The first iteration of the workflow accomplished one of our two initial goals, i.e., it identified which biaryl aldehyde (10j) would lead to assemblies with large enough CD signals to accurately determine the ee of both 11a and 11b. To our knowledge, this is the first chiroptical sensor that can assess a stereocenter so remote to the binding functional group. However, the second primary goal, to deconvolute the NCIs that underpin a successful sensor, was not yet realized. The model depicted in Figure is statistically sound, but the descriptor terms do not give clear insight into the NCIs that determine the magnitude of the CD signal. For instance, it is challenging to understand the physical significance of the NBO charge on the ipso carbon (NBOipso, highlighted with a green sphere). Furthermore, the need to classify two aldehydes that incorporate an ortho-substituted A-ring (only 10j and 10k) reduces the utility of the statistical modelling approach.