The purpose of this study was to investigate the problem solving strategies, problem solving episodes, and metacognitions of five Turkish high school freshmen and explore the interplay of these on their problem solving success in mathematics. Participants worked on ten problems selected among the released mathematical literacy items used in Programme for International Student Assessment (PISA) 2003. The research data had been collected through clinical interviews and a self-monitoring questionnaire filled by the participants. The data were coded and analysed according to a framework adopted from various researchers in the field. Our results have confirmed that the problem solving success is too complex to be clarified by a unique property or behaviour of the solver. It requires overcoming various obstacles to reach a successful result. Therefore, not only the students should have the required mathematical knowledge and a good repertoire of different problem solving strategies, but also they should know when and how to use those strategies, along with monitoring and regulating their problem-solving processes using their metacognitive skills.