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I'd received a letter of bounty from Riverwood while searching for a job. I killed all the bandits, and I can officially claim the reward, but since I'm a wanted man, I'm unable to collect my reward. Do I have to pay my dues before receiving the bounty reward? I've been going in circles talking to all the guards to no avail.

3

In the Elder Scrolls franchise, it very much feels like there's a conditional statement set when interacting with authority. The assumed logic would be something like:

If PC has bounty and bounty region equals current region, then set default dialog for guards to "uphold the law" (criminal scum).

you're best bet is to pay the bounty, and next time - try not to get caught in your crimes :)

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