This dissertation consists of two essays related to dynamic debt contracting and financial economics. The first chapter studies key determinants of inclusion of a financial covenant in corporate loans from theoretical and empirical angles. Using a novel manually collected loan dataset of small to medium-sized publicly-listed U.S. firms, I find that firms that issue loans without financial covenants tend to have (i) lower accounting quality, (ii) lower assets, and (iii) are experiencing faster growth in profitability relative to firms that issue loans with financial covenants. I build a theoretical model of project financing in which there is noisy public information about the project’s profitability, and the lender can privately monitor to improve the information quality. I show that if the signal precision without monitoring is sufficiently low (high), the equilibrium contract does not include (includes) a covenant. Covenant inclusion plays a key role in providing incentives to the lender to monitor. I show that the lender monitors less often relative to the first best. Insufficient monitoring leads to “excessive risk-taking,” namely, bad quality firms continuing with the project too often. Relatedly, I also show that covenants are used less often in equilibrium relative to the first best. The second chapter examines equilibrium consequences of litigation by holdout creditors in sovereign debt renegotiation. I show that given a sufficiently high probability of winning the litigation case against the borrowing country and/or a high enough defaulted sovereign debt, the presence of the holdout creditors increases the expected debt recovery rate, which makes the default option less attractive, and decreases the country’s default probability and the interest rate on the country’s debt. The country responds by borrowing more but defaults less often along the equilibrium path as it wants to avoid default and facing holdout creditors. Having a non-zero probability of successful litigation is welfare improving for the country as it sustains higher debt and defaults less frequently.