Satellitosis or in-transit metastasis (S-ITM) has clinical outcomes comparable to node-positivity in cutaneous squamous cell carcinoma (cSCC). There is a need to stratify the risk groups. To determine which prognostic factors of S-ITM confer an increased risk of relapse and cSCC-specific–death. A retrospective, multicenter cohort study. Patients with cSCC developing S-ITM were included. Multivariate competing risk analysis evaluated which factors were associated with relapse and specific death. Of a total of 111 patients with cSCC and S-ITM, 86 patients were included for analysis. An S-ITM size of ≥20 mm, >5 S-ITM lesions, and a primary tumor deep invasion was associated with an increased cumulative incidence of relapse (subhazard ratio SHR: 2.89 95% CI, 1.44-5.83; P = .003, 2.32 95% CI, 1.13-4.77; P = .021, and 2.863 95% CI, 1.25-6.55; P = .013), respectively. Several >5 S-ITM lesions were also associated with an increased probability of specific death (SHR: 3.48 95% CI, 1.18-10.2; P = .023). Retrospective study and heterogeneity of treatments. The size and the number of S-ITM lesions confer an increased risk of relapse and the number of S-ITM an increased risk of specific-death in patients with cSCC presenting with S-ITM. These results provide new prognostic information and can be considered in the staging guidelines.