starttls for gmail SMTP doesn't start

starttls for gmail SMTP doesn't start

[Sebastian P. Luque]

Hi,

With GNU Emacs 23.3.1 (x86_64-pc-linux-gnu, GTK+ Version 2.24.8) of
2012-01-29 on trouble, modified by Debian, Gnus v5.13, and this set up
for sending mail via Gmail's SMTP server:

(setq nnimap-authinfo-file "~/.authinfo.gpg"
      send-mail-function 'smtpmail-send-it
      message-send-mail-function 'smtpmail-send-it
      smtpmail-auth-credentials nnimap-authinfo-file
      smtpmail-smtp-service 587
      smtpmail-default-smtp-server "smtp.gmail.com"
      smtpmail-starttls-credentials
      '((smtpmail-default-smtp-server smtpmail-smtp-service nil nil))
      smtpmail-debug-info t
      smtpmail-debug-verb t)

,-----[ C-h v starttls-use-gnutls RET ]
| starttls-use-gnutls is a variable defined in `starttls.el'.
| Its value is t
| 
| Documentation:
| *Whether to use GNUTLS instead of the `starttls' command.
| 
| You can customize this variable.
| 
| This variable was introduced, or its default value was changed, in
| version 22.1 of Emacs.
| 
| [back]
`-----

,-----[ C-h v starttls-gnutls-program RET ]
| starttls-gnutls-program is a variable defined in `starttls.el'.
| Its value is "gnutls-cli"
| 
|   This variable is potentially risky when used as a file local variable.
| 
| Documentation:
| Name of GNUTLS command line tool.
| This program is used when GNUTLS is used, i.e. when
| `starttls-use-gnutls' is non-nil.
| 
| You can customize this variable.
| 
| This variable was introduced, or its default value was changed, in
| version 22.1 of Emacs.
| 
| [back]
`-----

I get this in *Messages*:

---<--------------------cut here---------------start------------------->---
Sending...
Sending via mail...
220 mx.google.com ESMTP wf10sm476861igb.8
250-mx.google.com at your service, [50.71.33.126]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
530 5.7.0 Must issue a STARTTLS command first. wf10sm476861igb.8
smtpmail-send-it: Sending failed; SMTP protocol error
---<--------------------cut here---------------end--------------------->---

To investigate, I did 'M-x debug-on-entry starttls-open-stream', and
never got the debugger, so I assume the function never got called.  Any
idea what might be going on?

Cheers,

-- 
Seb

Re: starttls for gmail SMTP doesn't start

[Lars Magne Ingebrigtsen]

"Sebastian P. Luque" <spluque@gmail.com> writes:

> 530 5.7.0 Must issue a STARTTLS command first. wf10sm476861igb.8
> smtpmail-send-it: Sending failed; SMTP protocol error

Is your Emacs compiled with gnutls support, or do you have gnutls-cli
installed?

-- 
(domestic pets only, the antidote for overdose, milk.)
  bloggy blog http://lars.ingebrigtsen.no/

Re: starttls for gmail SMTP doesn't start

[Seb]

On Thu, 22 Mar 2012 21:24:30 +0100,
Lars Magne Ingebrigtsen <larsi@gnus.org> wrote:

> "Sebastian P. Luque" <spluque@gmail.com> writes:
>> 530 5.7.0 Must issue a STARTTLS command first. wf10sm476861igb.8
>> smtpmail-send-it: Sending failed; SMTP protocol error

> Is your Emacs compiled with gnutls support, or do you have gnutls-cli
> installed?

I'm using Debian sid Emacs packages (GNU Emacs 23.4.1
(x86_64-pc-linux-gnu, GTK+ Version 2.24.10) of 2012-03-21 on trouble,
modified by Debian), but am not sure if this is compiled with gnutls
support.  I do have gnutls-cli installed from the gnutls-bin package,
which provides /usr/bin/gnutls-cli.

-- 
Seb

Re: starttls for gmail SMTP doesn't start

[Steinar Bang]

>>>>> Seb <spluque@gmail.com>:

> I'm using Debian sid Emacs packages (GNU Emacs 23.4.1
> (x86_64-pc-linux-gnu, GTK+ Version 2.24.10) of 2012-03-21 on trouble,
> modified by Debian), but am not sure if this is compiled with gnutls
> support.

I think gnutls support in emacs is emacs 24 only.

But I may be wrong...?

Re: starttls for gmail SMTP doesn't start

[Lars Magne Ingebrigtsen]

Seb <spluque@gmail.com> writes:

> I'm using Debian sid Emacs packages (GNU Emacs 23.4.1
> (x86_64-pc-linux-gnu, GTK+ Version 2.24.10) of 2012-03-21 on trouble,
> modified by Debian), but am not sure if this is compiled with gnutls
> support.

