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At this point my question might be obvious, but... if I roll my Rollover IRA into my 401K, could I then - in the same calendar year - contribute to a Non-deductible IRA and convert it tax free to a Roth IRA? Or would I have to wait until the following calendar year?

I believe - looking at form 8606, that the answer would be yes - but before I go forward with something like that, I wanted to see if anyone on here had a different opinion or any words of warning.

I read it the same way you do.

P.S. I don't think it will make a difference, but my Rollover IRA to 401K conversion looks like it would have to happen via check & not direct (my current 401k custodian looks like they don't support direct trustee-to-trustee transfers).

That's not a problem. Unlike 401(k)'s, withholding from IRA distributions is not mandatory. Just make sure you specify no withholding.

Rule Your Retirement Home Fool
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