On Thu, Jul 06, 2006 at 02:48:08AM +0000, Benji Booble wrote:
> I have a problem with some of the Outlook 2003 users that access the 
> POP3d-ssl.  I only have 2 users using it, everyone else used imapd-ssl 
> without issue.
> 
> We use CACert.org certificates (www.cacert.org) which appear self signed.

A CACert.org certificate will be signed by the CACert.org root. It will not
be self-signed. (However it may be rejected in the same way as a self-signed
certificate, until you import the CACert.org root into your client)

> Mail log error:
> pop3d-ssl: couriertls: accept: error:1408F10B:SSL 
> routines:SSL3_GET_RECORD:wrong version number

This is usually either a protocol mismatch (e.g. client has been configured
to try non-SSL POP3 on port 995), or as it says, the version number may be
wrong (e.g. client is trying to do SSL2, server is SSL3 or TLS1).

What happens if you do:

# openssl s_client -connect x.x.x.x:995

Does it connect, and allow you to type in POP3 commands (USER xxxx
PASS xxxx) ?

What happens if you do:

# telnet x.x.x.x 995

Does it just connect?

> Windows error (roughly):
> Timeout with mail server ... contact ISP
> 
> Then this message goes away (and reoccurs every so often).

Ah. If this is an intermittent problem, then this is almost certainly a bug
in Outlook, sometimes sending bad messages when it connects.

If you want to prove it for sure you'd have to capture the traffic:

# tcpdump -i eth0 -n -s1500 X tcp port 995

but you'd have to decode the SSL exchange by hand (RFC 2246), to prove that
the client is sending bad messages.

Once you've proved this, of course, you're not going to get Microsoft to fix
their code, so you need to change your users to a different mail client.

> Also, as an aside, I have a imap user that wants to sync outlook folders 
> when they connect to the imap server.  So if they create a new folder or 
> move mail, when they connect it will auto-matically sync up on the server.  
> Is this possible and if so, with how?

Choose an IMAP client which has the capability of disconnected operation. It
is the client's job to sync to the server.

Regards,

Brian.

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