My iPhone is (seemingly randomly) deleting songs from my playlists. How do I get it to stop?

I don't know why it's happening, but it's really annoying. My first one was a 3GS, and I had made a playlist for all the songs in one CD, because i'd gotten a single and then the rest of the CD once it actually came out, and even though iTunes counted the single in completing the album they wouldn't play together without the other albums by the artist. It would work fine while i was listening to it, and then when i would leave Music for a while, usually at most a day, some of the songs would be missing! They weren't in much of an order, and both times i paid much attention to whether they were the same, a couple of songs had vanished one time and not the other, so it wasn't the same songs leaving the playlist every time. Now I'm on a 4S, and it's doing the same thing with a different playlist, which has my Purchased songs and one other one.. Both times it's done it there have only been 3 songs left, the first one the same and i think the second one, and the third one different. Normally there are 8 songs in the playlist. The first time, it was only one day after i made the playlist, and the second time it was a few days after i repaired the playlist. Both playlists mentioned were made on my iPhone, not in iTunes.
My phone is not 100% up to date, there was a new update since November, and I don't know if there's a fix there, but I don't want to download the update in case I have to put my songs back on my phone, because some of my favorites have stopped working properly in iTunes. If anyone knows a) whether the update(s) have a fix for this, or b) whether songs I've bought since the Cloud became a thing will be damaged on my iPhone if they're damaged in iTunes, I would appreciate it.

Turn off repeat.
This is covered in the manual.
iPhone User Guide (For iOS 4.2 and 4.3 Software)
Play the song, tap the screen, tap the repeat icon until it is white= off.

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