BACKGROUND AND PURPOSE: Transoral robotic surgery is an emerging strategy for treating human papillomavirus-positive cancers, but the role of MR imaging in predicting the surgical outcome has not been established. We aimed to identify preoperative MR imaging characteristics that predispose the outcome of transoral robotic surgery toward an insecure (positive or close) surgical margin in human papillomavirus-positive tonsillar squamous cell carcinoma. MATERIALS AND METHODS: Between December 2012 and May 2019, sixty-nine patients underwent transoral robotic surgery at our institution. Among these, 29 who were diagnosed with human papillomavirus-positive tonsillar squamous cell carcinoma, did not receive neoadjuvant treatment, underwent preoperative 3T MR imaging, and had postoperative pathologic reports and were included in this retrospective study. Two neuroradiologists evaluated the preoperative MR imaging scans to determine the tumor spread through the pharyngeal constrictor muscle using a 5-point scale: 1, normal constrictor; 2, bulging constrictor; 3, thinning constrictor; 4, obscured constrictor; and 5, tumor protrusion into the parapharyngeal fat. The risk of an insecure surgical margin (involved or ,1 mm) according to the MR imaging scores was predicted using logistic regression with the Firth correction. RESULTS: The interobserver agreement for the MR imaging scores was excellent (k = 0.955, P , .001). A score of $4 could predict an insecure margin with 87.5% sensitivity and 92.3% specificity (area under the curve = 0.899) and was the only significant factor associated with an insecure margin in the multivariable analysis (OR, 6.59; 95% CI, 3.11-22.28; P , .001). CONCLUSIONS: The pre-transoral robotic surgery MR imaging scoring system for the pharyngeal constrictor muscle is a promising predictor of the surgical margin in human papillomavirus-positive tonsillar squamous cell carcinoma. ABBREVIATIONS: AUC ¼ area under the curve; cN ¼ clinical node; cT ¼ clinical tumor; HPV ¼ human papillomavirus; pN ¼ pathologic node; pT ¼ pathologic tumor; ROC ¼ receiver operating characteristic; SCC ¼ squamous cell carcinoma; TORS ¼ transoral robotic surgery O ropharyngeal squamous cell carcinoma (SCC) is a head and neck cancer with increasing prevalence as a consequence of rising human papillomavirus (HPV) infections. 1,2 HPV-positive oropharyngeal SCC is known for its excellent prognosis with substantially improved survival compared with HPV-negative SCC. 3-5 Surgery, radiation, and chemotherapy are the main treatment methods for oropharyngeal SCC and can be used alone or in combination depending on the cancer stage. 6