Wicked problems have no clear definition, multiple possible but arguably correct solutions, numerous stakeholders, and no clear point of completion. Every possible solution has ramifications, and the problems are so unique as to require one-shot solutions. This researcher-designed, cross-sectional, mixed-methods study gathered information about wicked problems from expert instructional designers in practice. Combining information from the fields of problem solving, experts and expertise, and instructional design, wicked instructional design problems were evaluated and described by the expert instructional designers who were the survey participants. These participants had a minimum of five years of experience in the field. They described their practice as filled with tasks and issues containing the characteristics typical of wicked problems. Designers described instructional design problems in their practice as frequently ill-defined, unique and uniquely complicated, and fraught with changing constraints and requirements. They believed that their problems were best solved through the use of personal experience, consultation with colleagues, instructional design models, and current instructional design literature. Designers with more experience in the field were less likely to rely on colleagues and models and more likely to rely on their own expertise and experience than their less-experienced counterparts. This study contributes to the field in the areas of wicked problems, general problem-solving techniques, expertise and expert behavior, and instructional design.