Read through the administrative rulings here to get a feel for the general approach FinCEN takes on these issues: http://www.fincen.gov/statutes_regs/rulings/

Read through the administrative rulings here to get a feel for the general approach FinCEN takes on these issues: http://www.fincen.gov/statutes_regs/rulings/ http://www.fincen.gov/statutes_regs/rulings/ If you read through those rulings, you'll see that FinCEN takes a very broad view on exchanges of value falling into the category of money transmission. Also, read through their new stringent guidelines for sellers of gift cards (sellers of prepaid access). Here's a good summary: http://www.dorsey.com/EU_giftcard_121211/ http://www.dorsey.com/EU_giftcard_121211/ In my case, I was planning on both buying and selling gift cards (digitally, for a mobile frontend to display barcode). My best hope was to be considered a seller of prepaid access, which brought some hope because the strict KYC guidelines didn't kick in until $1000, if I recall correctly. However, since I bought and sold, I was pretty sure that FinCEN would instead consider me a money transmitter, whose KYC requirements start at $0. It's totally possible for these kinds of businesses to fly under the radar for years, and never be affected. But the moment some ambitious bureaucrat learns about a project like this and decides to made a federal case of it (literally), or some kid's arrested for possession of marijuana who moved money through this type of business, then it's misery for everyone on the receiving end.