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I Tried to Venmo $12.66 for 'ISIS' and the Government Was Pissed

It turns out the Treasury Department doesn't appreciate my sense of humor.

This past April, I found myself in a familiar situation: contemplating a Venmo payment to my roommate for Thai food. It wasn't the amount—$12.66, to be exact—that gave me pause, but what to type in the comments section. The "what's it for" box is a required element of the app, ostensibly designed to help you remember whatever it is you bought. In practice, however, it's also a chance to make a joke, swear, or toss around the eggplant emoji. I suspect most people feel un-fun if they don't inject some kind of witticism or silliness into what is an otherwise banal transaction.

That night, under "what's it for," because I have the emotional maturity of a 12-year-old, I wrote "Isis"—you know, like the terrorist group. This is the message I got as soon as I hit "send."

Evidently, by typing "Isis," I had drawn the attention of some algorithm or another, and my account was immediately frozen. Later, when I looked it up, I learned that there is a whole list of sanctioned people, places, and entities, which includes ISIS. Use any of these flagged terms—or even pay someone with a Middle Eastern–sounding name—and there's a chance your account could get automatically suspended until the problem can be investigated.

My first move was to apologize to my roommate, promising to Venmo him as soon as my account was back up. The next morning I awoke to a new vague email, explaining that I had tripped up some security alerts as I suspected and should contact them should I have any questions (I did), or want to reactive my account (I did).

I immediately responded with a request to reactivate my account, and soon an employee curiously identified as "Steph J." was able to confirm that my account had been unfrozen.

Which was great, although also disturbingly easy. After closing my account for issues of national security, a simple email request had cleared my name? Had a government agent gone through my tweets to find out I am not a jihadist sleeper cell? At first, the whole ordeal seemed unnecessarily alarmist; now it seemed too simple.

It turns out, I was right—it was, in fact, too simple. Although my account had been reactivated, the $12.66 had yet to be returned or properly deposited in my roommate's account. I continued to make and receive transactions, but my Thai food funds remained stuck somewhere in the Venmo ether.

A week later, I received another email, this time from Steph J.'s surname-less colleague "Josh." I must say, when you're dealing with a company that has all your bank account information like Venmo, it is somehow comforting to know you are talking to a real human with a name and an occasional last initial.

Josh provided a bit of background, explaining that Venmo, as a regulated Money Service Business, is responsible for complying with US sanctions administered by the Office of Foreign Assets Control (OFAC), and that I would need to provide some clarification on what I meant when I said I was paying for ISIS.

I responded immediately, emailing an explainer for a joke that's barely even a joke, and making it clear I am not, nor do I ever intend to be, involved with the Islamic State.

After my response I waited again, more worried this time. My $12.66 was not lost in some Silicon Valley server farm, but rather, in a different, scarier ether: It was with the US government. The US Treasury's Office of Foreign Assets Control, to be exact. I have never heard of the Office of Foreign Assets Control, but they sound legit as hell.

It turns out this OFAC wasn't letting me off, simple explainer or not. Ten days later, I received a new email from anonymous "Compliance Team," informing me that my request for the return of funds was blocked after a review. They provided no criteria for my denial but assured me that my $12.66 would be held in a "special interest-earning account."

My only option was to follow the link and "apply to get my money back" from OFAC. I was directed to a Treasury.gov URL, a government website. Thankfully, Venmo provided me with a list of things I would need to know to start my application.

Maybe it's good to know that the Department of Treasury is very thorough with this process. As I started the application, a dropdown gave me a list of release of program options including "Rough Diamonds," "Non-Proliferation Weapons of Mass Destruction," and something called "Lybia2," among others.

I completed all eight steps (my contact info, my roommate's contact info, Venmo's contact info, my bank, my roommates' bank) to the best of my knowledge.

This—the Thai food, the joke, the emails—was all in April. Eventually, I forgot about my run-in with the Treasury Department and that $12.66 earning "special interest," wherever it was. I continued to use Venmo and eat Thai food, occasionally referencing my ISIS anecdote as a warning for other dumb jokes friends might post on Venmo.

I had thought this was the end of it until October, nearly seven months later, when I received an email from an Aidan Orsino with a dread-inducing Treasury.gov email address with the subject line "OFAC License Application No [redacted]."

More than half a year later, my application was finally being reviewed! All I needed to provide was two forms of government IDs (in .PDF form, they specified), and fill out the same eight-part application again. I took photos of my passport and driver's license and sent them off. I could sense I was closer than ever. With a newfound vigor and sense of purpose, I powered through the same eight-part form as before, this time making sure to get all of the information right. Still, I wasn't expecting much. Maybe another runaround in what had turned into a laughably Kafkaesque experience. After more than half a year of periodic email correspondence with anonymous Venmo employees and government officials, I had grown oddly fond of these interactions.

And then, on November 16, 2016, exactly eight months from that day when I paid my roommate for "Isis" instead of Thai food, I received an email notifying me that my payment had been unblocked. The "UNBLOCKED" glowed on the page in bright green capital letters. With the $12.66 deposited in my roommate's Venmo account, the saga had come to a close. I felt triumphant—and a little empty.

Though I'm sure my name and Venmo photo still live somewhere on a watch list at the Treasury Department, everything turned out fine now that my roommate and I are squared away. I've learned some things, too, through this process: that you shouldn't joke online about ISIS, that the feds have a vice grip on financial tech companies, and that "Lybia2" is a thing to look out for. Venmoing "Isis" was dumb, and not even an actual joke. Maybe next time I should stick to the eggplant emojis and keep the government out of it.

Follow Andy Verderosa on Twitter.