The purpose of this study was to investigate the challenges that affect Grade R (kindergarten) learners’ readiness for learning, and the strategies used to ensure learner-readiness when entering Grade 1. Learning readiness is an ongoing process from the beginning to the end of an individual’s life. Learners at this early point in their lives (Foundation Phase) begin with their formal learning based on play, arithmetic, cultural activities, and reading and writing practice. The study engaged four teacher-participants: two Grade R teachers, and two Early Learnerhood Development practitioners from Grade 1. The case study research design was selected to elicit data through semi-structured open-ended interviews in natural settings to gain in-depth information which was analysed via the thematic analysis approach. The study findings revealed that teachers experienced challenges due to poor infrastructure, overcrowded classrooms, lack of resources, policy of passing all Grade R learners, admission of non-documented learners, and learners who skipped pre-school. To address these challenges which impacted Grade R learners’ readiness to enter Grade 1, teachers were resourceful and planned innovative and interesting play-based lessons. This ensured that Grade R learners’ readiness is largely play-based to develop them holistically by involving them in creative indoor and outdoor activities.