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Lets say I contributed $18,000 to my 401(k) this year, and my employer matched 50%, so I have a total of $27,000 contributed this year. This money I invested and made $1000, so now I have $28,000. At this point, however, I realized I originally wanted to contribute to my Roth 401(k) and not my 401(k). Is there a way to "roll over" this contribution so I pay taxes on the $27,000, or would I have to pay taxes on the $28,000?

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This is called an in-plan Roth conversion and is discussed by the IRS here. If your 401(k) has a Roth option then it likely also has a provision to convert pre-tax dollars, but you'll have to check with the administrator to be sure. They could also potentially limit the type of money that can be converted. But most likely you should be able to convert any amount you want, and since it's all pre-tax (your contributions, employer matching, and earnings), it doesn't really matter which money is converted because it's all equivalent. One caveat is you won't able to convert any employer matching that hasn't fully vested.

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    I don't believe that employer match contributions can be rolled over into the Roth part of a 401(k) plan. Employer match is a pretax contribution and stays in the tax-deferred part of the 401(k); ditto the earnings on the employer match. Commented Mar 5, 2017 at 22:13
  • @DilipSarwate I think the IRS says this is allowed here.
    – Craig W
    Commented Mar 5, 2017 at 22:14
  • @CraigW - nice citation, would you mind adding it into the answer? My inclination is to clean up comments,but that link is great. Commented Mar 5, 2017 at 22:17
  • You are correct, but the operative words are "The plan can allow..." and "The plan can specify which of these amounts are eligible for in-plan Roth rollovers and how often these rollovers can be done." and so it is entirely possible that the OP's plan might either not allow such rollovers at all, or permit in-plan rollovers for employee contributions but not for employer match, etc. Commented Mar 5, 2017 at 22:22
  • @DilipSarwate I clarified that the employer/administrator could potentially limit what types of money can be converted.
    – Craig W
    Commented Mar 5, 2017 at 23:02

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