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I have a ShoreTel phone system. The voicemail server utilizes the IIS SMTP Virtual Server to send email (at least, it's supposed to). Specifically it sends a .WAV attachment when a voicemail is recorded.

The problem I'm having is that no matter what I put in for the smart host the emails are being sent to my website's IP address and this just doesn't make any sense.

Let me give you examples of the information I'm working with:

domain: DomainA.com (hosted at Media Temple) MX for DomainA.com: filter.DomainA.com and mail.DomainA.com (Barracuda Spam filter and Exchange 2010 hosts respectively; onsite)

For the smart host I've tried the internal IP addresses of both my Exchange server and spam filter (wrapped in brackets) and both the internal and external FQDNs for my Exchange server and spam filter.

No matter what I try the SMTP server, as reported by the logs, is sending to the IP address of the website at DomainA.com.

Any ideas on this?

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File a bug report that your phone doesn't comply with RFC 5321. – mailq Oct 28 '11 at 21:35
I understand your sentiment but that's not actually helpful. Wouldn't this issue be the "fault" of the SMTP Virtual Server in IIS vs the ShoreTel system? – cparker4486 Oct 28 '11 at 23:39
Maybe not. Otherwise there would be more complaints that Microsoft's SMTP is faulty. But you can verify it by sending mails manually via IIS SMTP. – mailq Oct 29 '11 at 19:05
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