Issue routing to single IP Address

qvfps
qvfps used Ask the Experts™
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Network DiagramPossible Routing issue.

I am trying to connect to a specific server over a vpn connection.    

I have configured the Firewall to provide an IP address in the 192.168.100.0 range.   When I connect to it I can see the local network.  I can ping and connect to the local servers.  The single server I can not connect to is 1.1.1.1.  I can ping and connect to other servers on the 1.1.1.0/24 subnet without issue.

I ran a tracert from my local computer and I get to 1.0.1.90 then 1.1.1.1.   If I run it from the remote computer over the vpn I get to 1.0.1.90 then nothing.  

I have checked the firewall and there are no rules specific to 1.1.1.1  on it or on 1.0.1.90 which is the default Gateway.  There is a route for the 192.168.100.0/24 on the Gateway
"Route 192.168.100.1 255.255.255.0 1.0.1.61"

I have talked to the vendor who provided the server and they say there is nothing on the server which would block any traffic.  

Any suggestions on what to check next?
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The underlying issue may be that you are both on the same subnets.  What is the netmask for your 1.1.1.207 and for the 1.1.1.1 server?

Also, are those the actual IP address or did you change them for this posting?  The 1.x.x.x addresses are public and shouldn't be used privately.

Author

Commented:
I am not using 1.x.x.x I changed the the first three octets.   1.1.1.  was just easy to type.      

I should have labeled the diagram better.  The laptop labeled 1.1.1.207 works but it is assigned an IP address on the local subnet and  I have been requested to separate these out.   The Laptop on the bottom labeled 192.168.100.50 is the one I am having issues with.    

When I connect to the second Firewallusing the the VPN I get an IP address of 192.168.100.x and I can ping/ssh/remote desktop/connect over Http and Https to all other servers.   The only one I am having an issue with is 1.1.1.1   I have gone through the configs on the firewall, switches and the router and there is no special routing for 1.1.1.1 anywhere I can find.    The 1.0.1.60 switch is connected to 10.0.1.90 over a fiber connection and is on the same subnet.

Author

Commented:
I argued with support for the server and they finally admitted there was routing on the server itself and posted the routing table for me to view.     They had a static route for 192.0.0.0/8 to an invalid address which was causing the issue.
Commented:
The issue was a static route directly on the server for 192.0.0.0/8

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