Thanks for starting this post. I use a Juicebox 40, so I also have the j1772 adapter in use.
1) The first time I unplugged, they both came out at once. Yay
2) The second time, I unplugged the J1772 and forgot I had a tesla, so had to manually pull the adapter our.
3) The third time, I unplugged the J1772 and the adapter would not come out. I had to use the app to “unlock the charge port” and it tried to close the door, make the clicking sound as it was blocked, then I was able to pull out the adapter.

I definitely need to figure out a method to have it work the first time every time. Opening a door in order to do that will get old quick.