I was recently hired to do some back end work on Church of Christ the King’s website. (Note that the site design is not mine.) In this case, the initial change I needed to make was small – trivial, even. However, I noticed as I made the change that the site was running WordPress 2.8.4. Unfortunately, that meant I was going to be upgrading WordPress manually.

For those of you (read: almost everyone) who doesn’t keep track of WordPress releases, the software is currently at version 3.3.1; version 2.8.4 was released back in August 2009. I suspected – and confirmed with a little searching – that there is no direct upgrade path from 2.8.4 to 3.3.1. That’s not a surprise; 2.8.4 is two and a half years old and five versions out of date.

There are two available paths for upgrading WordPress. First, you can automatically upgrade as each new version comes out. This is the easiest and generally the best practice: many version updates provide both better security and new functionality. The second option is to do the upgrade manually. Upgrading WordPress manually is not hard, per se, just potentially headache-inducing if you don’t do it carefully. In some cases, upgrading manually is the only option – as in this case, where the install was years out of date and the automatic upgrade path was no longer available within the application.

Potential pitfalls

There are a number of things that can (and will) go wrong in any upgrade:

• Your theme may break.
• Some plugins may break.

When performing a manual upgrade, however, things can get even more interesting:

• You can lose data if you don’t export a backup carefully ahead of time.
• You will lose all plugins and associated data.

In this particular upgrade, I took care of some the sorts of problems that arise in an ordinary upgrade by creating a version of the site on my local test server and checking the theme. I noticed that the plugins had gone missing, but I mentally attributed this to being on a local install and moved on. My assessment was accurate, but ignored the fact that the conditions after upgrading the live site would be the same. WordPress keeps plugins around when automatically upgrading, but when upgrading manually, all plugins get deleted. Even if you include the plugins in WordPress’ plugins directory when uploading the application files, the settings will be lost.

Thankfully, recovering the functionality of the website was fairly simple. The site was only using a few plugins, and I ended up replacing the old ones with slightly or dramatically better options.

Upgrading the hard way

Note that the safest way to perform manual upgrades is still incrementally, stepping from major release to major release. However, seeing as there were five major releases to go through (2.8.4 → 2.9 → 3.00 → 3.1 → 3.2 → 3.3), I decided to take a look at the theme. Since there were no major problems with the theme in relation to WordPress 3.3, it made sense to jump all the way at once.

There were other benefits to this approach, as well: for reasons beyond me, there were over 50 different themes and quite a few plugins installed, almost none of which were being used. The database was undoubtedly very messy and the site structure was a mess. Upgrading WordPress by doing a clean install eliminated all of that.

In general, I’d prefer not to do full removal and installations again. Upgrading this way is a last-ditch approach, though it was necessary in this case. It’s much less of a hassle to follow the standard upgrade path, and whenever possible users should keep upgrading. That means that it’s incumbent on theme and plugin authors to keep their themes up to date. It may also require replacing plugins, changing designs, or paying for maintenance to keep the site working correctly over time.

Lessons for everyone (but especially professionals)

Regardless, whenever possible, users should keep their installations up to date. That will make for better security and lower costs in the long run. For many clients, however, this will not be intuitive, especially in the world of bold prompts and automatic updates they are used to in their operating systems.

It also might behoove all online application developers to make their upgrade prompts a little more noticeable and a great deal more informative, WordPress included. In any case, the onus is on designers and developers to communicate with their clients, many of whom are non-technical, the benefits of keeping the software up to date and the potential costs of not upgrading it.