Close to 50% of municipal bonds are prepackaged with insurance at the time of issue. We offer a tax-based rationale for the emergence of third-party insurance of tax-exempt bonds. We argue that insurance adds value as it allows a third party to become, in a probabilistic sense, an issuer of tax-exempt securities. Insurance however reduces value by eliminating the possibility of a capital tax loss. While the net benefit from insurance increases with bond maturity, the benefit may not increase monotonically with default risk. We also provide empirical evidence supportive of the model's predictions.AS WITH SECURITY MARKETS EVERYWHERE, new financial products and institutional arrangements have radically altered the nature of the municipal bond market. A major development is the explosive growth in insurance for municipal bonds, in which a third-party insurer promises to step in and make timely payments to the bondholder in the event of a default. From humble beginnings in the 1980s, insurance is now commonly provided and about 50% of municipal bonds are prepackaged with insurance at the time of issue. Insurance can also be purchased directly by investors. Our objective in the paper is to understand why it is attractive for municipalities to issue bonds bundled with third-party insurance.We show that the demand for insuring municipal bonds can be attributed, at least in part, to an indirect form of tax-arbitrage. Critical to our argument is the fact that unlike other forms of credit-enhancement, insurance maintains the timing of payments in the event of default, and thus preserves the taxstatus of the payments received by the investors.