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I am currently trying to deploy a Server which is supposed to connect via a deman-dial in connection to a different companies network.

The demand dial in connection has been set up on Windows Routing and Remote Access role, and is listed as "Connected" there. Traffic from the other network is coming through to it as well.

There are static routes set up that are supposed to go through that connection, one of them being 10.150.0.0 with a subnet mask of 255.255.0.0. This route should allow all traffic in the range of 10.150.0.0-10.150.255.255 to pass through that connection.

But upon trying a traceroute on one of the available IPs, it gets stuck. The first hop is, of course, the local server itself, but after that it doesn't get redirected anymore, the request times out.

How may I debug this further, so traffic is properly routed "into" the connection and towards the other network?

bjoster
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CodingWolf
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  • Did you create a two-way connection and made sure, the route on the other side points to your server? – bjoster Mar 31 '21 at 12:31
  • Yes, the other side is configured correctly. – CodingWolf Apr 01 '21 at 08:46
  • The *route* (on the Client), not the RRAS Server. In many Cases, the Gateway is a security solution, that drops connections when it can not see the SYN for a conneciton. – bjoster Apr 06 '21 at 15:18

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