I need your network expertise because I have been looking at this for the past 3 hours and got nowhere. Migrating from ESX 4 to ESX 6, used Veeam to migrate a test server from one vCenter to another, before migrating it was all working OK. Using a Windows 2K8 server to relay email traffic to Office 365 via IIS as some devices such as copiers don't have a method for connecting to cloud exchange. Need to use a specific WAN gateway as email routing isn't setup with the provider on the other and it will bounce, call this WAN 2. ESX host public IP 192.168.0.222, mask 255.255.255.0, gateway 192.168.0.251 VM IP 192.168.0.229, mask 255.255.255.0, gateway 192.168.0.252 In this setup I cannot ping other subnets in the network (other offices), 192.168.1.0 and 192.168.2.0 etc but it worked fine on the old ESX host. If I add persistent routes in Windows with Route add -p 192.168.1.0 mask 255.255.255.0 192.168.0.251 then it can ping the 1.0 subnet but when I remove it stops working. If I set the default gateway on the windows server to 0.251 then it can ping the other subnets BUT although 0.252 is set to route all internet traffic from 0.229 to WAN2 it seems to ignore this when it comes from 0.251 first and sends it via WAN1. If it is set with 0.252 as the gateway then it routes via WAN2 but I lose the routing to other subnets without persistent route. 192.168.0.251 is a CISCO 2811 192.168.0.252 is a Draytek Vigor 2850 If I hit the 2811 first I can't route via WAN2 on the Draytek but if I hit the Draytek first it doesn't route internal WAN traffic to the Cisco without persistent routes in Windows! As I say it all worked perfectly on the old ESX host but it is set up the same and even tried adding the 2 routes into ESX CLI but still won't work. On ESX 4 the routing table for the public vmk0 is simply 0.0.0.0 192.168.0.251 and on it the VMs all are able to route to the other subnets even if they have 0.252 as a gateway. At the moment I have the extra routes to 1.0 and 2.0 in the ESX routing table and it still won't work. I even have an old server 2003 server with gateway 0.251 and have that set to go via WAN2 on the router and that works fine so I don't get why this 2K8 server is being so annoying! Before we completely blame ESX6 know that this non routing to WAN2 from 2K8 on 0.251 was happening on ESX4 too. I am guessing that when the gateway is set to 0.252 then the draytek isn't routing the stuff to the other subnets properly but this is only happening when it comes from a VM, when it comes from a physical system it works fine. I have persistent routes in the Draytek to all other subnets. It isn't the end of the world as I only need this one server to have 0.252 as a gateway address, all the others can have 0.251 and go out via WAN1 but I just don't feel it is a very elegant solution having to add the persistent route in Windows, I just want it to work automatically as it should! None of this probably makes sense.... Perhaps Server 2K8 R2 is just crap when it comes to IPv4.