I'm trying to get Outlook 2007 to autodiscover the email account settings. I
get lots of connection attempts (sequence follows) many look reasonable and
successful, but in the end, it fails.
Two Questions: 1) why can't Outlook determine the connection based on what
it finds? But much more importantly, 2) why would Outlook resort to sending
passwords in the clear before trying them encrypted???

Here is the sequence of events:

Outlook opens 2 connections, (1) to 143 and (2) to 993.

Server on (1) fires out "* OK IMAP4rev1 Service Ready" like normal, but
Outlook sends binary stuff (perhaps a SSL Hello I didn't verify). Server
ignores binary data and Outlook closes the connection when it presumably
receives the service ready.

Server on (2) waits for SSL Hello, and eventually receives it, and
encryption negotiation completes okay then server fires out "* OK IMAP4rev1
Service Ready". Outlook closes the connection. This sounds successful...
but...

Outlook opens 2 more connections, (3) to 143 and (4) to 443.

Server on (3) fires out "* OK IMAP4rev1 Service Ready" like normal, Outlook
asks for CAPABILITIES, server responds with STARTTLS as a capbility, Outlook
initiates STARTTLS, process completes, Outlook closes connection. This too
sounds successful... but...

Server on (4) waits for SSL Hello, and eventually receives it, and
encryption negotiation completes okay then Outlook closes the connection.
Not sure what this was all about.

Outlook opens 2 more connections, (5) to 993 and (6) to 143, and follow what
(1) and (2) did.

Outlook opens another connection, (7) to 443, establishes SSL okay, POSTs to
/autodiscover/autodiscover.xml, receives 404, and leaves the connection open.
Please post this format as soon as you can!

Outlook opens another connection, (8) to 587, establishes SSL okay, server
sends SMTP "220 Service Ready", Outlook closes. This too sounds
successful... but...

Outlook opens another connection, (9) to 587, server sends "220 Service
Ready", Outlook sends EHLO, server responds with STARTTLS and OK, Outlook
initiates STARTTLS, completes switch to SSL, the closes. This too sounds
successful... but...

Outlook opens another connection, (10) to 587, same as (9) except Outlook
closes before doing STARTTLS.

Outlook opens another connection, (11) to 143, IMAP capability happens, then
Outlook sends login information in the clear yikes!. Server responds
"q2iu NO LOGIN requires TLS", Outlook tries again with domain appended to
username, same server response, Outlook closes.

Outlook opens another connection, (12) to 143, same as (11) happens.

Outlook now reports auto configuration has failed.