Writing job application letters remain a major challenge for vocational high school students in learning English as a foreign language. Students must use proper grammar, professional language, and genre appropriate writing style as they prepare to enter the workforce. This qualitative case study examines the use of LinkedIn as an authentic professional learning environment. This use shapes the writing process, classroom engagement, and the challenges students face. The study involved 31 of 11th-grade Hospitality students at a vocational high school in Yogyakarta over two genre-based learning cycles. Data were collected through classroom observations, interviews with students and teachers, and analysis of students’ writing drafts in order. Data were analysed thematically following Miles and Huberman’s interactive model. The study’s credibility was supported by triangulation of sources and time. Triangulation also included the investigator and theory. These procedures align with the five established criteria for the validity of action research found in the action research literature. The findings indicate that LinkedIn helped students’ progress from generic self-introductions to more organized and professional letters. Class participation increased, and students became more willing to revise their writing. Some students began to demonstrate an awareness of professional identity while reviewing authentic profiles. Students found that viewing real professional writing was more helpful for understanding formal vocabulary and organizing information than textbook exercises. But, the challenges remained in four areas. Linguistic and cognitive difficulties were reflected in limited grammar and trouble constructing coherent paragraphs. Technological and affective difficulties were reflected in unfamiliarity with the platform and limited peer feedback. These findings suggest that authentic digital platforms like LinkedIn can enrich writing instruction in vocational schools. These benefits are maximized when accompanied by ongoing support that addresses all four challenges together.