The COVID-19 pandemic posed many challenges to student learning, classroom instruction, and the management of school systems. Media, think tanks, and education groups have warned of a post-COVID fiscal cliff for K-12 schools after the $190 billion from the federal government in the form of the Elementary and Secondary School Emergency Relief (ESSER) funds expire. The impending expiration poses both a challenge and an opportunity for district leaders to prove their mettle as advocates for their students and their communities and find creative ways to reform a funding system that is intricate at best. This brief highlights three dilemmas and seven considerations to help district leaders bridge over the ESSER funding cliff.