All,

I've just spent a good hour or so looking at this and scratching my head so I thought I'd share it with everyone else.

A number of my customers are now using Google Apps, and would like Kentico to send e-mail from their domain via Google Apps' smtp server.

Doesn't sound unreasonable right?

OK, so since 2008 Kentico CMS has allowed you to specify the smtp server and the port in the format smtpserver:port in the SMTP Server field under Settings > E-mail and you can select the box to use SSL (both seemingly fulfilling Google's requirements), but entering the SSL port as found on this page (465 at time of posting), doesn't work:
http://mail.google.com/support/bin/answer.py?hl=en&answer=13287

I was left scratching my head as the mail queue attempts to send, but then times out. I didn't know if I'd missed something.

Anyway, you need to enter the port as the TLS port from the page above instead (587 at time of posting).

Hey presto, you can then use GMail as your SMTP server, which is particularly useful if the DNS is configured with an SPF record.

Hope this helps,

Kurt Farrar
Small Business IT Consultant
MyDigitalMedia (Kentico Gold Partner)