U.S. GAAP currently mandates that convertible debt be reported as a liability in its entirety, despite the hybrid nature of convertibles. I examine the degree to which financial reporting for convertible debt is consistent with the views of market participants, and effects debt contracting outcomes. In the first essay I use market measures to determine whether three different approaches to convertible debt accounting correspond with views of shareholders and creditors: 1) liability measured at fair value FV), 2) the debt component measured as comparable non-convertible debt and the incremental conversion option value as equity FC), and 3) debt and equity components measured using probability-weighted discounted debt and equity settlement values PB). My tests relating leverage to credit risk suggest that creditors view convertible debt consistent with the FC method. In contrast, my tests linking leverage to systematic equity risk suggest the PB method corresponds best with shareholder perceptions. My results suggest that neither creditors nor shareholders view convertible debt as a homogeneous liability. Instead, investors recognize the debt and equity components of convertible debt differently according to their different purposes for distinguishing liabilities and equity. The evidence suggests supplemental disclosures can improve convertible debt accounting by helping investors more accurately and efficiently estimate the debt and equity components of convertible debt. Current reporting requirements for convertible debt assign the value of the conversion option to debt, and as a result distort both the firms cost of debt and measures of debt and equity. In the second essay, I test whether these distortions affect two aspects of debt contracting: pricing and covenant selection. I analyze a large sample of private debt contracts and find that after controlling for firm, issue, and macroeconomic risk factors, interest rates for borrowers with outstanding convertible debt are lower than those for borrowers with no convertible debt. The result is stronger for high credit risk firms, and firms that rely more heavily on convertible debt financing. Also, the results hold after controlling for the higher growth options, lower cash interest payments, and lower relative seniority generally associated with convertible debt issuance. These findings are consistent with creditors taking into account the equity characteristics of convertible debt when determining loan pricing. Lastly, I analyze the effects of post-loan-issuance increases in covenant slack caused by conversion, and find that loans to firms with convertible debt at loan issuance have more financial covenants, specifically those covenants that rely on debt and equity measures. Overall, I find that lenders do not rely solely on financial reports, but rather incorporate additional information when measuring firm credit risk, and designing loan contracts for borrowers with convertible debt.