It's hard to reproduce and seems like a race condition, but in one of 20 runs I could follow the steps:

• create Console Application from template
• without adding breakpoints or disabling 'Run in Terminal' start debugging
• as soon you think inferior is up and running hit 'Stop Debugger'
  • debugging finishes
  • if now the ProgressIndicator is not triggered start debugging again

Note: might be that the log gives a hint... (attached debug.log and the last entries of the command log left to debug log)