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And it seems that the WebIDE approach cannot be used if the watch does not start up properly anymore
Yes it can. :-) I was also in the situation shown in first picture above.
You need to release the button while the "=" move.
Have the WEBIDE prepared (navigate to update button via settings already (gear symbol upper right) and start update (dont take too long, there seems to be a timeout)
(Make sure that no other bluetooth device like your computer does interfere. Also make sure there is no coupling from android itself)
Thanks for the clarification. I'm using the nRF Toolbox without any success.
And it seems that the WebIDE approach cannot be used if the watch does not start up properly anymore.