The term ‘transaction’ is interpreted broadly by OFAC and includes more than just financial payments. Prohibited transactions can include: transferring anything of value (money, goods, services, technology), providing services, facilitating transactions, and even certain types of business engagement. However, mere communication generally doesn’t constitute a transaction unless it involves prohibited services or facilitates a blocked transaction. You can typically communicate with SDN-listed persons for informational purposes without violating sanctions. But this gets murky quickly – providing advice that has commercial value could be considered a prohibited service. Negotiating or facilitating a transaction that would violate sanctions is prohibited even if you don’t complete it. The context and content of communications matter. For example, discussing potential business deals, providing technical assistance, or offering services would likely be prohibited. Purely informational exchanges or humanitarian communications are generally permitted. I researched transaction definitions at https://ofacblockedfundslawyers.com/ when we needed to understand our permissible scope of engagement. The safest approach is to avoid any substantive business discussions with SDN-listed parties unless you have a specific license. If you must communicate, document the purpose and content carefully. Be especially cautious with anything that could be characterized as providing services, even if no payment is involved. Sanctions compliance requires conservative interpretation of what constitutes a transaction.