Nontraditional students enrolled in online courses tend to drop out within their first year because they do not have the basic literacy skills or essential college skills needed for success. They often need the guidance of an online instructor. The purpose of this case study was to explore the perceptions of instructors and students about the effectiveness of Skype as a scaffolding tool for increasing academic achievement for underprepared students in online remedial English composition courses through interactions with their instructor. The conceptual framework included Bruner's cultural-psychological theory of education, Vygotsky's social constructivist theory, and Siemens's connectivism theory. The study was centered on 4 research questions; the first 2 focused on students' and instructors' perceptions of student writing based on student-instructor Skype interactions, and the last 2 concentrated on students' and instructors' perceptions of Skype's effectiveness to scaffold English composition skills to remedial online students. The data sources were 6 student interviews, 2 instructor interviews, and 12 audio recordings of Skype sessions. Data were analyzed for patterns and themes using open coding. The key findings were that students and instructors perceived the Skype interactions created changes in students' writing because of ease of use, indispensableness, rapport, and skill acquisition. This study may affect positive social change by informing online instructors and other personnel of online institutions of higher education about the importance of real-time interactions between students and instructors and providing services for underprepared students using Skype to help enhance their learning of critical writing skills.