Can I deduct health insurance premiums taken from my pension check?

[sampena1]

I don't have any Federal Income tax withheld from my monthly pension check, but I did pay $4,138.32 for medical insurance this year (deducted from my check).  Why do I have to pay taxes on that portion of my income?

[ehbono]

On my 1099R what does the amount in box 5 mean?

[WillK · Accepted solution]

You can deduct your health insurance premiums as long as they are paid with after-tax dollars. If you pay for your health insurance premiums with pre-tax dollars then you cannot deduct the premiums.