Do I check "paid family leave" for uncommon situations question on my employers W2 if I received a separate W2 from the insurance company (hartford) who actually paid me?

No, you would not check "paid family leave" when entering the W-2 from your employer.

Thank you David for answering! I had this same question with the same insurance provider and wanted to confirm.  It was a W-9. Thank you, Great Day!