qbteachmt
Level 15
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"Both taxpayer and spouse are under age 59 1/2."

Which means they might have nontaxable and/or no penalty distributions, if the distributions meet specific reasons or amounts. Or, for a specified purpose, such as home purchase provisions. And, the five-year rule. And any conversion timing considerations. Otherwise, the earnings would be taxable, but not their own basis. I don't see where you addressed that the distributions were the full balances of the accounts. As I pointed out, this is typical: "It appears that his contributions over the years is greater than that distribution." If the entire account balance doesn't reach his basis, then he lost money, which means there are no earnings to tax. What about conversions?

"As the provision relates to conversions, each conversion has its own five year period of time that begins with Jan. 1 of the year in which you made the conversion. If you do end up taking money before the five years is complete, the IRS treats the order of withdrawals for Roth IRAs to starts with contributions, followed by conversions and then earnings."

The phrase you are trying to confirm is "qualified distribution."

I would start with the steps provided here:

https://www.irs.gov/help/ita/is-the-distribution-from-my-roth-account-taxable

And the Retirement/IRA/1099-R worksheet in the software should walk you through most of what you asked.

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