[stunnel-users] Stunnel 4 failing to connect to gmail

Mon Dec 15 22:49:57 CET 2008

"Asif Iqbal" <vadud3 at gmail.com> writes:

[...]

> I said it too soon. It passed that bind error but it still failing in ssl.
> I am seeing   `SSL alert (write): fatal: handshake failure'

Hello again Asif, glad you decided to try out stunnel!

Try using port 465 instead of 587.

It looks like Google's STARTTLS command requires an EHLO to be sent
first, which is a someqhat unusual requirement.  I don't think stunnel
does that.  Port 465 will start talking SSL directly, without
requiring SMTP commands first.

Good luck!

----Scott.