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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.

Yes, contributions can be withdrawn at any time, so if only contributions were withdrawn, there would be no penalty owed. However, the original post said "spending his.....Roth IRA" which indicated to me that the entire account was spent, including any earnings.

Additionally, if there were losses in the Roth IRA, rather than earnings, and the entire amount was withdrawn, the OP's son could actually have a potential deduction.

And if he doesn't have money to pay the IRS on 4/15, he still needs to file a tax return showing what he owes. Any payment plan set up that way will be far more lenient than failing to file his tax return on time (or file an extension).

Yes, although he would still be subject to additional penalties and interest if he fails to pay by 4/15.

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