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When you have wi-fi debugging enabled, (MonoDevelop Preferences->Debugger->iPhone Debugger), the dialog that pops up when debugging attempts to show the port it is connecting on.
Instead, you get a ':0..'
'Waiting for debugger to connect on port 6789'
Debugging over wifi does work and I am able to receive application output after disconnecting from the USB, so the port is found at some point, it just isn't displayed.
This has been fixed in master (it's the fix in bug #4900) - now it says:
Waiting for debugger to connect...
The device must be connected with a usb cable for debugging to start. You can
unplug the cable once this dialog disappears.
i.e. no mention of a port at all.