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Problem with Relay to Gmail

I am hoping for advice on how to track down an issue sending email from our managed GoDaddy Windows 2012 Server. The server uses ColdFusion to generate emails that send out appointment confirmations. Generated emails get passed through Smartermail and then relayed through GoDaddy's relay. The problem is that most of the emails we send get through, unless they are sent to an address. Then they only get through sometimes and I don't know what is causing it.


I recently got a bounce message from from a message directed to a recipient. It simply read: 

Delivery to the following recipients was aborted after 20.6 hour(s):


Reason: There was an error while attempting to deliver your message with [Subject: "xxxxx"] to It has been in queue too long, and will not attempt delivery again.
I know my setup is a bit convoluted, but if anyone could give me some troubleshooting tips, that would be appreciated.