@heybrian1 wrote:
I think it would be a bad idea for me to deselect the IRA/SEP/SIMPLE box on my own in TT as it would not match the 1099-R my 401k administrator sent to the IRS. Yet deselecting the box is the only way forward with the TT software. There must be a work around in "forms" right?
I do not think that TT is sending the IRS a 1099-R based on what you type in.
Rather it is using the information you type in (and your answers to its questions) to determinate what numbers to put on 1040 line 5a and 5b and perhaps a few other places. (E.g. Form 8606).
What really matters is that the correct amounts appear on 1040 line 5a/5b.
If the IRS does question you, then you just show them your records. Keep your forms requesting the direct rollover, keep the statements showing it leaving the 401k and arriving in the IRA. Writing a letter and showing them the documentation will likely solve the matter. Might take a long time, but should make it right. What's in the 1099s are information to the IRS. So they can find non-reporters or incorrect reporters. But they can be wrong or incomplete. You can only be taxed on your actual income. The burden of proof is certainly on you if the 1099 is wrong I wouldn't worry too much about this if you retain easy proof of the direct rollover.
Of course I could easily be wrong here. And if you are in doubt it is always a good idea to consult with a a CPA, enrolled agent, or tax attorney, who does this for a living, has malpractice insurance, etc.
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