The chiral recognition mechanism for a derivatized polysaccharide chiral stationary phase (CSP) under reversed phase conditions was investigated (Chiralcel OJ-R). While enantiorecognition mechanisms have been proposed for these types of phases under normal phase conditions, it is unlikely that they would apply to reversed phase conditions due to the high polarity of the eluent. Indandiol was utilized as the main probe. The effect of organic modifier, eluent anion, and temperature on enantioselectivity for indandiol was determined. Additionally, a number of structurally related probes were also investigated to define the role of various functional groups on enantioselectivity.