This qualitative study examines leadership challenges and lessons learned from 27 months of crisis during the COVID-19 pandemic as described by educational leaders in an urban public school district. Interviews were conducted with sixteen public school administrators: the Superintendent, Assistant Superintendent, Principals, Assistant Principals and Department Directors. The following themes emerged from qualitative interviews: leading in a crisis, leadership practices critical in overcoming challenges, VUCA, lessons learned. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]