All my songs are checked in iTunes but if I have my phone plugged in and iTunes open. If I click on my phone and then music I don't have them all checked to be synced to my phone. Could this be your problem?
My daughters 8g Touch has a weird problem. There are songs on the iPod that won't sync to iTunes on the computer. The iPod has songs on it that don't show up in iTunes, even when selecting My iPod. There are 40 or so songs affected. I've messed with sync settings and still can't get it to work. All of the songs that won't sync were downloaded from iTunes but directly onto the iPod. It's running 3.1.2 and it is jail-broken with blackra1n. I would just restore it and update to 3.1.3 but she doesn't want to lose those songs. There was a decent amount of money spent getting them. She also can't update any of her apps. We have the latest version of iTunes on the computer.
Question #1: has anybody seen anything like this before?
Question #2: is there any way of getting those songs off of the iPod so they can be saved when I restore?
Well, oddly enough, when I had her hook it up again she said all the songs were there now. I haven't seen it with my own eyes yet though. That would be very odd, considering I've fooled around with it for quite some time trying to figure out what the problem was. I'll report back when I see it for sure.
Not realizing it would wipe everything off the iPod she started to update the IOS. It restored and synced ok. She says she has all of her songs still.
The problem she still has is that when she's on iTunes it won't show how much credit she has in her account. It won't show anything at all where it's supposed to show the dollar amount. I've deactivated and reactivated the computer. She's logged out and back in a few times. We've rebooted the computer. Still nothing. We can't get a response from Apple. Anyone have a clue?
I had a similar problem when I used a PC with my iPhone. I have never jailborken my iPhone so I hope what I am about to tell you will help.
When I had a PC and my iTunes was acting funny, I always knew it was because of the PC and the iTunes not getting along. I eventually had to completely uninstall iTunes and then reinstall it to get it to work properly. I think that is your best move. Uninstall iTunes completely, you won't loose your music or videos. U might have to put any special settings you had in iTunes back, but that'll be it. It sounds like your best bet is to uninstall this copy of iTunes, as it is probably corrupted and redownload and install a fresh copy from the Apple web site.
Now, I can't stress this enough, there is a particular way to uninstall iTunes to be sure you get it all out. Call the Apple 1-888-659-5840 select 3 for Tech support and follow the promps from there. When you get someone on the phone, tell them what your problem is and ask them to walk you through uninstalling iTunes on your PC.
I had unauthorized it and reauthorized it several times without success. I also tried the Transfer Purchases. It all of a sudden synced all of the songs one day on it's own. Perhaps it was a result of one of the above. I still think it was an issue with having an older OS (3.1.2) and being J/B. She's running IOS4 now and has all of her songs. I'm not going to J/B it again. The only thing she misses, because it's a gen1 Touch, is being able to change her desktop background. But she can live with it.