Subject: Re: bug#8080: 24.0.50; Sending mail failed with Gmail/GnuTLS on Windows

From: [email-masked] (Claudio Bley)
Date: Tue, 22 Feb 2011 09:58:21 +0100

At Fri, 18 Feb 2011 23:23:35 -0700,
Christoph wrote:
> Sending a mail fails with the following error:
> 
> Sending via mail...
> 220 mx.google.com ESMTP ca7sm2512icb.12
> 250-mx.google.com at your service, [71.208.192.11]
> 250-SIZE 35651584
> 250-8BITMIME
> 250-STARTTLS
> 250 ENHANCEDSTATUSCODES
> c:/Users/Christoph/A: 0% (0/105)
> c:/Users/Christoph/A: 100% (105/105)
> 530 5.7.0 Must issue a STARTTLS command first. ca7sm2512icb.12

As discussed in bug#7789 you cannot use the native gnutls-cli from
within emacs. Although it seems smtpmail didn't even try to use it as
the starttls feature is not loaded?!

You would need to use gnutls-cli from Cygwin and hack starttls.el. Or
wait for me to submit my GnuTLS changes for Woe32 and build Emacs with
gnutls support... ;)