What’s this auto-upgrade thing?
To make this simple, if you use DreamPress or our One-Click installer, we automatically upgrade WordPress for you! It doesn’t happen the very second WP has a new version, mind you, we spread it out to not destroy our servers, but you will get upgraded unless the upgrade feature was disabled (of course, you would never disable them, right?). Any time you want to see if you have automatic upgrades enabled, or want to run your own, head over to the DreamHost Panel.
Why not plugins and themes?
So why do we only do this for core WordPress? Because plugins and themes are messy.
The safest upgrade in the world is the minor upgrade (like WP 3.6 to 3.6.1), as it’s exceptionally rare that it breaks anything. It’s not perfect, of course, sometimes we find out that a plugin or theme was doing something in a very non-optimal way before (if you hear ‘doing_it_wrong()’ please keep in mind that is not a value judgement, just a code comment, we all do it wrong in the beginning). But rarely will this kind of upgrade break your site.
Similarly, the major releases (3.5 to 3.6) are perhaps surprisingly stable. They’re tested, a lot. At DreamHost there are two people (me and Shredder) on the core contributor list, and we’re heavily involved in WordPress development every single day, at work and at home. We keep up with WP changes, test them on DreamHost, and work with the core team to resolve issues before they even release a beta! We’re on the job!
“But hang on!” I hear you say. “I upgraded to 3.6 and it broke my theme!”
And THAT is why we don’t upgrade themes.
I know, I know, it sounded counter-intuitive. You have to look at it a different way. Your theme stopped working with WordPress 3.6. That means something in the theme is not compatible with the best practices in WordPress core. Translation: WP didn’t break, your theme had a bug.
It sounds like semantics, or hair-splitting, and I totally get that. It also sounds like we’re passing the buck. We’re not! And we’re not trying to imply the theme (or plugin) developer who now has a broken product is a bad coder, or doesn’t pay attention to WordPress. What we mean is that themes and plugins, as they are used by much smaller segments of the WordPress community (everyone uses core, but maybe only 1000 use that theme), it just can’t be tested as robustly. This is especially true of the solo-developers. Speaking as one, I used to develop WP only in my free time, so any time WP had a new release coming up, I had to take days to test all my plugins, and pray I got everything. Invariably I missed stuff. It happens. We’re humans.
Breaking isn’t the only reason, though. Sometimes an upgrade is messy and complicated. Take, for example, NextGEN Gallery. When version 2.0 came out, it inadvertently broke a lot of installs. There was chaos, drama, and finally an open letter. How did this happen? It happened because NextGEN is hella complex, and it’s used in myriad different ways. It happened because plugins and themes can do anything with WordPress.
Blindly updating core is safe. It’s tested and easy to roll back. Blindly updating themes and plugins are not always easy to roll back, they’re not always easy to upgrade (some require a massive upgrade script to run), and they may require you to make other changes in your theme. For that, we just don’t.
If DreamPress is MANAGED Hosting, like WordPress.com, how come THEY do it?
You mean why do the plugins on WordPress.com get auto-updated? Because you can’t install any plugins on Wordpress.com! That’s all. They control everything, and simply activate various plugins depending on what package you buy. It’s not really the same thing at all, but I get why people think it is.
I don’t care! Can I auto-upgrade anyway?
Are you sure? Okay, then! Install the plugin Automatic Updater (by Gary P.) and set it to upgrade your themes and plugins. I personally use it on all my sites, but I’ve also personally vetted each and every plugin on my sites.