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Here are some tips for making an upgrade to Vanilla 2.3. less challenging. Many of these are general tips for managing any website or web software, but some are specific to Vanilla.

Platform maintenance:

• Upgrade PHP to version 5.6. (As low as 5.4 is supported, but we do not recommend it. Note that Vanilla 2.2 and below did not fully support 7.0 so if you want to jump straight to that, wait until after you upgrade).
• Upgrade to MySQL 5.6 or higher. (As low as 5.0 is supported for basic features, but starting in Vanilla 2.4 it will not provide 100% functionality).
• Are your server software (e.g. Apache) and operating system (e.g. CentOS) up to date and secure?

Forum maintenance:

• If you're not using Garden.RewriteRules = true in your config, enable it and see if it works. It will be auto-on in 2.3.
• Maintain a backup of you .htaccess file (if applicable), conf/config.php file and database on a different system.
• Check to see if your theme and addons are all compatible with 2.3. If you aren't sure, consider disabling them while you upgrade.

Testing the upgrade ahead of time:

• Consider doing a test upgrade on a copy of your entire forum (files + database) on another server or on your localhost environment.
• If that is not possible, consider copying the database and testing it in a new subfolder on your existing server (changing the copied config.php to point at your copied database, not the original).
• Don't forget to run /utility/update to update your database. On sites with millions of users or comments, this may take significant time so make plans for that.
• In addition to upgrading, perform key tasks (posting, registering, moderation actions) on your test install.

What to do if you run into issues:

• Use our troubleshooting guide.
• Start a new discussion on this forum to determine whether you have a setup issue or have found a bug.