Problems sending mail with Exchange SBS 2003 / apple mail

Here is an odd one. I can easily sync up with the exchange server at my office using my mac. I can view new mail, view sent mail and drafts easily.
When sending e-mail, it is a crap-shoot if it actually will send it or not. Sometimes it goes through, but the majority of the time it does not. I get delay messages from the server, and ultimately I get the "failed to send" message. But the mail is getting to the exchange server because I can see it in the queue.
Through Parallels, I was able to successfully configure and run Outlook 2004. When testing the same e-mail addresses, the Outlook mail went through easily, but the apple mail stalled and eventually failed.
On top of this, I can send e-mails to certain domains without ever getting an error through apple mail (i.e. a local company, hotmail.com, etc). Whereas others always or most of the time give me errors (cox.net, yahoo.com, another local company).
I checked the message queue on the exchange server and sure enough they were stuck trying to resend every 5 minutes - with no luck. There has to be a security setting or something preventing me from being able to send mail through my apple mail app.

This was an issue with my Exchange server.

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