Xbox 360 - DLC doesn't work on one Console with both Profiles.

Okay so, My boyfriend and I share an xbox 360 console. Its our main console in our living room. He had money on his account so I went ahead and downloaded the dlc for kingdom of keflings (lame i know, but i enjoy it). When it was all done downloading I went
to go play it on my profile with his signed in as well and it keeps telling me that I dont have it. I went through and did a license transfer to the console and it still tells me that I can't do it, or it doesnt show up. I've tried re-downloading it and still
nothing. It shows up on his but not mine.. Which is weird because we play COD Ghosts together and anything he downloads on there, I can use as long as he's signed in.. I've even tried turning it off and turning it back on to see if it would work.. and still
nothing.

Has Xbox changed how this works? or is it some glitch that I have to wait on to be fixed?

Would be helpful if I could get some answers..

:)

 

DLC Problem

I was wondering if anyone could help me out with a problem I have getting DLC to work on my brother's profile. I recently bought a new xbox 360 and, using a USB stick, moved all the Game Data, Save Data, DLC, etc from my old Xbox to my New one. The problem
is that the DLC worked for both my account AND my brother's account (both are Xbox Live Gold) on the old Xbox, but now it only works on my account on the new xbox. I tried looking online, but I only really gathered that it had something to do with DRM and
I might have to redownload everything. I was wondering if there was a way to get my DLC to work for both accounts on my new Xbox without having to redownload everything. So, to sum it up:

DLC used to work for Profile A and Profile B on old Xbox.

DLC now only works for Profile A on new Xbox.

 

My DLC will not work.

I have just recently purchased a new Xbox 360 because my old one had broken. I originally had a profile called "insanechipmunkz", but now i use a different one. I use now "" and "Altomphion" for my gamertags. Anything that I downloaded on one
profile doesn't work on the other. I did download the DLC on the other Xbox, but even the DLC that I downloaded on the new Xbox doesn't work. I tried the License Migration thing but that still didn't work. The problem is mainly with Rock Band DLC, but other
games like Guitar Hero and Halo do this too.

 

It's been awhile since I've worked with Xbox 360, but from what I remember the ability to share DLC between profiles varied, it was up to the developer if they wanted to allow The games will always work that way, as long as the console you're playing on
has the primary license for the game (that's when the license transfer would come into affect).

You may get a more informative response if you check with the Xbox 360 forums.