Critical thinking is a skill that school systems are trying to develop in their student populations. Numerous studies have been conducted on developing critical thinking skills such as self-regulation, interpretation, and analysis. However, available data on the use of learning management systems (LMS) as a means to develop critical-thinking skills have been opaque. This study examined the perceptions of local stakeholders and the impact of confidence-based assessment (CBA) on secondary students at one high school. The conceptual framework guiding the study represented a synthesis of theoretical perspectives on critical thinking and its development with the current research on the pedagogical foundations of LMS applications. This qualitative case study project was designed to understand the perceptions of teachers, administrators, and content developers regarding the viability of a LMS with CBA embedded to increase students' critical-thinking skills. The research question focused on the use of Moodle, an LMS option, modified to use CBA to measure, improve, and enhance critical thinking skills. Qualitative data from open-ended questionnaires and interviews were gathered from teachers, administrators, and content developers who had taken a CBA within Moodle, and then coded using typological analysis to explore the respondents' perspectives. Since compelling evidence was found that a cost-effective LMS with embedded CBA may provide a positive benefit to students, a project consisting of a detailed program implementation plan was proposed to the school district. If implemented, the program can be replicated by educational institutions, potentially contributing to social change by democratizing access to a testing methodology that increases students' background knowledge while measuring their critical thinking skills.