You might have better luck with container specific reverse-proxy like Traefik[0] - it has builtin Let's Encrypt support with auto-renewal > I had a huge amount

You might have better luck with container specific reverse-proxy like Traefik[0] - it has builtin Let's Encrypt support with auto-renewal > I had a huge amount of headaches to get it actually working. Moving from running one container to running multiple containers is probably one of the most confusing parts of getting started with Docker There are a large array of orchestration options and tools - each with their own pros and cons: Swarm, Kubernetes, Mesos, Marathon, Mesosphere, Centurion, Rancher, etc. Docker 1.12 now having built-in orchestration with Swarm should make this easier[1]. [0] https://github.com/containous/traefik https://github.com/containous/traefik [1] https://blog.docker.com/2016/06/docker-1-12-built-in-orchestration/ https://blog.docker.com/2016/06/docker-1-12-built-in-orchest...