Are we required to run an OFAC check on every person we hire? For example, if we hire a landscaper or a roofer, do we need to run an OFAC check on those individuals?

We are not aware of any rule or law that would require you to perform an OFAC check on bank employees or independent contractors hired for projects such as landscaping or roof repair.

We should note that since some of the OFAC regulations contain very broad definitions of what are considered to be blockable assets or transactions, a broad argument could be made that even a payment made to an independent contractor might constitute a blockable financial transaction. For example,  the Cuban Assets Controls Regulations, 31 CFR 515.201(a), prohibit “all payments . . . if . . . such transactions involve property in which a foreign country designated under this part . . . or any national thereof has . . . any interest in any nature whatsoever, direct or indirect.”  The regulations define “transactions” very broadly to include “any payment” to a national of a designated foreign country. 31 CFR 515.309(a).  Read together, the regulations could be interpreted to apply to all of your vendors (and even your employees) — i.e., to any person or entity who receives payments from your institution. We are not suggesting that the OFAC regulations require you to include the names of all of your independent contractors (or employees) on your OFAC scrub list, but it may be prudent to do so to the extent practicable.