Re: SMPT no longer works in Starttls upon upgrading from emacs-22.3-bin-i386 to emacs-23.1-bin-i386 on Windows XP Professional, Service Pack 3.

[Benjamin L. Russell]

Marco Maggi <mrc.mgg@gmail.com> writes:

> "Benjamin L. Russell" wrote:
>> When  I  renamed  C:\bin\emacs-23.1 to  C:\bin\emacs,  the
>> previous error  message went away, only to  be replaced by
>> the following error message:
>> [...]
>> Any ideas?
>
> I am not a Windows user,  I cannot help with that, but first
> I  would   make  sure  that  you  can   send  email  through
> gnutls-cli.   Can you  try  it in  an  "M-x eshell"  session
> following, for example, the instructions at [1]?
>
>   We cannot  send a SIGALRM POSIX signal  under windows, but
> we  can  send an  EOF  to  the  process through  the  eshell
> function   "eshell-send-eof-to-process".    So,   when   the
> instructions  say  "send SIGALRM  to  gnutls-cli", you  "M-x
> eshell-send-eof-to-process".
>
>   If that works we can try to debug the rest.
>
> [1] <http://marcomaggi.github.com/docs/mbfl.html#sendmail-gnutls>

Apparently, it is possible to send e-mail through gnutils-cli
successfully using an immediate encrypted bridge, according to section
"A.4.1 Immediate encrypted bridge" of your page "Marco's Bash Functions
Library" (see
http://marcomaggi.github.com/docs/mbfl.html#sendmail-gnutls); _viz._:

----- quoted text follows immediately after this line -----
c:/home $ gnutls-cli --crlf --port 465 plus.smtp.mail.yahoo.com
Resolving 'plus.smtp.mail.yahoo.com'...
Connecting to '98.136.44.53:465'...
- Successfully sent 0 certificate(s) to server.
- Certificate type: X.509
 - Got a certificate list of 1 certificates.

 - Certificate[0] info:
 # The hostname in the certificate matches 'plus.smtp.mail.yahoo.com'.
 # valid since: Sat Jan 26 07:37:33     2008
 # expires at: Fri Jan 25 07:37:33     2013
 # fingerprint: C1:28:CE:65:18:00:ED:FC:B7:51:B6:AF:7F:AE:26:03
 # Subject's DN: C=US,ST=California,L=Santa Clara,O=Yahoo! 
Inc.,OU=Yahoo,CN=*.smtp.mail.yahoo.com
 # Issuer's DN: C=US,O=Equifax,OU=Equifax Secure Certificate Authority


- Peer's certificate issuer is unknown
- Peer's certificate is NOT trusted
- Version: TLS1.0
- Key Exchange: RSA
- Cipher: AES-128-CBC
- MAC: SHA1
- Compression: NULL
- Handshake was completed

- Simple Client Mode:

220 smtp109.prem.mail.sp1.yahoo.com ESMTP
auth login
334 VXNlcm5hbWU6
<the-base64-username>
334 UGFzc3dvcmQ6
<the-base64-password>
235 OK, go ahead
mail from:<dekudekuplex@yahoo.com>
250 OK , completed
rcpt to:<dekudekuplex@yahoo.com>
250 OK , completed
data
354 Start Mail. End with CRLF.CRLF
From: <dekudekuplex@yahoo.com>
To: <dekudekuplex@yahoo.com>
Subject: interactive attempt

Text for interactive attempt.
--
DekuDekuplex
.
250 OK , completed
quit
221 Service Closing transmission
- Peer has closed the GNUTLS connection
c:/home $ 
----- quoted text ends immediately before this line -----

However, when I try to send an EOF to the process through the Emacs eshell
function "eshell-send-eof-to-process", for some reason, the TLS
handshake fails; _viz._:

----- quoted text follows immediately after this line -----
gnutls-cli --crlf --starttls --port 587 plus.smtp.mail.yahoo.com
Resolving 'plus.smtp.mail.yahoo.com'...
Connecting to '98.136.44.53:587'...

- Simple Client Mode:

220 smtp103.prem.mail.sp1.yahoo.com ESMTP
*** Starting TLS handshake
----- quoted text ends immediately before this line -----

At this point, the process hangs.  When I then enter "ehlo
localhost.localdomain" and wait, the TLS handshake eventually fails, as
follows:

----- quoted text follows immediately after this line -----
> ehlo localhost.localdomain
> *** Non fatal error: Function was interrupted.
> *** Fatal error: A TLS packet with unexpected length was received.
> *** Handshake has failed
> c:/home $ 
----- quoted text ends immediately before this line -----

Here are the relevant portions from my ~/.gnus.el file:

----- quoted text follows immediately after this line -----
(setq send-mail-function 'message-send-mail-with-sendmail)

(setq message-send-mail-function 'message-send-mail-with-sendmail)

; The following settings were adapted from the article "Re: Debugging msmtp in 
gnus," by Sivaram Neelakantan <nsivaram.net@gmail.com>, dated "Wed, 02 Sep 2009 
22:36:12 +0530," on gnu.emacs.gnus
(setq sendmail-program "c:/cygwin/usr/sbin/msmtp.exe")
; (setq sendmail-program "c:/bin/msmtprc/1.4.17/msmtp.exe")
(setq message-sendmail-extra-arguments '("-a" "dekudekuplex"))
(setq mail-host-address "yahoo.com")
(setq smtpmail-debug-info t) ; only to debug problems set to t if needed
(setq smtpmail-debug-verb t)

(setq starttls-use-gnutls t)

; (setq starttls-gnutls-program "c:/Program 
Files/GnuTLS-2.9.3/bin/gnutls-cli.exe")

(setq starttls-gnutls-program "c:/usr/bin/gnutls-cli.exe")

;; Configure outbound mail (SMTP)
(setq smtpmail-starttls-credentials '(("plus.smtp.mail.yahoo.com" 587 nil nil))
      smtpmail-smtp-server "plus.smtp.mail.yahoo.com"
      smtpmail-default-smtp-server "plus.smtp.mail.yahoo.com"
      send-mail-function 'message-send-mail-with-sendmail
      message-send-mail-function 'message-send-mail-with-sendmail      
      smtpmail-smtp-service 587
      smtpmail-auth-credentials '(("plus.smtp.mail.yahoo.com"
                                   587
                                   "dekudekuplex@yahoo.com"
                                   nil)))
----- quoted text ends immediately before this line -----

Additionally, here are the relevant portions from my msmptrc.txt file

----- quoted text follows immediately after this line -----
########################
defaults
tls on
tls_certcheck off
tls_starttls on

account dekudekuplex
host plus.smtp.mail.yahoo.com
domain plus.smtp.mail.yahoo.com
tls on
tls_certcheck off
tls_starttls on
auth on
user dekudekuplex@yahoo.com
from dekudekuplex@yahoo.com
password 
port 465

logfile c:\home\.msmtplog.txt
########################
----- quoted text ends immediately before this line -----

Any ideas on what is wrong?

-- Benjamin L. Russell
-- 
Benjamin L. Russell  /   DekuDekuplex at Yahoo dot com
http://dekudekuplex.wordpress.com/
Translator/Interpreter / Mobile:  +011 81 80-3603-6725
"Furuike ya, kawazu tobikomu mizu no oto." -- Matsuo Basho^