Menopause driven decline in estrogen exposes women to risk of osteoporosis. Detection of early onset and silent progression are keys to prevent fractures and associated burdens. In a discovery cohort of 120 postmenopausal women (aged: 49 – 90 years), we combined repeated quantitative pulse-echo ultrasonography of bone, assessment of grip strength and serum bone markers with mass-spectrometric analysis of exhaled metabolites to find breath volatile markers and quantitative cutoff levels for osteoporosis. Obtained markers and cutoffs were validated in an independent cohort of 49 age-matched women with 6 months apart seasonal follow-ups. Within the discovery cohort median concentrations (ppbV) of exhaled end-tidal dimethyl sulfide (DMS), allyl-methyl sulfide, butanethiol and butyric acid increased significantly (p≤0.005) by 45.24%, 42.83%, 38.29% and 33.66% in subjects (n=27) with bone density at high-risk of osteoporosis and fracture, when compared to subjects (n=62) with normal bone mineral density (BMD). Increased age and decreased grip strength were concomitant. All these changes were reproduced within the independent validation cohort including seasonal follow-ups. Exhaled metabolite expressions remained age independent in either cohort. Serum bone markers showed random expressions without any reproducibility. DMS exhalations even differed between patients with recent (<1 year), old and without fractures. Metabolite exhalations and BMDs were down-regulated during winter mirroring the regional climate change. ROC analysis in the discovery cohort yielded high classification accuracy (AUC=0.86) of DMS with a cutoff at 15.88 ppbV for osteoporosis, which predicted subjects at high-risk within the independent validation cohort with high (>91%) sensitivity and specificity during both follow-ups. Non-invasive analysis of exhaled DMS allowed more reliable classification of osteoporosis risk than conventional serum bone markers. We identified associations of exhaled organosulfur and short-chain fatty acid markers to bone metabolism in postmenopausal osteoporosis via a gut-bone axis.