diff --git a/ApplicationView/ApplicationController.cs b/ApplicationView/ApplicationController.cs
index 80d0e829e..98c3b55a4 100644
--- a/ApplicationView/ApplicationController.cs
+++ b/ApplicationView/ApplicationController.cs
@@ -179,7 +179,7 @@ namespace MatterHackers.MatterControl
 				{
 					UiThread.RunOnIdle(() =>
 					{
-						printer.Settings.printer.Connection.Connect(false);
+						printer.Settings.printer.Connection.Connect();
 					}, 2);
 				}
 
diff --git a/PartPreviewWindow/View3D/PrinterBar/PrinterConnectButton.cs b/PartPreviewWindow/View3D/PrinterBar/PrinterConnectButton.cs
index 764f6e612..7ab342a02 100644
--- a/PartPreviewWindow/View3D/PrinterBar/PrinterConnectButton.cs
+++ b/PartPreviewWindow/View3D/PrinterBar/PrinterConnectButton.cs
@@ -32,6 +32,7 @@ using MatterHackers.Agg.Platform;
 using MatterHackers.Agg.UI;
 using MatterHackers.Localizations;
 using MatterHackers.MatterControl.PrinterCommunication;
+using MatterHackers.MatterControl.PrinterControls.PrinterConnections;
 using MatterHackers.MatterControl.SlicerConfiguration;
 using MatterHackers.SerialPortCommunication.FrostedSerial;
 
@@ -49,6 +50,9 @@ namespace MatterHackers.MatterControl.ActionBar
 		private EventHandler unregisterEvents;
 		private PrinterConfig printer;
 
+		private bool listenForConnectFailed = false;
+		private long connectStartMs;
+
 		public PrinterConnectButton(PrinterConfig printer, ThemeConfig theme)
 		{
 			this.printer = printer;
@@ -77,6 +81,7 @@ namespace MatterHackers.MatterControl.ActionBar
 			cancelConnectButton.ToolTipText = "Stop trying to connect to the printer.".Localize();
 			cancelConnectButton.Click += (s, e) => UiThread.RunOnIdle(() =>
 			{
+				listenForConnectFailed = false;
 				ApplicationController.Instance.ConditionalCancelPrint();
 				cancelConnectButton.Enabled = false;
 			});
@@ -121,6 +126,21 @@ namespace MatterHackers.MatterControl.ActionBar
 
 			printer.Connection.EnableChanged.RegisterEvent((s, e) => SetVisibleStates(), ref unregisterEvents);
 			printer.Connection.CommunicationStateChanged.RegisterEvent((s, e) => SetVisibleStates(), ref unregisterEvents);
+			printer.Connection.ConnectionFailed.RegisterEvent((s, e) =>
+			{
+#if !__ANDROID__
+				// TODO: Someday this functionality should be revised to an awaitable Connect() call in the Connect button that
+				// shows troubleshooting on failed attempts, rather than hooking the failed event and trying to determine if the
+				// Connect button started the task
+				if (listenForConnectFailed
+					&& UiThread.CurrentTimerMs - connectStartMs < 25000)
+				{
+					// User initiated connect attempt failed, show port selection dialog
+					DialogWindow.Show(new SetupStepComPortOne(printer));
+				}
+#endif
+				listenForConnectFailed = false;
+			}, ref unregisterEvents);
 
 			this.SetVisibleStates();
 		}
@@ -135,6 +155,9 @@ namespace MatterHackers.MatterControl.ActionBar
 		{
 			if (printer.Settings.PrinterSelected)
 			{
+				listenForConnectFailed = true;
+				connectStartMs = UiThread.CurrentTimerMs;
+
 #if __ANDROID__
 				if (!printer.Settings.GetValue<bool>(SettingsKey.enable_network_printing)
 					&& !FrostedSerialPort.HasPermissionToDevice())
@@ -146,7 +169,7 @@ namespace MatterHackers.MatterControl.ActionBar
 #endif
 				{
 					printer.Connection.HaltConnectionThread();
-					printer.Connection.Connect(true);
+					printer.Connection.Connect();
 				}
 			}
 		}
@@ -191,6 +214,7 @@ namespace MatterHackers.MatterControl.ActionBar
 					break;
 
 				default:
+					listenForConnectFailed = false;
 					SetChildVisible(disconnectButton, true);
 					break;
 			}
diff --git a/PrinterCommunication/PrinterConnection.cs b/PrinterCommunication/PrinterConnection.cs
index 605ad452d..29bc72e1f 100644
--- a/PrinterCommunication/PrinterConnection.cs
+++ b/PrinterCommunication/PrinterConnection.cs
@@ -42,7 +42,6 @@ using MatterControl.Printing;
 using MatterHackers.Agg;
 using MatterHackers.MatterControl.DataStorage;
 using MatterHackers.MatterControl.PrinterCommunication.Io;
-using MatterHackers.MatterControl.PrinterControls.PrinterConnections;
 using MatterHackers.MatterControl.SlicerConfiguration;
 using MatterHackers.SerialPortCommunication;
 using MatterHackers.SerialPortCommunication.FrostedSerial;
@@ -854,7 +853,7 @@ namespace MatterHackers.MatterControl.PrinterCommunication
 			}
 		}
 
-		public void Connect(bool showHelpIfNoPort = false)
+		public void Connect()
 		{
 			// TODO: Consider adding any conditions that would results in a connection failure to this initial test
 			// Start the process of requesting permission and exit if permission is not currently granted
@@ -1044,14 +1043,6 @@ namespace MatterHackers.MatterControl.PrinterCommunication
 				OnConnectionFailed(
 					ConnectionFailure.PortUnavailable,
 					$"{this.ComPort} is not available");
-
-#if !__ANDROID__
-				// Only pop up the com port helper if the USER actually CLICKED the connect button.
-				if (showHelpIfNoPort)
-				{
-					DialogWindow.Show(new SetupStepComPortOne(printer));
-				}
-#endif
 			}
 		}
 
diff --git a/SetupWizard/AndroidConnectDevicePage.cs b/SetupWizard/AndroidConnectDevicePage.cs
index 6040b47ee..24cd63fe9 100644
--- a/SetupWizard/AndroidConnectDevicePage.cs
+++ b/SetupWizard/AndroidConnectDevicePage.cs
@@ -142,7 +142,7 @@ namespace MatterHackers.MatterControl
 
 		void ConnectButton_Click(object sender, EventArgs mouseEvent)
 		{
-			ApplicationController.Instance.ActivePrinter.Connection.Connect(true);
+			ApplicationController.Instance.ActivePrinter.Connection.Connect();
 		}
 
 		void NextButton_Click(object sender, EventArgs mouseEvent)