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I asked Venmo what it was exactly about “iced coffee obama nsa inside job syria” that prompted the company to raise an alarm. According to a company spokesperson, it was the last word. Since Syria is under sanctions in the US, payments that appear to involve the country get extra attention:

Venmo is a fully regulated Money Service Business committed to providing our users a safe and easy way to send and receive payments, which means that we are responsible for complying with U.S Sanctions administered by the Office of Foreign Assets Control (OFAC). To minimize account interruptions, we are reaching out to Venmo users on an individual basis to inquire about posts, which contain words or phrases that could be considered unsanctioned and clear up any confusion.

As you probably know, Syria is a sanctioned country and we are obligated to follow up when we see payments that are related to a sanctioned country, individual or entity.

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So it looks like “obama nsa inside job” is cool to write on Venmo if you want to avoid getting bugged by Venmo. Of course, whether that word string will trigger an NSA inquiry is another matter.