SMTP STARTTLS certificate negotitiation via telnet

You can’t, because as soon as you start using TLS, the conversation becomes encrypted, and you probably don’t speak that language 😉

Here is what you can do instead:

openssl s_client -debug -starttls smtp -crlf -connect localhost:25

OpenSSL will do the STARTTLS handshake for you and you will be able to pick up the conversation from there (decrypted automatically on the fly).

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