How do you correctly report RETIRED PUBLIC SAFETY OFFICERS after tax health insurance to get the $3,000 deduction?

[dag999]

If the box on the 1099R is not checked...and the amounts not accounted for, won't the IRS catch it as an error, especially if you add or change it?  Plus, if the box 2a already has an amount -- but you leave it blank, won't they see something is wrong?  The same thing goes for box 2b if it's blank on the 1099R.

[IsabellaG]

First of all, don't change anything about your 1099-R. Report it as it appears to you, because that's what the IRS will receive. Don't leave anything blank if there's an entry on your 1099-R.

• After you enter your 1099-R, you'll continue in TurboTax, and check that you were a Public Safety Officer. 
• On the screen Did the Pension Administrator Pay for Health Insurance? answer yes, if that's true.
• On the next screen, enter the amount taken out of your pension to pay for health insurance.

That's it. TurboTax will calculate the amount of your exclusion, which is the lesser of $3000 or your actual payments for medical insurance. It will show up on your return, Form 1040, on line 16b as a reduction in your taxable pension, with PSO notated next to line 16a for Public Safety Officer.

[NielES]

Does it matter if the amount came out after taxes?

[BillM223]

Having an entry in boxes 2a or 4 does not mean that the premium was paid before or after tax. Box 4 is just withholding for tax on whatever the taxable income is going to be.

Just enter the 1099-R as is.

Then check Isabella's answer above (except that for tax year 2019, the pension lines were moved to 4a and 4b on the 1040).

[NielES]

I see how to enter it, what I'm wondering is if it matters that the health insurance payment came out of my pay after my pay had been taxed. Does the health insurance payment need to be pre tax?

[MaryK4]

No, the health insurance does not need to be pre-tax, but it seems there would be less benefit. @NielES