diff --git a/MareSynchronos/Managers/TransientResourceManager.cs b/MareSynchronos/Managers/TransientResourceManager.cs
index d82c61a..620f620 100644
--- a/MareSynchronos/Managers/TransientResourceManager.cs
+++ b/MareSynchronos/Managers/TransientResourceManager.cs
@@ -106,11 +106,11 @@ public class TransientResourceManager : IDisposable
         var replacedGamePath = gamePath.ToLowerInvariant().Replace("\\", "/", StringComparison.OrdinalIgnoreCase);
 
         if (TransientResources[gameObject].Contains(replacedGamePath) ||
-            SemiTransientResources.Any(r => r.Value.Any(f => string.Equals(f.GamePaths.First(), replacedGamePath , StringComparison.OrdinalIgnoreCase) 
+            SemiTransientResources.Any(r => r.Value.Any(f => string.Equals(f.GamePaths.First(), replacedGamePath, StringComparison.OrdinalIgnoreCase)
             && string.Equals(f.ResolvedPath, filePath, StringComparison.OrdinalIgnoreCase))))
         {
             Logger.Verbose("Not adding " + replacedGamePath + ":" + filePath);
-            Logger.Verbose("SemiTransientAny: " + SemiTransientResources.Any(r => r.Value.Any(f => string.Equals(f.GamePaths.First(), replacedGamePath, StringComparison.OrdinalIgnoreCase) 
+            Logger.Verbose("SemiTransientAny: " + SemiTransientResources.Any(r => r.Value.Any(f => string.Equals(f.GamePaths.First(), replacedGamePath, StringComparison.OrdinalIgnoreCase)
                 && string.Equals(f.ResolvedPath, filePath, StringComparison.OrdinalIgnoreCase))).ToString() + ", TransientAny: " + TransientResources[gameObject].Contains(replacedGamePath));
         }
         else
@@ -141,6 +141,8 @@ public class TransientResourceManager : IDisposable
             return;
         }
 
+        SemiTransientResources[objectKind].RemoveWhere(p => !p.Verify());
+
         var transientResources = resources.ToList();
         Logger.Debug("Persisting " + transientResources.Count + " transient resources");
         foreach (var gamePath in transientResources)
diff --git a/MareSynchronos/Models/FileReplacement.cs b/MareSynchronos/Models/FileReplacement.cs
index 238bdc1..4dcb8c7 100644
--- a/MareSynchronos/Models/FileReplacement.cs
+++ b/MareSynchronos/Models/FileReplacement.cs
@@ -25,7 +25,7 @@ public class FileReplacement
 
     public bool IsFileSwap => !Regex.IsMatch(ResolvedPath, @"^[a-zA-Z]:(/|\\)", RegexOptions.ECMAScript) && !string.Equals(GamePaths.First(), ResolvedPath, System.StringComparison.Ordinal);
 
-    public string Hash { get; set; } = string.Empty;
+    public string Hash { get; private set; } = string.Empty;
 
     public string ResolvedPath { get; set; } = string.Empty;
 
@@ -41,6 +41,14 @@ public class FileReplacement
         });
     }
 
+    public bool Verify()
+    {
+        var cache = fileDbManager.GetFileCacheByPath(ResolvedPath);
+        if (cache == null) return false;
+        Hash = cache.Hash;
+        return true;
+    }
+
     public FileReplacementDto ToFileReplacementDto()
     {
         return new FileReplacementDto
diff --git a/MareSynchronos/WebAPI/ApIController.Functions.Files.cs b/MareSynchronos/WebAPI/ApIController.Functions.Files.cs
index 5ac17b8..f78a562 100644
--- a/MareSynchronos/WebAPI/ApIController.Functions.Files.cs
+++ b/MareSynchronos/WebAPI/ApIController.Functions.Files.cs
@@ -187,6 +187,8 @@ public partial class ApiController
 
         if (unverifiedUploadHashes.Any())
         {
+            unverifiedUploadHashes = unverifiedUploadHashes.Where(h => _fileDbManager.GetFileCacheByHash(h) != null).ToList();
+
             Logger.Debug("Verifying " + unverifiedUploadHashes.Count + " files");
             var filesToUpload = await FilesSend(unverifiedUploadHashes).ConfigureAwait(false);
 
@@ -235,16 +237,24 @@ public partial class ApiController
             {
                 var compressedSize = CurrentUploads.Sum(c => c.Total);
                 Logger.Debug($"Compressed {totalSize} to {compressedSize} ({(compressedSize / (double)totalSize):P2})");
-            }
 
-            Logger.Debug("Upload tasks complete, waiting for server to confirm");
-            var anyUploadsOpen = await FilesIsUploadFinished().ConfigureAwait(false);
-            Logger.Debug("Uploads open: " + anyUploadsOpen);
-            while (anyUploadsOpen && !uploadToken.IsCancellationRequested)
-            {
-                anyUploadsOpen = await FilesIsUploadFinished().ConfigureAwait(false);
-                await Task.Delay(TimeSpan.FromSeconds(0.5), uploadToken).ConfigureAwait(false);
-                Logger.Debug("Waiting for uploads to finish");
+                Logger.Debug("Upload tasks complete, waiting for server to confirm");
+                var anyUploadsOpen = await FilesIsUploadFinished().ConfigureAwait(false);
+                Logger.Debug("Uploads open: " + anyUploadsOpen);
+                double timeWaited = 0;
+                const double waitStep = 1.0d;
+                while (anyUploadsOpen && !uploadToken.IsCancellationRequested && timeWaited < 5)
+                {
+                    anyUploadsOpen = await FilesIsUploadFinished().ConfigureAwait(false);
+                    timeWaited += waitStep;
+                    await Task.Delay(TimeSpan.FromSeconds(waitStep), uploadToken).ConfigureAwait(false);
+                    Logger.Debug("Waiting for uploads to finish");
+                }
+
+                if(timeWaited > waitStep)
+                {
+                    await FilesAbortUpload().ConfigureAwait(false);
+                }
             }
 
             foreach (var item in unverifiedUploadHashes)