Why Can I Not Update My Windows?

Episode 1603 (1:29:30)

Carmine from Chicago
1903

Carmine is having issues updating Windows. He's behind and can't update to "1809." He's on 1803. Leo says that 1809 wasn't a good update, and Microsoft just skipped it and moved on to 1903. Eventually, Carmine will get it. There are ways to force it, and he can "check for updates." But Leo says that feature updates aren't as important as security updates. Eventually, it'll come.