I have received different answers regarding how the five year holding period works when taking distributions from a Roth IRA. In this instance the client is well past the 59 1/2 requirement. He wants to contribution to a Roth by converting his IRA to a Roth, however, the taxation on the conversion is such that he would like to stage his contributions. For this example let’s say he has a $100,000 Traditional IRA and would like to convert (and pay the resulting taxes) over five years. The first year 20,000 would be converted to the Roth, second year 20,000 ….and so on.

So for the purposes of distributions is the five year Qualified Distribution period beginning with the initial tax year deposit or does it start with each subsequent contribution?

Here is something I found online (does this apply?):

“Notably, under Treasury Regulation 1.408A-6, Q&A-2, for the purposes of this 5-year rule the clock starts the first time any money is funded into any Roth IRA, whether by contribution or conversion. There is not a new 5-year clock for each Roth contribution, nor for each Roth account that is held. All Roth IRAs (but not Roth 401(k)s) are aggregated together to determine whether the 5-year rule is met for any/all of them (which indirectly means that rollovers from one Roth IRA to another do not change or reset the 5-year requirement). In the case of rollovers from a Roth 401(k), any years in the Roth 401(k) are not added to the years for the Roth IRA; thus, if the individual did not otherwise have a Roth IRA already, the rollover from a Roth 401(k) begins a new 5-year period, even if the Roth 401(k) itself had already satisfied the 5-year requirement (per Treasury Regulation 1.408A-10, Q&A-4(a)).