This study aimed to investigate children's performance and perception of problem difficulty in solving everyday mathematical problems with familiar versus unfamiliar contexts. In addition, the ways that children identify the similarities in problem-solving approaches between problem settings and everyday shopping were also examined. Forty-eight 4th-grade children participated in this study. Both quantitative and qualitative analyses were used. The results demonstrated that the familiar contexts neither enhance children's problem-solving performance nor decrease problem difficulty. More than half of the children did not identify the similarity in problem-solving approaches between problem settings and real shopping. When making judgments, even good problem-solvers were found to be distracted by superficial features in outward appearance and global mapping in similarity. This research highlights that children in the process of solving problems tend to be distracted by non-mathematical features in the problem settings. Some implications for instruction are given. (Contains 2 tables.)