Background: Segmental bone defects pose a major, unsolved clinical challenge and may be the result of high-energy trauma, infection, and tumour resection or revision surgery. Several options exist to reconstruct, including Ilizarov bone transport, Masquelet technique, cylindrical mesh technique, allografts, and vascularized bone autografts. We present a patient with a delayed union of the tibia with concomitant chronic osteomyelitis treated with anterolateral thigh (ALT) flap and double-barrelled vascularized fibula graft. Case presentation:A 60-year-old male with a chronic pretibial wound with underlying osteomyelitis of the right leg presented himself at the emergency department and was admitted to the surgical ward. He had complex chronic osteomyelitis of a tibial non-union after an earlier right crural fracture (a previous work-related accident). He was treated with an ALT flap and double-barrelled vascularized fibula graft, which was complicated with an additional fracture and breakage of osteosynthesis material. Conclusion: Segmental bone defects pose a major, unsolved clinical challenge in orthopaedic, trauma-surgical, and plastic surgical practice. Concomitant infections and fractures can be part of the postoperative course. Patients with complex segmental bone defects need to be treated by a multidisciplinary team including at least an (orthopaedic) trauma surgeon, a plastic surgeon, and an infectiologist.