Are there different kinds of design problems? Jonassen (2011) argued that problems vary in terms of structuredness, complexity, and context. On the structuredness and complexity continua, design problems tend to be the most ill-structured and complex. Brown and Chandrasekaran suggest that design problems may vary along a continuum from well-structured to ill-structured, depending upon the context in which they are solved. In formal, school contexts, design problems are often more constrained, allowing many fewer degrees of freedom in their representations, processes, or solutions and are therefore more well-structured. Context also plays an important role in specifying the nature of design problems. In formal classrooms, it is important that problem solutions can be evaluated on stated criteria, because that is a cultural expectation in classroom instruction. For purposes of learning how to design, Jonassen (2011) has argued that design problem solving can be represented as a series of decisions. Those design decisions are based on multiple constraints and constraint operations in the design space. At the beginning of the design process, functional specifications and initial constraints are specified by some sort of needs analysis process. The author's recommendation for supporting engineering design problem solving among high school and university students is to present initial specifications and goals, and then require learners to analyze the problem in order to identify additional constraints. Learners then begin to make design decisions and to construct a model that reflects those decisions. For each decision, students construct arguments supporting their solutions. With each set of design decisions, the mode becomes more elaborate as the problem space becomes more circumscribed. (Contains 1 figure.)