You can enter your insurance premiums in box 5 only if they are listed there on the actual form 1099-R. The form must be entered into the program exactly as it appears.
However, you can enter your insurance premiums as medical expenses if they are paid with post-tax dollars:
- Federal Taxes
- Deductions and Credits
- Scroll down to Medical, select Medical Expenses, enter the total amount for all medical insurance premiums that you paid