It depends on the update/upgrade available. For security updates, I will read what the security update is for and determine if it effects my clients’ sites. Some of the security updates only affect some of my clients’ sites because it might fix a problem with Author users for example, but most of my clients don’t have author users. Also, the little security patches from 3.0.4 to 3.0.5 for example usually never affect plugins, so you don’t have to worry about plugins breaking.

With major upgrades (from 3.0.5 to 3.1), I usually wait quite awhile until the plugins I’m using are also working. I have a locally installed version of WordPress on my computer, so I can test whether or not the plugins break with the update. You can check the plugin repository at http://WordPress.org/extend/plugins to see what other people are saying about your plugins and if they say they are working or not.

So, definitely update if you think the security risk may effect your site, and you can wait to do the major upgrade a bit until your plugins are updated or you know they won’t break or until the current version also uncovers some security loophole related to your version.

Good luck!
~Angela

- Do you have to keep updating WordPress every time?
- I have a web site with few plugins. If I have to update versions because of security reasons, that means that all my plugins or work will get messed up or even worse, will they stop working at all? What would happen?

Thanks for the information and for this useful posting.