To improve student learning outcomes within online learning platforms, struggling students are often provided with on-demand supplemental instructional content. Recently, services like Yup (yup.com) and UPcheive (upchieve.org) have begun to offer on-demand live tutoring sessions with qualified educators, but the availability of tutors and the cost associated with hiring them prevents many students from having access to live support. To help struggling students and offset the inequities intrinsic to high-cost services, we are attempting to develop a process that uses large language representation models to algorithmically identify relevant support messages from these chat logs, and distribute them to all students struggling with the same content. In an empirical evaluation of our methodology we were able to identify messages from tutors to students struggling with middle school mathematics problems that qualified as explanations of the content. However, when we distributed these explanations to students outside of the tutoring sessions, they had an overall negative effect on the students' learning. Moving forward, we want to be able to identify messages that will promote equity and have a positive impact on students.