Which app did you open? (wondering if that app does some setup that kicks the Teensy off for some reason)

The serialosc question - I asked this because sometimes when I have serialosc running I will need to manually reboot a Teensy to get it to program - what’s happening here is that serialosc is holding on to the serial port. Alternately I need to kill serialosc in order to get the Serial Monitor to show me debug.

I use launchctl unload /Library/LaunchAgents/org.monome.serialosc.plist to deactivate serialosc.

You can then reactivate it with launchctl load /Library/LaunchAgents/org.monome.serialosc.plist

I don’t think this should make a difference with MIDI, but it might be worth trying to program the teensy as MIDI only to see if the problem persists. Or also deactivate serialosc and test.

I don’t think the custom name should matter (I do this all the time now) However, if you’ve used the same custom name for the Teensy with multiple, different Teensy’s then I would suggest deleting all of those objects from AudioMIDI Setup. It should re-instantiate itself the next time you plug it it.

Edit - also if this seems Teensy specific, asking on the PJRC forum might be better than the Arduino forum.