Q: I just bought a new iPod 8GB Nano (video). I’ve transferred or “synced” my music library up to it just fine, and I’ve even converted and transferred a couple of videos from youtube.com. However, when I went to transfer a few different TV shows that I PURCHASED from iTunes, I couldn’t. I received a message that—“TV Show” was not copied to the iPod “HG Nano” because it cannot be played on this iPod. I thought all iTunes purchased videos were supposed to be compatible with the new iPods. What do I need to do?
A: As a rule, any video content purchased from the iTunes Store via the iTunes application should play on all video-capable iPods and the iPhone, so this is not a specific compatibility issue with the iPod nano (video) in this case. Note that podcasts are a different matter, however, as these are not created by Apple, but rather by third parties and the iTunes Store simply maintains a catalog of available podcast content. Many podcasts are not released in an iPod-compatible format.
There are a couple of things that could be causing this problem, however.
Firstly, if you have never played back purchased video content on your computer prior to this, your computer, and therefore your iPod itself may not actually be authorized to play that content. iTunes will not transfer content to an iPod unless iTunes itself is also authorized to play that content back. Although this will usually result in a more specific error (that your iPod is not authorized to play that content), this is not always the case.
You can ensure that your computer is authorized by selecting Store, Authorize Computer from the iTunes menu and entering your iTunes Store user id and password. Also try to play back the video content in iTunes itself to see if it plays properly on your computer.
You should also check to ensure that your iPod is running the latest firmware. As of this writing, that would be version v1.1 for the iPod nano. Although with the exception of video rentals we are not aware of any incompatibilities with video formats and older firmware versions, it is certainly possible that there may be a limitation with certain types of content, or even simply a bug in an older firmware version preventing this from working properly.
You can check your firmware on the iPod “Summary” tab that appears in iTunes when your iPod is connected and highlighted in the left-hand source panel. The “Check for Updates” button will allow you to download a new firmware update (if one is available) and install it onto your iPod.
If the above steps still fail to resolve the problem, it’s also possible that you received a bad download. In thi scase, you can contact iTunes Store Customer Service, who can assist you further and allow you to re-download the TV show in question.