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I have configured a Server 2008 R2 instance in a VPC with 2 subnets. The server is configured as a DC, RRAS and CA and a NIC in each VPC subnet. SSTP VPN clients can reach the server but either the connection fails to register on the network or a 169.x.x.x address is provided to the client with no network connectivity.

I would prefer to have the 2K8 server also be the DHCP server, but a few resources have suggested to use the VPC DHCP server instead. I previously had an EC2 instance with a single NIC working properly, but ever since migrating to a VPC, it no longer works. I added the DHCP Option Set to my VPC that provides domain-name and domain-name-server. Also the DC NIC DNS points to 10.0.0.2. But still no worky :(

Here is a diagram of what I would like to accomplish.

Any ideas? enter image description here

John R
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1 Answers1

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You must use Amazon's DHCP server in cloud part, since they have their own SDN solution (software defined networking) you can not use your own DHCP on premise server for this.

169.254.0.0/16 is defined as APIPA (Automatic private IP addressing) where IPv4 gets its own IP without DHCP server. This subnet is not routeable. In your case it means that you are missing DHCP server.

For more info check offical documentation - http://docs.aws.amazon.com/AmazonVPC/latest/NetworkAdminGuide/CustomerGateway-Windows.html

Hrvoje Kusulja
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