Over the last five years, Collegiate School in New York City has made institutional decisions that have been challenging for its alumni community to accept: in 2018, it left its home of 125 years, where alumni "grew up," for a gleaming new building a mile away; and, this past year, it redesigned its long-serving mascot. Add to these the limitations on in-person events imposed by the pandemic, some unwanted publicity, and the way that all independent schools have been caught in the middle of the culture wars, and the result is disruption to the usual means of alumni engagement. In this session, we will discuss we were able to maintain and expand our engagement with alumni through creative programming and by taking advantage of the unique strengths of Collegiate's alumni community.