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Over the past four decades, work at the intersection of Arabic and technology has evolved alongside major technical breakthroughs and shifting regional and global political dynamics. In this talk, I revisit the development of Arabic NLP and AI, from early foundational efforts to today’s large-scale generative systems, and highlight how each phase has engaged with distinct aspects of Arabic’s linguistic complexity. I reflect on the language’s ambiguous orthography, rich morphology, diglossic landscape, and wide geographic and historical reach, and on the growing research community committed to ensuring that AI technologies meaningfully support Arabic and its diverse cultural expressions. I conclude with a forward-looking vision for building a cohesive and sustainable ecosystem that advances Arabic in AI through strengthened training, deeper collaboration, and sustained innovation for the next generation of researchers and practitioners.