Over five years ago Singtel embarked on an ambitious journey to expand beyond connectivity and tap into growth opportunities in digital advertising, OTT video-on-demand and big data. The results have been mixed so far. This report provides a summary of Singtel’s efforts in digital content and media, and identifies some key challenges facing its OTT video joint venture, HOOQ, and video content app, CAST on Digital Life Group’s path to profitability.