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Tun/Tap Suggestion #1

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@jaredjones

Back in 2011 a company called Tether implemented full scale tethering almost identically to how you are doing it now with one small caveat. They created a virtual network interface on your Mac which routed the networking over the virtual interface into a local program running on OS X and then they muxed over USB to the iPhone via a socks proxy. The reason they created a virtual networking interface for this is because SOCKS tethering is not real tethering. A lot of applications do not support SOCKS and most of the OS doesn't support it as well. With the use of Tun/Tap you can create a virtual network that can route your Mac's network requests into a listening/running OS X program which can forward the requests to a socks server listening on your iPhone. You might want to check this out.
http://tuntaposx.sourceforge.net

I noticed that you were mentioning tun2socks, however an actual virtual network interface would likely cause less headaches and would work loads better.

;)

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