Many mathematics students require support for learning challenges, such as those invoked by mathematics anxiety. Support for these learning challenges is imparted through personal interactions between the student and the instructor, support staff or their peers. The online delivery of mathematics classes and support meetings reduced the quality of the interactions compared to face-to-face interactions. This article presents an alternative approach used to support students with learning challenges in a virtual learning environment. The approach reported was used in a four week online preparatory mathematics subject. Most of the students were mature age, some years out of formal mathematics education, and low in confidence. In preparing the modules the nature of the subject and the cohort was considered and additional content called Checkpoints was added. The Checkpoint pages were designed to alleviate the learning challenges the students faced by including signposting, supporting positive dispositions, providing alternative learning strategies, and sharing assessment strategies. Feedback showed students engaged with the Checkpoints and found them helpful, leading the students to reflect on their learning. The checkpoints also 'chunked' the math content, resulting in a 'nice break', and provided students with reassurance they were on-track.