When can I withdraw Roth IRA earnings tax-free, not just my contributions?

Contributions come out anytime tax- and penalty-free because you already paid tax on them. Earnings are trickier: to withdraw them completely tax-free you must meet two tests. First, the account must satisfy the five-year rule, meaning five tax years have passed since your first Roth contribution. Second, you must have a qualifying reason, most commonly being age 59 and a half, but also death, disability, or up to $10,000 for a first home. Miss either test and the earnings portion is taxable and may face the 10% penalty. The IRS applies ordering rules so contributions always come out first, then converted amounts, then earnings, which protects most early withdrawals.