Reactions of ozone with ethenes through the 1,3-dipolar cycloaddition (Criegee) mechanism are furthermore prototypical for reactions of electron-rich olefins and aromatic compounds in treated waters and their kinetics and mechanisms are well-documented with experimental data. Moreover, ozone has biradical and thus multireference character and its computational identification and optimization of molecular structures and predicting the reaction energies may not be accurate with fast DFT methods, as illustrated in studies of the Criegee mechanism. Instead, single-reference coupled cluster methods are recommended, though they can be challenging to use given the large number of molecular structures in CRNs. The specific objectives of this study were threefold. (i) We identified the optimal computational methodology for automated CRN explorations with the Chemoton software 29 through systematic evaluation of the Criegee mechanism for ozone and ethene against benchmark studies of Wheeler et al. (ii) We tested the predictive capabilities of automated CRN explorations by investigating two model reactions of ozone with ethene and tetramethylethene, respectively. These processes were selected as benchmarks because they both proceed through the Criegee mechanism but generate different stable products under identical experimental conditions. Here, we performed the CRN evaluation with methods identified in specific objective (i) and evaluated their utility for future automated CRN explorations involving ozone and organic compounds. (iii) Finally, we analysed the outcome for the lowest energy path reaction mechanism between the reactants and the experimentally observed products with Pathfinder 32 as well as through microkinetic modeling.