Controling iOS Ports and URLs Via VPN and UTM

Question

I'm new to actual Network Security. My dad's worked network security, I've taken Security and programing classes. But in short, I have no real money and I'm too busy living the college life (Homework tell you're hired 3 years from now.) My goal this winter is to set up a UTM in the house. I'll probably go with Astaro. If not, WS2008 is my next choice. It's a bit harder on resources, to my experience, but I'm still new, so studying is required.
my ultimate goal is to lock down my network. No uncleared Ports or URLs. I've learned with ZoneAlarm how much I love manual control of my network and thus the applications within it. I'm not a pirate, but I don't like programs validating. It seems insulting for my computer not to trust it's creater. so I block that. My goal is to lock down my more portable systems and reroute them back into the LAN via VPN and block outgoing and incoming ports and URLs from the UTM here.
I realized that I can apply this technique to the iOSs as well, in theory. I'm here to ask for help with this.
My questions:
1. Can you forward ALL networked data to and through the VPNed Network without a single leek?
2. Has anyone tried this and what problems have you had? (Exp: some apps might not like this. I can't imagine them wasting the processor power to check for his, but it's happened with countless PC programs)
3. In regards to question number two's tangent, I'm making a special goal to block the new iAd Urls. I'm assuming they use the commonly open port 80. they don't want people to be without ads at school.
Has anyone seen a problem with this?
thank you in advance. I want to publish my findings in an easy How To Manual later. Sharing is caring. haha.

Answer 1

Smith Comma John wrote:
I was asking if anyone had actually tested the IOS for leaks. either Apple making a backdoor for their sake, or one of the apps exploiting a fault somewhere.
Given the intense scrutiny that Apple is under, I doubt either scenario is a possibility.
What I really ment to ask was "has anyone had problems with the apps not liking URL/Port limitations forced upon them". With ZoneAlarm, you can do exactly this and all of the programs I've used cannot access the internet without concent from the user. If blocked, the end up thinking that they're off line, but Crysis, for example will not intstall unless it get's an authentication check from crytec's server. You cannot install it without internet access (Assuming no workarounds/spoofing is used). Has anyone had problems with the applications after firewalling their ipad with in a similar fashion.
On a Mac, people use Little Snitch for this. It is very handy to make sure SPAM in your inbox doesn't phone home if you accidentally open it.
Because all such tools are system-level, you aren't going to run the on iOS. What you can do is run DD-WRT on your router. You could control and log all inbound and outbound traffic. It is essentially a port of Linux for your router. I used it for many years until I got a Time Capsule. As far as routers go, my ancient Buffalo router with DD-WRT was significantly better than the Apple Time Capsule. My iPad works great with it. I expect DD-WRT would be able to keep you suitably entertained.
Frankly I'm not too happy with apple right now. Tryrony comes to mind.
Don't believe what you read on the internet, especially if Apple is the subject.