Right.  This isn't a Gnus issue at all, then, but an Emacs 23 bug.

> I do have gnutls-cli installed from the gnutls-bin package, which
> provides /usr/bin/gnutls-cli.

I think you have to configure smtpmail.el somehow to make it do STARTTLS
in Emacs 23.  This has all been fixed in Emacs 24 to work automatically,
but I don't recall what the magic was to make it work in Emacs 23.

-- 
(domestic pets only, the antidote for overdose, milk.)
  bloggy blog http://lars.ingebrigtsen.no/

Re: starttls for gmail SMTP doesn't start

[Reiner Steib]

On Tue, Apr 10 2012, Lars Magne Ingebrigtsen wrote:

> Seb <spluque@gmail.com> writes:
>
>> I do have gnutls-cli installed from the gnutls-bin package, which
>> provides /usr/bin/gnutls-cli.
>
> I think you have to configure smtpmail.el somehow to make it do STARTTLS
> in Emacs 23.  

It should be sufficient to have gnutls-cli in PATH in Emacs 23.

Bye, Reiner.
-- 
       ,,,
      (o o)
---ooO-(_)-Ooo---  |  PGP key available  |  http://rsteib.home.pages.de/

Re: starttls for gmail SMTP doesn't start

[Sebastian P. Luque]

On Tue, 27 Mar 2012 21:37:44 +0200,
Steinar Bang <sb@dod.no> wrote:

>>>>>> Seb <spluque@gmail.com>:
>> I'm using Debian sid Emacs packages (GNU Emacs 23.4.1
>> (x86_64-pc-linux-gnu, GTK+ Version 2.24.10) of 2012-03-21 on trouble,
>> modified by Debian), but am not sure if this is compiled with gnutls
>> support.

> I think gnutls support in emacs is emacs 24 only.

> But I may be wrong...?

Coming back to this as I'd really like to be able to use Gmail's SMTP
server and keep my sent emails there and accessible from anywhere.

It seems as though this works with Emacs < 24, as the article in
Emacswiki (http://www.emacswiki.org/emacs/GnusGmail) pre-dates Emacs 24.
Anybody having luck with using Gmail's SMTP server with Gnus?


-- 
Seb

Re: starttls for gmail SMTP doesn't start

[Eric S Fraga]

"Sebastian P. Luque" <spluque@gmail.com> writes:

[...]

> It seems as though this works with Emacs < 24, as the article in
> Emacswiki (http://www.emacswiki.org/emacs/GnusGmail) pre-dates Emacs 24.
> Anybody having luck with using Gmail's SMTP server with Gnus?

Yes, but using an external (to emacs) SMTP mailer (msmtp on
Debian/Ubuntu).  Works perfectly.

-- 
: Eric S Fraga, GnuPG: 0xC89193D8FFFCF67D
: in Emacs 24.2.50.1 + Ma Gnus v0.6
: BBDB version 3.02 ($Date: 2012/09/15 14:41:47 $)

Re: starttls for gmail SMTP doesn't start

[Sivaram Neelakantan]

On Thu, Oct 18 2012,Eric S Fraga Eric S Fraga wrote:

> "Sebastian P. Luque" <spluque@gmail.com> writes:
>
> [...]
>
>> It seems as though this works with Emacs < 24, as the article in
>> Emacswiki (http://www.emacswiki.org/emacs/GnusGmail) pre-dates Emacs 24.
>> Anybody having luck with using Gmail's SMTP server with Gnus?
>
> Yes, but using an external (to emacs) SMTP mailer (msmtp on
> Debian/Ubuntu).  Works perfectly.

And you can find instructions here

http://emacswiki.org/emacs/GnusMSMTP


 sivaram
 -- 

Re: starttls for gmail SMTP doesn't start

[Sebastian P. Luque]

On Sat, 20 Oct 2012 16:54:39 +0530,
Sivaram Neelakantan <nsivaram.net@gmail.com> wrote:

> On Thu, Oct 18 2012,Eric S Fraga Eric S Fraga wrote:
>> "Sebastian P. Luque" <spluque@gmail.com> writes:

>> [...]

>>> It seems as though this works with Emacs < 24, as the article in
>>> Emacswiki (http://www.emacswiki.org/emacs/GnusGmail) pre-dates Emacs
>>> 24.  Anybody having luck with using Gmail's SMTP server with Gnus?

>> Yes, but using an external (to emacs) SMTP mailer (msmtp on
>> Debian/Ubuntu).  Works perfectly.

> And you can find instructions here

> http://emacswiki.org/emacs/GnusMSMTP

Thanks so much.  For GNU/Linux users, is it really necessary to:

(setq message-send-mail-function 'message-send-mail-with-sendmail)
(setq sendmail-program "c:/gnu/bin/msmtp.exe")

The latter would obviously be different, but I'm not sure I understand
why the former is necessary anyway.

