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One of the main skills of engineers is to be able to solve problems. It is generally recognized that real-world engineering problems are inherently ill structured in that they are complex, defined by non-engineering constraints, are missing information, and contain conflicting information. Therefore, it is very important to prepare future engineering students to be able to anticipate the occurrence of such problems, and to be prepared to solve them. However, most courses are taught by academic professors and lecturers whose focus is on didactic teaching of fundamental principles and code-based design approaches leading to predetermined “right” answers. Most classroom taught methods to solve well-structured problems and the methods needed to solve ill-structured problems are strikingly different. The focus of our current effort is to compare and contrast the problem solving approaches employed by students, academics and practicing professionals in an attempt to determine if students are developing the necessary skills to tackle ill-structured problems. To accomplish this, an ill-structured problem is developed, which will later be used to determine, based on analysis of oral and written responses of participants in semi-structured interviews, attributes of the gap between student, faculty, and professional approaches to ill-structured problem solving. Based on the results of this analysis, we will identify what pedagogical approaches may limit and help students’ abilities to develop fully-formed solutions to ill-structured problems.