In this work, the Outlet Stream Swing (OSS) non-conventional operation technique is compared with a classical Simulated Moving Bed (SMB) unit, for the separation of a racemic mixture of guaifenesin. A methodic approach, based on the complete separation and regeneration regions, is used to evaluate the performance of the OSS extract-raffinate, as well as the OSS raffinate-extract, operating strategies with the classical SMB in terms of purity, productivity and eluent consumption requirements. The variants of the OSS technique: OSS extract-0 and OSS raffinate-0 are presented, simulated, and used not only to introduce more simplistic OSS modes of operation, but also to better understand the influence of specific OSS operating parameters. The experimental validation of OSS extract-0, operated by means of the FlexSMB-LSRE (R) unit, is also presented as part of this work, demonstrating the potential, as limitations, of such operating techniques.