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Bone-derived osteocalcin has been suggested to be a metabolic regulator. To scrutinize the relation between osteocalcin and peripheral insulin sensitivity, we analyzed changes in serum osteocalcin relative to changes in insulin sensitivity, low-grade inflammation, and bone mineral density following lifestyle-induced weight loss in individuals with metabolic syndrome (MetS). Participants with MetS were randomized to a weight loss program or to a control group. Before and after the 6-month intervention period, clinical and laboratory parameters and serum osteocalcin levels were determined. Changes in body composition were analyzed by dual-energy X-ray absorptiometry (DXA). In participants of the intervention group, weight loss resulted in improved insulin sensitivity and amelioration of inflammation. Increased serum levels of osteocalcin correlated inversely with BMI (r = −0.63; <i>p</i><i><</i> 0.001), total fat mass (r = −0.58, <i>p</i> < 0.001), total lean mass (r = −0.45, <i>p</i> < 0.001), C-reactive protein (CRP) (r = −0.37; <i>p</i> < 0.01), insulin (r = −0.4; <i>p</i> < 0.001), leptin (r = −0.53; <i>p</i> < 0.001), triglycerides (r = −0.42; <i>p</i> < 0.001), and alanine aminotransferase (ALAT) (r = −0.52; <i>p</i> < 0.001). Regression analysis revealed that osteocalcin was independently associated with changes in CRP but not with changes in insulin concentration, fat mass, or bone mineral density, suggesting that weight loss-induced higher serum osteocalcin is primarily associated with reduced inflammation.