WordPress is a very powerful and convenient tool for your website to live in. However, if you let the software get too old, it can also become a very easy way for hackers to compromise your website. To increase the odds that you will avoid spam, viruses, and embarrassing defacement, be sure to keep up to date.
The main WordPress application itself will have updates available from time to time, but every plugin installed on your website has different developers, and different times where updates are published. Fortunately, it's not difficult to stay on top of things. A good rule of thumb is that you should be logging in to your WordPress admin at least once a month. When you do so, watch for the orange numbered circles, especially next to "Plugins" in your left-side admin menu. If you see the orange circle, the number inside of it tells you how many plugins currently have updates available. Hover over the plugins menu and click on "installed plugins" to bring up the plugin list.
In the section for each plugin, there's a link that reads "update now" at the end of a sentence that tells you what version is available. Typically, all you'll need to do is click that link for each one, and you'll be good to go. NOTE: depending on your web hosting, you might need to enter an FTP password to proceed after clicking the link (if you're on our web hosting, this won't be the case.)
Unfortunately, yes. Most of the time, it won't, it'll all go fine... but from time to time plugins can conflict with each other or fail to install properly, causing strange behavior. You should always check to see that everything looks to be running fine after an update.
It's also best practice to download a backup of your website files, and your MySQL database, prior to performing updates. This way, if something goes wrong, you'll always be able to recover to a previously working version of the website. If your hosting provides you with cPanel access, both types of backups can be obtained through the backup wizard.
If you are the type who likes to avoid risk wherever possible, or don't want to deal with all the steps involved on a regular basis, My Web Maestro does provide a maintenance plan that covers WordPress updates. Most of our plans are geared toward those who need ongoing help updating website content, but our smallest plan is WordPress specific. Every month, we'll make sure your core WordPress is up to date, along with any plugins, and will maintain an off-server backup of the website (in addition to the regular automatic backups your website is set up for if you're on our hosting server.) If anything goes wrong, we'll track down the issue immediately and correct it, keeping you posted on the status. Learn more about our maintenance plans.