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Is there some step order to access last selected song/audiobook/music file?

FR955, updated to 14.20

I put Audible audiobooks split by chapter on the device, they are all correctly linked under Audiobooks category in the My Music widget. I also have paired Powerbeats Pro, however I only connect them to the watch when I run, not all the time (they are also).

I noticed a few times when I press down the music button it doesn't go directly to the last file played, but to the main menu for selecting content (Playlists/Albums/Audiobooks, etc.). I have to fiddle with pairing and unpairing for it to work. This is very important as the audiobook chapters go for 30-40 minutes each and I do not want to risk it by selecting a chapter I was listening to and have it start from the beginning.

Did anyone else experience this and if so - is there any correct sequence of actions e.g. have it connected all the time, then press the music button down, etc. that I am supposed to know in order to always correctly arrive at the last played file?