The management of multiple dilemmas became a norm overnight for Catholic school superintendents navigating the COVID-19 pandemic as they quickly moved to making decisions that would have long-term effects on the system of schools they led. This paper attempts to make sense of the new educational dilemmas that have confronted Catholic school superintendents during these past several months. Utilizing the 2019 framework for navigating and managing professional dilemmas in educational leadership (Spillane & Lowenhaupt), we explore educational dilemmas Catholic school superintendents face during this pandemic. We show in this paper that Catholic school superintendents have drawn on their professional expertise and tailored their responses to these COVID-19 dilemmas in illustrative and instructive ways for considering how the U.S. Catholic school system may better respond as the pandemic continues.