I’ve used it recently on IDE 1.8.19 under Windows. (I’ve never migrated to 2.x because portable mode isn’t implemented: the issue raised over 5 years ago is locked for further comments with a dev comment that it’s “low priority” - now
that’s abandonware

)
The installation instructions given in the ReadMe should work for IDE 1.x - have you tried that? It should give the extra menu options, use a slightly different loading procedure (which calls the standard Teensy loader so you still see it happening), and pop up a debug window after the Teensy reboots.
If the Teensy doesn’t reboot properly (USB doesn’t enumerate) then the debug window doesn’t appear, and the IDE gives a message. If using dual serial then the ports can sometimes be named the wrong way round, which causes gdb not to attach to the remote, but at least it’s started - doesn’t sound like this is your issue, though.
There does seem to be an outstanding issue with Teensy startup code which causes it to crash very early. I usually provoke it when trying to debug a sketch using the Audio library; typically it hasn’t shown up with simple sketches but there’s no obvious reason for it one way or the other, so I guess it could do so. I’ve put in
PR#673 which is a reliable fix for me - on the comments Paul said he’d committed a fix, but that’s not working for me. The fix is simple, changing the optimisation level for
reset_PFD()
in cores/teensy4/startup.c thus:
C++:
__attribute__((optimize("O2")))
FLASHMEM void reset_PFD()
I’ve definitely seen the red flash when the debugger has been stopped at a breakpoint for a while.
It‘s a good test to turn on the LED, wait for Serial, output and flush a message, turn the LED off, and only then execute
halt_cpu()
; this tells you quite a lot about whether your Teensy has started and which port is which.