It’s usually an excellent idea to update WordPress. After all, it’s an important part of keeping your website secure and running well.
The danger comes with major updates to WordPress. These updates bring significant changes in how the core of WordPress works. They can break themes and plugins and leave your website a total mess if you aren’t careful.
What Is a Major Update?
A major update is something that makes fundamental changes to the way the software operates, adds new features, and adds or removes files from the underlying codebase.
It’s these major changes that can cause problems. If WordPress makes major changes to its core files and a theme or plugin author isn’t keeping up, then your site could end up broken.
Version Numbering
Like most software, WordPress and its plugins use numbers to keep track of the software versions as they’re produced. At the time of writing, the current version number for WordPress is 5.4.2.
WordPress Versioning
The core of WordPress does things a little differently than other software, including WordPress plugins. The first two numbers in the sequence together denote a major update, not just the first number by itself. From the WordPress documentation:
“A major WordPress version is dictated by the first two sequences. For example, 3.5 is a major release. So is 3.6, 3.7, all the way up to 4.0. Version 4.0 is no different than 3.9 and 4.1. There isn’t a “WordPress 3” or “WordPress 4” – we’re weird like that for historical reasons.”
And:
“A release, identified by the first two numbers (3.6), which is the focus of a full release cycle and feature development. WordPress uses decimaling count for major release versions, so 2.8, 2.9, 3.0, and 3.1 are sequential and comparable in scope.”
How Do I know What Version I’m On?
To know if you’re facing a major update, you need to know what version you’re currently on. This should be trivial, but most of the places where you’d go to look at your version number only show it when you’re on the latest version. Otherwise, you’ll see a prompt to upgrade instead with no clue if this is a major update or not.
The one place that’s usually reliable is in your admin area. Look for a box titled “At a Glance” like the one above. It’ll show you what version you’re on and a button with the latest version number if an update is available.
Wait a Minute
If you do have a major update available, wait before updating. Get ready first.
Quite often, there’ll be a bug fix release a few weeks after the major update. I recommend to my clients that they wait for this release to come out before upgrading. At the time of writing, the next major release of WordPress will be 5.5, so I recommend waiting until version 5.5.1 comes out before doing the update.
Example: WordPress version 5.0 came out on Dec 6, 2018. Version 5.0.1 came out 6 days later and 5.0.2 came out 7 days after that. Between those two subsequent versions, more than 80 bugs were fixed!
You can view the WordPress changelog here.
Make a Backup
Before doing any updates, I always recommend making a backup of WordPress files and the database. You must get both; the files are useless without the database and vice versa.
I use the UpdraftPlus plugin to do this. I set up UpdraftPlus to automatically backup my site to off-site storage. While I pay for UpdraftPlus, the free version will do this too. Offsite backups also protect me should anything ever happen to my hosting provider.
Pro Tip: Before doing anything else make sure you have backups in place and know how to restore from them. If you’re not sure, install UpdraftPlus and make a backup before doing any updates.
Another great option is a service like VaultPress. This is a premium service that’ll also make regular off-site backups for you.
Your hosting provider may also be making regular backups for you. Double-check to make sure and make sure you know how to restore from a backup or where to get help if needed.
You can also use FTP to download all of your files and phpMyAdmin (or equivalent) to get a copy of your database. This is a little advanced for this article, so search Google if you’d like to learn more.
Get Prepared
Before doing a major WordPress update, update all the plugins first.
This is crucial. Good plugin developers will make changes ahead of a major release to prepare for it. Updating the plugins first can save you from a world of hurt.
The same is true for your themes. Make sure that they’re updated as well. Select the themes you wish to update and click on the Update Themes button.

Pro Tip: Have a look at your pages, posts, membership areas, your shopping cart, any calendars, etc. Use a desktop and a phone to look at your site. Take a screengrab of your various page types. The goal here is to make sure that you have the “before” view of your site in mind.
Do it!
Now it’s time. Do the update by clicking on the button on the WordPress Updates screen. Your site will go into maintenance mode for a few moments while the update takes place.
Review the site again to make sure everything is working. If you’re not sure that everything is right, refer to the screen grabs you took earlier. Make sure to try your contact forms and make a test purchase if you have a store.
What About Automatic Updates?
This all seems like a lot of work, and many hosting providers will do automatic updates for you.
It sounds easy, shouldn’t you just do that?
The problem with automatic updates is that they’re thoughtless. Updates are applied as soon as they are available, whether or not your plugins or themes are ready. They can, and do, easily break WordPress websites.
Automatic updates will break your site without you knowing because you’re not even there to notice any problems. It’s not uncommon for a site to be messed up for days before the owner notices, and it’s oftentimes because a client told them. Panic time!
Summary
It seemed like this was a lot of work to do the upgrade. It kind of was if you had to get backups in place first. Once you’ve done this once or twice, it’ll go much smoother.
The good news is that you now have the confidence to do this the right way! You know how to be thoughtful about updates and what steps to take to ensure success.
P.S. If you’d rather not have to mess with any of this, I do have WordPress Maintenance Plans available. I manually update WordPress sites in this thoughtful manner, and I automatically take care of any issues depending on the plan you choose.