Apparently, this achievement is bugged. I just went on a rampage to all 9 holds, and double-checked the stats page which confirmed I had more than a 1000 gold bounty in all 9 locations. No achievement. I'm playing on X-Box 360. I figure it has something to do with me being the head of both the Dark Brotherhood and the Thief's Guild?

If anyone can confirm this is bugged, or how to unbug it, that'd be greatly appreciated.

My statistics don't even change. The total bounty amount increases but every location shows zero. I completed College of Winterhold, Thieves Guild, Companions, Dark Brotherhood and the Civil War (sided with the Imperials) LazyTiger ^(talk) 11:15, January 5, 2012 (UTC)

It isn't bugged, you are killing too many witnesses. Which removes the bounty, leave some alive to tell the tale. Mictlantecuhtli ^(talk) 12:51, January 5, 2012 (UTC)

82.160.166.50 15:13, January 16, 2012 (UTC)I can confirm it is bugged (for me, that is).