Software companies have trained me to not update my software. By now, when an update for an application or OS is available, I assume the new version is worse, and am usually right. Either I'm going to lose some functionality that I relied on, the UX is going to get shuffled around on me, or it's just going to get bigger and slower on my old machine.
Instead of doing automatic updates, I delay updating until the company forces me to choose between updating and not using the software--and only then do I make the hard choice. I wish that every software would provide security updates on a separate track from the usual "UX rewrite" and "Feature cram" downgrades. That way, I can stay on the oldest version (the one that works the best), yet get critical security updates so I can use it safely.
Web software, too! Reddit is the obvious example, but everywhere they're changing for the sake of change and usually making it worse. For example, Vanguard (the brokerage) recently did a site-wide update. They basically removed lots of critical functionality (including the only thing I actually visit their web site to do regularly) and replaced it with whitespace and fluff. For a while, they let you remain on the old site. Then they made it more difficult to find the link to the old site. Finally I got an E-mail saying that they'd charge my account a fee unless I "migrated" my account to the new site. Talk about end-user hostility. Now I just call them on the phone to do my rollovers, likely costing them more money. Good job, morons.
