
While it started with a single update to the IDE, I cannot eliminate either software component as the culprit.

I ask here because I lack the knowledge/experience to analyze what happens between the Teensy loader and the IDE to develop a credible root cause for the problem. I tried to get some help on the Arduino forums, but so far it no one else has noticed this. It happens in a short time frame (just a second or so longer), but it is detrimental to my work (or play, whatever) here, as the shutdown/restarts are not instant. The progress bar on the IDE itself seems to be still moving after the Teensy Uploader has said it was done. There seems to be a timing issue involved. I sometimes encounter this problem on every upload, sometimes I get a random few before it happens. Of course, the UNO upload happens much faster than the ~80K code++ I am pumping out at this point.

This does not happen on a UNO (other boards not tested here).

This problem was not there in 2.0.1 and prior, but what happens is after SOME uploads to my Teensy 4.1, the "Upload" menu-item gets greyed out (and requires a program restart to clear it up).
