Setting up my iPhone with VPN at my school

I am pretty new at using OS X Server, I've only had it for a day. I set up my Open Directory, DNS, and VPN when I got it. I've correctly port forwarded the ports needed. When I try connect to OS X Server from school with my iPhone, it won't connect to it for some reason. What do I need to do? It works fine over LTE when using my IPhone. I know the school network is somehow blocking the ports I need to access. Is there a way to change the port my Phone goes through?

OS X Mountain Lion (10.8.4)

Posted on Aug 15, 2013 3:28 PM

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3 replies

Jun 13, 2014 12:40 AM in response to Mac_Genius101

So the first thing you have to do before picking up your iPhone to configure your VPN, is to identify which VPN service provider you want to use. Ipvanish, hidemyass, express vpn are some of those top VPN service providers serve iPhone-friendly VPN services so that the installation and setup process is as easy as a walk in the park and you can easily access VPN from school or any other place. Also, they will even go so far as to setup VPN on your iPhone for you if you find their tutorials to be too complicated (which they never are).


This is a how-to tutorial to setup VPN on your iPhone 4S. Don’t worry if you are using any other version of the iPhone though because they all have the same VPN configuration features – more or less.


Source: http://www.vpnranks.com/how-to-setup-vpn-on-iphone/

Aug 16, 2013 3:10 AM in response to Mac_Genius101

Check with your school networking folks.


It's quite possible to substantially lock down a network at the firewall and at the switches used in larger networks, and to monitor what's not locked down for purposes of security, accountability and compliance. (VPNs can be a means for circumventing established security, so it wouldn't surprise me to see those ports blocked from primary schools, and from various other security-conscious organizations.)


It's also possible that there's a misconfiguration within the network, and that's blocking access. Multiple layers of NAT can play havoc with various VPN connections, for instance. (IP networks can be large and complex, and errors happen.)


Ask. That approach will also reduce the changes of getting in trouble with the school if the blocks are intentional, and can potentially also help the school networking folks sort out any unintentional network misconfigurations. Why? In general, intentionally circumventing network blocks can be viewed... dimly... by various organizations. Sometimes just dimly, sometimes with administrative consequences, and sometimes with legal consequences.


But since you have LTE mode, you can use that, and avoid the school network entirely.


As for your question, the iOS clients provide L2TP, PPTP and Cisco support, and those protocols have fixed port assignments. You'd likely need both a different client and a different VPN server, or command-line or port-forwarding connections with ssh on if-it-is-open TCP port 22 and related, but — if the port blocks are intentonal — that's just asking for administrative problems if (when?) the traffic gets noticed.


Ask. If you ask nicely and if the blocks are intentional, they might even open a route for you. If the blocks are not intentional, you can help test the configuration corrections.

Jun 13, 2014 4:26 PM in response to AmmarNaeem

AmmarNaeem wrote:


This is a how-to tutorial to setup VPN on your iPhone 4S...


Documentation on setting up an iOS VPN client does not seem relevant to the original question of setting up a VPN server running within an OS X Server system, to allow remote access into that server and its local network.


FWIW, the VPN cloud hosting gateway providers might be useful for bypassing some poorly-locked-down networks, but I'd tend to avoid sending anything sensitive through one of those providers — the VPN hosting provider has full and unencrypted access to all traffic traversing their gateway, after all. The VPN cloud hosting provider would also not grant access into the target (private) network — that still requires port forwarding for VPN passthrough at the firewall, or a firewall with an embedded VPN server.

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Setting up my iPhone with VPN at my school

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