For the purpose of “proof of concept” I needed to join a client to a domain over the internet via Logmein Hamachi network, and keep it managed.

I decided to setup a Gateway network, setting up the gateway as a Win7 guest virtual machine, on a 2012R2 Hyper-V Server.

The process was far from smooth, and it took hours of Googling and a support request with Logmein support to get it sorted.

So for the purpose of personal documentation, and in the spirit of helping other IT pros. who may struggle with it, this is how to setup Logmein Hamachi Gateway as a guest on Hyper-V server.

I have encountered two major issues:

  1. An error message during Hamachi client setup, saying the Hamachi drivers are not digitally signed.
    As a result, at the end of the process no Hamachi network adapters were installed. (That proved to be the easy one to solve).
  2. As soon as I was able to complete the setup and connect the Hamachi client to the network, and specify the computer as Hamachi Gateway, the gateway lost all network connectivity.
    I couldn’t even ping the internal IP address.

Working the problems

The solution to the first issue (drivers digital signature) was simple enough.
All I had to do is to make sure that the Windows machine (Win7) was fully patched with the latest updates.
As soon as I finished patching the machine, and Windows Update said that there are no more updates available, I was able to complete Hamachi client setup with no errors at all.

The second problem was a hard one to crack.
Googling the issue I found quickly many posts saying that I should use the “Legacy Network Adapter” on the virtual machine instead of the standard one.
But by itself that didn’t work out.
So I have opened a support ticket with Logmein. After going back and forth with no success that suggested to make sure that the VM setup is Promiscuous Mode.
While Promiscuous Mode is a VMware term, it got me thinking that there are two VM network settings worth of taking another look.
Port mirroring and Mac address spoofing.

At the end, the solution to the problem was to enable Mac address spoofing (check the image at right for details).

After enabling this option, I rebooted the VM, and run Hamachi setup again from scratch.

After a successful setup, I attached the client to my account and to the network and configured it as the Gateway.

At this point a short provisioning process has begun, as Hamachi configured the bridge network between the LAN and the Hamachi adapters.

During this process the Gateway lost connectivity for about 30 seconds (which is normal!), but then it reconnected again and the GW was operational.

Problem solved!

Best practice advice

During my attempts to setup the Gateway I had to run Hamachi setup process several times.

One of the troubleshooting suggestions I got from Logmein support was to completely remove Hamachi and start from scratch.

While I was provided a detailed document on how to perform the removal, I strongly suggest that you work around the issue simply by creating a snapshot (or checkpoint) of the VM before attempting the setup for the first time.

Trust me it will save you a lot of time later.

I do realize that if you landed on this post you’ve probably already encountered the problem, and this maybe too late, but just in case you didn’t run through the first Hamachi setup already, you’d be wise to snapshot before.

Another advice I would like to share is to use Win7 as the operating system for the Gateway machine.
At the time when this post is written, win 7 is known to be the most reliable operating system for Hamachi Gateway.

Conclusion

Setting up Logmein Hamachi gateway on a VM can be a very easy task, if you know what to do.

Following these guidelines should help you get over the setup process smoothly.

  1. Use Windows 7 as operating system
  2. Make sure that the operating system is fully patched with the most recent updates from Microsoft.
  3. Use legacy network adapter, and not the standard one
  4. Enable MAC address spoofing on the VM.

Good luck!

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