To describe the growing importance of enthesitis in patients with psoriatic arthritis (PsA) and discuss the advantages and disadvantages of clinical and imaging methods currently used to assess enthesitis. PubMed literature searches were conducted using the terms psoriatic arthritis, entheses, enthesitis, pathology, imaging, ultrasound, magnetic resonance imaging, clinical, and indices. Articles were deemed relevant if they provided insight into the pathology, monitoring, and/or diagnosis of enthesitis in PsA, or if they discussed clinical or imaging indices used to assess enthesitis. Enthesitis is an early manifestation of PsA that is associated with increased disease activity and reduced quality of life. A variety of clinical indices exist to assess enthesitis in PsA; however, the Leeds Enthesitis Index and Maastricht Ankylosing Spondylitis Enthesitis Score index have been the most frequently used indices in recent clinical trials. Limitations of these indices include an inability to discern structural involvement, risk of missing subclinical enthesitis, and lack of sensitivity in detecting enthesitis, especially in patients with central sensitization and/or pain amplification. Such limitations have led to the emergent importance of imaging techniques in the assessment of enthesitis. Although there have been recent advances in magnetic resonance imaging, ultrasound (US) appears to be the preferred method for detecting enthesitis because it allows for accurate assessment of the soft-tissue components of entheses and also for new bone formation. Hypoechogenicity, increased thickness of tendon insertion, calcifications, enthesophytes, erosions, and Doppler activity have been identified as important US characteristics of enthesitis. Enthesitis is thought to be integrally involved in the pathogenesis of PsA and is associated with worse prognostic outcomes in patients with PsA. A validated US index with entheses that are less confounded by mechanical factors and obesity would be the most effective measure of enthesitis in PsA. As imaging techniques continue to advance, our understanding of enthesitis and its involvement in PsA will also improve.