Purchased Music Videos won't Sync to iPod?

I have the exact same issue, I have purchased 20 music videos that wont sync, when I look at the file shows protected MPEG-4 file, all my others show purchased MPEG-4 file, and the same as crystalrose22, I have tried converting the files to strip the drm and reinstalling itunes now on version 12.2.2.25.

So far I have almost £40 of videos that I cannot watch unless I ferry my Mac-book pro around with me! This has only started with videos purchased from the beginning of July 2015.

Does anyone have any ideas

This appears to be a bug introduced with iTunes 12.2. If you download the same video files using an older version of iTunes they will be purchased or protected as appropriate, but can be transferred to your devices.

tt2

I have tried version 12.2.1 this gives the same results as previous and version 12.1.2 will not open without upgrading to a newer version.

To use an older version of iTunes you also have to roll back your library file as described in Empty/corrupt iTunes library after upgrade/crash. Weirdly it seems that 12.2.2.25 isn't visibly applying the Fairplay Version 2 DRM on a Windows machine that I'd previously rolled back to 12.1.2.27, but it is on my Mac that hasn't ever been downgraded. Once I try to sync however the redownloaded videos won't go. I'll roll back to 12.1.2.27 and test again, but it was successful when I tried it a few days ago. See Re: Fairplay 2 music videos won't sync to iPod classic.

You could install the older build of iTunes (see the Older versions section of Troubleshooting issues with iTunes for Windows updates for download links), use the shift-start-iTunes method to make a new empty library simply for the purpose of downloading the videos, copy these into the Automatically Add to iTunes folder of your main library, reinstall the current build, then shift-start-iTunes to reconnect to the main library where your videos will have been added.

tt2

Thanks for the info it's starting to get a bit complicated for my abilities, plus I have just realised this is for windows itunes.

I have a new MBP comming next week so it should have an older version on and I will see what I can do with that.

Again thank you for your help.

I've just double-checked and iTunes 12.1.2.27 downloads videos that will go onto an older clickwheel iPod nano (so presumably any non-iOS device). Anything I download with 12.2.x won't go on.

tt2