17 Jan 2016 16 Jan 2016 17 Jan 2016
From what I learned an update broke the saving on the playlist. To work on this achievement little by little. You can do a workaround with the disc version. Take your console offline and uninstall the game. Then, reinstall the game and play it offline. I have tested it and it doesn't send you back to the second level of halo ce. I am on Cairo station of halo 2 and I can resume it. The bad news of this solution is that I think that when you finish the playlist. It will give you the achievement offline so no time stamp. I'm not 100% sure about the time stamp thing unless it glitches with the achievement popping. If it does glitch, which for me I'm hoping it does just simply reconnect to Xbox live and it should give it to you.
Update: As of January 16th 21:40 eastern time USA I was able to get the achievement with a time stamp:)