Background: Os trigonum and Stieda process are common etiologies for posterior ankle impingement syndrome (PAIS), and diagnosis is typically made by radiographs, computed tomographic, or magnetic resonance imaging. However, these static tests may not detect associated soft tissue and bony pathologies. Posterior ankle and hindfoot arthroscopy (PAHA) is dynamic, providing at least ×8 magnification with full anatomical visualization. The primary aim of this study was to report the prevalence of associated conditions seen with trigonal impingement treated with PAHA. Methods: In this retrospective comparative study, patients who underwent PAHA for PAIS due to trigonal impingement, from January 2011 to September 2016, were reviewed. Concomitant open posterior procedures and other indications for PAHA were excluded. Demographic data were collected with pre- and postoperative diagnosis, arthroscopic findings, type of impingement, location, associated procedures, and anatomical etiologies. Trigonal impingements were divided in os trigonal or Stieda and subgrouped as isolated, with flexor hallucis longus (FHL) disorders, with FHL plus other impingement, and with other impingement lesions. Results: A total of 111 ankles were studied—74 os trigonum and 37 Stieda. Isolated trigonal disorders accounted for 15.3% of PAIS (n = 17). Cases having associated conditions had a mode of 3 additional pathologies. FHL disorders were found in 69.4%, subtalar impingement in 32.4%, posteromedial ankle synovitis in 25.2%, posterolateral ankle synovitis in 22.5%, and posterior inferior tibiofibular ligament impingement in 19.8% of cases. Associated pathologies were observed in 58.6% of cases when FHL was not considered. Significant differences were noted comparing os and Stieda (isolated: 20.3% to 5.4%, P = .040; FHL plus others: 35.1% to 59.5%, P = .015). Conclusion: Trigonal bone (os trigonum or Stieda) was found to cause impingement in isolation in a small proportion of cases even when the FHL was considered part of the same disease spectrum. This should alert surgeons when considering removing trigonal impingement. Open approaches may limit the visualization and assessment of associated posterior ankle and subtalar pathoanatomy, thus possibly overlooking concomitant causes of PAIS. Level of Evidence: Level III, retrospective comparative study.