diff --git a/ErsatzTV/Controllers/Api/PlayoutController.cs b/ErsatzTV/Controllers/Api/PlayoutController.cs
index 27b9f8f99..eeb29ff4c 100644
--- a/ErsatzTV/Controllers/Api/PlayoutController.cs
+++ b/ErsatzTV/Controllers/Api/PlayoutController.cs
@@ -148,25 +148,28 @@ public class PlayoutController(IMediator mediator) : ControllerBase
             }
         }
 
+        // the schedule-file update is the only step that can fail after the pre-checks,
+        // so it goes first — a rejected file must not leave DailyRebuildTime applied
+        if (hasScheduleFile)
+        {
+            foreach (PlayoutNameViewModel playout in maybePlayout)
+            {
+                Either<BaseError, PlayoutNameViewModel> scheduleFileResult =
+                    await UpdateScheduleFile(playout, request.ScheduleFile, cancellationToken);
+                foreach (BaseError error in scheduleFileResult.LeftToSeq())
+                {
+                    return error.ToErrorResult();
+                }
+            }
+        }
+
         Option<TimeSpan> dailyRebuildTime = request.DailyRebuildTime is { } t ? Some(t) : Option<TimeSpan>.None;
         Either<BaseError, PlayoutNameViewModel> result =
             await mediator.Send(new UpdatePlayout(id, dailyRebuildTime), cancellationToken);
 
-        return await result.Match(
-            Left: error => Task.FromResult(error.ToErrorResult()),
-            Right: async playout =>
-            {
-                if (!hasScheduleFile)
-                {
-                    return (IActionResult)new OkObjectResult(ToResponse(playout));
-                }
-
-                Either<BaseError, PlayoutNameViewModel> scheduleFileResult =
-                    await UpdateScheduleFile(playout, request.ScheduleFile, cancellationToken);
-                return scheduleFileResult.Match(
-                    Left: error => error.ToErrorResult(),
-                    Right: updated => (IActionResult)new OkObjectResult(ToResponse(updated)));
-            });
+        return result.Match(
+            Left: error => error.ToErrorResult(),
+            Right: playout => (IActionResult)new OkObjectResult(ToResponse(playout)));
     }
 
     private async Task<Either<BaseError, PlayoutNameViewModel>> UpdateScheduleFile(