During the COVID-19 pandemic, the switch to online training exposed the digital divide between higher education institutions, with some significantly superior to others in terms of equipment and experience, as well as among students enrolled in the same institution. The purpose of this study was to investigate online training and educational inequality in TVET (Technical and Vocational Education and Training) delivery in Kenya, during the COVID-19. A total of 16 unstructured discussions were conducted in four TVET institutions in the Western Kenya Region. Each college organized four conversations (two males only and two females only groups). The study took into account various reports and literature to provide the background and analyze the data to respond to the research questions. Additionally, the study collected data through desk reviews, unstructured conversations, reports, emails, WhatsApp messages, and phone calls that aid in situation analysis, utilizing a qualitative research methodology of situational analysis. Lack of experience with online training by trainers and trainees, along with inadequate training assistance, resulted in feelings of anxiety and unease. Trainees were frequently incapable of self-regulation and remained motivated to learn at home and they were unsure about the quality of the materials accessible to them. Recommendations on four major issues are given: providing complete support to trainees, trainers, and other institution personnel; improving remote and online training; ensuring policy certainty, implementation, and monitoring; and discovering and implementing effective interventions and innovations.