I had an 8GB iPod Touch 1G. The home button broke, so I had it jailbroken, and then things were fine, for a while. But after a while, things stopped syncing properly. Songs I put on my iPod suddenly started showing up scrambled; they didn't skip, per se, but were totally scrambled. The song would play, then there would be a few random seconds of other parts of the song, then it would play a completely different part of the song, do it again, and then resume where it left off the first time. Sometimes, parts of songs would just be missing completely. Then photos began to scramble, too. Parts and squares of pictures would be mixed with other pictures, or just be completely blank and gray. Then the problem expanded, and it started to happen to songs and photos that had been on my iPod forever, without me having made any changes to them whatsoever. For my birthday, my sister bought me a new iPod, a 32 GB 3rd Generation Touch. I set it up as a new ipod and transferred my library to it. Today, I bought an album from iTunes, and I put it on the iPod. At least two of the songs are doing the silent thing again. I read around and found that some people had the problem fixed if they restarted their ipod or used different headphones. I've done both, and it didn't fix anything. I also checked to make sure it wasn't the files themselves; the songs play just fine on my computer. So far, I haven't run across any songs doing the scramble thing (though with over 1300 songs on my iPod, I haven't listened to every one of them yet, so I can't confirm the issue.) I checked my entire photo library, and none of those are scrambled either. I should mention that I've been using the brand new USB cable that came with the new iPod, so I know the issue doesn't lie in the cable (I had assumed there was an issue with my former iPod's USB port itself, though it would appear that may not have been the case.) So wtf is going on here? Because of the nature of the glitches, I can't even do any type of controlled experiment to nail down the source of the problems. Changes made to files don't take effect unless they're removed from the iPod and then put back onto it; but that usually takes care of the problem anyway (but with the former iPod, doing so didn't fix the other files on it.) Because of this, I can't simply sync from a different USB port or a different computer, or delete and reinstall iTunes and verify that fixes it; re-syncing alone could've been what fixed it. Apple's support site was of absolutely no use whatsoever (as usual,) and in searching, I've seen cases featuring some of these symptoms, but not all of them, and definitely not all of them involving two completely different sets of iPods, charge cables, and headphones. Does anyone have any insight on this? Or any ideas on how I could even try to narrow down the issue? Since the new iPod isn't scrambling songs or photos, I can't even tell if it's the same glitch, or just a coincidence that two of them are having similar problems. The fact that they are makes me think it's a problem with either my USB port, my computer, my copy of iTunes (though it's been updated many times and the problems have persisted,) or even if it's my firewall (for some reason, I can't sync some apps through iTunes unless I completely shut down my firewall.) If the problems would stay consistent, I could easily just try a few times, and narrow down where the problem is coming from. But since I have to completely remove and re-add the files, that method is of no use to me. I really don't want to have to inspect, remove, and re-sync every single file I ever put on the device. I don't think restoring will fix it, either (since it's now happened on two iPods.) I should mention, though, that when I first set this iPod up, I tried to update to 4.0, and ran into a fatal issue requiring me to restore. I then was stuck in a restore loop, where the restore would fail at the last second. I don't recall how I fixed it; it might've been shutting down my firewall again (if so, that would make me think all of these issues are firewall related, and if that's the case, I guess I'm just going to go without a firewall. I'm currently using the free edition of ZoneAlarm, and I've made sure all iTunes-related programs have full access to everything, but that doesn't seem to help.) Anyway, any help would be greatly appreciated. This is incredibly and ridiculously frustrating; I already feel bad that my sister bought me a $300 birthday gift, but I'll feel even worse should it turn out that my former iPod wasn't even having the problems I thought it was having. I don't know what to do, or where to even begin.