Probably not the most helpful answer, but I would bet the Shuffle function isn't the problem. I believe shuffle just creates a "playing now" list that should play just like any other selection of tracks. Seems like a connection issue. Maybe post some detail on your "playing to" setup. Are the speakers wireless? Is there a receiver or other DAC in the mix?
I agree it is not related to shuffle, because I experience the same issue as the OP for both shuffled and non-shuffled playlists. My setup is very simple - audio output from my computer straight to speakers/sub.
As best I can recall, I believe this began approximately 6 months ago. I start a playlist, and anywhere between 3 and 10 songs in (sometimes more), play will just stop right near the end of the track. Without any intervention by me however, MC will resume playing after approximately 10 to 15 seconds. It then replays the final 10 seconds or so of the track, and then advances to the next track and resumes playing normally. If I listen to say 50 to 100 tracks, this stop behavior right before a track ends will occur several times.
It is not related to any specific tracks, and it does not happen at the exact same point in a playlist. What is consistent is that it WILL happen at some point when I listen to 10+ songs in a row. My guess is it's related to the settings for
Track Change in Audio options - maybe the checkbox for
Do Not Play Silence? Unfortunately, there are literally thousands upon thousands of permutations amongst those settings making diagnosing the issue, if it is related to that, extremely arduous.
It may only occur 3 or 4 times in 100 tracks, but it is still very annoying. Hopefully Master Matt can solve it.