PPTP VPN Problems on VMware ESXi 5.5

I’ve just discovered an interesting feature of virtual machines running on ESXi 5.5.  Skip to the bottom if you just want the skinny and not my anecdote.

I set up a couple of Windows 7 VMs for testing purposes for a client, and it came to pass that I was asked to deploy a PPTP VPN configuration to all the laptops at this company.  This is a fairly straightforward job, and there’s a number of ways to accomplish this using group policy.  (eg. Using a powershell script and XML file; Using the Connection Manager Administration Kit (CMAK); Using Group Policy Preferences.)

I configured the VPN in the normal way using group policy preferences, and pushed the policy to 2 of my test VMs.  I then rebooted these machines and tested the VPN.  Nothing.  ‘Error 718: The connection was terminated because the remote computer did not respond in a timely manner.’

VPN-718

This was unexpected, but I remembered encountering a few problems previously with a GPP deployed PPTP VPN config, so I assumed that I’d fat-fingered some of the settings.  Back to the group policy editor for some checking and changing!  I rebooted the VM, picked up my new config and tested it – still failing with error 718!  I carried on in this manner for … some considerable time.  With success still firmly at zero I decided to work backwards and try manually creating VPNs from my test VMs to known good VPN endpoints.  I was a little taken aback to discover that all these bombed out with a 718 error.  “Jeeves!  Fetch me my best Googling googles”

A depressingly brief trip to the search engines turned up this VMware KB article, titled “Point-to-Point Tunneling Protocol (PPTP) connections may not work on ESXi 5.5”.  A possible clue?  Indeed it is.  The very simple fact is that in ESXi 5.5, the E1000 and E1000e vNIC doesn’t support PPTP connections at all.  Change the adapter type to vmxnet3.  (Right-click the VM > Edit Settings > Remove the existing vNIC and add a new network adapter of type VMXNET 3)

VMXNET3

Hope this helps someone and saves a little troubleshooting time.

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