Chuck - Jail Updating

Hi Allan and Kris,

Thanks for all the knowledge you share on this show. When I recently had
the opportunity to setup a new webserver, I decided to give FreeBSD a
try. I have been running Linux servers for years, but after listening to
you guys for a while now, I decided to give it a go (on Digital Ocean no
less!).

I blogged about the setup at
https://techielibrarians.com/index.php/2017/02/02/setting-up-this-website/
and am very happy with the setup. Basically I have a FreeBSD server
running apache and mysql within a jail hosting wordpress. I am using
iocage to manage the jail and PF to take care of NAT and port forwarding
for IPv4.

Now to my question, since this system uses ports and packages and has a
jail, what is the best way to keep everything up to date? I want the
base system of the server, the packages and ports of the server, the
jail, and the packages and ports of the jail all to be updated. Coming
from Linux where I could just run a sudo yum update and have everything
updated this seems more complex.

Thanks

Chuck