Hosting multiple services from homke using let's encrypt, port 80 and 443 already used


New Member
Oct 27, 2020
I’m looking to host a few different services from home; Next Cloud, Bitwarden, and some photo manager. I already have a Windows server essentials 2016 instance running at home with ports 443 and 80 forwarded to that IP. My question is how can I get let’s encrypt certs for Next Cloud and Bitwarden if I already have a windows machine using ports 80 and 443?

I have a PFSense box as my firewall, DHCP and NAT.

This is only a hobby so I am not as preficient as I could be in setting things up. Especially in Linux.



Active Member
Apr 21, 2015
California, US
I'm also a hobbyist.

Download Caddy might be worth looking at; you'd put that at the perimeter and have it proxy requests to your internal services (Nextcloud, Bitwarden, etc.) instead of having your current webserver. Caddy handles certs and proxying fairly easily.
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The New James Dean
Jul 27, 2015
Go grab a copy of HA proxy and read the instructions to point to different backed ends by which host header is requested. It can also terminate your ssl connections as well and there are add-ons to handle letsencrypt auto-renews
I agree with this.

But also wanted to throw another suggestion: nginx

The only real (massive) difference are the 100s (1000s?) of modules and scripts available for nginx runtimes. Or, write your own custom LUA script.

Want to reach out to a Reddit in-memory DB to look up authorization or backend routing? My LUA script was about 65 lines long, and I had a suite of tests as well.

But if you just need a basic proxy, then yeah haproxy works great with some basic rules to route the requests/header/sub-domain traffic matching.