I have my 1099R (official).  Wondering why the value I entered into Turbotax wasn't automatically entered when I was asked the question above.  Thank you!

The reason is that Box 5 can contain Employee contributions /Designated Roth contributions or insurance premiums, so Turbotax wants to know whether it was insurance premiums or not. If you are not sure, call your provider and ask what the Box 5 amount is for, don't guess.

Great.  Makes sense now.  Thanks a lot!

I retired effective March 1st, 2016.  Is it possible health insurance premium payments from my salary during Jan/Feb would also be listed in Box 5 of the 1099R?  Or would those payments be reflected on my W-2?

You will need to ask your employer that question.

Ok thanks again.