This paper analyzed the effects of boundary conditions on the stress distribution of hydraulic support with the static finite element (FE) model. Five loading conditions are considered in this study, including: 1) canopy torsional loading, 2) canopy eccentric loading, 3) base torsional loading, 4) base diagonal loading, and 5) base symmetrical loading. In order to verify the simulation results obtained from the FE model, the corresponding experiments have also been performed. Based on the comparison between simulation and experimental results, the effects of pin-joint simplified methods and boundary conditions are evaluated in terms of accuracy and efficiency. Moreover, the new elastic-support boundary is also proposed to improve the simulation accuracy under conditions 2, 3, 4, and 5. The results show that bonded contact between the pin and shaft hole has high efficiency and accuracy compared with the frictional contact. The frictional contact boundary is reasonable under condition 1. However, the elastic-support boundary is suggested to be adopted to improve calculation accuracy for the stress distribution of the constraint components (canopy or base) under conditions 2, 3, 4, and 5.