Parents nowadays face tough questions about whether to monitor or (try to) control their kids’ use of the Internet, and if so, how. Although my personal opinion is that trying to restrict access is a losing battle, I understand why the idea is appealing. You’d like your kids to have some maturity and some perspective under their belts before encountering some of what the Internet so readily brings to their attention. When my kids were younger, the Internet was younger too. I guess if they were still that young I’d be wishing I could create a sandbox for them, even though I don’t think you can. But they’re teenagers now, and they have their own computers. For two reasons, activating the parental controls on those computers isn’t the strategy I want to pursue.

The first reason is that I don’t think filtering the Internet is feasible. Even if we could agree on a definition of what may be harmful, which we never could, people will find ways to route around censorship. Meanwhile we’ll inevitably censor things we never meant to — like, for example, my InfoWorld blog.

The second reason is that I don’t want to incent my kids to route around controls I might try to impose. Nor do I want to force them to go elsewhere to experience an uncensored Internet. The reality of the Internet, like the reality of the world, is something they’ll be dealing with for the rest of their lives. I’d rather they engage with that reality at home where I can more easily keep track of their activities.

If you want to be able to monitor without imposing explicit controls — in other words, trust but verify — then it’s worth knowing about the feature of Windows Vista that supports that preference. It’s in Control Panel -> User Accounts and Family Safety -> Parental Controls. There are two On/Off choices. The first, Parental Controls, enforces any of the controls you elsewhere define. These include restrictions about which websites are accessible, when the computer may be used, and which games or other programs may be used.

My strategy is to leave Parental Controls off, but switch on the second On/Off choice: Activity Reporting. That produces a detailed report about which websites were visited, which applications were used when, which games were played, messages sent/received and contacts added (if the kids use Outlook and Windows Messager, which mine don’t), and more.

The crucial item here, for me, is websites visited. That’s recently become an issue that I want to keep an eye on. With this setup I can, in a way that’s browser-independent, persistent across flushes of the browser cache, and very unlikely to be disabled.

Windows XP and Mac OS X don’t offer the same capability out of the box, but there are of course lots of third-party add-ons. Not ever having tried them myself, I’d be interested to hear how effectively they can be used to implement a “trust but verify” policy. And more generally, I’d be interested to hear about how other parents of teenagers are dealing with the difficult tradeoffs involved in this thorny issue.