Why don't my purchases from itunes work on my iphone?

I have bought several songs and music videos with itunes on my computer they work fine on my computer but on my iphone they don't work at all. What happens is if click one it skips to next track and keeps going they won't play so wondering what to do and I bought them several years ago if that matters thanks.

I would try restoring your iphone to its factory settings (with a backup first), and then syncing it to your library.

  • What happens to the purchases I made on iTunes if my info on my iPhone gets deleted? So my phone got deleted completely not the phone just the information all of it what's happens to my purchases that I made on the App Store and iTunes do I have I re-buy everything or is there a way I can get it back for free
  • Transfer purchases from iPhone with Itunes 11? Now I want to transfer purchases from my iPhone to my PC using iTunes 11. Now I know that with iTunes 10 I could do it simply by right clicking my connected device and selecting "Transfer Purchases". How can I achieve this with iTunes 11 as the documentation from Apple is not updated to reflect recent interface changes done in iTunes 11. Thank you for your replies! Fixed. Go File -> Devices -> Transfer Purchases and way you go
  • Transfer purchases from iPhone to iTunes? I connected my iPhone to my laptop and I clicked the update option to update my software. But it shows a message saying "There are purchased items on your iPhone that have not been transferred to your iTunes library before updating this iPhone. Are you sure you want to continue?" There are a few songs from my desktop on my iPhone but I just want to continue the update. Is that going to cause a problem with my songs/iPhone/iTunes?
  • My iPhone will only transfer iTunes purchases to my computer? I went from a 3gs to a 4. I transfered my purchases to my iTunes and it only transfered my purchases. How do i transfer all my music to my computer?