Hi! This is a great idea. The Chrome APIs needed to do this are in the experimental phase and we'll keep an eye out for when they are released.
Great idea! We have been thinking about this one for a while. Blocking searches is actually surprisingly tricky. If you search "porn" or "p o r n" or "porrn" on Google you get the same inappropriate results. That means that URL blocking won't really work. When you add in the numerous websites that searches can be performed on (Bing, Baido, Yahoo, Excite) this becomes a really intense engineering problem. Creating a solution inline with our quality standards would be nearly impossible. Very open to ideas!
Thanks for your request! We just added another 3000 proxy sites to our blacklist. However, we also realize that proxy mirror sites are being added daily, so we are working on a way to automatically categorize new proxy sites that students visit as well as improving flagged activity so that even if a student is using a proxy, we are giving you insight and awareness about what they are doing.
Here is an article we wrote to elaborate on using wildcards for use cases like this one!