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I'm considering getting a Router that is supported in the DD-WRT database.
Before I do that I would like to know, would it be possible to make the router
connect to a VPN on the router level (so all the computers that would be connected will be automatically connected via the VPN server) ?

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Yes, most DD-WRT routers support VPN connections through PPTP, OpenVPN, & L2TP through WAN connection type or as a VPN Client. You can see the option available on the DD-WRT Demo.

The prime issue is getting a build where all these services work and on which router which can take some digging, testing and frustration. I am running two router with the second being a VPN-dedicated E4200 V1 with DD-WRT big that I connect to HMA VPN.

My cousin in the military had a similar desire for his battalion and told me he didn't want to go through the trouble so he a Netgear WNDR4000 with DD-WRT already installed from a company called FlashRouters.

He said that it worked right out of the box for his VPN connection and that their support team is very responsive and well-informed when it comes to configuring VPN on a router. Once you order, they ask you what VPN service you are using and how you planon using the router in your network and then they configure the device before shipping.

They seem to support a lot of different providers as well and while their prices are above standard device pricing the piece-of-mind and ease of use was worth it for him.

Personally, I can't wait when the RT-N66U gets supported fully by DD-WRT then I will be making an upgrade myself.

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For your RT-N66u, check out Tomato, e.g. from this site. It also has full OpenVPN support (even two connections at the same time) and has some very good features. – Stefan Seidel Jan 30 '13 at 12:32

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