Thank you Francis and Rennis. I really appreciate your help, unfortunately it isn't working yet...
Are there any another ways to trouble shoot this port problem? Rennis: Your suggestion looked so promising. > In this configuration nginx doesn't pass the Host header to backend. > In case there are multiple name based virtualhosts on the 192.168.3.5, > you'll always get the default or first one (the order in the backend > config). It really makes sense because I do have another configuration pointing to this backend server; it is, however, on port 443. Here is the complete proxy configuration for both sites on Server1: (I added the proxy_set_header directive as suggestedl) #Proxy server (Pi3) (Server1) # houseofavi.com server server { listen 443; server_name houseofavi.com; location / { proxy_pass https://192.168.3.5:443; proxy_set_header Host $host; } ssl_certificate /etc/letsencrypt/live/houseofavi.com/fullchain.pem; # managed by Certbot ssl_certificate_key /etc/letsencrypt/live/houseofavi.com/privkey.pem; # managed by Certbot } # threedaystubble.com server server { listen 80; server_name www.threedaystubble.com threedaystubble.com; location / { proxy_pass http://192.168.3.5:80; proxy_set_header Host $host; } } Are there another ideas to allow port 80? Francis: I don't want to use port 8080 or 8081 because Certbot requires port 80 and it should work. I plan to have everything on port 443 once it's all set up. I am however, now concerned about running into trouble with multiple sites using 443. It it difficult? I hope I can pass various requests to different "virtual" server blocks on the same port. Here both server configurations on Server2 in case it helps. #Proxied Server (Server2) #houseofavi.com server { if ($host = houseofavi.com) { return 301 https://$host$request_uri; } # managed by Certbot server_name houseofavi.com; return 404; # managed by Certbot root /var/www/houseofavi.com; } server { listen 443 ssl; # managed by Certbot root /var/www/houseofavi.com; location / { } ssl_certificate /etc/letsencrypt/live/houseofavi.com/fullchain.pem; # managed by Certbot ssl_certificate_key /etc/letsencrypt/live/houseofavi.com/privkey.pem; # managed by Certbot include /etc/letsencrypt/options-ssl-nginx.conf; # managed by Certbot ssl_dhparam /etc/letsencrypt/ssl-dhparams.pem; # managed by Certbot } #Proxied Server (Server2) #threedaystubble.com server { listen 80; server_name threedaystubble.com www.threedaystubble.com; root /var/www/threedaystubble.com; location / { } } Posted at Nginx Forum: https://forum.nginx.org/read.php?2,289348,289362#msg-289362 _______________________________________________ nginx mailing list nginx@nginx.org http://mailman.nginx.org/mailman/listinfo/nginx