCount, maxRetries);
+
+                if (retryCount >= maxRetries)
+                {
+                    Logger.LogError("Max retries reached for {requestUrl} after TaskCanceledException", requestUrl);
+                    throw;
+                }
+
+                await Task.Delay(retryDelay, ct).ConfigureAwait(false);
+            }
+            catch (OperationCanceledException) when (ct.IsCancellationRequested)
+            {
+                response?.Dispose();
+                throw;
+            }
             catch (HttpRequestException ex)
             {
                 response?.Dispose();