Car: 2017 Honda Civic Hatchback
Phone: Samsung Galaxy Note 9 - Stock ROM
Poweramp version: 3.0 build 856
I typically listen to very long DJ sets (think 4+ hour long MP3s) in the car when I'm driving to and from work. The commute is only 20-25 minutes, so I obviously can't listen to the whole set in one drive.
Something I've noticed is that, after a few drives, the audio playback does not match the timestamp in the UI. You can definitely tell by the "end" of the track, when audio playback continues while the UI reports that the song has finished (4:00:00/4:00:00 for a 4 hour set). I don't immediately notice it because I listen to a lot of trance; it takes me a few more drives to realize that I've listened to that particular section. I don't know how long of a set you would need to actually trigger this, but it usually happens around 1.5-2 hours in.
If you need an example of what should trigger it: