As with all separations, enantioselective chromatography can span the gamut from straightforward to highly challenging. Such separations can involve analytical and/or preparative procedures, high throughput or fast separations, complex matrices, unknown synthetic impurities, etc. Often an SFC approach may be preferable for prep but an analytical reversed phase HPLC method is wanted for reaction/product monitoring/quality control. Over the years we have dealt with numerous such situations some of which needed interesting or unusual approaches which we hope will become routine in the future. A selection of examples will be given which will involve HPLC, SFC, chiral detection and data proces...