Prolonged exposure of deep coal mines to erosion from groundwater results in a gradual accumulation of rock mass damage, which can lead to geological hazards such as deformation and instability. These challenges significantly impact the safe operation of deep coal mines. To understand the mechanisms behind siltstone damage progression related to water content and confining pressure, this study explores the influence of these factors on the deformation and damage evolution of siltstone, employing a combination of rock mechanics testing, numerical simulation, and CT scanning techniques. Results demonstrate that increasing water content reduces the compressive strength of rock, leading to more complex failure modes. In contrast, higher confining pressure strengthens the compressive capacity, thereby suppressing the formation and growth of transverse cracks under compression. Using Avizo software, a three‐dimensional model of siltstone was developed to visualize the distribution of fractures in a three‐dimensional field. In the MATLAB platform, a box dimension algorithm based on three‐dimensional digital volume imaging was developed, employing box dimension theory and digital image storage methods. Fractal analysis reveals that the fractal dimension of internal fractures in loaded samples increases linearly with water content, indicating more extensive fracture development and greater specimen damage. Applying the box dimension from three‐dimensional digital volume images as a metric facilitates characterizing the damage evolution in siltstone under different water content conditions. This approach provides a new means to quantitatively evaluate the growth and complexity of internal fractures in siltstone, offering insights into rock damage progression under varying moisture conditions.