Hopefully this should help me keep WordPress more up to date: Installing/Updating WordPress with Subversion (without manually maintaining my minor modifications)

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Are you thinking about creating a script to run subversion then automating it with cron? Doing that with a stable release version could be wicked cool.

How would a script know when a new stable release of WP is available?

Nah, I was just going to do it manually when I hear a new release is out. So much easier to so a little svn sw http://... than the normal upgrade process, esp with local mods.

There’s probably some way to set up a script to ping trac.wordpress.org to determine when a new ver is released, but I’d rather do it manually so I make sure to hit upgrade.php and backup the db if necessary. And to make sure everything goes smoothly.