The use of technology as a pedagogical practice is growing at a phenomenal rate due to the availability of numerous computer mathematics software. As a result, conscientious efforts need to be made by teachers to integrate technology effectively to enhance the teaching and learning processes and consequently learning outcomes of students. This non-equivalent quasi-experimental study sought to explore students’ achievements and their attitudes after using a dynamic Autograph software technology to learn circle theorems. One hundred and fourteen Senior High School students purposively selected from three different schools participated in the study. While students from two of the schools were taught using the Autograph technology in a social-interaction and self-exploration environment respectively, the group of students from the last school were taught conventionally without the use of the Autograph technology. The findings of this study showed that the three teaching strategies had a significant positive effect on students’ achievements. However, the social-interaction Autograph-assisted group significantly outperformed, followed by the self-exploration Autograph-assisted group, and then the conventional group. The study also showed that though the self-exploration group showed higher positive attitudes than the social-interaction, the Autograph-assisted groups in general reported overall positive attitudes towards using the technology indicating further that the Autograph-support made lessons practical, stimulating, and provided imagery simulations and multiple representations that enhanced visualisation and understanding. Implications of the Autograph technology use in teaching, while engaging students in small groups are discussed.