Purpose Treatment package time (TPT) prolongation is associated with lower overall survival and locoregional control in mucosal head and neck squamous cell carcinoma (SCC), but there are few reports in cutaneous HNSCC (cHNSCC). We sought to test the effect of TPT in a cohort of patients with cHNSCC. Methods This is a single institution retrospective study of node-positive cHNSCC patients involving either the parotid or cervical nodes treated with curative intent surgery with macroscopic tumor clearance followed by standard fractionation postoperative radiation therapy (PORT) from 2001 to 2014. We assessed the effect of TPT and other prognostic variables on overall survival (OS), cHNSCC specific survival (CSS) progression free survival (PFS), and freedom from locoregional failure (FFLRF). Results In the present study, 152 patients met the inclusion criteria. The 5-year OS, CSS, PFS, and FFLRF were 62% (95% confidence interval [CI], 54-71), 78% (95% CI, 71-87), 54% (95% CI, 46-64), and 76% (95% CI ,68-85), respectively. In a multivariable model, TPT ≥14 weeks was associated with worse outcomes in all endpoints (OS [hazard ratio (HR) 4.93; 95% CI, 2.54-9.56, P < .001], CSS [HR 6.09; 95% CI, 2.33-15.92; P = .001], PFS [HR 4.29; 95% CI, 2.21-8.34; P < .001], and FFLRF [HR 4.63; 95% CI, 1.71-12.51; P = .007]). Immunosuppression and the presence of ≥2 pathologically involved lymph nodes were also significant adverse factors for both OS and FFLRF, although extracapsular extension was also associated with lower FFRLF. Delays to commencing PORT rather than treatment breaks accounted for the majority of cases with prolonged TPT. Conclusions Prolongation of TPT to 14 weeks or longer may confer a lower probability of locoregional control and survival in patients with lymph node–positive cHNSCC treated with surgery and PORT. Timely referral and commencement of PORT is necessary to maximize long-term disease outcomes.