Headphone Connections and Output Modes

^ All that makes sense. However, when I play ALAC content to my MacBook Pro, set to Built-in Output in Exclusive Mode, Roon shows a lossless signal path, with or without headphones wired into the MBP’s headphone jack. Is this an error? Or is it just not characterizing the complete signal path?

When I play ALAC content to my MacBook Pro, set to System Output, Roon shows a “high quality” signal path (with a green light at the Output stage.) Isn’t this what I also should expect to see with wired headphones while in Built-in Output in Exclusive Mode?