This paper reflects on twenty years of building NLP resources and research infrastructure for Arabic, a language spoken by hundreds of millions yet historically underserved relative to languages such as English or Chinese. The first decade focused on foundational linguistic infrastructure; the second shifted toward computational social science, social media analysis, and socially oriented applications. Rather than cataloguing outputs, the paper examines what the experience of building them revealed. Three counterintuitive lessons emerge: building datasets is as much a social process as a technical one; communities formed around shared tasks often matter more than the tasks themselves; and moving from language resources to computational social science exposes challenges that traditional NLP training does not address. We discuss three failures: a depression detection corpus that never reached clinical practice, a period of spreading across too many shared tasks without sufficient depth, and a long-standing assumption that Modern Standard Arabic infrastructure would transfer cleanly to dialectal tasks. These experiences suggest that the hardest problems in developing NLP for underserved communities are not linguistic but social, institutional, and epistemic, and require competencies the field rarely teaches.