Bone tumours and tumour-like lesions come with a wide and often deceptive spectrum of radiographic appearances, making their detection and diagnosis a challenging task—even for seasoned radiologists. Although primary bone cancers are rare, their subtle and varied imaging features can easily lead to missed or delayed diagnoses. This chapter explores the key challenges in detecting bone tumours on plain radiographs, highlights their limitations in early diagnosis, and presents practical strategies and imaging workflows to overcome these hurdles. We take a structured approach to evaluating bone lesions. The chapter also examines the expanding role of other cross-sectional imaging modalities and recent technological advances—including AI—that are enhancing diagnostic accuracy and streamlining workflows. Setting the foundation for tumour-specific discussions in the chapters that follow, this chapter serves as a practical guide through the nuanced and evolving landscape of bone tumour diagnosis, where the radiologist plays a pivotal role.