How do I determine the five-year minimum holding period for my Roth IRA contributions?
The five-year holding period begins on January 1 of the year for which your first Roth IRA contribution was made or in which your first Roth IRA conversion was completed, whichever is earlier. So if you opened your first Roth IRA on April 15, 1999, with a contribution for tax year 1998, you will have met the five-year minimum on January 1, 2003. For the sake of this requirement, the IRS treats all your Roth IRAs as one. Once your first Roth account has met this requirement (and you’ve reached age 59½), then you can make tax-free withdrawals from any of your Roth IRAs.