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Personal Finance (Not Investing) • Roth 401(k) rollover resets 5-year rule

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I have a question for the posters in this thread.
In my last job I was able to contribute to after tax 401k and then immediately roll over into a In-Plan Roth account (mega backdoor Roth). I did that every year between 2016 and 2021. I have a separate Roth IRA account R1 that was funded entirely with conversions from non deductible annual traditional IRA contributions (backdoor Roth). That Roth IRA was opened in 2014 and conversions were done form traditional IRA from 2014 until 2021.
  • If I want roll over the entire balance of the 401k In-plan Roth account in my 401k into a new Roth IRA account R2, what will the distribution and withdrawal rules be for that new Roth IRA?
  • Will it be any different if decide to roll over from 401k In-plan Roth account into the existing Roth IRA R1?
I am now 58 years old and retired at 55.
It will be very simple if you can delay any Roth IRA distributions until you reach 59.5 because your Roth IRAs will then be qualified and completely tax and penalty free. In addition you will no longer have to complete Form 8606 to report distributions and will no longer have to track your Roth IRA contribution and conversion basis.

Not as simple as the above, but if you can delay any Roth IRA distributions until 1/1/2026, all your IRRs and conversions including the final ones in 2021 will have completed their 5 year aging with respect to the 10% penalty on the taxable portions of those conversions. This will eliminate having to deal with a nasty Appendix C in Pub 590 B to determine this small penalty. Even though you never made any regular Roth IRA contributions or Roth 401k elective deferrals, these converted amounts can all be distributed tax and penalty free from your Roth IRA. But any gains (which is the amount in excess of your conversion basis) will come out last and will still be taxable and subject to penalty up to the day you reach 59.5. You will still have to file the 8606.

As retiredjg indicated, when you do the Roth 401k direct rollover to your Roth IRA, there is no tax related reason to create a new Roth IRA. Just roll into your existing Roth IRA.

Statistics: Posted by Alan S. — Sun Sep 07, 2025 11:16 am — Replies 21 — Views 2808



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