(i am not fully understood what happens there, but here some thought which might be useful).

��About that popup:

��- if its a warning, then you can see it in interactive mode.

in headless mode all warnings are ignored and program just continues to run.

This is equivalent as if user pressed 'proceed' when he sees warning.

If you don't want to proceed at such point, then you should throw an error instead of warning,

then in headless mode the process abort and quit, and as result, integration will fail.

And of course, you can do even smarter things like:

Smalltalk isInteractive ifTrue: [ self showWarning ] ifFalse: [ self throwError ].

--
Best regards,
Igor Stasenko.