I've been using the following setup Gnus SMTP

;;; SMTP
(defun email-settings ()
  (setq message-send-mail-function 'smtpmail-send-it
        starttls-gnutls-program "gnutls-cli"
        starttls-use-gnutls t
        smtpmail-stream-type 'starttls
        smtpmail-default-smtp-server "smtp.mail.me.com"
        smtpmail-smtp-server "smtp.mail.me.com"
        smtpmail-smtp-service 587
        smtpmail-smtp-user "john.doe@mac.com"
        smtpmail-debug-info t
        smtpmail-debug-verb t))

for years to send the email via Gnus using gnutls-cli. This setup stopped working recently on the starttls call:

Opening STARTTLS connection to ‘smtp.mail.me.com:587’...

When debugging the STARTTLS with gnutls-cli I am seeing this:

(~)[498]$ gnutls-cli --verbose --starttls --tofu -p 587 smtp.mail.me.com
|<1>| There was a non-CA certificate in the trusted list: O=Entrust.net,OU=www.entrust.net/CPS_2048 incorp. by ref. (limits liab.),OU=(c) 1999 Entrust.net Limited,CN=Entrust.net Certification Authority (2048).
Processed 175 CA certificate(s).
Resolving 'smtp.mail.me.com:587'...
Connecting to ''...

- Simple Client Mode:

- Received[47]: 220 mr85p00im-zteg06012001.me.com 3.3.1 v.666`

and it never completes. Does somebody know what's changed and what's wrong and how to fix that?

  • Is Emacs' smtpmail broken? #smtpmail – The Dude Jan 19 '19 at 18:16
  • Have you tried using 'gnutls-cli --insecure' to skip the certificate verification? (not recommended for production use). Longer term you might want to try using Emacs' builtin TLS support. – rpluim Jan 21 '19 at 9:20
  • Unfortunately, the --insecure parameter doesn't solve my issue. – The Dude Feb 4 '19 at 10:55
  • After switching to the internal TLS support I am getting this log sequence: Sending via mail... Opening TLS connection to ‘smtp.mail.me.com’... Opening TLS connection with ‘gnutls-cli -p 587 smtp.mail.me.com’...failed Opening TLS connection with ‘gnutls-cli -p 587 smtp.mail.me.com --protocols ssl3’...failed Opening TLS connection with ‘openssl s_client -CAfile /etc/ssl/cert.pem -connect smtp.mail.me.com:587 -no_ssl2 -ign_eof’...done Opening TLS connection to ‘smtp.mail.me.com’...done network-stream-command: Process smtpmail<2> not running – The Dude Feb 4 '19 at 10:56
  • I don't think you're using the builtin support, those messages come from tls.el. Have you unset starttls-gnutls-program and starttls-use-gnutls? – rpluim Feb 4 '19 at 12:46

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