Mulling over the FreeNAS 11.2 Upgrade

I have been debating updating or not updating my home server to FreeNAS 11.2. It is a big update for me because of this one change:

The Plugins and Jails backend has switched from warden to iocage and warden will no longer receive bug fixes. The new UI will automatically use iocage to create and manage Plugins and Jails. Users are encouraged to recreate any existing Plugins and Jails using the new UI to ensure that they are running the latest supported application versions.

I have one FreeBSD jail on my server with lots of customized software on it (most notably, a custom build of OpenVPN and two standard FreeNAS plugins. It has run rock solid for 2-3 years, but I can’t update it for various technical reasons, the underlying OS software is out of date, and rebuilding it will be a pain in the neck. I should probably wait until I can set aside a few hours, completely uninterrupted, to work on an upgrade—which probably won’t happen until sometime in January. Part of my wants to just let it run, updated, until the server dies—even if the software is very out of date—because it is behind a firewall and is largely shielded from cyberattack. I just never have been able to live like that before.