Keeping servers up to date with security patches is a challenging task. No one likes server outages, upgrades could break things, etc. This is what I do on FreeBSD systems to safely manage updates.
First, login as root. Then make sure that /etc/aliases is configured to forward root's email to your email address. This makes sure that you get the notifications of updates. It will also cause you to get nightly, weekly, and monthly updates about important things like how full the hard drives are and if any of the installed ports or packages have known security bugs. Once /etc/aliases is updated, type "newaliases" to activate the changes. Then email root to see if it worked.
Then, add this to /etc/crontab. (Note: Press "Tab" five times between "@daily" and "root".)
# Get OS updates every day @daily root freebsd-update cron
This will make the system check every night for important upgrades. If there are any, it will download them to a staging area and not install them. Instead, it will email you a list of the pending changes. This email will only happen when there are recommended updates to install, so you won't see it every day.
That is all the setup work. Now just wait for an email about a pending upgrade.
When you get one of these messages, read it over to make sure it wouldn't affect anything that you've customized. If it would, you might want to take a closer look at that system to put your mind at ease.
When you're ready to activate the upgrade, login as root again and type this:
freebsd-update install shutdown -r now
This will cause it to install the pending updates and restart. If everything goes as planned, you're all set. Really. That is it.
If anything doesn't go to your liking, you can revert to the pre-update system by logging in as root and typing:
freebsd-update rollback shutdown -r now
If the FreeBSD system is running as a virtual server in VMware, Digital Ocean, etc., then you may wish to make a snapshot of the server right before the "freebsd-update install" command. That gives a very convenient way to roll back to pre-update conditions. I haven't heard of anyone breaking their system with freebsd-update before, so this is really just an extra precaution more than a necessity. With servers, its always nice to have extra backups.
By keeping on top of updates regularly with a (mostly) automated system like this, your servers will be more secure, more trustworthy, and more stable. More importantly, you won't accidentally forget to update a random server for two years and then worry about breaking it during the next upgrade. Based on that stress-reduction alone, I highly recommend this approach.