The Contextualize to Learn team met for our second annual cross-institutional meeting, which took place March 23, 2018 in Milwaukee, Wisconsin. Team members from Madison College, Milwaukee Area Technical College, and UW-Madison gathered to share findings to date, discuss project progress and future plans, present contextualized course outcomes and lesson development, and share upcoming professional development opportunities. Faculty and institutional researchers engaged in a breakout session to discuss their experiences with and challenges around contextualization, as well as present contextualized lesson plans.