This study investigated Korean middle school students’ English essay writing performance and perceptions related to prior writing experiences. Seventy-nine students completed one of three essay tasks aligned with the Korean national curriculum and the International Baccalaureate (IB) Middle Years Programme (MYP). They then responded to a survey on their writing experiences, task difficulty, and task selection rationale. Student responses were scored using four IB MYP writing assessment criteria: vocabulary, grammar, organization, and communication. The results revealed differences between students with and without prior writing experience. Experienced students showed greater confidence and achieved higher scores across all scoring domains, while inexperienced students reported higher difficulty and adopted avoidance-based task selection strategies. Regardless of experience, vocabulary and grammar were the most challenging, whereas communication scores were higher. These findings suggest that prior writing experience is linked to task engagement and writing quality. The results underscore the need to provide diverse, curriculum-aligned writing opportunities to support students’ growth in written communication.