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

Alex Limberis alex at limberis.net
Mon Dec 15 23:10:20 CET 2008

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: stunnel-users-bounces at mirt.net
[mailto:stunnel-users-bounces at mirt.net] On Behalf Of Asif Iqbal
Sent: Monday, December 15, 2008 2:06 PM
To: Scott Gifford
Cc: stunnel-users at mirt.net; nullmailer at lists.untroubled.org
Subject: Re: [stunnel-users] Stunnel 4 failing to connect to gmail

On Mon, Dec 15, 2008 at 4:49 PM, Scott Gifford
<sgifford at suspectclass.com> wrote:
> "Asif Iqbal" <vadud3 at gmail.com> writes:
> [...]
>> I said it too soon. It passed that bind error but it still failing in
>> 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 `vadud3 at gmail.com'
instead of the sender, which is me at myhomecomputer.domain

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.

Asif Iqbal
PGP Key: 0xE62693C5 KeyServer: pgp.mit.edu
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