Frustration is a problem common to all people learning a new technology, particularly computing technology. Intelligent Tutoring Systems (I.T.S.) can offer help based on a users goal or ability. What these systems fail to take into account is that help is useless if the user is not ready to accept it. This research has two main aspects: the content of help and the timing of that help. Thus the goal of this research is to develop a program, called Mentor, which first offers good helpful direction to the user and second, learns the appropriate time to intervene. Mentor is being developed in modular form; the modules areas follows: (1) observing the user's behavior within a software environment, (2) statistical analysis of the users behavior, (3) a set of heuristics to decide what help to offer and when, (4) a means of presenting help to the user, and (5) a feedback system to measure user responses to the help offered.