Elbow stiffness is a condition that can be effectively diagnosed through a comprehensive assessment, including a thorough medical history, physical examination, and appropriate imaging studies. The elbow stiffness may arise from osseous or soft tissue abnormalities, either within or outside the joint. Intra-articular causes encompass posttraumatic arthritis, joint incongruity, loose bodies, ankylosis, primary osteoarthritis with bone spurs, and proliferative synovitis, while extra-articular factors include heterotopic bone formation, capsular thickening, and musculotendinous contracture. Soft tissue abnormalities like synovitis, tendinopathies, and capsuloligamentous lesions are best evaluated using ultrasound or magnetic resonance imaging (MRI). On the other hand, osseous abnormalities such as loose bodies, osteophytes, are best accessed using radiographs and computed tomography (CT) scan. Key elements to be evaluated in imaging include soft tissue integrity, remaining bone stock, bone alignment, articular congruency, severity of osteoarthritis, including impact of osteophytes on joint mobility and relation to neurovascular structures, loose bodies, and assessment of surgical implants. Imaging plays a crucial role in determining the cause and extent of elbow stiffness, guiding treatment planning and procedures, aiding in formulating effective treatment strategies.