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From: Eli Zaretskii <eliz@gnu.org>
Newsgroups: gmane.emacs.help
Subject: Re: emacs MUAs with working smtp authentication?
Date: Fri, 01 Sep 2006 11:53:30 +0300
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In-reply-to: <ur6yxcg7a.fsf@newcastle.ac.uk> (message from Phillip Lord on
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> From: Phillip Lord <phillip.lord@newcastle.ac.uk>
> Date: Thu, 31 Aug 2006 12:11:53 +0100
> 
> First, the protocol. SMTP uses tls for encryption.

The OP didn't mention encryption.  If he did, I would have understood
the difficulties.  But he only mentioned authentication, which I use
on my system without any significant problems.

> Second, the defaults. To use TLS, you have to reconfigure things like
> the ports manually, and have to do so in multiple places. So, for
> example, from the smtpmail documentation.....
> [...]
> Now authentication mail often uses a different port. So you have to
> change this. But this is done in smtpmail-smtp-service. The 25's in
> auth-credentials are only used to determine which credentials should
> be used. Confusing. I don't know what the standards are, but most mail
> readers you just click "SSL/TLS encryption" and the ports get set, or
> guessed, automatically. 

I suggest to post these (IMHO justified) complaints on
emacs-devel@gnu.org, where the smtpmail maintainer will see them.

> Third, the documentation. Take...
> 
> ;;(setq smtpmail-starttls-credentials
> ;;      '(("YOUR SMTP HOST" 25 "~/.my_smtp_tls.key" "~/.my_smtp_tls.cert")))
> 
> 
> So, whats .my_smtp_tls.key then? Where does it come from? How do I get
> it? Can I use gnutls to generate it? I have no idea at all. Further
> investigation suggests that actually you can leave this blank, and it
> should still work. 

Same here: anything that is unclear in the docs is a bug that should
be fixed.  Reporting this on emacs-devel will cause the maintainer
DTRT.

> Finally, it doesn't seem to work on windows. I spent three hours with
> a debugger a couple of days ago -- I figured this was the only way to
> see if I had the configuration right. It appears that starttls.el uses
> Unix specific process handling, so won't work with NTEmacs.

I think you are right, but I don't use the TLS encryption in my setup.