Abstract: Air injection technique for developing shale oil has gained significant attention. However, the ability of the heat front to consistently propagate within the shale during air injection remains uncertain. To address this, we investigated the heat front propagation within oil–detritus mixtures, shale cores, and fractured shale cores using a self-designed combustion tube (CT) and experimental schemes. By integrating the results obtained from high-pressure differential scanning calorimetry and CT, we developed a comprehensive reaction kinetics model to accurately analyze the main factors influencing the heat front propagation within fractured shale. The findings revealed that in the absence of additional fractures, the heat front failed to propagate within the tight shale. The flow of gases and liquids towards the shale core was impeded, resulting in the formation of a high-pressure zone at the front region of the shale. This pressure buildup significantly hindered air injection, leading to inadequate oxygen supply and the extinguishment of the heat front. However, the study demonstrated the stable propagation of the heat front within the oil–detritus mixtures, indicating the good combustion activity of the shale oil. Furthermore, the heat front successfully propagated within the fractured shale, generating a substantial amount of heat that facilitated the creation of fractures and enhanced gas injection and shale oil flow. It was important to note that after the heat front passed through the shale, the combustion intensity decreased. The simulation results indicated that injecting air into the main fracturing layers of the shale oil reservoir enabled the establishment of a stable heat front. Increasing the reservoir temperature (from 63 to 143 °C) and oxygen concentration in the injected gas (from 11% to 21%) promoted notable heat front propagation and increased the average temperature of the heat front. It was concluded that temperature and oxygen concentration had the most important influence on the heat front propagation, followed by pressure and oil saturation.