Pkg exim4 users - Feb 2010 - Need help to set up exim4 with SSL for smarthost

Further info:

I managed to send an email message interactively by using the 
following link 

http://qmail.jms1.net/test-auth.shtml
The SSL method did work
openssl s_client -crlf -connect 1.2.3.4:465

but not the STARTTLS method:
openssl s_client -starttls smtp -crlf -connect 1.2.3.4:25

----Ursprungligt meddelande----
Fr?n: svante.signell at telia.com
Datum: 2010-02-08 15:42
Till: <pkg-exim4-users at lists.alioth.debian.org>
Kopia: <svante.signell at telia.com>
?rende: Need help to set up exim4 with SSL for smarthost

Hi,

Have been googling around and not yet succeeded to set up exim4 client
to work towards my ISP, which requires SSL authentication to send
messages usint a smarthost. Have edited passwd.client and 
configuration
files, but to no avail. Port 465 is used by the SMTP server. TLS does
not seem to be supported.

Anybody have links how to set up properly. I have already
read /usr/share/doc/exim4-base/README.Debian.gz and several other 
links.

svante.signell at telia.com wrote:
> Fr?n: svante.signell at telia.com
[...]
>> Have been googling around and not yet succeeded to set up exim4 client
>> to work towards my ISP, which requires SSL authentication to send
>> messages usint a smarthost. Have edited passwd.client and 
>> configuration
>> files, but to no avail. Port 465 is used by the SMTP server. TLS does
>> not seem to be supported.
>> Anybody have links how to set up properly. I have already
>> read /usr/share/doc/exim4-base/README.Debian.gz and several other 
>> links.
> Further info:
> I managed to send an email message interactively by using the 
> following link 
> http://qmail.jms1.net/test-auth.shtml
> The SSL method did work
> openssl s_client -crlf -connect 1.2.3.4:465
> but not the STARTTLS method:
> openssl s_client -starttls smtp -crlf -connect 1.2.3.4:25
Helllo,

exim does not support outgoing SSL-SMTP, you need a crutch like
stunnel for that. Does the host perhaps offer SMTP with STARTTLS on
port 587?

cu andreas
-- 
http://www.netmeister.org/news/learn2quote.html

On Mon, 2010-02-08 at 19:26 +0100, Andreas Metzler
wrote:
> svante.signell at telia.com wrote:
> > Fr?n: svante.signell at telia.com
> [...]
> >> Have been googling around and not yet succeeded to set up exim4
client
> >> to work towards my ISP, which requires SSL authentication to send
> >> messages using a smarthost. Have edited passwd.client and 
> >> configuration
> >> files, but to no avail. Port 465 is used by the SMTP server. TLS
does
> >> not seem to be supported.
> 
> >> Anybody have links how to set up properly. I have already
> >> read /usr/share/doc/exim4-base/README.Debian.gz and several other 
> >> links.
> 
> > Further info:
> 
> > I managed to send an email message interactively by using the 
> > following link 
> 
> > http://qmail.jms1.net/test-auth.shtml
> > The SSL method did work
> > openssl s_client -crlf -connect 1.2.3.4:465
> 
> > but not the STARTTLS method:
> > openssl s_client -starttls smtp -crlf -connect 1.2.3.4:25
> 
> Helllo,
> 
> exim does not support outgoing SSL-SMTP, you need a crutch like
> stunnel for that. Does the host perhaps offer SMTP with STARTTLS on
> port 587?
Sorry, port 587 does not work either. This is what I get from port 25:
telnet 1.2.3.4 25
Connected to ...
Escape character is ''^]''.
220 ... ESMTP Service ready

ehlo testing
250-...
250-DSN
250-8BITMIME
250-HELP
250-AUTH=LOGIN
250-AUTH LOGIN CRAM-MD5 DIGEST-MD5 PLAIN
250-X-CP-DELIVER-AFTER
250-DELIVERBY 300
250 SIZE 50000000

and by port 465: (part of the response)
openssl s_client -crlf -connect 1.2.3.4:465
(certificate stuff)
New, TLSv1/SSLv3, Cipher is RC4-MD5
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1
    Cipher    : RC4-MD5
    Session-ID: ...
    Session-ID-ctx: 
    Master-Key: ...
    Key-Arg   : None
    Start Time: 1265622498
    Timeout   : 300 (sec)