To address childhood obesity, several states and local school districts across the United States have adopted body mass index (BMI) measurement initiatives. This descriptive case study explored psychosocial, environmental, and behavioral factors among parents of sixth-grade students who received BMI Health Letters (BMIHLs) in one Florida County. A nonexperimental postintervention design was employed to gather quantitative data via self-report Likert-type questionnaire. Participants were parents/guardians of sixth-grade students attending one Hillsborough County public middle school (n = 76). Results indicate three main findings: (a) most parents in this study (67.4%) who discussed the BMIHL with their child reported their child as “very” or “somewhat” uncomfortable with the discussion; (b) some parents of normal weight (NW) children responded by taking their child to a medical professional to control their weight; and (c) more parents of at risk of overweight/overweight (AR/OW) children (vs. NW) reported greater concern about their child’s weight, using food restriction and physical activity to control their child’s weight, and giving negative weight-related comments/behaviors. This case study illustrates the importance of adapting and tailoring state mandated BMIHLs for parents based on child’s BMI status.