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Outgoing SMTP Server for MAC Mail To Internal Mail Server

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Last Modified: 2013-11-30
Well here is the problem.

Recently did a migration to Exchange 2007. Everything more the most part is working great. The VP of the company uses a Mac with OS 10.5.1 and Mac Mail 3.1.

I have configured IMAP for this user to allow for retrieval of mail. Externally from the site I am able to recieve mail without a hitch. However I am only able to send mail to employees within the company. Any external mail just seems to vanish.

I am currently using the internal mail server as my Outgoing SMTP Mail Server. It is going through port 587 with SSL and NTLM for authentication.

At this point I think it is having a problem relaying mail from an authenticated user to an external source, but I need some insight.

Thanks
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Commented:
what's the server role for your exchange 2007 server?
Did you setup the send connector under the hub transport?

Author

Commented:
Well this is a smaller organization so it is just a Hub Transport Server with Anti-Spam Enabled.

Yes there is a Send connector for outgoing for " * " Domain.

Commented:
is all the external email stuck in queue?   right now under the queue it tell you why it's not going out...

Author

Commented:
I see nothing under the queues to the differnet domains that I have sent out to that would indicate they are stuck in the queue.

Commented:
did you relay the email to another connector?   What happen if you send out a fake email say abcde@abklsdf.com?  Will that show up from the queue?  You check the queue using the queue viewer right?

Author

Commented:
Yes I am using the queue viewer

Well internally I get a NDR saying it is a non existant domain. From the external Mac User I get nothing, even trying search for the Subject of the Email with the queue viewer I get no results.....

Author

Commented:
Sorry I didn't wait long enough I did get the NDR from the External Mac account.
Commented:
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Author

Commented:
I am currently running RPC over HTTPS to all my mobile Windows based client without any issues. I can access Web-based Outlook externally and internally without any issues.

I'll run the tool.....

Author

Commented:
There was a couple things that it detected.

First, it said that no external DNS servers were configured. Not sure that this means as I am able to resolve to any external address.

Second there is no MX or A records found for the local domain. (This is because the DNS is hosted outside the clients offices)

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