Ipod nano accepts itunes update - but then doesn't play the track

I have posted this problem somehwere else on this site - there's so many forums nt sure which one I should be in - hope someone here can help. I have a nano and a Dell PC Windows XP. I purchase from itunes and update ipod with no problems. I send a track that was purchased from itunes by email to my son on his pc. It's there and can play in itunes. I have deauthorised iti several times and played it in his itunes. We have updated his ipod and it shows on his ipod - BUT - it will not play - it just skips over it or defaults back to the main playlist. I have tied resetting the ipod, I have followed some advise on folder options and reset to show hidden files and then removed file SC Info.sid but it still doesn't work. Is there a different way of sharing downloaded itune tracks without so mu hassel - should I have emailed it? We are not on network. Many thanks for any help anyone can offer. SM

Hi there
Found your problem in discussions.apple.com
In this case what you can do is -
Go to Apple.com/support
In there you would be able to find a search box given
Type in this number there 303854 and click on search box
It will give you certain trouble shooting steps
Follow that and check whether it works or not
If it does not work
In that case you will have to call tech support
as there is some emerging issue going with song purchased from itunes music store

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Hello ariani,
Thank you for the details of the issue you are experiencing with Home Sharing in iTunes. I recommend the following steps for the issue you described:
4. Check your network connection
Home Sharing requires a home network with an active Internet connection. All the devices you want to use with Home Sharing need to be connected to your home network.
In addition, verify that:
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Block all incoming connections
Allow only essential services
If you use another security/firewall software on your computer or router, follow this article or contact the manufacturer or check the documentation on how to open TCP ports 123 and 3689 as well as UDP ports 123 and 5353.
6. Quit and reopen apps and iTunes
If connectivity issues persist, quit and reopen iTunes on your computer. Then, quit and reopen the apps on your iOS device.
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Restart your home network router using the method recommended in documentation from the manufacturer. This may include disconnecting the power cord for thirty seconds or more.
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Troubleshooting Home Sharing
http://support.apple.com/kb/TS2972
Thank you for using Apple Support Communities.
Best,
Sheila M.

Ipod nano and itunes update not working

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poisonserpent

Alright.
Thanks for the help.
poisonserpent

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Thanks!
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Try:
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How to put iPod touch / iPhone into DFU mode « Karthik's scribblings
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Apple Retail Store - Genius Bar

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Ipod nano accepts itunes update - but then doesn't play the track

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