I earlier wrote that I would provide more detail on using gnutls-cli (from cygwin) with Emacs 24.2 on my Windows XP Home laptop. I now provide more detail.
The following are copied from my customization file: '(mail-default-reply-to "alan.wehm...@gmail.com" nil (sendmail) "use Gmail") '(mail-from-style (quote angles)) '(mail-interactive t) '(mail-self-blind (expand-file-name "~/mail_rmail/XMAIL_sent_mail") nil (sendmail)) '(mail-signature t) '(mail-signature-file "c:/cygwin/home/.gmail_signature" nil (sendmail) "use Gmail") '(mail-user-agent (quote vm-user-agent)) '(pop3-stream-type (quote ssl)) '(query-user-mail-address nil) '(send-mail-function (quote smtpmail-send-it)) '(smtpmail-smtp-server "smtp.googlemail.com" nil nil "use Gmail") '(smtpmail-smtp-service 465) '(smtpmail-stream-type (quote ssl)) '(tls-program (quote ("gnutls-cli --x509cafile /usr/ssl/certs/ca-bundle.crt --insecure -p %p %h"))) In this example I am using the smtp server "smtp.googlemail.com" (there is another, "smtp.gmail.com", which uses a different port on the same server). Info node "(smtpmail) Authentication describes the use of the ~/.authinfo file to do the necessary authentication. As a test I invoked the following in my Emacs shell buffer (which is using bash from Cygwin to interpret commands): gnutls-cli --x509cafile /usr/ssl/certs/ca-bundle.crt --insecure -p 465 smtp.verizon.net This specifies a location for a file with CA certificates. I created the Certificate Authority cert file from the Mozilla cert bundle, using the advice given in http://www.mail-archive.com/modssl-users@modssl.org/msg16980.html But I'm still using the --insecure option on the gnutls-cli command, so the checking on the server certificate is not necessary (I should be able to remove that option and thus insist that the server is valid). After invoking the gnutls-cli command in the shell buffer, there is some output about the certificates and the TLS handshake takes place and the server identifies itself. I can then type "EHLO DELLLAPTOP" and the POP server will give me some status codes. One of these assures me that the authentication done by Emacs will work (this isn't true for the smtp server email.fnal.gov, at the lab where I used to work). I wasn't interested in doing anything further, so I gave the command "QUIT" to the POP server at this point. I can initiate writing email with the command "compose-mail", or I can use the methods specified in info node "(vm) Sending Messages". -- Alan Wehmann alan.wehm...@gmail.com