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Any idea what proportion of merchants using Stripe's bitcoin handling actually do this automatic refunding?

You only need to find one. Or sign up as a Stripe customer yourself -- they'd have a hard time proving that it was you who made the overpayment rather than one of your customers.

I think an overpayment and refund request weeks after the initial payment (when coincidentally the BTC value has reduced) would definitely ring some alarm bells

Maybe... but "oops I sent the coins to the wrong address" is a pretty plausible story. If there's one thing I've learned from accepting bitcoin payments at Tarsnap, it's that poor bitcoin client UIs seem to be responsible for a very large number of mistakes. (The most common one I see is failing to adjust for the miner fee.)



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