This dissertation uses administrative tax data to study behavioral responses to taxation and tax enforcement. Chapter I focuses on the two tax penalties associated with Individual Retirement Accounts (IRAs). Chapter II considers the impact of a temporary suspension of tax collection efforts on future tax compliance and income. Chapter III investigates the use of professional tax preparation services by the top 1% of the income distribution. Chapter I, which is co-authored with Victoria Bryant, focuses on tax-benefited retirement savings accounts. These accounts have features designed to encourage retirement savings, including a penalty for withdrawing before age 59.5. Account holders also face a penalty for failing to take required minimum...