In this work, we present the development of an automated extension tool to assist educators and increase the success and well-being of students by implementing flexible extension policies. Flexible extension policies materialize in many ways, yet there are similarities in students’ interactions with them; students tend to request multi-day long extensions repeatedly. In courses with hundreds or potentially thousands of students, providing a system to support this extension request demand is not possible given most currently available resources and limited staff. As such, a tool is necessary to help automate flexible extension processes. The development of this tool should reduce staff load while increasing individualized student support, which can be used in varying ways for different extension policies. Our research questions are: RQ1: Does the extension tool reduce barriers and stigma around asking for assistance? RQ2: Does the tool lessen the wait time between requesting and receiving an extension, and how does the tool improve students’ learning experience in the course? These questions will help inform us about how an automated tool for flexible extensions helps support growing course sizes and students who may not otherwise receive the support they need for their success and well-being in the course.