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I have somewhat of a complex configuration question for you.

I would like to share my VPN connection to other devices, iPad and Apple TV via Wi-Fi using my Mac Book Pro and Airport.

I know that OSX Supports sharing of VPN connections via Airport, as there is the option to share my Ethernet and Strong VPN Connection via Airport.

However, when I attempt to connect my iPod Touch to my shared VPN connection via Wi-Fi (from MBP) the iPod gets a full signal but nothing will load in Safari.

Yet, if I disconnect the VPN, then my iPod works fine with the shared Ethernet (Broadband) via Wi-Fi.

This leads me to think that there are specific IP Address details that need to be entered for the iPod or Apple TV to make this work.

Does anyone have any past experience with this type of setup?

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Here is a tutorial (minus the VPN config):… – Jessica Taylor Dec 20 '10 at 20:17
Your VPN software may prevent this configuration. – Chris Nava Apr 7 '11 at 4:32

This link has it documented well: Using (and sharing) a VPN connection on your Mac – Rodrigo Sieiro

It involves using an OpenVPN server and setting up Tunnelblick.

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Would be nice if you could include the most essential points here in the answer in case the link ever goes down. – slhck Jan 14 '13 at 15:37
Unfortunataly that blog post is no longer relevant for Mac OS X 10.7 or 10.8 – Simon Woodside Sep 26 '13 at 2:16

To share a VPN connection on 10.7, using WaterRoof, follow these directions.

To share a VPN on 10.8 and above, do the same thing with IceFloor

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I didn't read your post, but here is how everything should go down.

Your Mac has two network interface devices (the wifi and ethernet card). You must be connected to the VPN via the ethernet card. You will see why in the next paragraph.

To make your Mac a wireless hotspot you can do so by using your wireless device in ad-hoc mode. Give your ad-hoc profile a name (aka ESSID), and a cryptographically strong password. Now, people can connect to your Mac as if it were a wireless router.

Now, to join the people connected via ad-hoc to go through the VPN, you need to create a bridge between your wireless and ethernet device. So, the traffic flows as such: Client -> ad-hoc -> bridge -> ethernet -> VPN -> Internet

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