https://bugs.winehq.org/show_bug.cgi?id=57804
--- Comment #2 from Dominik-Home@gmx.de --- I see and confirm the behaviour you're describing. Windows is showing the prompt after calling issue.bat, i.e. there is still a bug present in Wine but under the changed circumstances it's not that critical anymore.
I'm going to change the title and priority of this issue report.
For reference, this issue is not the root cause why PlanAhead does not start, I have to investigate a bit further to find the actual issue.