When the post-secondary institution's insurer completed its initial assessment of the March 2024 incident at the Thornbury, Ontario campus, the coverage picture appeared manageable: a remediation contractor had retained an electrical subcontractor whose electrician performed unauthorized work, that work caused $340,000 in additional damage beyond the original remediation scope, and the subcontractor's commercial general liability policy would respond to the loss. Within 6 weeks of the loss, however, the electrical subcontractor had ceased operations, its principal had filed for personal bankruptcy, and its insurer had issued a reservation of rights letter questioning whether the policy remained in force at the time of the unauthorized work. The institution's insurer now faced a familiar but formidable problem in construction-related subrogation: the entity most directly responsible for the loss lacked the assets or coverage to satisfy a judgment, while the parties with solvent balance sheets and responsive policies each pointed to contractual provisions, policy exclusions, and equitable doctrines that ostensibly placed the loss elsewhere. This lesson examines the legal architecture of layered coverage disputes when the most proximate wrongdoer is judgment-proof, focusing on the doctrines that govern priority among insurers, the contractual mechanisms that shift or preserve coverage obligations, and the strategic considerations that shape recovery efforts when subcontractor insolvency transforms a straightforward tort claim into a multi-front coverage battle.