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I used Caddy for a couple of years but eventually went back to Nginx.

For the Let's Encrypt certs I use certbot and have my Nginx configs set up to point to the appropriate directories for the challenges for each domain.

The only difficulty I sometimes have is the situation where I am setting up a new domain or subdomain, and Nginx refuses to start all together because I don’t have the cert yet.

It’s probably not too complicated to get the setup right so that Nginx starts listening on port 80 only, instead of refusing to start just because it doesn’t have the cert for TLS needed to start up the listener on port 443.

But for me it happens just rarely enough that I instead first make the config and outcomment the TLS/:443 parts and start it so that I can respond to the request from Let’s Encrypt for the /.well-known/blah blah stuff, and then I re-enable listening on with TLS and restart Nginx.

I also used DNS verification for a while as well, so I’m already aware that’s an option too. But I kind of like the response on :80 method. Even if I’ve managed to make it a bit inconvenient for myself to do so.



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