This paper reports on a longitudinal phenomenographic inquiry into understanding how two postgraduate Syrian students' ways of approaching English language learning in their homelands influenced the shape of their personal study abroad goals, language strategy use and L2 identity. It is guided by Norton's (2013) conceptualisation of motivation as investment in learning a new language, and Hajar's [(2016) distinction between compulsory and voluntary strategies. The qualitative data suggest that the two participants acted agentively to accomplish their academic qualifications in the UK. However, the adjustments of the participant raised by a well-off, well-educated family and educated at outstanding private establishments to the new context appeared to be less taxing than the case of the other participant who came from a disadvantaged background in Syria. The former's positive prior language learning experiences along with the assessment methods of his MA programme helped him to build a positive linguistic self-concept in the UK, using diverse voluntary language strategies. This study reveals how strategy use and L2 identity development of learners in similar contexts might be influenced by educational policy and distribution of resources. From this qualitative longitudinal study, pedagogical implications and areas for ongoing research are suggested.