The assumption that only biological processes are enantioselective introduces challenges in the reliability of enantioselective analysis as a tool for discriminating biotic and abiotic processes in the environmental fate of chiral pollutants. Enantioselectivity does not depend on the nature of the fate process a chiral contaminant undergoes but on the interaction of the chiral contaminant with homochirality inducing external agents (e.g. chiral molecules, macromolecules or surfaces such as enzymes, blood plasma, proteins, chiral co-pollutants, humic acid and soil organominerals). The environmental behavior of a chiral contaminant is difficult to anticipate because the interactions between the chiral contaminants and the homochirality inducing external agents is often complex and strongly influenced by local environment conditions such as pH, redox conditions, organic carbon, organic nitrogen, humic acid, and redox conditions. Furthermore, the use of enantioselective analysis in environmental forensics depend on the adequate separation and accurate identification and quantification of the enantiomers of the chiral contaminant. Matrix effects, instrument effects, inadequate enantioselective separation, and poor quantification techniques introduce uncertainties in the determination of enantiomeric composition. Here we present the weaknesses of this assumption and recommend using enantiomeric fractions as chemical markers of biotransformation with caution. We recommend using stable isotopes, including abiotic controls to determine if enantioselective sorption occurs, and determining stability of enantiomers in solvent or at elevated temperatures to account for confounding factors arising from matrix effects, enantioselective abiotic processes, and enantiomerization due solvent and thermal lability of the chiral analyte, respectively to maintain the integrity of the utility of enantiomeric composition changes as an environmental forensics tool.