MacOS native Cisco VPN cannot access remote network

[nathang01]

I have the Cisco VPN client 5 installed on a Windows 10 computer and using the Native Cisco IPSec client on MacOS10.12.  I can successfully connect to the VPN on both computers however, on the Mac, I cannot RDP to any of the servers on the remote side.  I can successfully RDP on the Windows 10 computer.  On the Mac, I can't even ping any of the servers.  

I ran the route get -n www.google.com which confirmed that my gateway was my local router.  I ran route get <server ip> and confirmed that the gateway listed was the utun1 adapter.

I really can't speak of what's on the other side as this is a remote network to me and belongs to another company.  They provided the windows client and the config file, however most of my work I do is on the Mac.  Any ideas that I can ask them to see why I cannot access their servers while on MacOS?

[Francesco Molino]

Hi

Are the ip address you get are in the same range on Windows and Mac machines?
You can ask them to check logs on their asa when you try to send traffic from your Mac.

On your Mac if you confirm that next hop IAS your tunnel interface, everything seems to be fine.

[nathang01]

Hi,

I’m on a 192.168.0.0/24 network and the remote network is 10.9.0.0/23 network.

When I connect to the VPN on either Windows 10 with Cisco VPN client or MacOS 10.12 with native Cisco IPSec, the IP address I get is 10.2.0.23.

When I do a route –r I can see:
10.0.0.0/8 10.2.0.23 utun1

When I do a route print I can see the same thing on the Windows 10 of access to the 10.0.0.0/8 network goes to the tunnel adapter.

I suppose I can try to see if I’m allowed to have multiple sessions open. I can then VPN on Windows 10 and see if I can access the Mac from a RDP session on the server from Windows.