This qualitative-phenomenological study aimed to explore the lived experiences of the Senior High School students in region 11, particularly their learning experience in contextualizing literature. This inquiry was gleaned from Vygotsky, Brunner, and Dewey (1997). Employing the sampling technique, snowball sampling, five (5) students were selected for the in-depth interview. Another five (5) students were selected for the focus group discussion with ten (10) students from five regions’ schools. As to the participants’ lived experiences in learning literature, the following four (4) significant themes emerged: Enjoying the familiarity of content, participating in discussions, developing knowledge expansion, and using familiar examples as learning guides. For the students’ perspective in situations that influence the challenges in contextualization, the following five (5) majors emerged: Listening carefully to the teacher, participating actively during classwork, acquiring life-long lessons, giving participation opportunities for community-based programs, and employing teaching materials. Finally, the students’ perspectives on overcoming contextualization issues were organized into three (3) primary themes. Improved knowledge through contextualization, effectively employing contextualization and learning to study well. The findings of this study are essential for academic institutions to comprehend students’ contextualization experiences.