This study aims to document the extent to which the use of digital technology enhances and extends high school teachers’ problem-solving strategies when framing their teaching scenarios. The participants systematically relied on online developments such as Wikipedia to contextualize problem statements or to review involved concepts. Likewise, they activated GeoGebra’s affordances to construct and explore dynamic models of tasks. The Apollonius problem is used to illustrate and discuss how the participants contextualized the task and relied on technology affordances to construct and explore problems’ dynamic models. As a result, they exhibited and extended the domain of several problem-solving strategies including the use of simpler cases, dragging orderly objects, measuring objects attributes, and finding loci of some objects that shaped their approached to reasoning and solve problems.