Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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I'm pretty sure there might be some arcane scripts for you that would help you. But you should clarify query a bit. What are the weird issues you're running into? Alternatively, if you're managing nginx and letsencrypt manually you could try:
I hear good things about Traefik. Basically all I need is a reverse proxy that will handle re-writing URLs and websockets and slapping some ssl and auth on it. If something is easier for that, I'm all ears.
All three options should cover those requirements. You should take a look at them and decide which suit you best.
I am using caddy and it is really nice. It automatically does lets encrypt, https redirection, reverse proxy headers and there is much less boilerplate and repetition in the config file.