The College is currently piloting a one-credit asynchronous online course for students who incurred academic probation in their first semester at UVA. This is part of a broader College Initiative to provide greater support to students experiencing academic challenges. In fall 2022, the class will also be required for students who incur probation in the spring of their first year. The course is an academic skills class that was first offered in spring 2021 and was significantly restructured in consultation with the Learning Design & Technology team to accommodate larger enrollments. The course redesign includes new assignments that leverage Collab functionalities to streamline assessment and grading. Although the changes have made it possible to triple course enrollment from 35 students in one section to 120 students across four sections, we have encountered technological and instructional challenges that are interfering with our ability to meet our course objectives. As a required course for new students on probation, it is essential that we offer engaging, meaningful, and timely content while also being able to track student involvement in real-time, provide feedback, and individualized outreach. Our course objectives are to provide students with effective academic life skills, connect them with academic and wellness resources, and assist them in their return to good standing, thus avoiding suspension. Funding from the Learning Technology Incubator Grand will allow us to explore software options to improve our ability to achieve course objectives and enable us to hire graduate and undergraduate students to help with course redesign, implementation, grading responsibilities, and assessment.