that certainly is a possibility Dave, however if that was the problem then
one would expect it to happen consistently not intermittently.
I can't say I have tested with CF, but in general SMTP over SSL should work
as long as there is a valid certificate regardless of the domain, when
using an email client you can choose to ignore any errors relating tot he
domain name.

Andrew did you try NOT spooling the emails to disk ?



On Mon, Aug 26, 2013 at 12:41 PM, Dave Watts <dwa...@figleaf.com> wrote:

>
> > The only thing that I see in the logs is the following.
> >
> >
> *"Error","scheduler-0","08/25/13","17:05:17",,"javax.mail.MessagingException:
> > Could not connect to SMTP host: smtp.domain.com, port: 465; nested
> > exception is: javax.net.ssl.SSLException: Server key"*
> > *
> > *
> > *javax.mail.MessagingException: Could not connect to SMTP host: **
> > smtp.domain.com**, port: 465;*
>
> That looks to me like a regular SSL/TLS error. It's looking for a TLS
> certificate from smtp.domain.com, but Gmail's certificate is going to
> return smtp.gmail.com.
>
> Dave Watts, CTO, Fig Leaf Software
> http://www.figleaf.com/
> http://training.figleaf.com/
>
> Fig Leaf Software is a Veteran-Owned Small Business (VOSB) on
> GSA Schedule, and provides the highest caliber vendor-authorized
> instruction at our training centers, online, or onsite.
>
> 

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