Abstract: The present invention is a system and method for the repeated, dynamic, and automated transformation and manipulation of strings of printable or typeable characters that are commonly used for passwords, PINs, keys, tokens, keys, encryption, and filenames forming a class of printable strings. The system and method described makes use of secured password “Hopping” to maximize data security and user's ease of implementation. “Hopping” refers to a method of automated random-password construction and serial substitution. The process of Hopping as described herein is based upon a set of user-selected transformation rules that employ, among other variables, easily accessible, time-variable, data as sources of randomized inputs. Use of randomized inputs and automated serial substitution at time intervals heightens the security of resulting generated passwords.