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Do not want to add to the confusion but did a get info on both files and there are some differences.
file size
creation date
enable app nap option

18930

I consider for myself this problem...

I have no idea either.
But I fixed the problem by copying Teensy.app 1.50 installed in Arduino 1.8.10 to Teensyduino Catalina 10.15 version.

iMac12,2 OS X 10.13.6 (17G10021)

Catalina 10.15 version -> show package content -> double click Teensy.app
result:
18927

No errors in the console.

No, the Teensy Loader window does not appear.
There is no process "Teensy" visible in the Activity Monitor.

Previous post was referring to iMac12,2 OS X 10.13.6 (17G10021)

different system, different result:
MacBookPro8,2 OS X 10.13.6 (16G29)
The Catalina 10.15 version runs without crashing, also...

The Catalina 10.15 version runs without crashing, also after a system reboot.
I can compile but not upload.

Opening Teensy Loader...
Unable find Teensy Loader. (p) Is the Teensy Loader...

1.49 runs fine with arduino 1.8.10 as does 1.50.
But cannot install 1.49 on arduino 1.8.11 which I think is normal since arduino 1.8.11 is only supported by td1.50.


Plain 1.8.11 does not crash....

Same behaviour with 1.50-beta1.

I spoke too soon. After shutting down both macs and have a good night sleep, today arduino crashes on startup on both systems.

Process: Arduino [917]
Path: ...

MacBookPro8,2 OS X 10.13.6 (16G29)
iMac12,2 OS X 10.13.6 (17G10021)

Arduino 1.8.11 & TD1.50 is running fine on both systems.