Italy has long been a key player in olive crop production, but the sector is currently facing an unprecedented crisis. This is evident by shrinking cultivated areas, farms, production levels, and investments. Multiple factors contributed to this decline, including traditional cultivation practices, limited innovation and competitiveness, siloed-oriented policies, landscape protection measures, and unsustainable agricultural systems. Phytosanitary issues, such as the spread of Xylella fastidiosa and the effects of climate change and drought, further compounded these challenges. Over the last decade, the sector has undergone preservation efforts focused on the perpetuation of traditional narratives and implementing policies to protect smallholder farmers, old cultivars, and safeguard traditional agri-food products. However, these approaches hinder the sector's ability to adapt and compete in the market, perpetuating stagnation rather than driving the necessary changes. To reverse this decline, the olive sector must undergo necessary evolution, as seen in other sectors, such as viticulture and tree crops. This entails embracing a comprehensive strategy encompassing research and development, infrastructure investment, the promotion of modern cultivation techniques, and policies that support the sector's evolution. Without such measures, the future of Italy's olive industry remains uncertain, with significant implications for its cultural heritage and economy. Italy must recognize the economic and cultural consequences of continued decline and take immediate action for long-term viability.