PPTP VPN aka GRE Not Working After VMware 5.5 Upgrade

One would think that updating VMware would be a pretty transparent task, I mean VMware is supposed to be absolutely transparent to the VM’s operating system…. right? – Not so with VMware vSphere 5.5; It broke my VPN, and here’s the story of how I fixed it:

Basically I have a Sophos UTM 9 Firewall system running as a VM Appliance (in VMware 5.5) It works great, but if you want to use the PPTP VPN feature, you have to make some modifications to the Virtual Machine Properties.

Change VMP, Guest Operating System from “Other Linux”:


to “Red Hat Enterprise Linux 6”:


This will allow you to add virtual network adapters other than the E1000 NIC:


Remove all existing NICS:

removed NICS

And finally, re-add your virtual networks card and use the VMXNET 3 device:


Like so:

added NICS

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