HT201272 I had to reinstall windows 7 on my computer and never backed up iTunes on a external drive. Two things, first, I have all my music on my iPod (which a lot of it was on cd's that I no longer own),if I back up my iPod to iTunes will I lose all that

I have all my music on my iPod ( which includes music from all my cd's that I bought from retail stores and I no longer have), if I back it up to ITunes will I lose it even though it is in iCloud ?
Also, I can not find any of my audio books that I bought and downloaded thru iTunes, why?

For music purchased from iTunes you might be able to re-download it via the Purchased link under Quicklinks on the right-hand side of the iTunes store home page on your computer's iTunes.
For music copied from CDs, and for purchases if you can't redownload them, then there are some programs listed half-way down this page which should be able to copy them back from your iPod : https://discussions.apple.com/docs/DOC-3991
There is also this page for syncing to a new computer (which, in effect, you will be) : https://discussions.apple.com/docs/DOC-3141
Where are you looking for the audiobooks ? They are currently a one-time only download from the store, so they won't appear in the Purchased tab for redownloading. If you don't have them on a backup nor on your iPod (if they are on your iPod then File > Devices > Transfer Purchases should copy them back to your computer's iTunes), then if they are still in the store then you can try contacting iTunes Support and see if they will grant you a redownload : http://www.apple.com/support/itunes/contact/ - click on Contact iTunes Store Support on the right-hand side of the page, then Purchases, Billing & Redemption

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