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Retirement tax questions
It depends. You said at the beginning of your question that the 1099-R was for your "post-tax" employee contribution". If they are post tax, then you should answer Yes. As the program mentions "This is not common." It usually only occurs when someone is making the maximum pre-tax salary deferral ($23,000 if you are under 50). This means you are paying tax on those contributions. It's similar to making a non-deductible contribution to a traditional IRA. The earnings are tax deferred, and the principal (the amount you contributed) is not taxable when it is withdrawn. In addition, The principal is eligible to to be rolled over to a Roth IRA.
If you rolled over funds from your 401(k) that were pre-tax salary deferrals, you will answer no.
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