Submitted as Ticket #16406. A bit of a rollercoaster ride there.

Can you please capture the problem with WASAPI switching in a debug log (step 4b) and attach the log to a Support Ticket: https://www.mediamonkey.com/forum/viewtopic.php?t=86643

I was on MediaMonkey WASAPI output. Switching to MediaMonkey DirectSound output indeed solved the problem. Thanks!

Which Output Plugin are you using, and does switching Output Plugin fix the issue?

Because I have several very long classical music tracks, such as a 2.5-hour-long opera CD that I've collapsed into a single FLAC file, I have enabled bookmarking for classical music files.

If I plug in my headphones, thus causing my computer to switch output devices, MMW briefly resets the location of the playback meter to 00:00, then jumps forward again to where it remembers that I last stopped. The trouble is it doesn't update the bookmark first; it only updates it when I last paused. So if I paused the track at, say, 04:41, then resume playing and listen for an hour, then plug in my headphones - it blinks back to 04:41. The same is true for unplugging them.

As a secondary issue, when I do this the playback meter ceases to visually update. The little white circle just sits at 04:41 forever, though the track plays normally.

As a tertiary issue, if I unplug my headphones while a track is paused, it immediately starts playing. That should not happen.

I'm on Windows 11, running MMW 2024.2.1.3212.