On Wed, Mar 18, 2015 at 05:46:45PM -0400, Postfix User wrote:

> The is the output from the "sendEmail" program:
> 
> Mar 18 16:57:29 scorpio sendEmail[29407]: SUCCESS => Received:  220 2.0.0 
> Ready to start TLS
> Mar 18 16:57:29 scorpio sendEmail[29407]: ERROR => TLS setup failed: SSL 
> connect attempt failed error:14090086:SSL 
> routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed
> 

Your "sendEmail" software is not configured to trust the certificate
of this Postfix server.

> I am using port 587 with authentication when I sent either to Yahoo directly
> or attempt to send through Postfix. I have also tried sending directly to
> GMail, and it works flawlessly too. So why the problem with Postfix on my
> server?

The problem is not with Postfix.  It is a configuration issue with
"sendEmail".  It needs to be configured to either not check the
SMTP server's certificate, or trust whichever CA signed the Postfix
server's certificate.

You can also obtain a DV certificate from one of the usual suspects,
and sweep the trust management problem under the rug (the DV CA
will make an unauthenticated email delivery to ad...@example.com
to confirm authorization to issue an example.com certificate).

-- 
        Viktor.

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