Focusing on private debt contracting, this dissertation investigates two pivotal events: loan covenant violations and renegotiation, in three chapters. Specifically, Chapter 1 presents the first research “Insider Trading Signals around Debt Covenant Violations: An Empirical Investigation”. Chapter 2 documents the second research “How Does Inside Information Impact Debt Renegotiation? The Role of Inside Trading”. Chapter 3 shows the third research “Credit Risk Transfers and the 20-year Decline in Loan Covenant Violations”.