diff --git a/DeepDrftCms/Pages/Tracks/TrackNew.razor b/DeepDrftCms/Pages/Tracks/TrackNew.razor
index 1f5c864..11f38a4 100644
--- a/DeepDrftCms/Pages/Tracks/TrackNew.razor
+++ b/DeepDrftCms/Pages/Tracks/TrackNew.razor
@@ -155,8 +155,8 @@
         }
         catch (Exception ex)
         {
-            Logger.LogError(ex, "CMS upload failed");
-            _errorMessage = $"Upload failed: {ex.Message}";
+            Logger.LogError(ex, "Upload failed in TrackNew");
+            _errorMessage = "Upload failed. Please try again.";
         }
         finally
         {
diff --git a/DeepDrftContent/Controllers/TrackController.cs b/DeepDrftContent/Controllers/TrackController.cs
index 767af0e..2bb7d59 100644
--- a/DeepDrftContent/Controllers/TrackController.cs
+++ b/DeepDrftContent/Controllers/TrackController.cs
@@ -138,7 +138,8 @@ public class TrackController : ControllerBase
         [FromForm] string? artist,
         [FromForm] string? album,
         [FromForm] string? genre,
-        [FromForm] string? releaseDate)
+        [FromForm] string? releaseDate,
+        CancellationToken cancellationToken)
     {
         _logger.LogInformation("UploadTrack called: trackName={TrackName}, artist={Artist}, size={Size}",
             trackName, artist, wav?.Length);
@@ -184,7 +185,7 @@ public class TrackController : ControllerBase
                 bufferSize: 81920, useAsync: true))
             await using (var uploadStream = wav.OpenReadStream())
             {
-                await uploadStream.CopyToAsync(tempStream);
+                await uploadStream.CopyToAsync(tempStream, cancellationToken);
             }
 
             var entity = await _trackService.AddTrackFromWavAsync(
diff --git a/DeepDrftWeb/Controllers/CmsUploadController.cs b/DeepDrftWeb/Controllers/CmsUploadController.cs
index 20fb571..2bc617f 100644
--- a/DeepDrftWeb/Controllers/CmsUploadController.cs
+++ b/DeepDrftWeb/Controllers/CmsUploadController.cs
@@ -67,10 +67,10 @@ public class CmsUploadController : ControllerBase
             return BadRequest("artist is required");
         }
 
-        var apiKey = _configuration["ContentApi:ApiKey"];
+        var apiKey = _configuration["DeepDrftContent:ApiKey"];
         if (string.IsNullOrWhiteSpace(apiKey))
         {
-            _logger.LogError("ContentApi:ApiKey is not configured");
+            _logger.LogError("DeepDrftContent:ApiKey is not configured");
             return StatusCode(500, "Content API key is not configured");
         }
 
@@ -118,8 +118,16 @@ public class CmsUploadController : ControllerBase
             if (!response.IsSuccessStatusCode)
             {
                 var body = await response.Content.ReadAsStringAsync(cancellationToken);
-                _logger.LogWarning("Content API rejected upload: {Status} {Body}", (int)response.StatusCode, body);
-                return StatusCode((int)response.StatusCode, body);
+                var statusCode = (int)response.StatusCode;
+                if (statusCode >= 500)
+                {
+                    _logger.LogError("Content API returned {Status} for upload of {TrackName}: {Body}", statusCode, trackName, body);
+                    return StatusCode(statusCode, "Upload failed on the content server. Please try again.");
+                }
+
+                // 4xx: body is user-friendly validation text from DeepDrftContent — relay as-is.
+                _logger.LogWarning("Content API rejected upload: {Status} {Body}", statusCode, body);
+                return StatusCode(statusCode, body);
             }
 
             TrackEntity? unpersisted;
diff --git a/DeepDrftWeb/appsettings.json b/DeepDrftWeb/appsettings.json
index 113f28f..6b30219 100644
--- a/DeepDrftWeb/appsettings.json
+++ b/DeepDrftWeb/appsettings.json
@@ -12,7 +12,7 @@
   "ApiUrls": {
     "ContentApi": "http://localhost:12777/"
   },
-  "ContentApi": {
+  "DeepDrftContent": {
     "ApiKey": "REPLACE_IN_ENV"
   },
   "ForwardedHeaders": {