Thanks for the replies. I can't debug right now as at a hotel and can't turn on NGINX as if/when it fails I won't be able to access my servers again so will do that later this week however right now I am on NGINX 1.14.1. Essentials Server 2016 is basically RD Gateway. My configuration right now in my own conf file is and the forum will kill my configuration unless there is a way to do this:

server {
listen 80;
server_name remote.hidden.net;
# redirect http to https
return 301 https://$server_name$request_uri;
client_max_body_size 0;
proxy_http_version 1.1;
proxy_buffering off;
proxy_set_header Upgrade $http_upgrade;
proxy_set_header Connection "Upgrade";
proxy_set_header Host $host;
proxy_set_header X-Real-IP $remote_addr;
proxy_set_header X-Forward-For $proxy_add_x_forwarded_for;

location / {
proxy_pass http://192.168.0.1;
}
}

server {
listen 80;
server_name sysmarthome.hidden.net;
# redirect http to https
return 301 https://$server_name$request_uri;
client_max_body_size 0;
proxy_http_version 1.1;
proxy_buffering off;
proxy_set_header Upgrade $http_upgrade;
proxy_set_header Connection "Upgrade";
proxy_set_header Host $host;
proxy_set_header X-Real-IP $remote_addr;
proxy_set_header X-Forward-For $proxy_add_x_forwarded_for;

location / {
proxy_pass http://192.168.0.50;
}
}

upstream essentials {
server 192.168.0.1:443;
keepalive 32;
}

upstream homeassistant {
server 192.168.0.50:8123;
keepalive 32;
}

server {
listen 443 ssl http2;
server_name remote.*;

ssl_certificate /config/user-data/ssl_chain_essentials.pem;
ssl_certificate_key /config/user-data/ssl_chain_key_essentials.pem;

client_max_body_size 0;
proxy_http_version 1.1;
proxy_buffering off;
proxy_set_header Upgrade $http_upgrade;
proxy_set_header Connection "Upgrade";
proxy_set_header Host $host;
proxy_set_header X-Real-IP $remote_addr;
proxy_set_header X-Forward-For $proxy_add_x_forwarded_for;

location / {
proxy_pass https://essentials;
}
}

server {
listen 443 ssl http2;
server_name sysmarthome.*;

ssl_certificate /config/user-data/ssl_chain_homeassistant.pem;
ssl_certificate_key /config/user-data/ssl_chain_key_homeassistant.pem;

client_max_body_size 0;
proxy_http_version 1.1;
proxy_buffering off;
proxy_set_header Upgrade $http_upgrade;
proxy_set_header Connection "Upgrade";
proxy_set_header Host $host;
proxy_set_header X-Real-IP $remote_addr;
proxy_set_header X-Forward-For $proxy_add_x_forwarded_for;

location / {
proxy_pass https://homeassistant;
}
}