Unable to Download Previously Purchased Content

With the recent update to the Xbox 360 to allow for larger external storage I purchased an external HD, and began the process of re-downloading all of my older content. I have run into issues with 2 different games so far, but worry there will be more.
The first is Lara Croft and the Guarding of Light which my last achievement shows a completion of the story on 9/30/2012. The game was a Games with Gold on 1/16/2014 so I would have acquired at some point regardless of having paid for it or purchased during
the give away. When I go through my account history through xbox.com there is just the generic place holder of points purchased for the relevant date/time no longer showing any actual purchase history. When I access directly the xbox download history on
the console there is no marked purchase for the content, and the store page asks me to purchase the content all over again.

The second game I have been having an issue with has been Halo 4. Going to the marketplace through either xbox live or the menu within the game indicates that I do not own the season pass to download the map packs. However, when I go to purchase history
in the console I am able to re-download all 3 map packs as well as all the content that came along with the limited edition version I purchased at launch (Skins, Emblems, Avatar gear can all be downloaded again). For this game I have a 100% completion across
base and DLC so there is no way I could have not purchased the content.

On my end I cleared the system and store cache data to no effect, checked all avenues of purchase history to try to find my missing content, and even attempted a license transfer to the console again just to make sure that something didn't get lost in the
translation. Any assistance would be appreciated since now I am worried about other content I have purchased digitally being removed from my purchase history forcing me to repurchase.

:)

 

Migrating accounts

Hello,

We're unable to tell you what content will be available for you depending on what country you decide to migrate to. You do keep your gamerscore, and your gamertag. The only thing that changes is the country/region and your ability to be able to re-download
previously purchased content. But, as I said we'd be unable to directly tell you what you would be able to re-download or not.

Sorry.

 

Please don't let it be true!

@Frontport.

support.xbox.com/.../download-content

You need to do a license transfer to get access to some of your previously purchased content.

 

Generally nothing gets removed from your download history. If it's not listed, it usually means it was purchased on a different account. If you're 100% sure you purchased it with this account and it's not showing in your download history, you would need
to contact support and see what they can do. 1-800-4my-xbox if you're in the US/Canada or
support.xbox.com/contact-us