Host Unreachable or Timeout

[everest12]

I am sure it is something really simple causing this Host Unreachable or Timeout error when trying to connect from the remote client but it would help if someone had the same issue and could help me get over the hump ...

Set up:

Windows 2008 Server DC (10.0.0.85/24) with the following:
1. OpenVPN VMware appliance on VMWare Workstation in Bridged VPN mode (10.0.0.87/24)
2. Windows 2008 Server (file server) virtualized on VMWare Workstation (10.0.0.89/24)
3. Firewall off for testing
4. IPForwarding enabled

So far I can connect successfully remotely (using AD) and ping & browse all internal accessible network resources EXCEPT the W2008 VM file server. What is interesting is out of about a dozen times I pinged the internal host name or ip address it returned a reply twice. From the W2008 VM I have the same results...can access and ping other network resources except the remote client (10.0.0.116/24).

[everest12]

I thought I would give a update on this. I used Wireshark to look at the traffic and interestingly when I ping other devices including the OpenVPN VM The ICMP requests show up but not the ones to the W2008 VM.

Also, periodically I see this:

Pinging SEP.domain.local [10.0.0.124] with 32 bytes of data:
Reply from 10.0.0.124: bytes=32 time=1841ms TTL=128
Reply from 10.0.0.124: bytes=32 time=69ms TTL=128
Reply from 10.0.0.124: bytes=32 time=78ms TTL=128
Reply from 10.0.0.124: bytes=32 time=70ms TTL=128

Ping statistics for 10.0.0.124:
Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),
Approximate round trip times in milli-seconds:
Minimum = 69ms, Maximum = 1841ms, Average = 514ms

C:\Users\User>ping SEP

Pinging sep.domain.local [10.0.0.124] with 32 bytes of data:
Request timed out.
Request timed out.
Request timed out.
Request timed out.

Ping statistics for 10.0.0.124:
Packets: Sent = 4, Received = 0, Lost = 4 (100% loss)

[everest12]

After further head banging I did a tcpdump and noticed that ICMP requests from the client connection (10.0.0.116/24) traversing the bridge were being broadcast to 10.0.0.1 (router) to provide the location of the file server (10.0.0.124/24).

So, my question is...what is the best way to add the route back to the OpenVPN AS? I tried to add a static route in the router but of course the static route destination and gateway cannot be on the same subnet.