The reduction ofcis-2,6-dimethylcyclohexanone with NaBH4in methanol is shown to produce predominantly the axial alcohol, an unexpected result based upon prior reports and current paradigms for similar cyclohexanone reductions. This finding prompted a careful and systematic investigation of the NaBH4and LiAlH4reductions ofcis- andtrans-2,6-dimethylcyclohexanones in various solvents, with additional results contrary to literature reports. Possible explanations for these discrepancies are given, an unusual solvent effect is noted, the rate of epimerization versus reduction is examined, molecular modeling results are reported, and an important caveat is offered for future stereochemical studies of this nature.Key words: cyclic ketone reduction, stereochemistry, molecular modeling.