How to manually launch Lua Debugger

In order to enable the Lua Debugger in the Simulator, you have to check the Enable Lua Debugger box in the Storyboard Simulator Configurations menu:

Normally this makes it so that once you simulate your application, the Debugger will automatically launch as well, connect to your app, and begin debugging.

However, there are scenarios where it may fail to connect to your application. This is a sort of timing issue that can be caused by a variety of factors.

Luckily, it is easy to work around. All we have to do is manually launch the debugger before simulating our application. 

First we have to change the perspective of Storyboard Designer to the Debug perspective. This will unhide the Debug Configurations dialog, which we will be needing to perform this operation. You can do this by clicking the bug icon on the top right of Designer:

Once the layout has changed, you will notice there is a new bug icon available next to the Storyboard Simulator Configurations icon:

Click this drop down and select Debug Configurations.
In this window, Right Click the Lua Attach to Application header and select New Configuration:

In your newly created configuration’s settings, simply ensure that the correct project is select under the Project header:

Once that is done, click Debug in order to launch the Debugger.

All that is left to do is to launch the Simulator as normal. The Debugger should output a message to the console stating that the connection has succeeded. 

Note: it is important that the Enable Lua Debugger option found in the Storyboard Simulator Configurations menu is turned on for this approach to work.