Mp3 file transfer not working right, not sure why

So I’ve been using my phone as my MP3 player and for the most part have had no issues with it. But for one odd thing:

Of all the music I’ve put on the phone, two songs simply won’t fully transfer over. Everything seems to work fine - i.e. no error messages, it takes a reasonable amount of time to do the transfer. I’ve tried having my media player sync the songs onto the phone (which works for everything else) and directly copying the files. Either way when I check the phone it only gives me part of each song, about the first minute or so. These are both fairly long songs, but other long songs have transferred without issue.

Can anyone think what might be causing this?

Maybe funky encoding settings, small write errors from a previous copy corrupting the mp3s, or even funny special characters in the id3 tags messing things up?

And sometimes you’re just shit out of luck. There’s one of my old Ayreon CDs I ripped years ago to iTunes that works fine on the PC, but when transferred to my iPod, it doesn’t play. Like, they show up on there and look okay, but when I select the album, it just races through all the tracks in half a second and stops -.-

If the file sizes seem right, but the playback cuts off, it’s probably not the transfer that’s at fault. Beyond that I dunno. Re-rip?