If your WordPress blog is outdated even by a few days and there's a security hole in your old version you could be seriously compromised without even knowing it. Trust me. This has happened to two of my clients and the fix is not easy. Usually, once compromised, you have to delete the blog and reinstall WordPress, then scour your theme and uploaded files before re-uploading to the server. Avoid this hassle (or worse damage to your blog) if you can.
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