My ISP requires all my mail to go to mail.myISP.net via SSL to port 465.

I have sendmail compiled with STARTTLS, configured authinfo and I've set up sendmail's smarthost to send everything to mail.myISP.net

I run stunnel like this.

stunnel /etc/stunnel/stunnel.conf -c -d 25 -r mail.myISP.net:465

There are no errors in the log. I can see stunnel listening on 25 with netstat. When I try to send mail I get:

bash-3.00# sendmail -v sc00b123@yahoo.com <test sc00b123@yahoo.com... Connecting to [127.0.0.1] via relay...

Which just hangs for ever.

My stunnel.conf looks like:

cert = /etc/stunnel/mail.pem chroot = /var/stunnel/ setuid = nobody setgid = nogroup pid = /stunnel.pid socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 debug = 7 output = /var/log/stunnel.log [smtp] accept = 25 connect = 465

Thanks for any help, hints, etc..

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