HI Asif, Unfortunately that is the way gmail works. It changes the from to the gmail address rather than the computer domain. Unfortunately, this mostly makes it useless if you are trying to use it as a smarthost.

-----Original Message----- From: [email protected] [mailto:[email protected]] On Behalf Of Asif Iqbal Sent: Monday, December 15, 2008 2:06 PM To: Scott Gifford Cc: [email protected]; [email protected] Subject: Re: [stunnel-users] Stunnel 4 failing to connect to gmail

On Mon, Dec 15, 2008 at 4:49 PM, Scott Gifford [email protected] wrote:

"Asif Iqbal" [email protected] 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!

Yep, as you suggested :-)

Try using port 465 instead of 587.

That worked! I were able to send an email and I did receive it. It says the email came from `[email protected]' instead of the sender, which is [email protected]

I am using this in /etc/nullmailer/remotes file

localhost smtp --port=25 --user=vadud3 --pass=s3cr3t

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.