Business schools have long valued case studies as a tool for both broadening a student’s perspective, and provoking them to deeper consideration of complex situations. The challenge with case studies is assuring the portability of the lessons; we don’t expect students to see situations imitating those they’ve studied, hence the goal must instead be habits of mind and principles of action which the student can portage to the circumstances of their professional lives. This paper evaluates the suitability of Richard Paul’s Critical Thinking model as a template for evaluating engineering enterprise thinking habits and organizational behavior, using the Columbia Accident Investigation Board (CAIB) report as a case study. With minor refinement, Paul’s model provides a powerful vocabulary for complicated case study analysis, and that familiarity with the model provides participants with both a mechanism for analysis and a means for portaging lessons to other professional situations and organizations.