-- 
Seb

Re: starttls for gmail SMTP doesn't start

[Eric S Fraga]

"Sebastian P. Luque" <spluque@gmail.com> writes:

> Thanks so much.  For GNU/Linux users, is it really necessary to:
>
> (setq message-send-mail-function 'message-send-mail-with-sendmail)
> (setq sendmail-program "c:/gnu/bin/msmtp.exe")
>
> The latter would obviously be different, but I'm not sure I understand
> why the former is necessary anyway.

The first is because the variable could be set to one of many different
options and this just makes sure sendmail.  It's probably not necessary
in that I think it's the default (or at least I cannot see where I have
set this in my configuration).

The second, by the way, is probably not at all necessary on some, maybe
all, GNU/Linux systems.  On Debian/Ubuntu, msmtp automatically links
/usr/lib/sendmail to /usr/bin/msmtp.

-- 
: Eric S Fraga, GnuPG: 0xC89193D8FFFCF67D
: in Emacs 24.1.1 + Ma Gnus v0.6
: BBDB version 3.02 ($Date: 2012/09/15 14:41:47 $)

Re: starttls for gmail SMTP doesn't start

[Sebastian P. Luque]

On Thu, 25 Oct 2012 20:41:19 +0100,
Eric S Fraga <e.fraga@ucl.ac.uk> wrote:

> "Sebastian P. Luque" <spluque@gmail.com> writes:
>> Thanks so much.  For GNU/Linux users, is it really necessary to:

>> (setq message-send-mail-function 'message-send-mail-with-sendmail)
>> (setq sendmail-program "c:/gnu/bin/msmtp.exe")

>> The latter would obviously be different, but I'm not sure I
>> understand why the former is necessary anyway.

> The first is because the variable could be set to one of many
> different options and this just makes sure sendmail.  It's probably
> not necessary in that I think it's the default (or at least I cannot
> see where I have set this in my configuration).

According to 'C-h v message-send-mail-function' the default is system
dependent, which for me it was 'smtpmail-send-it'.  It seems like this
automagically uses exim4 in my system, which in turn uses my default ISP
smtp server.


> The second, by the way, is probably not at all necessary on some,
> maybe all, GNU/Linux systems.  On Debian/Ubuntu, msmtp automatically
> links /usr/lib/sendmail to /usr/bin/msmtp.

In my Debian sid, I have:

,-----[ ls -alh /usr/lib/sendmail ]
| lrwxrwxrwx 1 root root 13 Sep 23 06:04 /usr/lib/sendmail -> ../sbin/exim4
`-----

Using:

(setq message-send-mail-function 'message-send-mail-with-sendmail
      sendmail-program "/usr/bin/msmtp"
      message-sendmail-extra-arguments '("-a" "gmail")
      mail-host-address "gmail.com")

works smoothly.

Thanks,

-- 
Seb

Re: starttls for gmail SMTP doesn't start

[Sivaram Neelakantan]

On Fri, Oct 26 2012,Sebastian P. Luque Sebastian P. Luque wrote:


[snipped 12 lines]

>> The first is because the variable could be set to one of many
>> different options and this just makes sure sendmail.  It's probably
>> not necessary in that I think it's the default (or at least I cannot
>> see where I have set this in my configuration).
>
> According to 'C-h v message-send-mail-function' the default is system
> dependent, which for me it was 'smtpmail-send-it'.  It seems like this
> automagically uses exim4 in my system, which in turn uses my default ISP
> smtp server.

"system dependent", that's the reason why.  I posted about this when
Emacs 23.1 was released, as on Windows, any arbitrary program can be
made as your mail client and it gets weird when Emacs launches Firefox
or Outlook when you least expect it.

http://lists.gnu.org/archive/html/info-gnus-english/2009-07/msg00126.html

 sivaram
 -- 

Re: starttls for gmail SMTP doesn't start

[Ted Zlatanov]

On Tue, 27 Mar 2012 21:37:44 +0200 Steinar Bang <sb@dod.no> wrote: 

>>>>>> Seb <spluque@gmail.com>:
>> I'm using Debian sid Emacs packages (GNU Emacs 23.4.1
>> (x86_64-pc-linux-gnu, GTK+ Version 2.24.10) of 2012-03-21 on trouble,
>> modified by Debian), but am not sure if this is compiled with gnutls
>> support.

SB> I think gnutls support in emacs is emacs 24 only.

It showed up earlier.  I did the initial work towards the end of 2010.
Use the presence and return value of `gnutls-available-p' to be sure;
it's defined at the C level so it doesn't required gnutls.el to be
loaded.

There have been some important bug fixes to the GnuTLS integration since
then, though, so if GnuTLS support is important to you, please upgrade
to the latest Emacs.

Ted