IPod to PC sync not working

I have both a 3rd generation iTouch and a 5th generation Nano and I can not sync items (audio or video files) from either unit to my iTunes page. I can sync from PC to iPod, though my understanding is that files should move seamlessly both ways right? This is very frustrating, and I am thinking because it is happening to both iPods that perhaps something is not set right (or did not download right) in iTunes? Thank you in advance for any insight.

iTunes will only give you the option to copy your iTunes Store purchases directly from an iPod to the computer, you'll find details in this article: Copying iTunes Store purchases from your iPod or iPhone to a computer
For everything else (music from CDs, other downloads etc) there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod. You'll find that they have varying degrees of functionality and some will transfer movies, videos, photos, podcasts and games as well. You can read reviews and comparisons of some of them here:
iTunes & iPod software
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
A selection of iPod to iTunes utilities:
TuneJack Windows Only (iPhone and iPod Touch compatible)
SharePod Windows Only (iPhone and iPod Touch compatible)
iPod2PC Windows Only
iDump Windows Only
YamiPod Mac and Windows
iPod Music Liberator Mac & Windows
Floola Mac & Windows
iPodRip Mac & Windows (iPhone and iPod Touch compatible)
iPod Music Liberator Mac & Windows (iPhone and iPod Touch compatible)
Music Rescue Mac & Windows (iPhone and iPod Touch compatible)
iGadget Mac & Windows (iPhone and iPod Touch compatible)
iRepo Mac & Windows (iPhone and iPod Touch compatible)
iPod Access Mac & Windows (iPhone and iPod Touch compatible)
TouchCopy Mac & Windows (iPhone and iPod Touch compatible)

Similar Messages

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    - Make an appointment at the Genius Bar of an Apple store. You likely have a bad headphone jack
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    my ipod nano 1g is not working, it will be replaced?

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    OK OK OK
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  • The earphone port on my ipod touch 4 does not work anymore, will I need to send it in for repairs?

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    A third-party place like this one is less expensive.  Google for more places.
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