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Retirement tax questions

You can include your Medicare premiums that you paid as health insurance premiums under medical expenses, or under self-employed health insurance, if you have self-employment income. 


The amount listed on your SSA-1099 automatically goes to medical expenses, so make sure you aren't duplicating anything first. 


  1. Use the search box toward the upper right corner to search for Medical expenses. 
  2. Next, click on Jump to medical expenses.
  3. The first question will say, Did you spend more than $XXXX on medical expenses in 2019?
  4. The figure quoted there is 7.5% of your AGI. That amount will be deducted from your total out of pocket medical expenses. 

If you think you have enough to make a difference, go ahead and add the information about your expenses.

There are other deductions that can be taken in this section too, such dental and optical insurance, eye exams, hearing aids, prescriptions, co-pays, etc.


You only get a benefit from itemizing if your total of itemized deductions is more than your standard deduction for your filing status. 

For instance if you are married, and file jointly, your standard deduction for 2019 is $24,400. To save money by itemizing your deductions, your deductions need to add up to more than $24,400. The standard deduction is even higher if you are over 65.


If you have self-employment income, you can claim the amount you paid as self-employed health insurance coverage.

  1. Login and continue your return.
  2. Select Federal on the left side menu.
  3. Find, Self-employment income and expenses, select Edit/ Add on the right.
  4. Select Edit to the right of your ride sharing business.
  5. Scroll down and select, Add expenses for this work.
  6. Find Health insurance premiums, select the circle to the left.
  7. Scroll to the bottom and select Continue.
  8. Enter the amount you paid for your health insurance. 


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