Bug? IDE debugging multiple apps concurrently

I have two apps that I am debugging simultaneously.

App 1 is a Non-UI app designed to accept TCP sockets and process requests. This app is always started first for debugging.

App 2 is a UI app designed to make connections to the App 1. This is where the issue begins.

What is happening when I attempt to debug App 2 is that I have to Run App 2 three times before the UI is started.

Attempt 1
The app compiles and nothing else happens. I do see the following...


Attempt 2
The app compiles but this time the debug windows are added to the IDE along with the same log messages from Attempt 1. Shortly after I get an error message popping up staing that the IDE was not able to connect.


Attempt 3
The app compiles, I see the same log messages from Attempt 1, the debug windows appear (as from Attempt 2) but the app now starts. The logs now also show the following


If I start App 1 in release mode so that it's not connected to the IDE Debugger then App 2 will start normally as expected.