Can i reduce my taxable pension by cost of the medical insurance being deducted from my paychecks?

[thatguyasking]

Why don't the pension payors adjust the Box 2a taxable income to $3000 less (the maximum you can take off even if you pay $4500 in medical/dental insurance from your pension)

[AnnetteB6]

Even though that seems like a logical thing to do, the number that is reported in box 2a is more complicated.  

Often box 2a is left blank for a reason.  If it is blank, additional calculations are needed in the tax return to determine what portion of box 1 is taxable.  So, it wouldn't be a good idea do adjust box 2a for the insurance premium payment made for a retired public safety officer.  Also, the financial institution issuing the Form 1099-R may not have the information that the payment is being made to a retired public safety officer.  

Therefore, the amount in box 2a and the amount paid for insurance premiums paid for a retired public safety officer must be handled separately.

@thatguyasking 

[rhsol]

This response applies to (firefighters) safety officers who pay health care premiums directly from their retirement annuity.  The provisions of the 2006 Pension Protection Act allow retired public safety officers up to a maximum of $3,000 in health care premiums paid directly from qualified retirement accounts as reduction to taxable retirement income.   The question I have is where this is reported.  I spoke with a TurboTax representative and he informed me that, when entering the 1099R data, I should not change any of the data reported on the form.  He said there are additional questions that TurboTax will ask regarding the amount reported in box 5 of the 1099R.  I am in the process of preparing a return and will provide an update on this response when I complete the return.  Hope this helps.