This study explores the perspectives and strategies of seasoned Teachers of Technology and Livelihood Education / Technical-Vocational Education and Training (TLE/TVL) in addressing the challenges posed by the Digital Divide in educational settings. The participants are four Master Teachers who have 10 or more teaching experience and currently teaching in the secondary school in the Province of Ilocos Sur. Two of them are from rural secondary schools while the other two are from secondary schools situated in urban areas. Through a phenomenology study and cool and warm analysis, the research investigates how these seasoned teachers view their teaching experience in using adaptive pedagogical approaches and perceive the impact of unequal access to technology and varying levels of digital literacy among learners on engagement and learning outcomes. Findings reveal that seasoned TLE/TVL teachers view the Digital Divide as both a dynamic challenge and a leveraging opportunity. They employ adaptive pedagogical approaches, including differentiated instruction, flexible grouping, and varied assessment methods, to cater to diverse learner needs. Continuous assessment of individual learner digital competencies and promotion of collaborative learning emerge as effective strategies to bridge digital gaps and enhance student engagement. The study underscores the importance of ongoing professional development in digital competencies and the need for institutions to prioritize access to technology and support flexibility in teaching practices. However, the study also identifies limitations, including potential sampling bias and the subjectivity of self-reported teacher experiences. Despite these constraints, the findings contribute valuable insights into effective strategies for fostering inclusive learning environments in vocational education amidst technological disparities.