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Iran is on the FATF black list and features a lot in the OFAC sanctions lists, any transaction mentioning Iran is going to be blocked.

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No idea why this is downvoted; it's the plain truth. The same thing goes for other sanctioned countries: (Cuba, North Korea, Sudan, and Syria), as well as for transactions mentioning sanctioned individuals or organizations.

Is Cuba still sanctioned? I thought the main embargo was lifted a few years ago.

Cuba was removed from the State Sponsors of Terrorism list in 2015, but it remains under heavy economic sanctions and travel restrictions -- enough so that mentioning "Cuba" or "Havana" in an electronic payment memo will probably get your account locked temporarily while the compliance department takes a look at it.

Interesting that that really seems to mean that you can't mention those countries in transaction messages. It seems insanely silly, but since it's US regulation I'm not at all surprised.

You can mention them but your transaction will be blocked until it is reviewed. The review process will depend on the FI in question with some not as efficient as others...

The fines for breaking US sanctions are just to big to ignore so risk appetites tend to err on the side of caution.

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