The dynamics of the cutting process is modeled for investigating the relationship between tool wear and sound generation during surface turning. The vibration of the tool holder, together with the cutting insert, is considered as the main source of sound associated with tool wear. In this research, the tool holder-cutting insert combination is simplified as a cantilever beam which is excited by an external force that is directly related to tool wear. Based on this model, the displacement of the cutting tool is shown to be directly affected by tool wear and process characteristics. Simulation results show a change in the sound signal distribution over frequency as tool wear increases. A transfer function that includes the process characteristics is also developed to investigate the capability of sound and vibration signals in tool wear monitoring for a specific process. This provides critical information for sensor selection in implementing a tool failure monitoring system in reconfigurable manufacturing.