Abstract Introduction The purpose of this pilot study was to assess the effectiveness of the revised My Body Knows When (MBKW) program to promote intuitive eating behaviors within a sample of a military population through an online or in-person delivery mode. Materials and Methods Fifty-six overweight or obese adults (70% female); military service members (20%), retirees (38%) and family (42%) participated in the 10-week MBKW program at two military installations from 2012 to 2014. Body Mass Index, Intuitive Eating Scale-2 (IES-2; 23-item) and Motivation for Eating scale (MFES; 43-item) were collected at baseline and 10-weeks. Data were stratified by sex. Descriptive data were reported as mean ± standard deviation (SD), frequency, or percentage. A paired t-test was conducted with data at baseline and 10 weeks (α = 0.05, 80% power). Results Participants were predominantly female (70%); mean age of 51 ± 13 years; and BMI of 34.1 ± 5.5 kg/m2. There were no demographic, MFES, or IES-2 baseline differences between groups (in-person vs. online) or location. All subjects were collapsed into one group for a pre-post MBKW implementation assessment due to small sample size despite the original intent to stratify by online and in-person grouping. At 10 weeks, the remaining 26 participants exhibited a significant improvement (mean ± SD) in BMI (−0.4 ± 0.6 kg/m2; p = 0.012), environmental/social eating score (2.7 ± 0.4 points [pts]; −0.5 pt change; p < 0.001), emotional eating score (2.2 ± 0.5 pts; −0.6 pt change; p = 0.001), unconditional permission to eat score (3.4 ± 0.4 pts; +0.3 pt change; p = 0.017), eating for physical rather than emotional eating score (3.7 ± 0.8 pts; +1.0 pt change; p < 0.001), and reliance on hunger and satiety cues score (3.6 ± 0.5 pts; +0.8 pt change; p = 0.001). High attrition rates at the 10-week follow-up assessment precluded accurate assessment of long-term intervention effects. Conclusions The MBKW program was associated with improved intuitive eating behaviors and with less external eating influence on behavior; however, a larger sample is required to assess the effectiveness of MBKW delivery mode. Modest weight loss was attained but testing the efficacy of the MBKW program in a large diverse sample with alternate scenarios may be worthwhile (e.g., primary prevention against weight gain, or during weight maintenance to prevent weight regain).