An amount for Medical Insurance or Employee Contributions can show in Box 5 on your 1099-R.
Since this amount may or may not be for Medical Insurance, it doesn't automatically go to Medical Expenses.
if it is for Medical Insurance in your case, you can enter the amount under Medical Expenses, in the Deductions and Credits section.
Here's more info:
https://ttlc.intuit.com/replies/6052375
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