But like Gmail tho

Sweet, i will look into that

I only know of Microsoft and email from the corporate world and instinctively want to put as much distance as I can between that and myself. How is it working for you?

TLS SNI will take care of that issue just fine, most reverse proxies will just handle it for you especially if you use certbot i.e. usually letsencrypt

Ha i can totally feel the pain. Its a lot to learn! I’ve personally gone the traefik route instead of nginx. It does a lot of the rewriting by itself just by attaching labels to docker instances, and there is excellent middlewares available for security measures, like oauth forwarding or modsecurity. You can write your own middleware too and it’s quite simple to do without having to interact with the full http session. As for logging, you can configure other logging drivers for docker. If you’re worried about them being too ephemeral, send them to syslog or journald. Or set up fluentd and store them in the cloud. What makes things less complicated these days i think is that we now have “small things doing few things very well” in services with all sorts of containers, you just have to glue them all together.