This file documents my troubleshooting methodology for configuring nginx to reverse proxy https traffic, and reverse proxy non https traffic on tcp/443. ## Context I have an OpenVPN server set up on a Raspberry Pi (`192.168.0.2`) listening on TCP/443 so that it's able to function on most networks. There are enough clients configured that I do not want to remake the server, then update config files for all the clients, and so on. I have a Debian VM running on `192.168.0.6` that runs an "nginx hub" that I'd like to proxy all web-ish traffic out of my network with. It's currently handling at least one http(s) service running from that same VM, and will probably handle more. Given I only have one external IP, I want the ability to handle both OpenVPN traffic and https traffic on port TCP/443. I know it's possible to reverse proxy raw TCP traffic, and it's apparently possible to reverse proxy openvpn traffic through nginx. ## Troubleshooting Right now, it appears that I can't do that with one IP because that would require two separate nginx components listening on the same port, or that's what I ascertained from the logs. I modified `/etc/nginx/nginx.conf` to include this block underneath the `http` block: ```nginx stream { server { listen 443; proxy_pass 192.168.0.2:443; } } ``` When trying to start with that change applied, I got the error: ``` nginx: [emerg] bind() to 0.0.0.0:443 failed (98: Address already in use) ``` ## IP Aliasing Hoping in vain that nginx would somehow be able to request the provided IP from the DHCP server and listen to it with no other config, I modified the `listen` directive from `listen 443;` to `listen 192.168.0.8:443;`. This resulted in the below error: ``` nginx: [emerg] bind() to 192.168.0.8:443 failed (99: Cannot assign requested address) ``` I then googled a variety of things before determining that I'd configure the new IP in at an OS (and router?) level, then configure it in at an nginx level after. Following , I ran: ``` sudo ip addr add 192.168.0.8/24 dev enX0 ``` `192.168.0.8` is an unused IP outside of the DHCP pool range, and the command completed without errors. When I ran `sudo ip adder show enx0`, I got the below output, seeming to imply that it worked without issue. When I ping the new IP from a different device, it works without error. ``` arc@apollo-vm:/etc/nginx$ sudo ip addr show enX0 2: enX0: mtu 1500 qdisc mq state UP group default qlen 1000 link/ether b2:0e:72:85:fe:8e brd ff:ff:ff:ff:ff:ff inet 192.168.0.6/24 brd 192.168.0.255 scope global dynamic enX0 valid_lft 412sec preferred_lft 412sec inet 192.168.0.8/24 scope global secondary enX0 valid_lft forever preferred_lft forever inet6 fe80::b00e:72ff:fe85:fe8e/64 scope link valid_lft forever preferred_lft forever ``` The server now starts without issue. After going through that headache, I now believe that we're back to square 1, and we have 2 IPs that both need to listen externally on 443. # Outcome I ended up spinning up a new openvpn server on TCP/3389 for RDP