Students from refugee background enter Australian schools to pursue their educational goal. Though most do well academically, a few encounter educational difficulties and struggle to acquire English language. An exploratory qualitative case study approach was used to investigate factors contributing to poor development of English language and academic progress and challenges associated with the assessment process. Samir, a 14 year old grade nine student from Syria, who has resettled in Australia took part in the study. The method involved generating hypotheses and collecting data from multiple sources. Samir, his teachers and parents were interviewed. A battery consisting of a receptive vocabulary screener, verbal and non-verbal cognitive tests and a phonological processing measure, was administered. Results indicated that Samir had an average nonverbal cognitive ability and emerged as a socially skilled student with good English language conversational skills. Nevertheless, he lacked academic-level English skills and had difficulties learning this language due to multiple factors, including a possible underlying Developmental Language difficulty and/or Specific Learning Disorder. These difficulties coupled with underlying stress led him to disengage with his studies, resulting in poor academic performance. The findings highlighted challenges associated with the assessment of a student with cultural and language barriers. Potential options for flexible assessment and teaching are discussed.