Open Educational Resources (OER) have been adopted by growing numbers in higher education during the last two decades. Online repositories contain a myriad of OER content, learning objects, and activities. This article presents six case studies from both new and experienced instructors across multiple disciplines at a single institution. It outlines varying motivations for selecting OER, problems encountered, and possible solutions according to when, how and why instructors started their individual OER journeys. Closer examination using thematic analysis reveals context and commonalities contributing to a more informed understanding of past experiences and more insightful strategies for the use of OER in the future.