The Commonwealth of Puerto Rico has been the center of attention as it faces mounting pressure from its unsustainable debt obligations. Puerto Rico’s current fiscal predicament is further complicated by the fact that it lacks a contractual mechanism that would help it obtain debt relief, if it ever seeks to do so, in an organized manner. The experience of the sovereign debt markets may yield the answer going forward. This essay will explore collective action clauses (CACs), a staple term in sovereign bonds, as a viable and practical contractual alternative to preventing this quandary from re-occurring in the future. The legal issues surrounding the current debt crisis and the remedies recently employed by the Commonwealth to address the current debt crisis are beyond the scope of this essay. Instead, I will employ a prospective, forward-looking approach and analyze the implications of including CACs in future Puerto Rican debt issuances. In particular, I will (i) provide a brief background on CACs within the sovereign and U.S. municipal debt context, (ii) survey empirical research on the borrowing costs CACs may impose, (iii) discuss recent developments, including their use by Belize — the only modern New York law sovereign issuer to activate CACs as part of a debt restructuring — and proposals by the IMF pushing for the strengthening of existing CACs and (iv) analyze CACs as viable tools for the Commonwealth’s future debt management.