Health Information Technology (HIT) is globally recognized as essential for enhancing patient safety and optimizing care delivery. However, its successful implementation in Low- and Middle-Income Countries (LMICs), faces persistent technical, financial, and organizational barriers. This study investigated the core barriers to HIT implementation in LMICs and identified targeted strategies to enhance digital transformation within resource-limited healthcare systems. A qualitative single-case study design was employed. Data were collected through semi-structured interviews with 40 diverse healthcare specialists and stakeholders. Template analysis was performed using the NVIVO software. Nine major barriers were identified: inadequate HIT policies, financial shortages, cultural and privacy concerns, structural characteristics of the healthcare sector, insufficient qualified personnel, infrastructure limitations, weak data integration, resistance to change, and poor system design. Human, organizational, and contextual factors have emerged as central determinants of HIT success or failure. Digital transformation in LMICs cannot advance without comprehensive policy reform, sustainable financing models, stronger governance, interoperability standards, and structured workforce capacity building. Human factors, not technology alone, remain the decisive element in HIT adoption. This research provides evidence-based, actionable strategies to guide policymakers and healthcare managers in Jordan and other LMICs toward sustainable and high-quality healthcare digitalization. This study addresses a critical knowledge gap by providing empirically grounded, context-specific recommendations essential for accelerating HIT maturity in LMIC healthcare systems.