Shortly after getting my iPad2 I was sitting in a hotel connected to their wireless network with my computer and fired up Wireshark to see what I would see floating through the air. I saw about what I expected, everything that everyone connected to the same access point was doing. I have known this was the case for a long time and have normally used a PPTP VPN to my house to get around this, but that didn’t always work as well as I would like. My roommate tunnels his traffic through a PC at the house over SSH, which I could also do, but it was the iPad that really got me thinking, what could I do that I could easily do on the iPad as well as any computer and not have connectivity issues. PPTP has issues getting through some routers and firewalls and the easiest way around this is to move to SSL so that was what I did. I opted to pick up a Cisco ASA and setup AnyConnect over SSL on it. There is an AnyConnect client for the iPad, it does require that you have the AnyConnect Mobile licenses on the ASA, but after I looked into the price was not too bad for the piece of mind that it would give me. Yes, it was somewhat of a pain to setup, but after a weekend of testing and working on it on and off I did get it to do everything I wanted it to and it has been working well for the last week. I will post some of what I learned along the way in the future.