Some people love to be on the bleeding edge of software updates however there are many times when installing a new update can break your website.

If you haven’t experienced a Plugin, Theme or Core Update failure then you should count yourself as lucky. Although a good amount of testing does go into every core roll out due to a small group of developers always using nightly updates for test sites the interaction of any update with the variety of addons and custom code you might write could throw your website offline for hours or maybe days.

This is why it is important to understand the roll out process for WordPress and the best methods for deployment.

Another serious problem we all will face soon is WordPress core auto updates that by default work without your intervention. I have serious concerns with this new update method that the core team has added to WordPress because there are times when WordPress Core updates can wipe out a well running and secure website.

However because WordPress wants to be able to feed your site security releases as soon as they are available the only thing that you can do is monitor your website and or turn off the auto updates.

For clarification it has to be explained that the Auto Updates that we use to use were really manual one click updates. The Auto Updates in future releases of WordPress will happen automatically and be activated by someone visiting your website and setting off a cron process that does not require you to press a button.

This will definitely cause millions of websites to go down automatically at some point in the future.

We will cover the method to turn this feature off in other How Tos.

When is it Safe to Install a WordPress Update?

Although I am not on the core team I have been providing tech support to thousands of you in the WordPress forms and in the IRC Freenode Chat Room for years now. If you have visited you have probably run into me and sorry yes I sometimes can be a little sarcastic .. on the other hand I am also someone who is going to answer your question rather than direct you to another chat room or website…

For this reason I do have some experience with thousands of plugins interacting with core updates and theme modifications.

I personally think its a bad idea for anyone to deploy first day patches unless they are security patches that have been fully tested. Most security patches will also sneak in other updates unrelated to security that can break your site.

As someone who has helped people through this thousands and thousands of times ..

I Personally do not run for every update. I have no desire to turn my production server sites into Beta Test sites for WordPress until they start paying me specifically to do this. And I do not have a desire to have my Client’s websites crash  due to the same.

To understand if a plugin is safe to update to your version of WordPress you should read the descriptions that the Plugin Authors include with their Updates.  Below you will see two plugins that are currently functioning properly that have updates available.

You will see that the Press This plugin has an Unknown Compatibility with the two most recent versions of WordPress and that the Sociable Plugin shows 100% compatibility with only the prior version.

Press This Reloaded
You have version 1.0.3 installed. Update to 1.1. View version 1.1 details.
Compatibility with WordPress 3.7.1: Unknown
Compatibility with WordPress 3.8.1: Unknown

Sociable
You have version 4.3.3.2 installed. Update to 4.3.4.1. View version 4.3.4.1 details.
Compatibility with WordPress 3.7.1: 100% (1 “works” votes out of 1 total)
Compatibility with WordPress 3.8.1: Unknown

If either of these plugins are not compatible with the version of WordPress you have installed then Updating them can cause your site to crash .. and you will probably be locked out of your website too.

The best situation here is to visit the Plugin Maker’s Support Form found on the Plugin Download page on wordpress.org

Each plugin will have a support area. Not all Authors are attentive to the questions because plugins are free and developers have lives like everyone.

And another thing is although a Plugin Author may test their update it does not go through nightly build or pre-deployment beta testing by thousands of users so it is highly possible that it may work for the author but not for you.

What is the Best Practice for WordPress Core and Plugin Updates?

I can only give you my personal opinion after using WordPress for many years.

If your website is not having a problem I would Normally wait a few days and double check the WordPress Help Forms … and also each one of the Plugins Support Forms before you deploy.

Make a Backup of your Files and Database.

Be Ready and Understand how to get yourself back in if a Crash Locks You Out.

Be Ready to roll back your update by uploading your backup files if necessary.

Keep Old Version Copies of all Plugins and Themes you use .. even if the new update works as the Author wants it to you may not like his new version… I have had this happen.

Also say a little Prayer .. heh hey it can’t hurt.