I have a Windows 2008 server running in country A and I am in country B with an iPhone.

Country B censors the internet. Obviously this is not acceptable, I want to make VoIP/Skype calls and access restricted sites on my phone.

All I need of course, is a VPN service which I can connect to - as the iPhone supports several types, and I'm home free. The problem is, I already have a perfectly good Windows 2008 server laying around in a data centre in country A doing not much. After unsuccessfully looking at dozens of complex howto's on VPNs, obscure Windows IPSec settings and advanced certification and authentication set-ups I am at a complete loss:

How do I set up an extremely simple, single-user, nothing-fancy VPN between a Win2008 server and an iPhone so that the phone can access the outside? Surely there is a simple, 3 minute-solution to this that doesn't involve getting my hands dirty?


Windows 2003 it was Routing and Remote access. If its the same in 2008 it should take you about 3 minutes.

Open the Routing and Remote access from the Administrative tools, enable it, step though the wizard. Open necessary firewall ports.

One word of caution....I have in the past when doing this remotely managed to knock the server off the network by messing up the routing, default gateway or something like that. A personal rule I have now is that I never do the routing and remote access unless I'm sitting infront of the computer or I have another way to get into it like DRAC or KVM over IP independant of the server.

Good luck.

  • Thanks. The wizard kept failing with 'Class not registered' In order to get this working you have to 'install' the Network Policy and Access Services 'role' (while reading Windows Server documentation I often wonder "is this the most useless information I will ever learn?", then I realise that no, learning about WoW would be only slightly more useless). It then of course, being windows, asks you to restart, fat chance. Then one can follow the VPN wizard – Jimmy Jun 22 '09 at 13:28
  • Ah right, I already had that installed so my wizard didn't fail. Sorry about that :) Glad it worked out though. – SpaceManSpiff Jun 22 '09 at 14:52

If at all possible I would do this in hardware not on a Windows server. If you do it on the server you need to install RRAS, which is not without it's complications, and then you have to worry about tunneling GRE or IPSEC through your firewall(s), which is again not without it's complications.

You don't say what firewall you have. We use Drayteks and they support PPTP VPN clients, which I'd guess (on the grounds it seems obvious) would be supported on an iPhone.


  • I was hoping to use the existing hardware I have. – Jimmy Jun 22 '09 at 10:04
  • OK, but make sure you read up on RRAS before you enable it as it isn't trivial to configure. Also make sure your current hardware can forward GRE or IPSEC to your server (if you use NAT many can't). Yes, changing the firewall costs money, but it's a lot simpler. – John Rennie Jun 22 '09 at 13:17

The nice thing is that so far, I've not yet encountered a VPN that my iPhone 3G could not connect to. Which means that you can probably safely remove the iPhone from the equation and just look at an easy-to-deploy VPN server.

  • I don't think iPhone has a client for the popular OpenVPN. (unless you jailbreak the iphone). At least that was the case last year. – Brent Jun 22 '09 at 13:47

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