I've been having this unusual issue lately with my Xbox and certain bits of DLC.
Typically when I start to download something, I can press B or the Guide button to send the download to the background, and then I can check on the status of the download and the queued downloads by using the "Active Downloads" entry on the Guide.
However, when I download DLC from in-game menus, if I back out while it is downloading the download seems to abort. The "Active Downloads" screen is blank, and if I go into the "Storage" view, it says the download is "Incomplete." I've been able to complete the download if I leave the Xbox turned on and don't back out of the initial status screen you get when you initiate the download, but this is inconvenient and irritating.
It seems to happen exclusively with DLC that is downloaded in-game, for instance, Borderlands 2 DLC with the Season Pass, and the Halo 4 Crimson Map Pack. Both of these aren't downloaded through the Live Marketplace, and must be chosen from in-game menus. I don't remember this issue when I was playing LA Noire, though (and I had a Season Pass for that game). I can also download or re-download items directly from the Marketplace and they end up in the "active downloads" menu with no issues.
What gives? Is there a setting I need to change, or something I can reset to get this functionality back for in-game DLC?