We lasted about a day with the new content filtering that I put in place before we switched the kids back to the old open WiFi network. We encountered two problems: Missing whitelist entries, and well built apps that depended on not messing with their certificates with a MITM attack.
Amazon Video, for one, will not communicate with its servers if you tamper with its certificates. Given that the sort of inspection I am doing is a Man-In-The-Middle (MITM) Attack, they have a point. I thought I had prevented this problem, but as it happens, I did not understand two things: SSL inspection, and how Squid decides to mess with certificates.
Continue reading “Keeping The Kids Safe Part 2: MITM Lessons Learned”