We help IT Professionals succeed at work.

Outgoing SMTP Server for MAC Mail To Internal Mail Server

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.

Watch Question

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


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.

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


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.

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?


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.....


Sorry I didn't wait long enough I did get the NDR from the External Mac account.
This one is on us!
(Get your first solution completely free - no credit card required)


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.....


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)

Gain unlimited access to on-demand training courses with an Experts Exchange subscription.

Get Access
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Empower Your Career
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE

Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Unlock the solution to this question.
Join our community and discover your potential

Experts Exchange is the only place where you can interact directly with leading experts in the technology field. Become a member today and access the collective knowledge of thousands of technology experts.

*This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.


Please enter a first name

Please enter a last name

8+ characters (letters, numbers, and a symbol)

By clicking, you agree to the Terms of Use and Privacy Policy.