For low permeability reservoirs, bailing oil is a flexible, low-investment, and environmentally friendly oil recovery method. In field work, a reasonable bailing system is quite important for improving the development effect and economic benefits of oil bailing wells. Starting from theoretical research and field management, two methods are used to greatly increase oil recovery and reduce oil recovery costs, namely optimizing bailing period and establishing a rainy season bailing management mode. Aimed at low permeability reservoirs, considering hydraulic fractures and threshold pressure gradients, a mathematical model for calculating depth of liquid level is established through applying the principle of seepage mechanics. By deducing and solving the model, wellbore liquid level build-up curve is obtained and thus optimum bailing time is determined for specific well. To reduce the impact of rainy season on bailing operations, bailing oil wells are classified into three categories based on rainfall and road conditions, and different management methods are formulated. Through example verification, error between calculated liquid level and measured value is within 5%, which meets field needs. After optimizing oil bailing period, bailing system becomes more reasonable. Oil wells with shortened period can obtain more oil yield while wells with extended period keep the same production. Applying the established management model to oil bailing during rainy season has significantly improved the compliance rate of bailing period, and thus ensured production supply. The two optimization methods of bailing well work system have strong applicability, which provide technical basis for economic and effective development of low permeability reservoirs and offer reference for production as well as management of bailing wells.