VMWare – Fix Windows 2008 Server Guest Can’t Ping Issue

NAT is the issue. Packets from the Ubuntu machine fly out of the machine, and onto the network. Router sees these, and sends them to your computer, because it knows where it is. then, VMWare ensures your VM gets the packets back, because that's its job. You get connection.

When pinging the guest, packets from the Windows host fly out onto the network and the router sees them. The router has no idea where your VM is, because VMWare has carved a tiny pocket out of your host for a private network. VMWare can't help the router find your VM, because at that point, it's outside of its sphere of influence. The router drops the packets, and moves on with life.

Here's VMWare's explanation of NAT configuration.

Put the VM on a bridged adapter. This allows your router to assign an IP address to it that it knows, and it sits on the network "next to" your computer. Then they can talk to each other.

Your routing table is correct, actually it is identical to mine.

But you state:

I run Wireshark on my host and monitor the traffic. Well, I can see ICMP request packets for both Linux guests and windows guests, but the reply from Gateway are for Windows guest only.

This means your gateway is responding differently to the two ping packets. The best way to proceed is to capture both packets and to compare them. Since you are running wireshark, listen on the Host outbound interface, restrict your capture to the icmp protocol and to destination 10.0.60.0, ping once only from host1 nd host2, save the 2 packets to a file, study what is different between them.

The difference between the two packets is what is triggering the different gateway behavior. If, at the end, the only difference is the source IP address, then it means there is a problem with your kali Ip address. If it is a static address make sure it is outside the DHCP range. If not you may try restarting gateway, host and VMs to ensure the release of the DHCP leases, in case of conflict with previously assigned addresses.