I have kids, one that is grown and finishing college and another in high school right now. My son who is grown went towards computers early and did his high school in one of the better public school robotics programs. I underestimated his sophistication & level of knowledge in his sophomore year of HS, primarily in his ability to get around the internet controls and filters I had setup. Honestly they were not primarily there for him anyhow, more so for his younger sister, but there was one that was aimed squarely at him which was a time limiter. I forced off time for all internet/electronic activities for him because if I didn't the kid would've been a vampire in his bedroom and turned pasty, which living in a sunny sub-tropical state wouldn't work out well for him.
Nothing I had setup initially was that difficult to defeat, but I realized pretty quick I had to step up my security as he was learning quite a bit as he was going through school, more than I expected him to at least. I never told him not to try or punished him for trying, in fact my wife was upset with me for a short time because I encouraged him to try. My thought was if he was trying to best me he'd learn something, and if he got past me I'd learn something. So to me, win-win.