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Leasing has become, throughout recent years, an increasingly important financing source for companies’ operational activities and has deserved some attention in the corporate finance literature. Understanding the leasing decision, through a comparison with other external financing options and an evaluation of its overall fit with firms’ specific characteristics has been the focus of existing investigations and it is the goal of this study. Our analysis is focused on the relationship between lease and debt financing and on an examination of firms’ leasing propensity, taking into account their particular features. With the adoption of three different, but complementary methodologies, we find that leasing propensity is greater for smaller firms, with more investment opportunities, in a worst financial condition, with relatively fewer specific assets and with lower availability of collateral. In addition, results suggest that lease and debt financing are seen as substitutes, as higher relative amounts of debt are associated with lower leasing intensity.