Core Points - The article discusses the rules surrounding Roth IRA conversions and the conditions under which individuals can withdraw earnings and principal without penalties [1][3][6] - It highlights two distinct five-year rules that may apply to Roth IRAs, which are independent of each other [3][8] Group 1: Roth Conversion Rules - Each Roth conversion has its own five-year waiting period that begins on January 1 of the year of conversion [6][7] - If an individual converts $50,000 on April 30, 2025, they must wait until January 1, 2030, to withdraw that amount without penalties [6] - Individuals under 59 ½ years old face a 10% early withdrawal penalty if they withdraw converted amounts before the five-year period ends [6][7] Group 2: Roth Contribution Rules - There is a separate five-year rule for Roth contributions, which states that if it has been less than five years since opening the first Roth IRA, earnings withdrawn are subject to income tax, even for those over 59 ½ [8] - Unlike conversions, this contribution rule only needs to be satisfied once [8]