As ocean engineering operations extend into deeper seas, the working environment becomes increasingly complex, making free fall lifeboats (FFLBs) more vital for maritime disaster rescues. Unlike traditional davit-launched lifeboats, FFLBs are propelled into the water at a specific velocity and angle, engaging in a complex motion process of launch, impact, submersion, and resurfacing. Therefore, to assess the safety of FFLBs, this paper regarding the lifeboat as a rigid body aims to investigate the six-degree-of-freedom motion characteristics of lifeboat entering the water with different entry angles θ and wave environment, with a specific focus on analyzing the primary causes of capsizing. The numerical simulations of water entry with various θ, wave heights H, and relative entry positions are carried out by combining large eddy simulation and overset mesh technology. The free surface is captured by the volume of fluid method, and the attitude change, acceleration change, motion trajectory, and free surface evolution law of lifeboats are analyzed. The findings suggest that lifeboats can enter calm water safely at θ of 20°–50° and maintain a stable posture. Moreover, in extreme conditions where θ is either 0° or 90°, there is a high risk of entry failure due to excessive vertical acceleration and poor motion attitude, respectively. Furthermore, when facing waves, lifeboats experience reduced horizontal displacement when entering at peak and downward zero point compared to calm water conditions, which poses challenges for avoiding potential dangers.