I'm achievement-hunting right now. I'm trying to get the Master Criminal achievement, which requires I have a bounty of at least 1000 in all the holds.

But, to get this achievement, must I have nine 1000-gold bounties at one time? Or, can I go ahead and go to jail and get rid of one bounty before moving on to the next one?

I think it has to be all at once, but I'm not entirely sure. Just save then run from hold to hold stabbing civilians until you get the achievement.

it is all at once

That achievement's name makes no sense. A "Master Criminal" doesn't get bounty But i suppose it sounds better than "Master Screw-Up"

good to know i always been wondering about that achievement as well

I think the same. If you truly were a master criminal, you would not ever get caught.

Get caught? Well, no. But getting caught and having a bounty placed on you aren't the same thing. Even master criminals aren't immune to bounties (pretty sure the Grey Fox had one in Oblivion ).

The good news is you can reload afterward, so the bounties vanish (as do the atrocities).

I actually want to have my Khajiit try for this one, but without killing or hurting anyone, since he's an essentially nonviolent character. He'll have to use his fear spells on 25 people per hold.

all you really have to do is fast travel to the stables kill a guard outside the gates make sure you were saw and flee till they stop the chase,then go to another hold and rinse and repeat

Sounds like a great way to get a shield from each hold. I guess I will have to try to get this achievement.