Despite advances in diagnostic tools and treatment options in the management of bone infection, osteomyelitis can still be a major cause of morbidity and even mortality, both in children and adults. According to clinical symptoms’ duration, osteomyelitis can be categorized as acute, subacute, or chronic. Each of these stages has its clinical, biological, and radiological peculiarities and its specific challenges and management. In acute osteomyelitis, it is most important to make an early diagnosis in order to provide adequate treatment and prevent complications and sequelae. The differential diagnoses are the major challenge in Brodie abscess, while in chronic osteomyelitis, diagnosing and treating infection relapse are the main concerns. In each stage, the different modalities of imaging play a key role in overcoming those challenges.