Profligate_parasite

Hello Self Hosters! I am new-ish... got Jellyfin working great with tailscale remote access! I love it! I keep getting deeper into this stuff and geeking out... really excited to add my next service: Self-Hosted Nextcloud.

Would someone kindly walk me through setting up reverse proxy to my stuff with Caddy? I really just want HTTPS support, as my media files are one thing, but hosting all my personal info/docs on NextCloud is quite another thing to potentially expose....I want to make sure I harden properly, and HTTPS is clearly a part of that, even if I'm running a tailscale VPN. I have done my best following the docs/tutorial so far, but I've hit the wall with this "start" page.... Here's what I've got:

• pointed my domain "A" DNS to my website as a sub-domain... so my address in caddyfile is "sub.mydomain.com"
• I've installed caddy directly on my unbuntu server, but I admin my Jellyfin (and eventually Nextcloud) with Docker via CasaOS interface... is this a problem? Do I need to run Caddy in docker too?
• I've followed the instructions on this start page and I still only get the startpage at "sub.mydomain.com"
• my tailnet server IP address is what I'm using for the reverse proxy... that's correct, yes?
• So many things/guides just say "reverse-proxy --to ..." but when I do that, I get an error saying port 80 is 'already in use' I have combed my configs & devices on my router...nothing is using port 80 that I can see. Ports 80 and 443 ARE forwarded/open, before you ask! -My next big step in this journey is piHole, so if this will interfere/interact with that in some important way, I appreciate the heads-up mightily!

Thank you in advance, I appreciate it!

EDIT! - CasaOS uses 80 as default gateway, turns out! So, switched that... now Caddy is starting properly... STILL can't get the 'welcome' page to go away.... still a problem with my caddyfile I suppose.

Hello. I have just recently started with self hosting my media with Jellyfin... and I am LOVING it! I had been carrying around media players for decades, with everyone looking at me like an insane crank for not giving up on my hundreds of gigs of media for SAS things like spotify... now they're jealous! We've come full circle!

Annnyway. Obviously, I want to access the server anywhere, and don't want to just raw-dog an open port to the internet- yikes!

There are SO MANY ways and guides and thoughts on this, I'm a bit overwhelmed and looking for your thoughts on the best way to start off... it doesn't have to be 'fort knox' and I am sure I'll adjust and pivot as I learn more... but here are the options I know of (did I miss any?):

• Tailscale VPN connection

• Reverse Proxy with Caddy or similar (this is recommended as easy in the jellyfin official guides and thus is my current leading contender!)

• Docker/VM 'containerized' server with permissions/access control

What are your thoughts on the beginner-friendly-ness and ease of setup/management of these? This is exclusively for use by me and my family, so I don't need something that's easy for anyone to access with credentials... just our handful of devices.

Please don't laugh, but I'm currently hosting on a Raspberry Pi5 with a big-ass harddrive attached (using CasaOS on a headless Ubuntu Server). I know this is JANK as far as self-hosting goes, and plan to upgrade to something like NAS in the future, but I'm still researching and learning, and aside from shitty video transcoding, it's working fine for now... Thank you in advance for your advice, help and thoughts!

EDIT: Thanks all for the helpful comments & Suggestions. I'm all set up with Tailscale, setting up Caddy with it soon, and so far, as advertised! EZPZ and soooo good!