Helicopter live line insulator cleaning is a kind of special flying operation. It can ensure the quality of the electricity transportation system of the electricity company. By using it will not waste electricity and can avoid power supply suspending which will lead to influence the development of industry–commerce and house living quality. At the same time, it will reduce the emission of CO2. With the progressive operation and advanced technical development, it can increase the effectiveness of insulator washing and replace the inconvenience of manual cleaning operation. This kind of flying operation makes a huge sacrifice to maintain the stability of electricity transportation. The working partners and equipments move continuously owing to the aerial working process. Therefore, workers should pay more attention to the safety due to the change of working spots. This operation is handled totally by workers and just like an airborne stunt. There must be a good cooperation relationship between team workers not only in the air but also at ground to avoid serious disasters. This thesis is to investigate the working process of the helicopter live line insulator cleaning. We understand the working process and confirm it as a system by focusing on the hazards of enterprise management and making use of the analysis and observation of practical working safety and various kind of risk assessments. From the beginning of plan and design, we use preliminary hazard analysis and what-if brainstorming to identify the initial hazards and risk assessments. We also use FMEA to analyze the system hazards digitally and the methods of hazards controlling to reduce the hazards to endurable and acceptable condition. In this way, this will match the analysis of events happened annually. In the end, we hope to combine the operation resource from the air and ground and use the system of TOSHMS to attain the goal of “0” item risk and establish one set of essential safety operation system .