Monitoring online activity

I’ve been thinking a lot these days about my DS’s online activity. When DD was his age, we had one desktop and it lived in our living room. She got a laptop when she was in middle school, so she could do homework and so that she and I didn’t fight over computer time.  She knew that I had her passwords, that I could check at any time, and that if I ever saw that “quick close” when I walked in the room we’d have a TALK.  It seemed to work for her – she was very open with me, and has made it to (almost) 21 successfully.

DS has had a different route.  He’s grown up with multiple laptops in the house, bought his own laptop last year with money he earned, and has a lot more time alone at home than his sister did.

My main worry so far is the AMOUNT of time he’s online.  But I know that MS/HS is a tricky time and I worry about where he will visit and who he will talk to.Mostly I trust him, and we talk about a lot of stuff, but I also know that there is a lot more “stuff” out there than there was 8 years ago with DD.

How have you all handled this?  If your kids are still young, what have your thoughts been?  Is the old-fashioned route of talking about it, open communication, and some clear boundaries enough, or do we need more?

I was interested in this article in the NYTimes

Have you used any of these tools?  Is this going too far (reading every text to your kid’s girlfriend?) or the appropriate caution with today’s technology?