With one of my email accounts I've been unable to send mail using Gnus (in GNU Emacs 23.0.60.5 (i686-pc-linux-gnu, GTK+ Version 2.12.0) of 2008-02-14 on escher). I use this setup (anonymized): (setq message-send-mail-function 'smtpmail-send-it smtpmail-default-smtp-server "mail.myprovider.com" smtpmail-smtp-service 465 user-mail-address "Stephen.Berman@myprovider.com" smtpmail-auth-credentials '(("mail.myprovider.com" 465 "myusername" "mypassword"))) I type `M-x message-mail', type the message and send it, and Emacs locks up for 20 minutes, then beeps and shows the message "smtpmail-send-command: Process SMTP not running". The buffer *trace of SMTP session to mail.myprovider.com* shows this: