I too have encountered this "hiccup" in TT 2021.
I have tried entering the payment from my former employer as a 1099-NEC entry and as a 1099-MISC entry. Neither works, and I end up having TT steer me towards treatment as a self-employed individual with all the accompanying complexities.
Searching through IRS documents also fails to provide any answers to this issue.
At this point, I may just have to ignore the whole issue and wait for IRS to audit me. Only then may I have the issue addressed and resolved!
In the mean time, one thing appears to be clear, and that is that employer payments to an employee for medical insurance premiums for insurance privately obtained by that employee are NOT considered as taxable income! So, does that also apply to retired employees?
Someone appears to have dropped the ball pin this issue at TT and/or IRS!
