Purchased TV Show won't sync to iPod with no error messages or action

I've ripped two seasons of a tv show onto my computer and they sync to my video iPod just fine. I purchased the only 3 episodes I wanted of a later season, but they won't sync to the iPod. It gives me no error messages about authorization, and it won't allow me to drag the files to the iPod. Do you think this is an authorization problem? This is the first macbook, iPod, and iTunes account I've ever had.

The key phrase is "iTunes includes the capability to convert SOME movies into a format that can be played on an iPhone or an iPod that supports video playback."
The original poster is a Mac user. I find QuickTime Pro to be an excellent tool on the Mac for converting video files to the touch.
There certainly are some file formats QT won't convert, but if the file he has plays in iTunes it should convert with QT Pro.

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In the course of your troubleshooting to date, Connie, have you worked through the following document?
[iTunes displays a -69 error when syncing iPod|http://support.apple.com/kb/HT1210]

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Hello jjos4,
It looks like the article below has some troubleshooting steps for this specific issue.
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Troubleshooting iTunes for Windows Vista or Windows 7 video playback performance issues
http://support.apple.com/kb/ts1718
Hope that helps,
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Hi kimcinma!
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1st - Sorry I can't help you.
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There is no Info tab in Mavericks
if you use OS X v.10.8.5 or earlier. If you use OS X Mavericks v.10.9 or later, your contacts, calendars, and other info are updated on your computers and iOS devices via iCloud. For more information, see iCloud Help at icloud.com.
iTunes 11 for Mac: Sync contacts, calendars, and other info with iPod, iPhone, or iPad

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Thanks
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Yup,
Me too...this is stupid, stupid, stupid. Just purchased my 200 (ish) mac and now I am told that my new Mac Book pro is not "authorized".
Which if my 200 macs are authorized. Can someone please tell me???
I "deauthorized" my old MBP and still told I cannot use my iPhone with iTunes.
Interesting that my old $2500 MBP, my new $3000 MBP and my $500 iPhone all cannot work cuz of some pinhead's decision to use this assorization process.
Yes I am very, very, very mad.

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Hello ThisIssue
Check out the troubleshooting assistant in the first article below. It will walk you through a few simple steps like restarting your iPod nano and changing ports on your Mac. Another troubleshooting option is to put your iPod nano into disk mode and then plug it in and see if iTunes recognizes it to be restored.
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https://www.apple.com/support/ipod/five_rs/nano2gen/
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http://support.apple.com/kb/HT1363
Restoring iPod to factory settings
http://support.apple.com/kb/ht1339
Regards,
-Norm G.

HT1212 I have previously synced my iPod with iTunes, but then I changed my computer and all the backups were there but i had to reinstall itunes and it won't sync, can you help?

I have previously synced my iPod with iTunes, but then I changed my computer and all the backups were there but i had to reinstall itunes and it won't sync, can you help?

See:
Syncing to a "New" Computer or replacing a "crashed" Hard Drive: Apple Support Communities

My laptop hard drive with my itunes library died and now itunes won't sync my ipod to the libary on the new drive without first deleting everything on my ipod. What can be done?

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Sync with new computer
https://discussions.apple.com/docs/DOC-3141

Purchased TV Show won't sync to iPod with no error messages or action

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