Chiroptical properties are of interest for various applications, including structure determination, polarized photodetectors, and spintronics. Inducing chiroptical activity into semiconductors is challenging because of difficulties in creating asymmetric crystal structures. One promising method is to use chirality transfer by deploying chiral organic molecules as capping ligands for nanocrystals. Experimentally, chiral-capped nanocrystals show emergent chiroptical signatures, but the mechanisms for chirality transfer remain unclear. Here we utilize atomistic modeling using time-dependent density functional theory calculations to explore chirality transfer in CsPbX3 (X = Cl, I) clusters capped with chiral diaminocyclohexane (DACH) enantiomers. When DACH enantiomers are bound to the cluster surface, the perovskite optical transitions gain chiral signatures. This observed chirality transfer is best rationalized by chiral molecular dipole-cluster transition dipole coupling. With multiple DACH molecules bound to the cluster surface, anisotropy factors are found to increase proportionally to the surface ligand density, providing mechanistic insight toward improving chiroptical functionality in semiconductor nanomaterials.