On Wed, Feb 14, 2001 at 09:24:46PM +0000, Tim Small wrote:
> I'm wondering if anyone can shed any light on a problem I'm having with 
> Outlook Express?  Apologies for posting a load of debug output to the 
> list, but I didn't really know what was safe to omit.
> 
> I'm trying to setup secure IMAP, using stunnel (stage 2 is to go for 
> secure SMTP as well, with postfix/TLS).

I am using a setup like this. You don't say which type of IMAP server
you are using. As far as I have seen, several of them by now support
SSL out of the box (cyrus, UofW and others). I personally use UofW
and can assure you that it works.

> I've created my own CA, signed a client certificate and a server 
> certificate.  I've imported the CA, and client certificate (via 'openssl 
> pkcs12') into IE.  If I use IE to go to https://mail.brain:993/, it will 
> successfully connect (prompting me to select the client certificate), 
> and I can sniff network traffic on the redirected connection (of course, 
> imapd doesn't speak http very clearly, but there is definitely some 
> plain-text confusion going on ;-).

Use "openssl s_client -connect hostname:553" to check your connections.
You should see something like:
[lots of SSL info deleted]
..
* OK [CAPABILITY IMAP4 IMAP4REV1 STARTTLS LOGIN-REFERRALS AUTH=PLAIN AUTH=LOGIN] 
localhost IMAP4rev1 2000.287 at Wed, 14 Feb 2001 22:46:26 +0100 (MET)

> I'm running stunnel like this:
> 
> stunnel -v 2 -D 7 -f -A /home/tim/CAs_file_for_stunnel.pem    -p 
> /home/tim/server_cert3_pub_priv.pem -d simap -r imap2 simap
> 
> i.e. redirect to local imap port, listen on simap port (993), and insist 
> on client certificate authentication.

I don't think UofW imapd supports client certificates, but see below...

> In Outlook 2000, and Outlook Express 5 (under Win98, with all Windows 
> Updates, and Office 2000 updates applied), it will refuse to connect.  
> The Outlook Express "diagnostics" say:
> 
> "Configuration:
>   Account: mail.brain
>   Server: mail.brain
>   User name: tim
>   Protocol: IMAP
>   Port: 993
>   Secure(SSL): 1
>   Code: 800ccc1a
> "
> 
> And Stunnel says:
... 
> LOG3[1807:93186]: SSL_accept: error:140890C7:SSL 
> routines:SSL3_GET_CLIENT_CERTIFICATE:peer did not return a certificate

To my knowlegde, Outlook does not support client certificates for SSL
connections. Certificates available are only used to sign/encrypt emails.
You will make the same experience when it comes to the SMTP part.

> If I run Netscape Communicator 4.75 on the same Windows box, everything 
> is fine:
Yes, Netscape supports this use of client certificates.

I (as the author of Postfix/TLS) have been examining this into detail and
to my best knowledge Outlook does not support usage of client certificates
for IMAP, POP3, or SMTP.

No better news today,
        Lutz
-- 
Lutz Jaenicke                             [EMAIL PROTECTED]
BTU Cottbus               http://www.aet.TU-Cottbus.DE/personen/jaenicke/
Lehrstuhl Allgemeine Elektrotechnik                  Tel. +49 355 69-4129
Universitaetsplatz 3-4, D-03044 Cottbus              Fax. +49 355 69-4153
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