This study was conducted while 9th grade students learn to solve inequalities and seeks to understand their approach to solving problems with a real-life context. Specifically, the aim is to understand: (1) What are the main characteristics of the students' approaches to the proposed problems? (2) What is the impact of the real context on the students' resolutions? A qualitative and interpretative methodology is adopted, based on case studies, with data collected through documentary collection and audio recording of discussions between a pair of students while solving problems. The main conclusions suggest a trend to approach problems without establishing immediate connections with what was being done in the classroom, with students' decisions being essentially guided by criteria of simplicity. The real context of the problems seems to have the potential to develop in students a more integrated mathematics, focused on understanding and not so much on the repetition of mechanical and meaning-independent procedures. The students' familiarization with the context in question is one of the aspects highlighted by this study.