URL Logging on home network

Question

I am interested in knowing what websites my teenage boy is going to from his Chromebook connected wireless to my home network. I have been open with him and have told him that I am not censoring him, but I want to help him make good choices by always knowing that his tracks are discover-able. My wife and I are most concerned about his productivity on the web - he has a super bad habit while studying for school to SEVERELY get distracted by time-wasting websites like youtube and others. He has been using incognito mode to circumvent web history logging.

I do not want to censor his web experience by blacklisting.

I am not concerned about monitoring his web activity when he is not on my home network (cellular or outside our home)

I can only think of three options:

1. disable incognito mode in ChromeOS (my web searches have only shown me that this can be done via a policy administrator on enterprise devices. I couldn't find out how to do it on a personal ChromeBook)

2. URL logging application - i could not find an app in the Chrome WebStore that could do it on personal devices - again only enterprise devices

3. URL logging at the router - my current router (cisco WRT54g2) appears to have limited logging capability that does not appear to be informative. I believe i need to see IP address (or URL), MAC address and a timestamp.

My web searches have shown me that i could set up a transparent web proxy (but i don't know how and it seems quite complex to set-up and maintain). Furthermore, performing the log analyses seems complex, too. I've found WallWatcher that claims to make it easier but that support for that program stopped in 2001. Link Logger also is no longer supported

i currently use a cisco router wrt54g2 v1.5, but would be willing to upgrade to a different router and/or purchase software if i could gain url monitoring capability.

Answer 1

First of all, you can assume that anything done on the machine itself, he'll find a way around it. This results in a man-in-the-middle setup being the best approach. I will have to be very abstract about this, as further info would be too long for a proper answer.

The best approaches here are:

1) A dedicated transparent proxy. To give you an idea, what you want is a linux machine running a software suite named squid. Once you have squid up and running, it's fairly trivial to log the URLs to a file for you to check.

2) See what you can do with the linksys router you have. You are in luck, because linksys wrt54 series is one of the most customizable routers out there (I have one myself). I know that DD-WRT, which is compatible with your wifi router, allows setting up a transparent proxy on the router itself. This involves flashing the firmware of the router, which is fairly complex, but doable if you follow the instructions carefully.

I think for your scenario, option 2 would be the better approach, as it doesn't tie up any additional hardware. Regardless how you go about this, it will involve fairly advanced stuff, but if you have time and determination for it, it's certainly doable.