The healthcare sector of the UAE is undergoing digital transformation. The policy support, along with the national vision, is providing dedicated support for accelerating this transformation. However, despite the government-led initiatives, there exist some critical gaps in the sector’s technological investments and actual care outcomes. This research work was conducted to synthesize the existing evidence and explore the current state of digital transformation in the UAE hospitals, evaluating the current trends and challenges. The analysis is anchored at the Technology-Organization-Environment (TOE) and Donabedian (Structure-Process-Outcome) framework, and secondary research findings reveal that although the UAE hospitals are proactively investing in the emerging technological tools, a deeper analysis highlights key gaps at the backend. Some commonly highlighted challenges currently being faced by UAE hospitals include interoperability crises, workforce capability gaps, and weak strategic leadership. Collectively, these challenges hinder the effective integration of digital technologies, reducing their beneficial impact on care outcomes. Based on the analysis, the study concludes that currently, the key challenge being faced by the UAE healthcare sector is not about the technology adoption, but about the managerial and organizational aspects that impact the wider and in-depth integration. The hospital management and policy makers should stretch their focus from the technological to the managerial side to achieve the desired outcomes from their digitalization investment.