We hereby report a remarkable mechanism by which stereoisomeric and twisted capsules P/M-1 direct their dynamic chirality in the presence of haloalkane guests. The capsule comprises a static, but twisted, cage that is linked to a dynamic tris(2-pyridylmethyl)amine (TPA) lid at its top. From the results of experimental (NMR spectroscopy and X-Ray crystallography) and computational (DFT) studies, the TPA lid was shown to assume clockwise (+) and counterclockwise (-) folds with diastereomeric (but racemic) capsules M-1(+) and M-1(-) interconverting at a rapid rate (ΔG‡189K = 9.1 kcal/mol). Larger guests, such as CCl4 (89 Å3) and CBr4 (108 Å3), however, formed M-1(-)⊂CX4 at the expense of M-1(+)⊂CX4 in circa 3:1 ratio. To account for the observation, we used theory and experiment (1H NMR spectroscopy) to deduce that CX4 guests become localized inside the twisted cage of the capsule by forming a C-X···π halogen bond (Nc = d / (rH + rX) = 0.91-0.92) with the benzene "floor" while encountering electrostatic repulsions with closer naphthalimide boundaries. At last, the TPA lid used its central methylene hydrogens to, within the M-1(-)⊂CX4, establish three stabilizing C-H···X-C interactions with the guest. The same C-H···X-C interactions, however, became weaker (or possibly vanished) after the conformational reorganization of the lid and the formation of less stable M-1(+)⊂CX4 complex.