It seems to be based on how much money I have *ever* taken out of any traditional IRA, vs the amount that I have ever paid MA tax on? And what does it mean to have paid MA tax when I'm making nondeductible contributions -- it's just arbitrary money at that point. Does it depend if I paid MA tax that year/lived in MA/filed an MA tax return? Do I basically have to pay tax up to the amount that I've ever contributed out of state? On the other hand, (https://www.mass.gov/info-details/tax-treatment-of-non-government-pensions-in-massachusetts) refers to "Any taxable parts of rollovers included in federal gross income", and my conversion doesn't seem like it would count as federal gross income. Extra confusingly, Turbotax erroneously claims it is federally taxable when it prompts me to fill the MA form, but doesn't show any income on my federal return.
If your history of non-deductible contributions is not carried on your Form(s) 8606 (required) , your distributions and conversions wll be taxable events.
It is carried on my 8606, so that in Turbtax the federal gain is listed as 0 -- except when I'm filling out my Massachusetts form, where it says "[Name]'s federally taxable IRA/Keogh plan distributions received during 2024 are [Amount of the conversion]".
You will have to manually adjust this amount on the Massachusetts return. Massachusetts follows the same rules for taxable rollovers as the federal government does so you just need to go through the Massachusetts return and adjust the taxable amount of the rollover to zero to match the federal amount. Massachusetts gets a copy of the federal return when you file so it will recognize the correct amount as long as you enter it.
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How long have you been doing that.?
if you did a tax-free Roth Conversion your IRA is not growing.
You need a better investment approach for your IRAs - Traditional or Roth.