Yea, it can be pretty easy in many cases, but it is case by case depending on the destination Country and citizenship of the receiver. This also gets more comp

Yea, it can be pretty easy in many cases, but it is case by case depending on the destination Country and citizenship of the receiver. This also gets more complicated if the contractor visits the US in relation to their business with you, at which it can be argued they have transacted business within the US and now that may change the status in the US too. It also makes a difference if they are contracted as a business in their home country or an individual, as that changes the rules some too. I don't disagree about using good people wherever they are, just I am cautious on blanket statements anymore cause so many things can bite you and the rules aren't always so straight forward when you cross international boundaries. So the key is just to get some legal/tax advice so you know the best way forward. It is definitely very doable and doesn't have to cost a fortune if like you said it is a true contractor and they do not hold US citizenship or travel to the US for business and they are working from a Country the US has a treaty with. It can get more complicated if those aren't the cases. edit to add this: Also if you do business in their home Country, e.g. sell a service even over the Internet that can change the tax situation too in their home Country for you (based on their Country's laws). Another thing to always consider, doesn't rule anyone out, just something to ask about.