EvilZone

Ok, so my high school just got their firewall/web filtering service upgraded from Barracuda to NetBox Blue.

As this is my second last year of high school, me and other technologically adept friends want to go out with a bit of finesse and screw with the IT guys a bit.
Does anybody know of some vulnerabilities in NetBox currently?
We are just getting past it with an SSH tunnel with a DNS leak fix in chrome command line.

Another strange thing I have noticed is that when they changed over, ironically from being frustrated with critical errors in barracuda, they asked every device on the network to download and install an app called BYODClient.exe (attached). The web page it comes from, hosted locally, claims it is to install a security certificate in the machine, but I've never seen a security certificate with a startup entry. Plus I can't find the cert on the machine anywhere.

I have broad capabilities and experience and therefore, should be able to cope with most technical jargon that you throw at me.

Thanks for the help