This article describes the chirality sensing systems based on changes in conformation of dynamic terephthalamide hosts from a nonhelical form to a helical form with biasing to prefer one handedness upon complexation with a chiral guest through supramolecular transmission of chirality. The syn form is endowed with the ability to capture a ditopic guest through hydrogen bonds at the amide carbonyls; thus in a complexed state, a strong CD signal is produced thanks to a helical conformation induced by the conformational change and a biased handedness. Attachment of chirality to the terephthalamide host itself leads to an intrinsic preference in the sense of dynamic helicity in a helical syn form. Cooperative transmission of chiralities within the host and from the guest enables to further design an advanced sensing system with stereospecific chiroptical modulation, based on a stereospecific change in conformation of the chiral dynamic host upon complexation with a pair of enantiomeric guests.