This research was conducted to find out how strategies primary school age children use to solve simple math problems are related to their understanding of mathematical concepts, how this impacts their ability to solve more complex word problems and what we can learn from analyzing the strategies. This research is important because there is a need to improve mathematics education so that children develop deeper, more connected, mathematical understandings. A multiple case study was used; each case was analyzed to see what could be learned. The data was collected in the form of videotaped interviews. These interviews were analyzed and a storyline was composed. The main finding was that the kinds of strategies children use to solve simple math problems do have an impact on how they approach more complex word problems. The implications are that children need to learn efficient strategies early so they can become successful mathematicians.