Venous leg ulcers (VLU) are a major complication of chronic venous disease, with compression therapy as the gold-standard treatment. This 2 × 2 factorial randomised open-label trial assessed the effect and three-month sustainability of a one-hour training intervention on compression bandaging quality among 50 advanced practice nursing students (APNS) in France, using two different compression bandage types (system A or system B) on a mannequin leg. The primary outcome was the Control Score of compression bandaging (CCB score, 0–7). Secondary outcomes included installation conformity, application time, and satisfaction. At baseline, mean CCB score was 3.78, with 52% installation conformity. The intervention did not significantly improve the CCB score compared to controls (adjusted difference: −0.43; 95% CI: −1.01 to 0.15). A significant interaction between bandage type and intervention was found for installation conformity: a tendency to improve with system B and decrease with system A. Improvements observed at 1 month were not sustained at 3 months. Application time decreased over follow-up, and system B was applied more efficiently than system A. Brief, behaviourist-based training was insufficient to achieve lasting skill improvement. Findings highlight the need for repeated group practice, feedback, and integration into relevant clinical contexts to enhance compression bandaging proficiency.