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Thank you for the thorough and thoughtful information. 

 

W-2 shows DD in box 12 (employer's contribution).  Box 14 shows - "pretax" and the dollar amount. Clarification was made with HR that this info in box 14 is the "sum of your medical, dental, and vision payments".  So unfortunately, not the no-brainer. 

There is no domestic partner in my scenario.  

 

What initiated my confusion is that TurboTax was forcing me to enter a "category" for this item when completing the W2.  That is how I discovered the link to IRC 125.  If I select the "NY IRC 125/sec 18 subject to NY tax" it generates the NY IT225 form and codes it under A-101 (New York City flexible benefits program).  If I select the "NY IRC 125/sec 18 NY tax exempt", then the IT 225 is not generated.