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Can I convert $50,0000 (to match the post tax contributions) to the Roth IRA without creating a taxable event? Since this amount was from post tax dollars it seems there would be no new tax due on this amount. Or is there a proration calculation or something else involved?

As Bill already pointed out, under current law, you must pro-rate the conversion. And if the House version of the Build Back Better plan isn't changed and it passes (2 very large ifs, I know), after Jan 1, 2022, you actually won't be able to do conversions of those after-tax amounts at all - only pre-tax amounts.

I will point out for anyone who has after-tax contributions in an IRA, wants to convert them, and is still employed at a company with an employer plan that accepts roll-ins from an IRA, you do have a short window of opportunity before 2022 to segregate the after-tax contribution amounts from the pre-tax amounts by rolling over all pre-tax funds in your IRA(s) into your employer's plan. Employer plans aren't allowed to accept the after-tax contributions, so those will remain in the IRA. At that point, your entire IRA balance will be after-tax, and under the current law, you can convert the entire amount to a Roth IRA without paying any additional taxes.

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