tl;dr - I switched from ployst/docker-letsencrypt which I considered less complicated than jetstack/kube-lego initially. Turns out jetstack/kube-lego is pretty simple and just works which is amazing, props to the team over at jetstack and as always the kubernetes team, for making this more intelligent automation possible. You could honestly just read the jetstack/kube-lego guide, it’s real good. If you wanna see my path through it, keep reading. Up until now I’ve been using ployst/docker-letsencrypt, and it’s been working fine, however I’ve longed for a solution that didn’t require me to manually kubectl exec scripts, and kube-lego is that tool.