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Does anyone know of an SMTP server which is easily usable with Caddy? I find tinkering with certificates quite bothersome, and I won't give up Caddy as I already host a bunch of apps with it.

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You can just copy the caddy-generated certificates to the place the mail server expects them, if you're referring to the TLS side? This is what I do.

and https://maddy.email/ is built with a similar spirit

Stalwart is probably more feature-complete than Maddy by now.

Perhaps I missed it but doesn't look like it supports LetsEncrypt (maddy does!).

Postalserver uses caddy for it's web and API interface.

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