Looking around here the every few weeks i do, It's seems to me a lot of us have dlc issues where it won't load offline and with the recent merge glitch, i saw some posts where people weren't even going to try without having their dlc available. I made the suggestion about having to update the licenses on the content to be able to work so i figure i'd maybe make a separate post to center the issue and possibly help more people out.

All i know was a few years ago after red-ringing or even after i upgraded my hard-disk/drive, i had those similar issues where download content didn't work offline and i wasn't happy about that. So i looked around the xbox support website and luckily found the the information about transferring digital licenses. After following the suggested steps i was able to use dlc offline and pretty much been steady since.

Suggestions:
Note If you are certain that you know the dlc has not been working since you upgrade xbox or got a different xbox you may want to jump right to license transferring

First thing i think you should try is re-downloading the dlc, i am not saying to delete the content and re-downloading but just re-downloading it with it still on the hard drive, it should only take a few seconds and you might just have refreshed the dlc.

You could also then try the whole delete and re-download and see what happens but check that you won't have to rebuy your dlc to be able to download it.

License Transferring
If both fail you may really need to preform a license transfer
Here is that link to how to do that.
HTML Code:
http://www.xbox.com/en-US/Support/LicenseMigration/Home
If anyone else want to add any other options/suggestions or want to say this worked or didn't work for them, feel-free to add on to this thread.