The second five-year rule relates specifically to Roth conversions and whether an early withdrawal of converted principal will be taxed. In effect, the rule only applies if you take a distribution before you turn 59 ½.If you are at least 59 ½ years old but have not met the five-year rule requirement, then you will pay income taxes on any earnings that are withdrawn. Since contributions to Roth IRAs are made with after-tax dollars, you can always withdraw the value of your contributions free of taxes and pen ...