Network Box SSL Proxy secures communication between two internet endpoints by decrypting secure connections on the way in, performing security analysis, then re-encrypting data on the way out. Incoming and outgoing SSL connections over the internet, are upgraded to use as secure settings as possible, following the approach of highest common denominator security, rather than the lowest. The engine also moves the choice of bypassing failed SSL server certificate validation away from the end-user, to the IT Manager.