What are the two different five-year rules for Roth IRAs?

Roth IRAs have two separate five-year clocks that trip people up. The first applies to earnings: to withdraw investment gains tax-free, your first Roth IRA must have been open for five tax years AND you must be 59½ (or meet another exception). This clock starts once and covers all your Roth IRAs. The second applies to conversions: each Roth conversion has its own five-year clock before you can withdraw that converted principal penalty-free if you're under 59½. So a conversion done in 2025 is penalty-free to withdraw in 2030. Note your own direct Roth contributions are always withdrawable anytime, tax- and penalty-free – the five-year rules only restrict earnings and converted amounts. Keeping good records of contribution, conversion, and earnings dates avoids unexpected penalties.