The random distribution of a complex joint network within a coal–rock mass has a significant weakening effect on its bearing capacity, making the surrounding rock of the roadway highly susceptible to instability and failure under the influence of in situ stress and mining-induced stress. This poses challenges in controlling the surrounding rock and seriously affects the normal production of mines. Consequently, it is imperative to conduct stability analysis on complex jointed roadway surrounding rock. Therefore, taking the transport roadway of Panel 11030 in the Zhaogu No. 2 Coal Mine as a case study, the microscopic contact parameters of particles and joint surfaces in each rock layer were calibrated through uniaxial compression and shear simulation tests using the particle flow simulation software PFC2D 5.0. Based on the calibrated microscopic contact parameters, a multilayered roadway surrounding rock model containing complex joints was established, and the joint density was quantified to analyze its effects on the displacement field, stress field, force chain field, and energy field of the roadway surrounding rock. The research findings indicate that as the distance to the sidewall decreases, the impact of joint density on the deformation of the surrounding rock of the roadway increases. The displacement of the roadway roof, floor, and sidewalls is affected differently by the joint density, predominantly contingent upon the properties of the rock mass. During the process of stress redistribution in the surrounding rock, the vertical stress of the roof and floor is released more intensively compared to the horizontal stress, while the horizontal stress of the sidewalls is released more intensively compared to the vertical stress. The increase in joint density leads to an increasing release rate of the surrounding rock stress, causing the load-bearing rock mass to transfer towards the deeper part. As the joint density increases, the force chain network gradually transitions from dense to sparse, resulting in a decrease in strong force chains and a decline in the bearing capacity of the surrounding rock, accompanied by an expansion in the range of force chain failure and deformation. With the continuous increase in joint density, the values of maximum released kinetic energy and residual released kinetic energy become larger. Once the joint density reaches a certain threshold, the kinetic energy stability zone consistently maintains a high energy level, indicating extreme instability in the roadway and sustained deformation. The results provide a valuable insight for analyzing the failure mechanism of complex jointed roadway surrounding rock and implementing corresponding support measures.