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You must be 59 ½ and have held your Roth IRA for at least five years before you withdraw investment earnings tax-free and penalty-free. You can withdraw your Roth IRA contributions at any age because you've already paid taxes on that money.
All Roth withdrawals are considered to be from contributions first, conversions second, and earnings last. You must have your own accurate records as to how much you have contributed in the past, and how much you have withdrawn in the past. The IRA custodian may be able to help you figure this out, but they can't provide the IRS a definitive answer, for various reasons. You will get a 1099-R and report the withdrawal on your tax return, Turbotax will ask you about your prior contributions and your prior withdrawals.
Withdrawal of contributions is always tax-free.
Withdrawal of conversions is not subject to income tax, but is subject to a 10% penalty if the conversion was less than 5 years ago and you are under age 59-1/2.
Withdrawal of earnings is subject to income tax unless you are over age 59-1/2 and it has been at least 5 years since you opened your first Roth IRA. Withdrawal of earnings is also subject to a 10% penalty if you are under age 59-1/2.
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