Andy Green on Mon, 19 Nov 2012 19:53:49

Hey guys!  I have a bit of an issue I'm hoping I can get some help with.

I have some Azure VM's on an Azure VPN that talks to our local private network.  Looks a bit like this:

Azure VM(s) ==> AzureVPN Endpoint ==> --- <== LocalVPN Endpoint <== Local Hosts

A.B,C                                xx                                              D                             E,F,G

Connectivity works great for all the VM's and they're able to talk to all the local hosts (A, B, and C can all talk to E, F and G just fine).  However, the VM's are unable to connect to the host that IS "LocalVPN Endpoint"... also known as Host D.  It's a Windows 2008 server, and the VPN is set up between it and the Azure VPN endpoint.  The problem is, that 2008 server is also our mail server, and we'd like the Azure VM's to be able to connect to it to send out mail, but alas... 'tis a no-go.

It doesn't appear to be a firewall issue... it seems as though it may be a routing issue. 

Does anyone have any suggestions as to what the problem could be, or maybe some tips for getting it ironed out?


Dino He on Tue, 20 Nov 2012 10:44:04


  This is a quick note to let you know that I am performing research on this issue and will get back to you as soon as possible. I appreciate your patience.

Andy Green on Tue, 20 Nov 2012 12:10:24

Great!  Thanks Dino!

Steve Espinosa [MSFT] on Tue, 04 Dec 2012 00:35:21

Hello Andy,

Thank you for posting your question here.

Unfortunately, this is an unsupported scenario. It is a known issue that an on-premises machine cannot simultaneously perform the Endpoint function and also participate in communications with the Virtual Network.

Best regards,