So I joined this forum specifically to ask this question. My roommate and I both play Skyrim together and the further we get into the game, the more this problem starts to come up.

We both have our own game files. I'm a Nord (Knutsac) and he's an Imperial Mage (Jaikobs).

We're losing our game files.
Now, I know this isn't an 'xbox' problem because last night my roommate saved 3 different files to make SURE he didn't lose his saved file. I just loaded mine and we were thinking maybe we had too many files and maybe it wasn't saving them properly. I accidentally (somehow) saved over my roomie's last file, but that's okay, he has 3.
So I leave Cidna Mines and it autosaves over his second copy of his save file.

At this point, we're both really confused. I tell him to let me kill the Forsworn so I don't jump into the file in battle and then he can resave his stuff. I finish the battle and I go to save it and his THIRD copy of the saved file is gone.

the both of us are really fucking confused right now.
anyone have an idea of what's going on?

Thanks so much, everyone
Zimothy