This chapter presents the environment in which the Dr Math project operates and the types of questions posed to the tutors. The mathematics tutors are primarily South African university students, but graduates and mature members of society are also welcomed as volunteers. The project was piloted at one inland high school in a small village and, at that point in time, no more than 20 to 30 pupils were expected to participate in the project. Dr Math platform currently uses software developed by the CSIR Meraka Institute, it is possible for individual teachers to create similar systems for use with their pupils using free resources found on the Internet. The Dr Math online scaffolding environment is built on the first two levels of Anghileri's three-level scaffolding framework and represents a range of teaching strategies that have been adapted for the mathematics tutoring of secondary school learners through the Dr Math platform.