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Federal law requires licensed gun dealers to conduct background checks on their buyers but exempts unlicensed, so-called “private” sellers from this requirement—sellers who increasingly use websites to facilitate their sales. Policymakers have long drawn attention to this loophole, but there has been no attempt to empirically measure how frequently unlicensed sales transfer firearms to unlawful possessors. We adopt a novel methodology to do so, by either posting ads offering guns for sale or responding to “want-to-buy” ads posted by people seeking guns in four states—Washington, Vermont, Oregon, and Nevada. Having identified 682 would-be gun buyers, we search for court records that document prior convictions or protective orders, and assess whether they prohibit firearm possession. Sampled gun buyers were almost exclusively male and the majority were aged 20-36. Overall, would-be online gun buyers were 10.3 times more likely to be federally prohibited from buying or possessing guns due to observable criteria than were individuals who attempted to buy firearms from licensed gun dealers in 2014. The share of online buyers who were prohibited varied across states from 4-10 percent, in part because of variation in the breadth of local laws restricting gun possession by domestic abusers.