diff --git a/LightlessSync/PlayerData/Pairs/PairHandlerAdapter.cs b/LightlessSync/PlayerData/Pairs/PairHandlerAdapter.cs
index 82c4a94..b0f2710 100644
--- a/LightlessSync/PlayerData/Pairs/PairHandlerAdapter.cs
+++ b/LightlessSync/PlayerData/Pairs/PairHandlerAdapter.cs
@@ -1423,7 +1423,7 @@ internal sealed class PairHandlerAdapter : DisposableMediatorSubscriberBase, IPa
     private Task _visibilityGraceTask;
 
     private async Task DownloadAndApplyCharacterAsync(Guid applicationBase, CharacterData charaData, Dictionary<ObjectKind, HashSet<PlayerChanges>> updatedData,
-        bool updateModdedPaths, bool updateManip, Dictionary<(string GamePath, string? Hash), string>? cachedModdedPaths, CancellationToken downloadToken)
+     bool updateModdedPaths, bool updateManip, Dictionary<(string GamePath, string? Hash), string>? cachedModdedPaths, CancellationToken downloadToken)
     {
         var concurrencyLease = await _pairProcessingLimiter.AcquireAsync(downloadToken).ConfigureAwait(false);
         try
@@ -1577,24 +1577,37 @@ internal sealed class PairHandlerAdapter : DisposableMediatorSubscriberBase, IPa
                 RecordFailure("Handler not available for application", "HandlerUnavailable");
                 return;
             }
+            _applicationCancellationTokenSource = _applicationCancellationTokenSource.CancelRecreate() ?? new CancellationTokenSource();
 
-            var appToken = _applicationCancellationTokenSource?.Token;
-            while ((!_applicationTask?.IsCompleted ?? false)
-                   && !downloadToken.IsCancellationRequested
-                   && (!appToken?.IsCancellationRequested ?? false))
+            if (_applicationTask != null && !_applicationTask.IsCompleted)
             {
-                Logger.LogDebug("[BASE-{appBase}] Waiting for current data application (Id: {id}) for player ({handler}) to finish", applicationBase, _applicationId, PlayerName);
-                await Task.Delay(250).ConfigureAwait(false);
+                Logger.LogDebug("[BASE-{appBase}] Cancelling current data application (Id: {id}) for player ({handler})", applicationBase, _applicationId, PlayerName);
+
+                var timeoutCts = new CancellationTokenSource(TimeSpan.FromSeconds(5));
+                var combinedCts = CancellationTokenSource.CreateLinkedTokenSource(downloadToken, timeoutCts.Token);
+
+                try
+                {
+                    await _applicationTask.WaitAsync(combinedCts.Token).ConfigureAwait(false);
+                }
+                catch (OperationCanceledException)
+                {
+                    Logger.LogWarning("[BASE-{appBase}] Timeout waiting for application task {id} to complete, proceeding anyway", applicationBase, _applicationId);
+                }
+                finally
+                {
+                    timeoutCts.Dispose();
+                    combinedCts.Dispose();
+                }
             }
 
-            if (downloadToken.IsCancellationRequested || (appToken?.IsCancellationRequested ?? false))
+            if (downloadToken.IsCancellationRequested)
             {
                 _forceFullReapply = true;
                 RecordFailure("Application cancelled", "Cancellation");
                 return;
             }
 
-            _applicationCancellationTokenSource = _applicationCancellationTokenSource.CancelRecreate() ?? new CancellationTokenSource();
             var token = _applicationCancellationTokenSource.Token;
 
             _applicationTask = ApplyCharacterDataAsync(applicationBase, handlerForApply, charaData, updatedData, updateModdedPaths, updateManip, moddedPaths, wantsModApply, pendingModReapply, token);