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Sorry if this is all rather vague. It feels like any time I try to get anywhere with this, I start to hit brick walls consisting largely of things I don't understand.

I'm trying to set up a VPN for my company (current setup is listed here). As mentioned in this question, I recently obtained a Cisco Wireless-N Gigabit Security Router with VPN (WRVS4400N). Unfortunately, my digging through the settings seems to suggest that it doesn't support more than five users. At all. Which means that it isn't fit for purpose. I probably need to support about 15 concurrent incoming connections; I don't really expect to hit that level often, but I want to be capable of it.

Is it actually possible using this beastie?

If it isn't, I'm going to have to sort out something that is capable of it. We have a Windows Server 2008 machine that someone tells me can do VPN. I don't know how feasible it is to set up. Can anyone tell me? Keep in mind that I'm starting from very little knowledge (I tried to set up the Cisco VPN as a test, and I kept getting error messages I didn't actually understand.)

Here's what we want to do. I may well be misinterpreting the capabilities of VPN; please tell me if I am.

  • Allow our remote users to enter a username and password, to get to the office network
  • Provide them with access to several machines on the network
  • Ideally, allow them to use Remote Desktop and file transfer

I'm allowed to purchase new hardware if necessary to achieve these goals.

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    The documentation pretty clearly states "Capacity - VPN tunnels (remote access) : 5" It's a "Linksys" SOHO router that costs $170.
    – Chris S
    Jun 30, 2010 at 22:50

4 Answers 4

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setting up vpn on windows server 2008 is not difficult, plenty of information online and how-to guides.

the most important thing to remember when doing that is to forward the correct ports form your internet router to your 2008 box.

This guy wrote a nice article: http://www.windowsecurity.com/articles/Configuring-Windows-Server-2008-Remote-Access-SSL-VPN-Server-Part1.html

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We wound up going in a slightly different direction; installing OpenVPN and doing things that way. Thus far, it seems to have been working quite well.

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openvpn is great for vpn connectivity - we use it at our office (we installed IPFIRE as our firewall/vpn/IDS) and we have had little problems. One problem we did have though is with the client vpn software - if it is older than the current 2.1.1 (i believe 2.0.9 was the last stable before 2.1.1) it can create a loop in the network and bring your office internet connection as well as the user's vpn connections to a crawl, so watch out for that. we mainly saw this on linux vpn clients, the windows clients seemed to be OK with the older versions. hope that helps, good luck!

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I agree with Luma. I have set-up 4 VPN's using windows 2000/2003/2008 and it is really quite simple.

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