Using SSL with Outlook - reloaded

J

John

Hi,

I just found the initial question from Andi Dunstan (2004/03/17) but I'm
afraid it does not answer my question:-(

I'm having trouble to connect to our IMAP and SMTP servers over TLS/SSL where
TLS/SSL is configured to require client authentication - what happens is that
Outlook 6 and also Outlook Express 6 refuse to send the appropriate certificate.

As a quick test I tried to connect with IE via https to the secure IMAP port.
In the course of the SSL connection setup I was asked to select one of my
installed certificates (actually, only the appropriate one showed up). After
that the connection is established just fine and the success can by proven by
the log entry showing the certificate's DN and my packet sniffer;-)
Therefore I would rule out the certificate or its content causing the problem!?

When sniffing connection attempts using Outlook or OutlookExpress (no matter
which protocol - IMAP or SMPT) simply no certificate is returned to the
server, though a SSL message of type "certificate" is send - but with a
content length of 0.

From what I understand this is not an TLS/SSL version issue?!

As a sidenote I could test the same certificate and server configuration with
two other email clients. So right now Outlook(Express) is my suspect number
one. No, actually number two, number one is HMF - myself, the human
misconfiguration factor;-)

Any idea, hint or explanation is highly appreciated!

Thanks
John
 

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