Florida school districts are facing increasing fiscal pressure as property and sales tax revenues continue to decline as a result of the national economic downturn. Further financial deterioration could render a school district unable to meet its financial obligations. This Article examines lease financing, Florida’s school districts’ preferred method of financing schools’ construction and improvements, and discusses some surprising aspects of this financing method that could be revealed in the event of a school district’s default. Tracing caselaw, this Article follows the evolution of lease financing, charting its increasing popularity since the landmark case of State v. School Board of Sarasota County. The Article asserts that lease financing’s popularity is tied to the perceived credibility of the remedy of cross collateralization of leased facilities. The Article further argues that the use of lease financing has become path dependent on cross collateralization of leased facilities. Next, this Article identifies the inherent risks in cross collateralization of school facilities and questions whether cross collateralization of school facilities is an enforceable remedy in Florida. If cross collateralization were deemed unenforceable, wide-ranging effects to investors and school districts alike could follow because of the widespread incorporation of cross collateralization as a lease financing remedy. Finally, this Article calls for school districts to reexamine their reliance on this method of financing and explore alternative means of funding the construction of schools in the future.