diff --git a/RELEASE-NOTES.md b/RELEASE-NOTES.md
index 520fc7e29b8..f0316a8742f 100644
--- a/RELEASE-NOTES.md
+++ b/RELEASE-NOTES.md
@@ -43,7 +43,7 @@ END TEMPLATE-->
 
 ### Bugfixes
 
-*None yet*
+* Clients connecting to a server now always load prototype uploads after resource uploads, fixing ordering bugs that could cause various errors.
 
 ### Other
 
diff --git a/Robust.Server/ServerIoC.cs b/Robust.Server/ServerIoC.cs
index 016e8271ee1..d69eb0f6eb5 100644
--- a/Robust.Server/ServerIoC.cs
+++ b/Robust.Server/ServerIoC.cs
@@ -93,8 +93,10 @@ internal static void RegisterIoC(IDependencyCollection deps)
             deps.Register<IServerNetConfigurationManager, ServerNetConfigurationManager>();
             deps.Register<INetConfigurationManagerInternal, ServerNetConfigurationManager>();
             deps.Register<IGamePrototypeLoadManager, GamePrototypeLoadManager>();
+            deps.Register<GamePrototypeLoadManager>();
             deps.Register<NetworkResourceManager>();
             deps.Register<IHttpClientHolder, HttpClientHolder>();
+            deps.Register<UploadedContentManager>();
         }
     }
 }
diff --git a/Robust.Server/Upload/GamePrototypeLoadManager.cs b/Robust.Server/Upload/GamePrototypeLoadManager.cs
index 3cc11c17a87..e1daf963a20 100644
--- a/Robust.Server/Upload/GamePrototypeLoadManager.cs
+++ b/Robust.Server/Upload/GamePrototypeLoadManager.cs
@@ -24,8 +24,6 @@ public override void Initialize()
         base.Initialize();
 
         _sawmill = _logManager.GetSawmill("adminbus");
-
-        _netManager.Connected += NetManagerOnConnected;
     }
 
     public override void SendGamePrototype(string prototype)
@@ -50,7 +48,7 @@ protected override void LoadPrototypeData(GamePrototypeLoadMessage message)
         }
     }
 
-    private void NetManagerOnConnected(object? sender, NetChannelArgs e)
+    internal void SendToNewUser(INetChannel channel)
     {
         // Just dump all the prototypes on connect, before them missing could be an issue.
         foreach (var prototype in LoadedPrototypes)
@@ -59,7 +57,7 @@ private void NetManagerOnConnected(object? sender, NetChannelArgs e)
             {
                 PrototypeData = prototype
             };
-            e.Channel.SendMessage(msg);
+            channel.SendMessage(msg);
         }
     }
 }
diff --git a/Robust.Server/Upload/NetworkResourceManager.cs b/Robust.Server/Upload/NetworkResourceManager.cs
index 8e324a1854f..e3fbe382412 100644
--- a/Robust.Server/Upload/NetworkResourceManager.cs
+++ b/Robust.Server/Upload/NetworkResourceManager.cs
@@ -27,7 +27,6 @@ public override void Initialize()
     {
         base.Initialize();
 
-        _serverNetManager.Connected += ServerNetManagerOnConnected;
         _cfgManager.OnValueChanged(CVars.ResourceUploadingEnabled, value => Enabled = value, true);
         _cfgManager.OnValueChanged(CVars.ResourceUploadingLimitMb, value => SizeLimit = value, true);
     }
@@ -65,14 +64,14 @@ protected override void ResourceUploadMsg(NetworkResourceUploadMessage msg)
         OnResourceUploaded?.Invoke(session, msg);
     }
 
-    private void ServerNetManagerOnConnected(object? sender, NetChannelArgs e)
+    internal void SendToNewUser(INetChannel channel)
     {
         foreach (var (path, data) in ContentRoot.GetAllFiles())
         {
             var msg = new NetworkResourceUploadMessage();
             msg.RelativePath = path;
             msg.Data = data;
-            e.Channel.SendMessage(msg);
+            channel.SendMessage(msg);
         }
     }
 }
diff --git a/Robust.Server/Upload/UploadedContentManager.cs b/Robust.Server/Upload/UploadedContentManager.cs
new file mode 100644
index 00000000000..3bea743a71d
--- /dev/null
+++ b/Robust.Server/Upload/UploadedContentManager.cs
@@ -0,0 +1,28 @@
+using Robust.Shared.IoC;
+using Robust.Shared.Network;
+
+namespace Robust.Server.Upload;
+
+/// <summary>
+/// Responsible for sending uploaded content to clients when they connect.
+/// </summary>
+internal sealed class UploadedContentManager
+{
+    [Dependency] private readonly IServerNetManager _netManager = default!;
+    [Dependency] private readonly GamePrototypeLoadManager _prototypeLoadManager = default!;
+    [Dependency] private readonly NetworkResourceManager _networkResourceManager = default!;
+
+    public void Initialize()
+    {
+        _netManager.Connected += NetManagerOnConnected;
+    }
+
+    private void NetManagerOnConnected(object? sender, NetChannelArgs e)
+    {
+        // This just shells out to the other managers, ensuring they are ordered properly.
+        // Resources must be done before prototypes.
+        // Note: both net messages sent here are on the same group and are therefore ordered.
+        _networkResourceManager.SendToNewUser(e.Channel);
+        _prototypeLoadManager.SendToNewUser(e.Channel);
+    }
+}
diff --git a/Robust.Shared/Upload/NetworkResourceUploadMessage.cs b/Robust.Shared/Upload/NetworkResourceUploadMessage.cs
index 7b7021b0820..0e7c62ff30f 100644
--- a/Robust.Shared/Upload/NetworkResourceUploadMessage.cs
+++ b/Robust.Shared/Upload/NetworkResourceUploadMessage.cs
@@ -8,8 +8,7 @@ namespace Robust.Shared.Upload;
 
 public sealed class NetworkResourceUploadMessage : NetMessage
 {
-    public override NetDeliveryMethod DeliveryMethod => NetDeliveryMethod.ReliableUnordered;
-    public override MsgGroups MsgGroup => MsgGroups.Command;
+    public override MsgGroups MsgGroup => MsgGroups.String;
 
     public byte[] Data { get; set; } = Array.Empty<byte>();
     public ResPath RelativePath { get; set; } = ResPath.Self;