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I have set up a server running Windows Server 2008 which two remote users can dial into using a VPN connection. It works fine unless they are both in the same location, in which case only one of them can connect.

I understand this is because the PPTP protocol cannot cope with two VPN connections from the same IP address. Is this correct? If so, what can I do about it?

Please note that the remote location in question is a serviced office, so we're not in a position to change or play around with their router.


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When you say "from the same IP address", you mean the endpoint of the TCP connection itself? There's no reason that should present a problem. PPTP is layered over TCP, which has no such limitation. – David Schwartz Apr 11 '12 at 10:53

Hamachi isn't an industrial VPN, but it provides a secure connection and is fairly simple to set up. VPNs like Hamachi with multiple networking modes may resolve the issue your having with PPTP.

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The only two problems I can think about is this is either a restriction on the VPN server and you may want to check settings, a bad/faulty/not powerful enough router that isn't handling multiple VPN connections well*, or you are using a web edition of Windows Server which is limited to one (I think) concurrent VPN connection.

* I have seen many routers that have their own VPN features fail when trying to use PPTP or VPN technologies behind

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