The use of assessment for learning (AfL) has been critical in improving students’ learning and teachers’ teaching as both respond to the information it provides. It is imperative that the information gathered through assessment is effectively utilized through a continuous process to provide the bridge between teaching and learning. With the advancement of technology, ICT has been leveraged to enhance assessment of learning that goes beyond simply diagnose and identify students’ learning needs; it can be used to provide feedback to inform teachers’ pedagogical approaches and help learners plan and manage the next steps in learning. This session discusses the development of digital learning environments for learning mathematics and AfL guiding principles / approaches adopted by a group of mathematics teachers in a primary school in Singapore. Through the observation of lessons held in the classrooms, the teachers identified the need to incorporate interactive assessments that gives students timely targeted feedback that communicates progress and directs subsequent effort in a collaborative and non-threatening environment. By tapping web2.0 technologies (e.g. paddlet, Kahoots etc) and learning through gamification, the group of teachers successfully redesigned the learning environment that empowers students to take ownership in learning to improve math literacy and take learning beyond the classroom environment.