EXTEND TOOL IS CRIPPLED
This was introduced RECENTLY.
As of Version 14.3.2.(Build 42), Extend no longer honors a Tail-back-to Playhead Reverse Extend with the tail cut SELECTED. All we get is Extend from the tail of the previous clip overwriting the head of the clip operated on. Unwelcome surprise.
Also, a repeated suggestion- make it so Extend draws all clip ends on all selected tracks with media to the Playhead. This is expected behavior in Avid and Final Cut Pro, and until recently right here in Premiere.
Best, as always,