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Obesity is a complex chronic disease conveying significant health risk. Women with obesity have greater risk for certain obesity associated conditions and midlife is when women experience an increase in their overall obesity prevalence and severity. Some midlife women experience treatment resistant obesity (TRO), a phenomenon not previously explored. The purpose of this research was to determine the prevalence of TRO, or failure to achieve ≥ 5% total body weight loss after one year of medically specialized obesity treatment, among midlife women and to identify factors associated with the phenomenon. A retrospective cohort study was completed using information from the electronic health records of 203 midlife women with obesity who received one year of medically specialized obesity care from providers certified in obesity medicine. Quantitative analysis determined the prevalence of TRO among midlife women and found associations between TRO and certain biopsychosocial factors. More than 27% of participants in this study demonstrated TRO. The use of FDA approved injectable medications and the dietary modification of lowering carbohydrates demonstrated associations with TRO. Participants were more likely to demonstrate TRO if they did not use FDA approved injectable medications (OR = 3.49, p = 0.0002) or follow a diet lower in carbohydrates (OR = 2.18, p = 0.035). More than a quarter of midlife women with obesity who receive medically specialized obesity care for one year may fail to achieve ≥ 5% total body weight loss and demonstrate TRO. The combination of lowering dietary carbohydrates and taking FDA approved injectable medications for weight loss in midlife women may reduce their risk of TRO. Incorporation of these two strategies alone does not eliminate the occurrence of TRO among midlife women and therefore additional research into this phenomenon is necessary to determine more efficacious treatment strategies.