I have a window nagging me to upgrade to Sierra. I don't want to because I'm afraid it will break things. Sure, there is the security aspect but that is mostly the browser and for apps I scan anything I install. The risk of everything slowing down is just a lot, lot greater than getting malware. What's the best way to do it? Let's not get into the specifics of 'Is your mac new?' or not. I am trying to learn the best way to upgrade or a way to handle not upgrading. I've heard some people say that missing an update actually is the worst - and that the next time you update you'll be in for trouble - by skipping that update the next one is more likely to break things. But on the other hand I've heard people say "Don't update - Apple will cripple your old hardware deliberately. They favour the newer hardware." ^ well, if that's the case at what point do you decide to stop updating? And, at what point do you consider an update fully tested to be safe to upgrade? How long do you wait to search for people who have written about problems? I'm coming from linux, windows and android. All of those had thier own best ways to handle. For linux I found it was best only to upgrade the browser. For Android I found it was best to wait about 2 months after the latest release had been tested. For Windows I generally upgraded a week after the update had been released but kept the browser as new as I can.