Newly Purchased iTunes Song Disappears from Shuffle After Disconnecting

Twice now I have purchased a song, have trouble getting it to my Shuffle. when I do, once I disconnect it from my PC, it disappears.
Action Taken to Resolve:
I have replaced the hardware (new Shuffle from HP)
Microsoft has helped me uninstall & reinstall iTunes twice, getting it to work; now problem is back!
OK Apple - the ball in in your court! I've tried everything else!!!!

swexan,
Do you have any other drives, or network shared folders you access from this machine? Sometimes Windows will confuse the drive letter and device ID's for drives and copy things to the wrong location.
Is the size of the iPod Shuffle being reported correctly in iTunes?
You may want to look at this knowledge base article:
http://docs.info.apple.com/article.html?artnum=93499

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Hello,
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crichton007 wrote:
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Apparently, something went way wrong SOMEWHERE, SOMEHOW... and now I'm afraid of losing ALL MY MEDIA considering I have NO ITUNES ON MY LAPTOP! I followed all appropriate steps found in trouble shooting, when I reinstalled iTunes though, the reinstalled music on my pc was a handful of songs that were triplicates, even listed some five TIMES! And maybe a total of 20-25 different songs, a fraction of what I had initially!
*N OVER MY HEAD! my iTunes library disappeared from my PC, TS said uninstall then reinstall, before I reinstalled though my ipad 2 said NOT ENOUGH MEMORY as I tried to update 1 app. What do I do now?

1, you can't at the moment, though with iOS 5 in the Autumn, from http://www.apple.com/ios/ios5/features.html#photos :
Even organize your photos in albums — right on your device
2, by removing it from you synced from and re-syncing. Only photos taken with the iPad, copied to it via the camera connection kit, or saved from emails/websites etc can be deleted directly on the iPad (either via the trashcan icon in the top right corner if viewing the photo in full screen, or via the icon of the box with the arrow coming out of it in thumbnail view)
3, the location of the photos that you synced to the iPad should be listed on the iPad's Photos tab when connected to your computer's iTunes.
4, you can copy the photos from your iPad to your computer : http://support.apple.com/kb/HT4083 . You should also be able to delete them from the iPad as part of the transfer process to your computer, and it's then your choice whether to add them to your sync photo list so as to copy them back to the iPad. Copying them to your computer would allow you to organise them into folders and therefore be able to sync them back into separate albums.
5, I don't use Dropbox either. There are some third-party browser apps in the iTunes App Store that allow you to download pages so that you can view them when offline e.g. Atomic Web (the whole page is saved within Atomic Web, it doesn't place a photo into the Photos app)
6, deleting content should help. If you remove an app from your iPad then you also remove the content that it's got on the iPad - so if you then decide to reinstall it back onto the iPad then you will need to manually add back any content that you want in it. None of the Apple built-in apps (including Photos) can be removed from the iPad

Newly Purchased iTunes Song Disappears from Shuffle After Disconnecting

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