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It depends. If reported on your 1099-R, your insurance premiums will be reported in box 5. This must be entered manually on Schedule A. To deduct medical expenses, you must have expenses at least 10% of your AGI unless you are over 65, which is still 7 1/2%. However, you also must be itemizing deductions to see the benefit on your return. This website linked to the IRS provides additional information: 1099-R Pension and Annuity Income - IRS.gov (see the box 5 information in the blurb).
Some states do allow for a health insurance deduction. If your state does, you may see a benefit on your state taxes even though you may not on the federal return.
The TurboTax page listing medical deductions, "your 2019 Deductions and Credits", has an amount for 2019 medical expenses that does not include the health insurance premiums indicated on my Federal (OPM) annuity1099-R, Box 5. On the TurboTax pages that asks, "How much did you spend on insurance premiums" Learn More link says, "If you have any of the below forms, enter then in Wages & Income. We'll include the deduction for you payment there". One of the listed forms is "Health insurance payments paid through your government annuity (Form CSA-1099-R)". Despite the wording of the above quotation, should I add the insurance payments, manually, in the box on the "How Much Did You Spend on Insurance Premiums" page?
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