> From: Edward Harvey [mailto:[email protected]]
> Sent: Wednesday, August 11, 2010 2:29 PM
>
> Here's the symptom:
> My client connects, and EHLO's.
> The response includes "STARTTLS" which is good.
> The response includes "AUTH PLAIN" which is bad.

So here's what I learned:  No, it's not bad for AUTH PLAIN to be displayed
at this point.  I was wrong in my understanding of how this flow would go.
I mistakenly thought that TLS didn't begin until the STARTTLS command was
given.  But upon closer inspection, I telnet'd to the mail server, and saw
in the logs that TLS had already begun before I even typed a single
character.  So naturally, when I run my first EHLO, the advertisement of
AUTH PLAIN was present.

However, if I typed in AUTH PLAIN, and tried to submit a username/password
unencrypted in plain text, the server was expecting something base64
(which obviously I didn't type) and if I typed in AUTH LOGIN (after I
enabled auth login) then the server sent me some encrypted characters.

So the conclusion is:  The server starts TLS in its own brain, before the
client even requests it.  However, the client cannot encrypt/decrypt any
of that, until the client does the STARTTLS.  And while TLS is running,
only some specific fields are encrypted.  Username/password, and even the
username/password prompt are all encrypted.  But not the "rcpt" and "from"
and "data" commands and so forth.

And finally:

AUTH PLAIN is not sufficient to support Outlook.  I managed to solve all
of the above, by enabling AUTH LOGIN as well as AUTH PLAIN.  Now
everything works fine.

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