The major challenge that was encountered involved the formation of a gel-like reaction mixture upon completion of the 1,2-rearrangement. This resulted in significant loss of material during the automated filtration to remove the lithium benzoate (LiOTIB) by-product. Fortunately, the issue could be resolved by concentration of the crude reaction mixture and redissolution in 1,2-dichloroethane (DCE), which provided a homogenous mixture that could be easily handled by the robot. With this modification incorporated into our workflow, the homologation of boronic ester 1 with 4-Li proceeded with high efficiency on the automated platform, producing product 5 in high yield (92%, average of four parallel reactions) and 99:1 enantiomeric ratio (e.r.). Furthermore, this automated homologation reaction could be performed iteratively, furnishing product 6 in 86% overall yield, in 99:1 diastereomeric ratio (d.r.), and with high reproducibility.