Having been with WordPress since v1.5 (2005), I have never once had a plugin break after a core update. Some didn't mesh well with the current interface years l

Having been with WordPress since v1.5 (2005), I have never once had a plugin break after a core update. Some didn't mesh well with the current interface years later so I'd replace them with something newer, but nothing ever stopped working. Plugins I wrote for WP 5 years ago, designed for a totally different admin interface than exists today, still work perfectly in 3.3.1. I have a feeling this isn't a real problem, it's an imagined one based on misunderstanding of the "compatible up to" label on WP's plugin directory. Most plugin authors don't log in to the site and edit their plugin to bump that number, but the plugins still work fine. Most WP core updates are just security fixes. You don't have to worry about breaking a plugin or theme by updating; security fixes don't add or remove any features the plugins use. There are 30 million sites running on WordPress, millions of those at organizations like yours, not just blogs. One reason it's so widespread is that this isn't an issue.