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That was my concern too. NGINX would need access to the internet in order to renew the certs.
Yes, that is how it is currently setup, and how I may end up leaving it. Right now, I can go to jellyfin.home, and that request gets routed to my pihole which has custom DNS entries, which then points to NGINX and NGINX forwards it to the correct IP/ port. All works as expected, except it is not https (which is not that big of a deal since all my stuff is restricted from the outside world). Just an OCD itch I'm trying to scratch.
Hey, I advocate https even for LAN only, most people don't think about the Wifi attack vector. That's why I use self signed certs on my LAN stuff, I just don't care about that yellow padlock that disappears when I trust the website. I've only experienced a single app ever that didn't accept self-signed (I'm looking at you wallabag app).
I can understand how it would be different if family members suddenly starts asking if it's true when their devices tell them the webside is potentially dangerous.
People... watching money?