I get this, but you say "very often", but it's not, and generally, looking at OFAC lists, there's only a few countries with personal carveouts (less than 5 of the countries on the list), usually for remittances, and in a few of those countries only to US persons residing there.
Generally the software carveouts are very limited - it's not just "providing IT services or technology to individuals for personal use", i.e. Sudan:
> software updates for medical devices to Sudan
Indeed, of the software carveouts listed on that page, only two are not related to the operation or update of medical devices:
- provision of Internet services to the people of the Ukraine (read: "Starlink")
- provision of messaging services to members of the Government of Venezuela.