The surgical treatment of the stiff elbow is a challenging condition that may lead to unsatisfactory clinical results and complications, even when performed by expert elbow surgeons. For this reason, accurate preoperative planning may be considered more important for this condition than for other types of elbow surgery. In order to properly address the causes of elbow stiffness, a systematic examination of the elbow is mandatory: this allows the surgeon to evaluate the components (soft tissues, bone, or both) that are potentially responsible for the stiffness. This evaluation should always be conducted by considering general factors such as age, functional demands, comorbidities, expectations, and the time of onset of stiffness. A proper imaging study protocol, alongside an accurate clinical evaluation, is the starting point for the surgical planning: a varying combination of different imaging techniques allows a comprehensive understanding of the pathology. In this chapter, for the sake of clarity, an introductory section on imaging techniques is followed by a separate discussion of bone and soft tissue disorders that may contribute to elbow stiffness. It should be borne in mind that soft tissue and bone disorders are generally not isolated: these two conditions are often encountered in a varying combination in clinical practice. In most cases of elbow stiffness, a custom surgical strategy is required.