Can I roll over my Roth 401K to a Roth IRA and then withdraw my contributions with no penalty? I know it’s not recommended, but have extenuating circumstances

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The first point is whether you can roll your 401k into an IRA. Most plans won’t let you while you are still employed at the company with the 401k. I believe you could take the 401k contributions out immediately if you have held the Roth IRA for 5 years or more.

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You can withdraw contributions anytime, penalty free. However, you you need to wait 5 years to withdraw conversions to avoid the penalty. I think the Roth 401k to Roth IRA may count as a conversion, but I'm not sure.

Take a look here and see if this answers your question: https://www.investopedia.com/articles/retirement/09/roth-401k-rollover.asp

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