Introduction Central to a functional public health system is a strong health information ecosystem and robust data use. Many low-and-middle-income countries (LMICs) face the task of digitizing their health information systems (HIS). For health leaders, deciding what to prioritize when investing in HIS strengthening is central to this daunting challenge. Objectives The study explores how HIS maturity assessment contributes to HIS strengthening, describes the facilitators and barriers to HIS maturity assessments, and how health leaders can prioritize conducting maturity assessments. Methods This descriptive qualitative study employed key informant interviews (KIIs) with fourteen eHealth leaders at national and international levels working or supporting Ministries of Health’s national HIS in LMICs. Results were analyzed using Dedoose Version 9.0 to develop themes based on the health systems' building blocks as a framework for identifying facilitators and barriers to conducting HIS maturity assessment. Results Participants identified maturity assessments as a critical beginning step to HIS strengthening, showing the system’s performance, and building a baseline response to systematic data quality challenges. Barriers to conducting HIS maturity assessment include lacking collaborators’ buy-in, fragmented vision, low financial/human resources, and overdependence on donor priorities. Non-supportive policies, a lack of execution champions, and an inadequately skilled workforce in conducting maturity assessments or negotiating for their prioritization hinder maturity assessment implementation. Frequently identified facilitators to promoting HIS maturity assessment include multi-stakeholder engagement, understanding the country’s HIS ecosystem, and priorities to appropriately integrate maturity assessment objectives. Recommendations include capacity building in data use and conducting maturity assessments at all health system levels to grow the demand and value of HIS maturity assessments. Conclusion Promoting HIS maturity assessments can help leaders prioritize areas to improve in the HIS ecosystem, making appropriate decisions that steward HIS maturity advancement. Addressing challenges that hinder HIS assessment implementation holds promise to identify a pathway to a strengthened health system.