There is no way to make plugin updates risk free. Anyone who tells you otherwise is selling something.
What you can do is make the risk small and recoverable. The goal is not "nothing ever breaks". The goal is that if something breaks, you notice before your customers do and you can undo it in five minutes. Here is the order of operations.
Step 1: take a backup, and know where it is
Before you click anything, take a fresh backup of both your files and your database. Not one of them. Both.
Then answer a second question that most people skip: where is that backup, and how would you restore it? If it is stored on the same server as your site, it is not much use when the server is the problem. If restoring means opening a support ticket and waiting two days, that is not a five minute recovery.
A backup you cannot reach quickly is a backup you do not have.
Step 2: write down what "working" means
You cannot tell whether an update broke something if you never decided what to check.
Take five minutes once and list the things on your site that actually matter. Usually it is a short list. The contact form delivers to the right inbox. The checkout completes. The booking calendar shows the right availability. The homepage looks right on a phone. Search returns results.
Five items is plenty. Keep the list somewhere you will find it again, because you will use it every single time.
Step 3: read the changelog before you update
Every plugin in the WordPress repository has a changelog, and most premium plugins publish release notes. It takes thirty seconds to look.
You are scanning for three specific words. Major, as in a version number jumping from 3 to 4, which usually means things were removed or rewritten. Breaking, which is the author telling you outright. And any mention of a new minimum PHP or WordPress version, which is how a plugin ends up refusing to activate.
Also glance at the plugin's support forum. If a release went badly, the complaints appear there within hours of it landing.
Step 4: update one at a time
This is the step people skip, and it is the one that costs the most when things go wrong.
WordPress lets you tick every checkbox and bulk update fourteen plugins in one go. If the site breaks afterwards, you now have fourteen suspects and no way to tell which one did it. Your only real option is rolling all of them back and starting over.
Update one. Load the front end. Check your list. Then update the next one.
It is slower, and it means that when something breaks you know exactly what broke it, which turns a debugging session into a one click fix.
The fix: if you have a long backlog, do the low risk utility plugins in a batch and the business critical ones, payments, forms, page builder, one at a time.
Step 5: pick a sensible time
Do not update at 5pm on a Friday. Do not update the morning of a campaign launch, before a sale, or the day you are travelling.
Update when you have an hour free and your traffic is low. Check your analytics for your quietest window if you are not sure. The reason is simple: the recovery is usually quick, but only if you are actually there to do it.
Step 6: check the site as a stranger would
After each update, open your site in a private browsing window. This matters more than it sounds.
Logged in, you often bypass caching entirely and you see admin-only versions of pages. Logged out and cached, your visitors can be seeing something quite different. Purge your cache first, then check in a private window, then check on your phone.
Run your five item list. Actually submit the form. Actually start a checkout. Do not just look at the pages.
Step 7: know your undo before you need it
If an update breaks something, you have three routes back, in order of preference.
Deactivate the plugin, if the site can survive without it for an hour. Roll back to the previous version, which some plugins and rollback tools support directly. Or restore your backup, which is the blunt instrument and the reason step 1 exists.
If the site is fully down and you cannot reach the admin, check your email for a WordPress recovery mode link. If there is none, renaming the plugin's folder over FTP or your host's file manager will deactivate it and usually get you back in.
The version of this that does not involve you
All of the above works. It also takes real time, every month, forever, and it competes with running your business.
There is a better way to do step 4, which is to apply the update on a copy of your site first and check it there, so a bad release never touches production at all. A staging environment for exactly that is included on the Professional plan, along with Wordfence firewall, iThemes hardening, two-factor login, Google PageSpeed work and 24 hour priority response.
Every Up Speed plan, including Starter, already covers the core of this process: we test each update before it goes live, and if one breaks something, we roll it back. Plus scheduled off-site backups with 30 day retention and a monthly report listing exactly what was updated. You do not log into anything and there is no dashboard to learn. The updates just get done, by a person, and someone checks afterwards.