A great number of homes in Florida are subject to the rules of homeowners’ associations (HOAs). HOAs have the authority, pursuant to their recorded declarations, to establish HOA rules and powers and, perhaps most importantly, to level assessments. Given the recent economic downturn, more homes than ever are being foreclosed upon and falling into the hands of financial institutions and lenders, and many of these properties are subject to unpaid assessments from HOAs. Liability for such assessment can sometimes survive the transfer of title through foreclosure and post-foreclosure sale; however, determining the amount of unpaid assessments owed by a new homeowner to an HOA can be quite difficult. This Article outlines the foundations of liability for assessments, the depth of assessment, and the extent of HOA powers regarding such assessments. It also analyzes the inherent conflict between HOA declarations and the Florida statutory provisions regarding HOA assessments. Because a Florida statute now permits joint and several liability amongst subsequent mortgagees or assignees with regard to unpaid HOA assessments, it is unclear whether financial institutions can limit their liability for unpaid HOA assessments through the HOA declaration itself, or whether the statute somehow alters the legal landscape. It is this paradoxical dynamic, created by the failure of a previous mortgagee to pay debts owed to both the lending institution and the HOA, that forms the backdrop for this problem, and for which this Article seeks to provide much-needed clarification.