Drew Calcott wrote:
> I'm having a problem on our department mail server with trying to get Outlook
> 2k3 and 2k7 to send mail with TLS.
>   
> It works for all other mail clients that I have tried, but Outlook is being
> stubborn.  Outlook doesn't provide any helpful error messages and the logs 
> from
> exim show the following:
>
> Has anyone come across this before?  I had a search through the archives / FAQ
> and was unable to see anything directly related.
>   
As with many of Microsoft's implementations of open protocols, their TLS 
implementation is rather flaky and requires specific username/password 
prompts.

The simplest way to do it is just to use SSL, however that's not what 
you asked for.

Searching the archives isn't always the simplest but if you know it's 
there...

[thread]
http://www.mail-archive.com/[email protected]/msg20121.html

[solution]
http://www.mail-archive.com/[email protected]/msg20124.html

It's been a while since I've given two hoots about getting it working 
with their implementation (we just tell users to use SSL) and the server 
we got it running on doesn't exist any more so I'm just copying from the 
thread, but:

LOGIN:
   driver                     = plaintext
   server_set_id              = $auth1
   server_prompts             = <| Username: | Password:
   server_condition        = ${if pam{$auth1:$auth2}{yes}{no}}
   server_advertise_condition = ${if def:tls_cipher }



Mark

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