Assessment practice in Maldivian schools is undergoing change. The newly developed draft of Maldivian National Curriculum with associated documents aligns assessment, instruction, and curriculum to provide optimum learning conditions for students. The Maldivian Ministry of Education (MOE), in collaboration with UNICEF, has introduced quality indicators for the Child Friendly Baraabaru School (CFBS) based on the Maldivian National Curriculum. These indicators stress the importance of maintaining a balance between assessment for learning (formative assessment) and assessment of learning (summative assessment). The dissemination and implementation of best practices in formative assessment are currently underway in Maldivian schools. This study portrays a “snapshot in time” of assessment practices of three teachers and utilizes the findings to provide an insight into the MOE’s initiative of assessment innovations in Maldivian classrooms and schools. The study found that the three teachers have to practice formative assessment within high quality interactions based on thoughtful questions, attend to responses, and with observation and documentation to reflect a valid picture of the whole child. Nevertheless, the study also showed how the three teachers separated assessment from teaching and learning as well as how the teachers documented and reported this assessment data. There is a strong element of competition for academic achievement, as reported in grades and numerical scores. The competition is amongst students, teachers and parents. This competition appears to get in the way of assessment being used to support teaching and learning. Nonetheless, when the research data was explored through a formative assessment lens, there was also evidence of formative assessment being used in the normal day-to-day happenings in the three classrooms. The teachers in this study were not always confident in their use of formative assessment, and did not necessarily recognize when they were using formative assessment strategies. They all wanted all of their students to be successful learners, and they wanted to be good teachers. The study shows some of the complexities that teachers face when implementing new approaches to assessment.