This study on the Schools Digital Maturity and Leadership of Administrators Towards a Contextualized Technology Empowerment Model aimed to determine the relationship between schools digital maturity and leadership of administrators among one-hundred fifty-six (156) public elementary schools in the Division of Laguna. This study used the convergent parallel mixed method design, which has been demonstrated to generate correct and reliable answers to the ten (10) basic problems. The researcher gathered all the data from the survey and interview results and conducted a statistical and thematic analysis. The findings revealed that there is a significant relationship between the extent of maturity of schools, the level of digital leadership of the school administrators, and the degree of challenges encountered by the school administrators in terms of digitalization revealed that only the school digital maturity and digital leadership of school administrators have a significant relationship with moderate positive correlation. The school administrators derived thematic experiences based on the best practices and issues encountered to strengthen the schools digital maturity. Utilization of ICT in instruction and school operation and management is themed as best practices for school administrators. It also revealed that the issues were lack of ICT training for teachers, poor / lack of internet connectivity and lack of ICT equipment. Lastly, the application of best practices and issues to strengthen the schools digital maturity were ICT in the teaching and learning process, implementation of ICT in institutional management like school learning action cell (SLAC) and support in accessible internet connectivity. It is proposed that school administrators and school digitalization be strengthened using the WIFI: Contextualized Technology Empowerment Model. This model promotes the strengthening of school administrators to survive the challenges and strengthen school digitalization so that they will continue to explore more opportunities in digital setup. The framework should be implemented progressively to ensure its long-term sustainability and effectiveness in strengthening digital practices in school operation and management.