The whole thing is talking about how dialog boxes confuse clueless users and they tend not to do the right things when they see them. OK, fine, I agree that that happens and that it is a very real problem with computer usability.
But then he (Jeff) makes this comment:
If you need to update, do so. if you need to download and apply security patches in the background, do so. If you need to send crash data, do so. Silently. And do it in the background, when the PC is idle-- without bothering the user.
AAAAAAAHHHHHH! NO, NO, NO.
I never want my computer to install anything unless I know that it is happening. I never want anything sent out of my computer unless I know that it is happening.
I run software to notify me when malicious software (and anything that does something on my computer that I am unaware of is malicious, even if Microsoft wrote it) tries to access the internet.
And I disable all automatic updates. Of course I want to have the latest security patches (and I do), but any install, no matter how innocent, can break my system and I at least want to be able to identify the culprit. If I install an IE patch and all of a sudden Firefox stops working or something, then at least I know what to blame and where to look for a fix.
That kind of automagical maintainance logic belongs in an appliance, not a general purpose computer. Only when all of the variables can be fully controlled does it make sense in my opinion. If it does exist in a general purpose computer, it should be something I can opt into, not opt out of.