So in order to run the iPad through a debug proxy (Burp Suite), and still be able to forward on the traffic to the net, I needed to be able to talk to it over USB. (yay limited tech to work with!)
This wasn't actually too hard to get going thanks to a little tool called usbmuxd.
- Install usbmuxd (i did this through homebrew: brew install libmuxd)
- Startup the included iproxy tool (
iproxy LOCAL_PORT DEVICE_PORT)iproxy 2222 22)
- Plug in your iDevice (I assume you already have SSH setup on it and enabled)
SSH to localhost:LOCAL_PORT, making sure to specify the account you want to logon as
ssh firstname.lastname@example.org -p 2222
Yay for things just working how they should!