Yes, if you are paying out of pocket for supplemental health insurance (assume in addition to Medicare?) then those premiums can be entered as medical expenses.
The medical expense deduction has to meet a rather large threshold before it can affect your return. The amount of medical expenses that will count toward itemization for someone under 65 is the amount that is OVER 10% of your adjusted gross income; for someone 65 or older it would be the amount over 7.5% of your AGI.
You should only enter the amount that you paid in 2016—do not include any amounts that were covered by insurance or that are still outstanding. Of course, your medical expenses plus your other itemized deductions still have to exceed your standard deduction before you will see a difference in your tax due or refund.
To enter your medical expenses go to Federal>Deductions and Credits>Medical>Medical Expenses
We have Medishare and supplemental insurance through Surbridge/Chesapeake Life Insurance (additional Hospital, Accident Companion and cancer coverage). We are NOT on Medicare. I understand that the Medishare premiums are not deductible as medical expenses but are the supplemental insurance premiums ? Thanks.