The study aimed to delve into the lived experiences of senior high school students as they navigate the complexities of writing mechanics in crafting position papers. A qualitative research design was used, specifically employing a phenomenological approach. In-depth interviews and focus group discussion were conducted with 14 senior high school students in the public secondary schools in Tagum City Division. The study uncovers recurring patterns of grammatical errors, vocabulary misuse, and syntactic issues that hinder effective argumentation. The findings also reveal the influence of students' prior language exposure, instructional methods, and self-perceived writing competence on their ability to construct coherent and persuasive position papers. This study is anchored on the theories of Cognitive Process Theory of Writing, Communicative Competence, and Argumentation Theory, which explain the experiences of students in their written works. This research highlights the critical need for foundational language support and targeted writing interventions in senior high school curricula. It underscores the importance of revisiting basic linguistic principles to enhance students’ proficiency and confidence in academic writing. Ultimately, the study offers practical insights for language teachers, curriculum designers, and stakeholders to address these challenges and improve the writing skills of students in argument-driven academic tasks.