Deepened periodontal pockets exert a significant pathological burden on the host and its immune system, particularly in a patient with generalized moderate to severe periodontitis. This burden is extensive and longitudinal, occurring over decades of disease development. Considerable diagnostic and prognostic successes in this regard have come from efforts to measure the depths of the pockets and their contents, including level of inflammatory mediators, cellular exudates and microbes; however, the current standard of care for measuring these pockets, periodontal probing, is an analog technology in a digital age. Measurements obtained by probing are variable, operator dependent and influenced by site-specific factors. Despite these limitations, manual probing is still the standard of care for periodontal diagnostics globally. However, it is becoming increasingly clear that this technology needs to be updated to be compatible with the digital technologies currently being used to image other orofacial structures, such as maxillary sinuses, alveolar bone, nerve foramina and endodontic canals in 3 dimensions. This review aims to summarize the existing technology, as well as new imaging strategies that could be utilized for accurate evaluation of periodontal pocket dimensions.