This chapter develops a practical framework for valuing stablecoins as a bridge between traditional finance and crypto assets. It explains major design types, including fiat-backed, crypto-collateralized, and algorithmic stablecoins, and analyzes how peg mechanisms, reserves, governance, and regulation shape peg reliability. The chapter links market behavior, conversion dynamics, and stress scenarios to expected loss and fair value estimates. It also discusses accounting treatment, disclosure, and risk-management implications for treasurers, investors, and regulators, providing concrete due diligence and monitoring guidelines for deciding which stablecoins to hold, how much exposure to take, and when to exit positions.