Workplace will check to see if you have your Windows or macOS Operating System set to update automatically, as per your applicable security policy. This is to ensure that you have all the latest security patches and fixes as soon as they become available. If Workplace indicates that this is turned off, it only takes a few clicks to turn it on.
On later versions of Windows, like Windows 10, it is really quite difficult to turn auto-updates off! You have to dig through really advanced settings and flip a bunch of switches. If it is off, (and you don't know how to turn it back on) you should contact your IT provider to help out.
On older versions of Windows like Windows 7 or 8.1, there is a setting found in the Windows Control Panel, under System and Security and Windows Update. Here you can select "Turn automatic updating on or off" and then "Change settings." Make sure to change it to "Install updates automatically (recommended)."
On a Mac, you open System Preferences, and select "App Store" or "Software Update," depending on your version of macOS. Select the box for "Automatically check for updates."
If for some reason you cannot currently configure auto-updates on your device to satisfy the device security check, you may be able to contact your local admin or IT support to grant you a one-time exception so you can continue on.
Once you've set your machine to automatically update your operating system, refresh the Workplace security checks page or go back to log into your portal and Workplace will indicate that you have passed the check and you can proceed!