I'm here upgrading several FreeBSD VPS instances and it's

# freebsd-update fetch # prepare to get up to date on current version
# freebsd-update install # get up to date on current version
# freebsd-update upgrade -r $VERSION # fetch new version
# freebsd-update install # install new version
# shutdown -r now
# freebsd-update install # install userland
# pkg update && pkg upgrade -f # upgrade packages
# freebsd-update install # why not?
# shutdown -r now # another reboot

Because of the full-disk encryption, I need to do this from the VPS control-panel VNC connection.

It makes me appreciate my OpenBSD upgrades where it's a straightforward

# sysupgrade
(it auto-reboots, installs, auto-reboots into the new system)
# pkg_add -u
# sysmerge

and done.