Basic Medical Insurance (BMI) has changed remarkably over time in China because of health reforms that aim to achieve universal coverage and better health care with adequate efforts by increasing subsidies, reimbursement, and benefits. In this paper, we present the development of BMI, including financing and operation, with a systematic review. Meanwhile, Pudong New Area in Shanghai was chosen as a typical BMI sample for its coverage and management; a stratified cluster sampling survey together with an ordinary logistic regression model was used for the analysis. Enrolee satisfaction and the factors associated with enrolee satisfaction with BMI were analysed. We found that the reenrolling rate superficially improved the BMI coverage and nearly achieved universal coverage. However, BMI funds still faced dual contradictions of fund deficit and insured under compensation, and a long-term strategy is needed to realize the integration of BMI schemes with more homogeneous coverage and benefits. Moreover, Urban Resident Basic Medical Insurance participants reported a higher rate of dissatisfaction than other participants. The key predictors of the enrolees’ satisfaction were awareness of the premium and compensation, affordability of out-of-pocket costs, and the proportion of reimbursement. These results highlight the importance that the Chinese government takes measures, such as strengthening BMI fund management, exploring mixed payment methods, and regulating sequential medical orders, to develop an integrated medical insurance system of universal coverage and vertical equity while simultaneously improving enrolee satisfaction.