This study examines a six-month pilot programme designed to empower youth entrepreneurs in South African informal settlements by enhancing their digital skills. A mixed-methods approach was employed, combining pre- and post-programme surveys with in-depth interviews to gather quantitative data on digital skills development and qualitative insights into participants' experiences and perceptions of the programme. Participants demonstrated a significant improvement in digital literacy, with an average increase of 45% in proficiency levels. Themes emerged around the need for tailored training resources and ongoing support mechanisms to sustain learning. The DSYE programme successfully enhanced youth entrepreneurs' digital skills, contributing to their confidence and entrepreneurial ventures. Ongoing support is crucial for sustaining these gains. Future interventions should include more interactive training materials and establish a community-based mentorship network.