iOS app on real iPad can't connect to the debugger

Airplane mode may be the culprit. On-device debugging does use networking over USB and it could be that Airplane mode interferes with that.

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Oh, good catch! That’s the issue, indeed.
And I can reliably replicate it (with airplane mode, won’t work, without, it works). Would be nice if it figured in the documentation.

A big thank you, Greg!

I have to admit that when I wrote all of that code last year, I never imagined that someone would try that. Glad you got it working.

You should file a bug report about that.