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In our office network we have a VPN setup to our datacenter. We are using a Sonicwall NAS. The VPN works fine for most cases. From our office we can connect to the servers in our DC but if I were to remote into a server in the DC and try to ping a local host then the requests time out.

We also have site-to-site tunnels between two other offices and if I remote into a machine in any of those two offices I can ping local machines.

So let's say we have our 4 networks which are as follows:

  • 10.10.10.0/24 (DataCenter)
  • 192.168.0.0/24 (Office 1)
  • 192.168.1.0/24 (Office 2)
  • 192.168.2.0/24 (Office 3)

Then the issue is that:

  • DataCenter can talk to: Office 1, Office 2
  • Office 1 can talk to Office 2, Office 3, DataCenter
  • Office 2 can talk to Office 1, Office 3, DataCenter
  • Office 3 can talk to DataCenter, Office 1, Office 2

I can't figure out why DataCenter can't talk to Office 3. As far as I can tell, all 3 tunnels are configured the same way and there is no non-standard/automatic routes, NAT rules, or firewall rules.

Unfortunately, I don't have access to the DG at the DC so I can't see the table, but the routes look like this:

Tracing route to 192.168.1.1 over a maximum of 30 hops

  1     1 ms    <1 ms    <1 ms  10.10.10.1
  2     9 ms    10 ms     9 ms  192.168.1.1

Tracing route to 192.168.2.1 over a maximum of 30 hops

  1    <1 ms    <1 ms    <1 ms  10.10.10.1
  2     *        *        *     Request timed out.
  3     *        *        *     Request timed out.
  4     *        *        *     Request timed out.
  ...
  30    *        *        *     Request timed out.
share|improve this question
    
Are you trying to ping a local host from remote by IP or DNS? –  Jason Huntley Mar 22 '12 at 20:04
    
I am trying to ping by IP. I cannot even ping our local gateway in Office 3 from the DataCenter while I can ping the gateways of Office 1 and Office 2 from the DataCenter. –  illvm Mar 22 '12 at 20:28
    
What kind of server? Windows Server or Linux? –  Jason Huntley Mar 22 '12 at 20:30
    
Run a tracert from the datacenter to office 3 and see what the results are. The traffic may be taking a path you're not expecting (and therefore not getting to office 3). If the path looks OK, then run a packet capture on both ends while you ping one from the other (and vice versa) to see if you're seeing the ICMP traffic going in both directions from both sides. –  joeqwerty Mar 22 '12 at 20:31
    
The tracert is definitely strange. Going from DC->O1 or DC->O2 it's a straight jump from gateway -> host while going from DC->O3 we see the gateway followed by lots of hops which timeout. Is it a routing issue on the gateway in the DC? –  illvm Mar 22 '12 at 20:38

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