I'm just starting the civil war on the side of the stromcloaks. And to make it feel a bit more realistic i want gain high bounties at all the holds that are controlled by the Empire. However, Post Civil War, after those Holds are controlled by the stromcloaks i don't want to owe a 20,000 gold bounty for acts of war.

Thus, my question is: If i get a bounty in a hold that was controlled by the Empire, will the bounty still be there after i eventually gain control of it with my stormcloaks?

Really, the game should automatically give you bounties in those Holds that are now your enemies of once you start the civil war. The game is too forgiving on so many levels, and it would be so much more interesting if it was like this. However, in correcting this problem, i don't want to get punished in the end by having to pay a bounty to my allies for acts of war on our enemies.

You lose the bounty when it switches sides.

The bounty will be gone.

ty