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Need Help With Exchange Setup in VMWare Workstation and Sending Mail Accross Internet.

RyanHartwick used Ask the Experts™
Basically I'm looking for some assistance with end-to-end e-mail delivery within Exchange 2010.  This is for a testing environment I'm using at home.  I've decided to include a diagram of my setup at home.
 My Home Network
Here's the network setup:

1) SMC Router is configured as a DHCP server.  All computers on my home network are part of the subnet.
2) I have a PC and Laptop with the addresses shown above.
3) My laptop is running VMWare Workstation with two Virtual Machines.  One is a Server 2008 R2 VM which has been promoted to a domain controller for the "testlab.com" domain, had the DNS role installed, and has a copy of Exchange 2010 runing.  The other VM is a Win 7 Enterprise VM with an Outlook client for testing purposes.
4) Both VM's are part of the subnet and use NAT in conjuction with VMWare through my laptop to access external resources.  My server is and the Win 7 box is dynamic.
5) Both VM's are currently able to access the internet and other external resources (they can ping the PC on my subnet for instance).  Also my VM server's DNS seems to be working correctly and I have no forwarder installed.  The default gateway for the virtual network is as configured by VMWare.

I've installed and configured Exchange 2010 SP1 and right now I'm trying just to be able to send mail to an external domain over the internet from the VM (if that's even possible given my network structure).  I'm not concerned about receiving mail at this point, just sending it out.  I set up the proper "Internet" send connector under the hub transport roll and configured it as follows:

 Exchange Queue Viewer Tool
When I try to send an e-mail from my Outlook client it goes into the sent folder, but the item appears to get stuck in the queue on my Exchange server:

 Send Connector Configuration
Excluding my ISP blocking this type of traffic is there any other configuration I could be missing.  I mean technically this server is not internet-facing.  I'm passing the request to a virtual router which then needs to pass through my home network router and to the internet.  I'm not sure if this type of functionality is possible, but I thought I'd ask the experts :)
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JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

This would be much cleaner if your VMware Workstation were Bridged instead of NAT. With NAT, you want to ensure that all firewalls in all machines allow the 192.168.0.x network and the 10.7.7.x network.

Check who is running DHCP. VMware NAT wants to assign addresses, your router is probably a DHCP server and the Server VM may also be a DHCP server.

... Thinkpads_User


Right now my SMC router is running DHCP for my home network and my VMWare NAT is running DHCP for my VM's.  Not sure how that is going to affect outgoing mail though.  In regards to firewalls I opened up port 25 on VMSRV01, but not my laptop I'll check that out.


Oh, I forgot to mention the main reason I didn't do this setup in bridged mode, because I take my laptop back and forth to work with me, so I wanted to isolate the subnet for the VM's.
JohnBusiness Consultant (Owner)
Most Valuable Expert 2012
Expert of the Year 2018

>>> I didn't do this setup in bridged mode, because I take my laptop back and forth   <--- I do the same thing with my own laptop, so I understand.

You might try Bridged mode to see if it helps resolve the problem. You can always change back. NAT is somewhat trickier because it adds firewall complexity and put the virtual machines on a different subnet. .... Thinkpads_User
What roles have you installed on your Exchange Server? I didn't hear anything about the Edge Transport role. You need to install this role on the Exchange Server as this will be required for mail routing internally and externally together with Connectors on the HUB.

See links for installation and configuration guide http://araihan.wordpress.com/2009/11/16/exchange-server-2010-edge-transport-role/ and http://www.msexchange.org/articles_tutorials/exchange-server-2010/migration-deployment/exchange-server-2010-edge-server-microsoft-threat-management-gateway.html

Note: you have an option of not using a TMG.

Hope this helps :)


As per the technet site you don't actually need an Edge server to get end-to-end mail flow:


I can try the bridged mode setup, but I'd prefer to keep the NAT if possible.


I've found the issue.  It was my ISP blocking traffic on port 25.  Once I configured it to port 587 the outgoing mail worked a treat.  Have to love virtualization; my Virtual Exchange server sending e-mail across the internet from a NAT virtual subnet, just awesome.
In order to change the port for your send connector you need to use the Exchange Management Shell, using the following command:

Set-SendConnector -Identity "SENDCONNECTORNAME" -port 587

Hope this helps!


Found this out through trial and error before getting a response from the forums.