Research examining the impact of water and mineral matter on the thermal conversion of crude oil has indicated that retaining these components during treatment affects cracking, hydrogen transfer, and addition reactions. However, the complex nature of a reaction medium containing crude oil poses a challenge in relating the influence of water and minerals to particular reaction pathways. To enhance understanding of the specific contributions of water and minerals to reaction chemistry during thermal conversion, a practical approach is to make use of simpler model systems to capture relevant information for petroleum processing. The current study explored the impact of water and kaolinite on the reaction rates and pathways during the thermal conversion of a model system comprising αmethylstyrene (AMS), tetralin, and n-pentadecane at 400 °C for 1, 5, 10, and 30 min. The effect of kaolinite at different concentrations was also compared to that of rutile and quartz during the conversion of AMS alone. Water and kaolinite, individually and collectively, affected the reaction rates. Water suppressed the AMS conversion rates, but no evidence was found that water affected reaction pathways. Kaolinite increased the conversion rates of both AMS and tetralin, while also enhancing the formation rates of cumene and naphthalene. This suggested that kaolinite somehow favored hydrogen transfer during the treatment. The presence of kaolinite also increased the formation rates of benzene by dealkylation and the tricyclic AMS dimer 1,1,3-trimethyl-3-phenyl indane, indicating that kaolinite was catalytically active, influencing reaction pathways by promoting cationic conversion. The adsorption of water on the surface of kaolinite appeared to contribute to reduced reaction rates when reacting AMS in the presence of both water and kaolinite. The deposition of carbonaceous material on kaolinite suggested that the mineral is rapidly fouled during the conversion.