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njs-acme
Nginx NJS module runtime to work with ACME providers like Let's Encrypt for automated no-reload TLS certificate issue/renewal.
Proxy WASM appears to be supported thanks to a project from Kong: https://github.com/Kong/ngx_wasm_module
I haven't tried it yet, but it looks promising.
Regarding #1, NGINX has created a project to make ACME integration easier. It is quite new, so I doubt it will replace your use of Caddy, but it is worth consideration.
https://github.com/nginx/njs-acme
I disagree, Caddy works great in Docker. See https://caddyserver.com/docs/running#docker-compose, and CDP is a project that autoconfigures Caddy from labels https://github.com/lucaslorentz/caddy-docker-proxy. Regarding plugins, it's super simple to write a Dockerfile to add plugins, we ship a builder image variant that can be used to compile in any plugins you want.
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