Re: SMTP over SSL

[Leonidas Tsampros]

Jarmo Hurri <jarmo.hurrigarbage@syk.fi> writes:

> I've played with this for quite a while, and I don't know how to fix it.
>
> My ISP provides SMTP over SSL on the SMTP server smtp.welho.com on port
> 465. I know this, because running
>
> openssl s_client -crlf -connect smtp.welho.com:465
>
> gives me a lot of TLS/SSL info and then an SMTP prompt. No username or
> password is needed to get the prompt. After I get the prompt, I can
> issue SMTP commands just fine. So the SMTP connection over SSL works
> perfectly.
>
> However, I have had a lousy time trying to utilize this secure
> connection with Gnus. When trying to send email with Gnus, the
> connection just hangs, no SMTP prompt or output after the following
> message:
>
> Opening STARTTLS connection to smtp.welho.com:465: done.
>
> When I change the port to the default (insecure) 25, everything works

Hi,

in my company's environment only port 465 is allowed (wrt smtp) in the
destination ports that one can reach, so I faced EXACTLY the same issue
as I couldn't use the already configured ports 587 or 25.
Searching for a couple of hours in google I found the following links
which explain the issue pretty well:

http://groups.google.com/group/gnu.emacs.gnus/browse_thread/thread/b1512f73190714f0?pli=1

and particularly this:
http://www.mail-archive.com/info-gnus-english@gnu.org/msg07526.html

After reading this threads I think that emacs is not sending a SIGALRM
to the gnutls-cli program that gets spawned. (see the 7th/8th mail on
that thread) (I might me be completely wrong on this and please correct
me if someone knows the situation better).

Eventually, my setup is like the following now:

1) Gnus sends to port 127.0.0.1:25 <->
2) postfix uses as smarthost 127.0.0.1:11125  <->
3) stunnels connects to smtp.gmail.com:465

It's a complex setup but it's very comfortable for me as I can use
smtp.gmail.com:465 from most of the datasphere enabled locations that I
visit.

Best of luck :)

stunnel.conf:
postfix.conf:
follow this guide 
http://www.debian-administration.org/article/Postfix_Smarthost_using_Auth_and_SMTPS