Universities are being asked to prepare our students to navigate successfully in a complex and interconnected world and to contribute to the solution of difficult problems at work and in the communities where they live. Our universities must do the same. We must adapt our approaches to education, scholarship, and community involvement in order to play a meaningful role in addressing the increasingly complex and wicked problems that our communities face. The housing crisis in Portland, Oregon offers an especially important example of a wicked problem that has developed slowly, will be very costly to resolve, and involves a lot of uncertainty due to unpredictable social, economic, and environmental factors. In 2015, policymakers in communities throughout Oregon began talking about a housing crisis as people searching for affordable housing found themselves competing with both the growing popularity of Oregon as a place to live and a real estate investment boom. Rents rose at a rate of $100/month and over 24,000 units were needed to meet the demand in 2015. The problem remains acute in 2016. This article uses community efforts to understand and address the housing crisis as a focus to explore the changing roles of the university in participating in and contributing to these new social networks, multi-stakeholder initiatives, and collaborations.