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I have a Windows 2008 R2 RRAS server set up for L2TP over IPSec, using DHCP to assign IP addresses to VPN clients and configured the DHCP options to send routes with DHCP option 121. This is working, and has been working for months, for any Windows client. When the client connects to the VPN the routing table on the client gets updated.

I have not been able to get this to work with and Mac OSX client or and Apple iOS device. The routes are not being taken by the Mac's, iPad's or iPhones. I have gone as far as jailbreaking my test iOD devices, installing a terminal and network tools to confirm that the routing has not changed as it did not in the Mac. My configuration looks like this (these are not IP's I use):

VPN Subnet:

Level 1 Subnet:

Level 2 Subnet:

Printer Subnet:

Server Subnet:

*Gateway is .250 on each subnet

In the DHCP option 121 for indicates for the VPN subnet is through, and in Windows clients it is updated when connected but not on any Apple devices.

The question would is: Does this feature work and should I continue trying to get the routing to work on Mac's and iOS devices?

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