[xenophonf]

The guy's wife didn't do anything wrong. Slack broke the law by providing an embargoed service to someone in Cuba. I'll bet money that when this was discussed with their compliance officer, the lawyers and engineers and everyone else agreed to use certain metrics (like source IP) to determine whether someone fell under the embargo. Otherwise, Slack would have to spend a lot of time and money validating people's identity, etc., in order to comply. I don't really fault them for taking this path because their exposure is huge and compliance is hard.

Your analogy about grocery stores doesn't really work because logging into Slack isn't the same thing as walking into a grocery store, because buying from a grocery store isn't the same thing as exporting food across a national boarder, and because neither food nor medicine is embargoed.