Woolworths has announced a significant upgrade to its Olive customer service chatbot, leveraging Google Cloud’s Gemini Enterprise platform to transition the tool into a personalized shopping assistant. The updated Olive will feature "agentic" capabilities, allowing it to perform multi-step tasks such as meal planning and building grocery baskets based on voice inputs or handwritten recipe photos. This report examines the operational changes, data privacy considerations, and commercial neutrality policies governing the new system, as well as how this move aligns with global trends in conversational commerce.