My 14 yo's computer skills have continued to be a real strength. Of course, being both 14 and having disabilities in executive function, he does not always use them wisely.
Years ago I hoped the iPhone and other iOS devices would provide app-restricted services while limiting web access. Sadly, I've been disappointed by Apple's deceptive iOS "parental controls" . That didn't work very well. On the other hand, monitoring his computer use and punishing misuse isn't working that well either. We can't be looking over his shoulder everywhere -- such as in his school room.
So now I'm trying Plan B, an educational program of trial and reward based on techniques that have worked before.
I've set up an account on a machine using OS X Parental Controls . I've whitelisted a number of sites he's interested in, including bing.com . I give him 10 minutes every day to use the machine without me watching. When he's done we review his history and log files together (in Parental Control mode history files can't be wiped -- he learned that trick at school).
If he's used the computer responsibly, he gets some reward tokens. If he hasn't he doesn't get any and I make the whitelist more restrictive. Since I'm trying to extinguish the bad behavior I keep things dull.
He's keen on this, and so far he's doing well. My plan is to keep broadening the list and reducing the parental controls, rewarding self-control over time.
I'm sure it won't fully succeed, but at the very least I'm hoping he'll learn some discretion. If he can think for a second before acting, he may avoid a lot of trouble.
 I'm trying various channels to get Apple to improve, including contacting legislators and this email to Consumer Reports ...
I'm writing to ask you to include 'parental control' functions in yuor next evaluation of smartphones.
We've been very disappointed in the parental controls Apple provides; in some ways they're worse than nothing. It seems we can limit web access by disabling Safari, but many, many apps contain embedded browsers. Once a child has access to an embedded browser, they can usually find their way to a Google search and abundant porn.
Embedded browsers are found in encyclopedias, MLB (major league baseball), reference works, educational materials, and many others.
The fix is simple. Apple needs to provide a parental control that restricts embedded browsers. Until they do, iPhone parental controls are a deceptive fake.
If you include parental control functions in your evaluations, Apple and other vendors will pay attention.
 They're mediocre at best, but they're (barely) enough for this experiment. See updated documentation below.
 Though Bing's parental controls are even worse than Google's he's less familiar with Bing so he doesn't dodge them as readily.
Update 5/29/11: This is working better than I'd hoped. The huge advantage of Bing.com over Google.com is that Bing doesn't use https. So OS X Parental Controls show a meaningful history of sites visited. I'm going to explicitly block Google.com but permit Bing.com.
Update 6/12/11: History files cannot be wiped in the most strict form of parental controls. In the "automatic detection" mode they can be wiped. See Gordon's Tech: OS X Parental Controls Review - State of the art in OS X 10.5 and 10.6.