We report on a study of mixtures of octylcyanobiphenyl (8CB) and equal amounts of two chiral agents (CE2 and CB15) as a function of chiral pitch (concentration). Bulk studies reveal a widening cholesteric temperature range with increasing chirality. The first order cholesteric-isotropic (Ch-I) transition shifts marginally to lower temperature with increasing chirality while exhibiting a pretransition feature near its C-p maximum. The smectic-A-cholesteric (SmA-Ch) C-p anomaly becomes smaller and continuously shifts to lower temperatures with increasing chirality while exhibiting the unique feature of a discontinuous jump on the low temperature side of the C-p peak. The increased chirality suppresses the smectic formation through twist elastic distortion. Upon Anopore confinement, the C-p maximum of the Ch-I transition increases as compared to bulk with the disappearance of the pre-transition feature; the SmA-Ch transition becomes extremely rounded and suppressed. The transitions shift to lower temperatures while retaining the bulk cholesteric temperature range.