Advances in remote-sensing, sensor and robotic technology, machine learning, and artificial intelligence (AI) – smart algorithms that learn from patterns in complex data or big data - are rapidly transforming agriculture. This presents huge opportunities for sustainable viticulture, but also many challenges. This chapter provides a state-of-the-art review of the benefits and challenges of AI and big data, highlighting work in this domain being conducted around the world. A way forward, that incorporates the expert knowledge of wine-growers (i.e. human-in-the-loop) to augment the decision-making guidance of big data and automated algorithms, is outlined. Future work needs to explore the coupling of expert systems to AI models and algorithms to increase both the usefulness of AI, its benefits, and its ease of implementation across the vitiviniculture value-chain.