Gastrointestinal stromal tumours (GISTs) have distinct biological and treatment-related features posing challenges for imaging. In this review the importance of imaging in different stages of patient management is discussed, emphasizing the unique characteristics of GISTs. Potential pitfalls of using the standard response criteria on conventional imaging have been highlighted. These include size measurements, which may not adequately reflect response rates, pseudo-progression, and spurious new lesions. Furthermore, the role of positron emission tomography/computed tomography (PET/CT) in early response evaluation and in the detection of both primary and acquired resistance is explored. The current role and future directions of use of both conventional and metabolic imaging in the management of GISTs are discussed.