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I worked at a big corp and we paid out randoms for a program (not bug bounty). It was an absolute minefield, people would lie to us about where they were located only for us to find out they’re in <insert sanctioned country here> and then legal tells us we have to pay them but we’re not allowed to at the same time.

Outsourcing all that mess is a great use of money.

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Yea we also handled it ourselves the first couple years but it was so painful. Literally the same thing you described happened - as well spending weeks+ how we need to file it as tax when we pay bounty to someone in Pakistan etc.

Are you in the US? You simply collect a W8 from them that you keep on file and then the payment would be counted as an expense on taxes. We do payout to hundreds o f affiliates every year and this is how we handle it, it's really not complicated. The actual payments are done via Wise batch payments which just requires their email address.

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