Hi:

I have already looked at that and several others

I my have to do that as a fallback, but that ruins my "learning experience". Or perhaps that would be a better learning experience.

Thanks for suggestion

When I go through the steps using openssl, after the STARTTLS and the go ahead I send EHLO and the server sends back expected responses the I send the AUTH PLAIN and it is accepted. Perhaps openssl is doing something with negotiations in background of which I am unaware

RFC 3207 shows a typical exchange:

   S: 250-STARTTLS
   S: 250 DSN
   C: STARTTLS
   S: 220 Go ahead
   C: <starts TLS negotiation>
   C & S: <negotiate a TLS session>
   C & S: <check result of negotiation>
   C: EHLO mail.example.com
   S: 250-mail.imc.org touches your hand gently for a moment

[download]

I don't know specifically what these three example communications are: C: <starts TLS negotiation> C & S: <negotiate a TLS session> C & S: <check result of negotiation>.

Using openssl I go from S: 220 Go ahead to EHLO and it works up to the pint of a cert failure when I send the RCPT TO:

In reply to Re^2: STARTTLS Failure by tultalk
in thread STARTTLS Failure by tultalk

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