Is there something in the config that might affect whether auto hotfix works? I'm seeing the same problem on my home Windows 10 PC. But if I start VS with a new config, it immediately notifies me that an update is available.
I do see under Application Options/Notifications that I don't have anything disabled and specifically, "Updates: Auto Hot Fix", is set to "Status line icon with pop-up", but I don't get any notification or pop-up when running with my normal config.