This scoping review employed the PRISMA-ScR framework to dissect the complexities of technological extension in agriculture within developing nations, where varying socio-economic, cultural, and environmental facets deeply influence extension strategies. Our study aimed to identify and expand upon the existing knowledge of critical factors—both challenges and opportunities—that affect the efficacy of agricultural extension, with a focus on contextual variations. To achieve this, we conducted a comprehensive review of the relevant academic contributions from 2013 onwards. This included articles, reviews, conference proceedings, book chapters, and data papers. Our analysis focused on scrutinizing the interaction dynamics between extension personnel and farmers, the adaptation of technologies to local contexts, and the significance of cross-sector collaboration. Through bibliometric analysis, we provide a synthesis of 32 pertinent records. Our findings advocate for a paradigm shift from the traditional linear knowledge transfer to a more encompassing approach that values bidirectional communication, cultural awareness, and the active involvement of local farming communities. We argue for extension practices that are attuned to environmental dynamics, promote long-term economic sustainability, and are informed by theoretical perspectives that can refine the design of extension systems and models. Our review posits that the enhancement of sustainable agricultural technology adoption lies in a profound reform of extension systems. Such reform should focus on design and operational models that are more inclusive, adaptive, and acutely attuned to the complex realities of farmers in emerging economies. This integrative, systemic, and holistic approach proposes a framework to bolster agricultural sustainability and rural development.