The primary aim of previous research has been to describe, using a constraint based planning strategy, the restructuring of architectural design problems. The present project aims to study the rationality of designer' behavior in structuring and especially restructuring design problems. The research will be performed in five steps. First, a model of problem structuring in space planning will be developed using optimization. To overcome problems inherent in space planning, such as, continuity of values and size of problem space, dynamic programming techniques will be exploited. Using model developed in the first step, optimal solution paths for the given problem structures will be determined. Protocol data of subjects and simulation program called HeGeL, from previous research, will be used to show factors that explain subjects' behavior, whether it be optimal, pareto optimal or non- optimal. A new version of HeGeL, HeGeL-II will be developed incorporating dynamic programming capabilities developed earlier. The optimality, Pareto optimality or other forms of "rationality" in the paths and solutions used by subjects will be compared against results obtained in the initial modeling step, using HeGeL- II. Finally, bounded rationality techniques and strategies for space planning which can be integrated into the designers' process will be proposed.