Ipod: Sometimes my playlist stops shuffling

Factual Questions
1

On my Ipod (classic), I have a playlist of holiday songs. I go to the playlist, select a track, and then keep clicking until I get to the shuffle option (off/songs/albums) and I choose “songs.”

What I expect is that it will then shuffle through the entire playlist. But if I leave it on for several hours, at some point it decides to just stop. And then when I select a track, it just plays that one track and stops. It doesn’t go through the rest of the playlist, either in order or by shuffling.

What’s going on?

2

It is possible that it shuffles the songs and the song you’ve already started playing is in the middle of the shuffled list of songs? Hence, it just plays any songs in the shuffled list that are after the track you’ve already started?

I don’t have an iPod classic, so am not sure how to best avoid this problem. I’d say selecting the shuffle option before playing any track.

And that doesn’t explain why sometimes you play a single track and then it just stops. Just guessing.