Setup for dual delivery with Google Apps

Hi,
I am trying to get SLS to funnel all outbound email through Google Apps Premium. The idea is to have Google Apps as a backup for my users (small company) in case I loose my internet connection or the server goes down.
Incoming email gets delivered to both my server and Google Apps. I can send email from both as well and it gets delivered. It looks like Google is correctly forwarding email to my SLS.
What I need is to have my server send outbound email through the Google Apps servers so that 'sent mail' in Google Apps matches my server's.
I tried to set this up in 10.6 server, by setting up the relay option to smtp.gmail.com in mail admin. I get an error message about STARTTLS. Is there a way to get Mail to connect with the google smtp servers via the required secure connection and port 587? Also, how do I set this up without all my email getting flagged as spam.
Thanks,

Hi,
Not quite the same situation but when I was testing the google apps migrator tool on my 10.5.8 server, I had similar issues getting it to connect over TLS/SSL. The google server didn't support cram-md5 login apparently which I believe is the default on most OS X servers. I had to enable either login or plan+clear (I can't recall the exact one that fixed it but I'm pretty sure it was the combo of plain+clear).
In doing this, make sure you're using SSL (I had issues getting google to use TLS, google lets you specify TLS or SSL) obviously since the password would otherwise be cleartext in doing the above as opposed to cram-md5 which at least has some level of encryption associated with it. SMTP has the same login options as IMAP so you very well could be experiencing the same issue.
Not sure this will help you since I understand your situation is different but just a heads up.

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