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I have been looking for hours, for a way to set up an OpenVPN server on an Amazon EC2 instance that's running Windows Server 2008 R2.

All of the tutorials I have found deal with EC2 Linux, Ubuntu, etc. And we have already bought a Windows Reserved instance, so switching is not an option.

I have tried translating the commands, but since I am not well versed in Linux, this has been a challenge. So I have been looking for a step by step guide to set up an OpenVPN server on an Amazon EC2 instance that's running Windows Server.

If anyone knows where I can find one that would be amazing.

Thank you in advance.

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2 Answers 2

up vote 2 down vote accepted

OpenVPN offers some installation notes with special considerations for installing on Windows. The fact that it's on EC2 is (mostly) irrelevant (except for network/IP considerations). Please also note that running it on Windows is not a workaround for knowing your way around the command line, or for understanding VPN and networking basics. Setting up a VPN is definitely not for novices. Your best bet is the OpenVPN Access Server Virtual Appliance.

A bit of googling led me to this tutorial, which seems 100% Windows-oriented.

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There is a problem which makes running OpenVPN on 2008/R2 impossible on Amazon EC2. – paradroid Mar 6 '12 at 14:55

There is a some sort of problem with running OpenVPN on Windows Server 2008 and 2008 R2 on Amazon EC2. I have been trying to get it working for a couple of days now, and there are many other people with the same problem. It seems to be impossible. See here, and all over the web.

If there wasn't such a problem, as I would have posted a detailed step-by-step guide on how to do this, as running a replica DC on a micro instance would be an ideal solution for small companies, and I have kept detailed notes.

I'm using Server Core, which has no PPTP VPN, so OpenVPN has been the only option, except that it doesn't work.

So, either PPTP on the full GUI version of 2008 or 2008 R2 (which is much easier to set up), or OpenVPN on Windows Server 2003 R2 are the only ways to go.

(Apparently PPTP does not work either and I have read some people report that OpenVPN does not work on 2003 either, but I have also read the opposite)

There is Amazon's Virtual Private Cloud, but you would need a business class router for that and micro instances are unavailable in VPC.

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