Premature failures in chemically stabilized expansive soils cause millions of dollars in maintenance and repair costs. One of the reasons for these failures is the inability of existing stabilization design guidelines to consider the complex interactions between clay minerals and the stabilizers. It is vital to understand these complex interactions, as they are responsible for the strength improvement and swell/shrink reduction in these soils, in turn affecting the overall health of the infrastructure. Hence, this research study examined the longevity of chemically stabilized expansive soils subjected to wetting/drying conditions with a major focus on clay mineralogy. Eight different natural soils with varying clay mineralogy were subjected to wetting/drying durability studies after stabilizing with chemical additives including quicklime and cement. Performance indicators such as volumetric strain and Unconfined compressive strength trends were monitored at regular intervals during the wetting/drying process. It was observed that clayey soils dominant in the mineral Montmorillonite were susceptible to premature failures. It was also noted that soils dominant in other clay minerals exhibited early failures at lower additive contents. Also, an attempt was made for the first time to address the field implications of the laboratory studies by developing a correlation that predicts service life in the field based on clay mineralogy and stabilizer dosage.