Yea, I’m feeling your pita… I updated my test unit and it still needs me to push the buttons also, Strange as well when it finishes uploading… and Resets (well it say’s it’s resetting RTS. ) but it never does I must manually reset it to start executing the revised code download. Something is WACK!
May need to CAD up a reset & boot helmet like the Xiao nRF52840 BLE Sense Reset Button(pic2) Helemet. LOL 
more testing… may jump over to VS_code and try it there.
GL :-p