Urbanization exacerbates climate change impacts, making it crucial to develop innovative strategies for adaptation and mitigation. In this context, the “smartness” concept must be seen as the technical capability to forecast and adapt to changing conditions while maintaining livability and safety. This paper investigates the use of Vertical Green Structures (VGSs) as a mitigation strategy. Through a critical review of technology-driven applications, this research identifies key motivations and challenges in VGSs’ technological integration and implementation, governance frameworks, and community engagement. Methodologically, it employs a critical case analysis and categorizes the technologies based on multicriteria; it also explores the potential to implement smart green infrastructure (GI) in cities and the GI urban governance that was developed in previous decades to adopt these systems at an urban scale and increase the community’s awareness of them. The findings reveal diverse motivations driving technology and VGS integration, ranging from economic incentives to environmental sustainability. Additionally, this contribution explores possible future directions for VGSs and highlights three scenarios derived after the multidimensional impacts of climate change with their pros and cons in future cities. Multidisciplinary collaboration emerges as a crucial factor in optimizing technology implementations in VGSs and fostering a transition from nature-based solutions to technology-based solutions in urban sustainability initiatives.