This thesis addresses various contractual solutions to firms' financial distress. The first chapter presents a unified framework for analyzing the holdout problem, a pervasive economic phenomenon in which value creation is hindered by the incentive to free-ride on other agents' participation. The framework nests many classic applications, such as takeovers and debt restructuring, and highlights the role of the commitment power: The holdout problem can be resolved using contingent contracts with commitment, e.g., by a unanimity rule if the principal can commit to calling off the deal when anyone holds out. In contrast, a lack of commitment substantially alters the optimal offers depending on the payoff sensitivities of the existing contracts, which explains the absence of the unanimity rule despite its efficacy and cross-sectional heterogeneity in offers. (E.g., senior debt is used in debt restructuring but not in takeovers.) Furthermore, I show that stronger partial commitment can backfire via renegotiation, exacerbating the holdout problem. This non-monotonicity reconciles contradictory empirical findings on the use of CACs in the sovereign debt market and sheds light on various policies. Lastly, the paper shows stronger investor protection could facilitate instead of hinder restructuring under limited commitment.The second chapter considers the role of institutions in financial distress. Distress can be mitigated by filing for bankruptcy (which is costly) or preempted by restructuring (which is impeded by a collective action problem). We find that bankruptcy and restructuring are complements, not substitutes: Reducing bankruptcy costs facilitates restructuring rather than crowding it out. So does making bankruptcy more debtor-friendly, under a condition that can be written in terms of a few easily observable sufficient statistics. The model gives new perspectives on relief policies (e.g., subsidies to bankrupt firms) and on legal debates (e.g., the absolute priority rule). The third chapter examines the optimal design of liquidity insurance contracts for firms that experience a quality shock concurrent with the liquidity shock, both of which cannot be verified and hence contracted upon. Due to the incompleteness of these contracts, firms cannot receive full liquidity insurance: If a firm is fully insured, it has little incentive to stop inefficient projects, as creditors bear the costs. Therefore, the optimal contract involves limited insurance and requires co-investment with internal cash. Interestingly, my findings challenge the classical theory that low-pledgeability firms rely more on liquidity insurance. Instead, I show that a lack of pledgeability prevents these firms from obtaining more liquidity insurance. In fact, I demonstrate a positive relationship between liquidity insurance and pledgeability, which sheds light on the seemingly paradoxical fact that smaller firms that need liquidity insurance the most are the least insured and face the highest risk of revocation. Furthermore, my results rationalize the common cash-related covenants in credit lines.