Yes, the holding period is measured from the year of your first Roth IRA contribution of any kind. Earnings become tax free when you reach 59.5 AND you first contributed to the Roth 5 years previously. Note that there is another 5 year holding period for conversions or rollovers from a qualified plan. This conversion 5 year holding period relates to the 10% penalty if you withdraw the conversion before 5 years, but only applies to the taxable portion of the conversion. For example, if you do a direct rollover from the after tax 401k sub account and this account balance consisted of 10k of after tax contributions and 1k of earnings on those contribution, then if you were to withdraw this rollover from your Roth IRA before 5 years, you would owe the 10% penalty on the pre tax portion of 1k. The pre taxc portion is treated as being the first dollars distributed if you withdraw any portion of a specific conversion.

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