The launch of lifeboats is commonly completed through freefall dropping from a considerable height, where the lifeboat is released from an inclined skid so that it can obtain a forward speed after being launched. The drop is followed by a water entry process that can induce high impact forces on the hull, which gives a significant risk of structural damages. Ascertaining the water entry impact is therefore a key step of lifeboat design; however, conventional methods have linear assumptions and assess the water impact following a quasi-static manner, which causes these methods to be not fully accurate and ignore some important details. To address this gap, this work developed a model based on Computational Fluid Dynamics to holistically simulate and analyse the process. An overset mesh technique was incorporated to reproduce the entire series of drop, water entry and resurfacing, in which the pressure distribution on the whole hull was obtained and recorded with a sampling frequency of 1000 Hz to ensure the peak impacts can be captured. Full-scale measurements were used to confirm the accuracy of the present computational model. Subsequently, a systematic series of simulations were performed to investigate how the water entry process is influenced by the inclined angle and height at which the lifeboat is dropped. The results show that a higher dropping angle can reduce the pressure impacts, but the dropping angle also dictates the lifeboat's motion pattern during the water entry. It was demonstrated that the best dropping angle is around 70° for the investigated case, since an either too low or too high dropping angle would cause the lifeboat to appear in an undesirable after-launch status. This indicates the great importance to assess the optimal dropping angle for every potential freefall lifeboat launch, and the present work proved an effective approach to perform the task.