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Depends on the contract between your employer and your insurer. In general, gynecomastia is considered a cosmetic defect (there is a mildly increased risk of breast cancer, but not enough to make surgery required). You might want to meet with a plastic surgeon to discuss whether he can come up with a way to justify the surgery, if your insurance will not cover it as a cosmetic procedure. You also need to call your benefits department, or the insurance company itself, and ask.