This case report describes the use of TIELLE™ Silicone Border in the management of a chronic venous leg ulcer of 3 years’ duration, in a patient with multiple relevant comorbidities. Despite several, ongoing prior interventions, the wound remained unhealed, and continued to present issues related to exudate levels and maceration. During the dressing evaluation period, the condition and depth of the wound improved overall. Moreover, the patient reported liking the dressing compared to previous regimens because it allowed him to use compression hosiery, wear normal clothes, maintain mobility and use the shower. Overall, the dressing represented a significant improvement in quality of life in a long-standing, hard-to-heal ulcer in a patient with multiple comorbidities.