This paper focuses on a group of mothers of immigrant origin as they engage in explorations and conversations about mathematics. We examine how bringing in tasks that draw on their children's school mathematics, and on the participants' knowledge and experiences, can inform us about their understanding of mathematics and provide opportunities to further enhance this understanding. Our analysis centers on two different types of mathematical tasks, both with rich potential for adult numeracy education. The first type of task engages the mothers in school mathematics through an exploration of addition and subtraction. In the second type of task, we look at mothers as adult learners working on two mathematical problem solving tasks, with different levels of connections to their everyday experiences. The findings point to a relationship between the type of context (everyday based versus school based) and the nature of the adult learners' mathematical sense making and engagement with the tasks. While there was some initial apprehension towards the school based tasks, the direct connection to what their children are learning was a strong motivator. The everyday based tasks bring up the potential tension between everyday mathematics and academic mathematics. The more the task connected to their everyday knowledge, the more the mothers drew on their experience to offer approaches that made sense from a practical point of view. We argue that these different types of tasks can complement each other in working with adult learners to enhance their numeracy skills.