diff --git a/src/csharp/Meadow/MeadowDeployer.cs b/src/csharp/Meadow/MeadowDeployer.cs
index 616469a..236b6c0 100644
--- a/src/csharp/Meadow/MeadowDeployer.cs
+++ b/src/csharp/Meadow/MeadowDeployer.cs
@@ -48,19 +48,15 @@ public async void Dispose()
             }
         }
 
-        public async Task<DebuggingServer> Deploy(string folder, int debugPort = -1)
+        public async Task<IMeadowConnection> Deploy(string folder, bool isDebugging)
         {
-            var isDebugging = debugPort > 1000;
-
-            await Task.Run(async () =>
-            {
                 if (meadowConnection != null)
                 {
                     meadowConnection.FileWriteProgress -= MeadowConnection_DeploymentProgress;
                     meadowConnection.DeviceMessageReceived -= MeadowConnection_DeviceMessageReceived;
                 }
 
-                meadowConnection = await MeadowConnectionManager.GetConnectionForRoute(PortName);
+                meadowConnection = new MeadowConnectionManager(new SettingsManager()).GetConnectionForRoute(PortName);
 
                 meadowConnection.FileWriteProgress += MeadowConnection_DeploymentProgress;
                 meadowConnection.DeviceMessageReceived += MeadowConnection_DeviceMessageReceived;
@@ -106,15 +102,7 @@ await Task.Run(async () =>
                 {
                     meadowConnection.FileWriteProgress -= MeadowConnection_DeploymentProgress;
                 }
-            });
-
-            // Debugger only returns when session is done
-            if (isDebugging)
-            {
-                Logger.LogInformation("Debugging application...");
-                return await meadowConnection?.StartDebuggingSession(debugPort, Logger, CancelToken);
-            }
-            return null;
+                return meadowConnection;
         }
 
         private async void MeadowConnection_DeviceMessageReceived(object sender, (string message, string source) e)
diff --git a/src/csharp/MonoDebugSession.cs b/src/csharp/MonoDebugSession.cs
index 40d0625..9ce5dfd 100644
--- a/src/csharp/MonoDebugSession.cs
+++ b/src/csharp/MonoDebugSession.cs
@@ -219,18 +219,23 @@ public override async void Launch(Response response, dynamic args)
 			try {
 				
 				var logger = new DebugSessionLogger(l => Log(l));
+
+				var isDebugging = launchOptions.DebugPort > 1024;
 				
 				// DEPLOY
 				meadowDeployer = new MeadowDeployer(this, logger, launchOptions.Serial, ctsDeployMeadow.Token);
 
-				meadowDebuggingServer = await meadowDeployer.Deploy(fullOutputPath, launchOptions.DebugPort);
+				var meadowConnection = await meadowDeployer.Deploy(fullOutputPath, isDebugging);
 
-				if (meadowDebuggingServer != null)
+				if (isDebugging)
 				{
+					var meadowDebuggingServerTask = meadowConnection.StartDebuggingSession(launchOptions.DebugPort, logger, ctsDeployMeadow.Token);
+
 					_attachMode = true;
 					Log($"Connecting to debugger: {address}:{launchOptions.DebugPort}");
 
 					Connect(IPAddress.Loopback, launchOptions.DebugPort);
+					await meadowDebuggingServerTask;
 				}
 
 				SendResponse(response);