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Does he have money to pay the IRS penalties for taking money out of the IRA before he's 59 1/2? If not, that needs to be his first priority from a money perspective - he needs to have the money to pay the IRS before April 15.

Since the amount owed will be small, if necessary he can arrange a payment plan with the IRS. Their interest rates are reasonable, and they must accept payment plans for amounts under $10,000.

I thought you could withdraw your contributions to a Roth IRA anytime? It's just any earnings that have to wait until 59 1/2.

Contributions can be withdrawn at any time. Roll-overs require aging. It depends on the history of the funds in the ROTH IRA.
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