This study describes the experiences of secondary-level mathematics teachers from the Department of Education of Puerto Rico implementing the strategy of contextualized teaching. Qualitative research framed in phenomenology was conducted, collecting data through semi-structured interviews and a review of normative documents from the Department of Education. The findings provide valuable information about the use of contextualized teaching, the perception that teachers have of this strategy, as well as the challenges that participants face in its implementation. Some of the challenges they face during its implementation are limited resources and needs of teacher support. As a contribution to this research, a manual and a website were designed as teacher support tools for the implementation of contextualized teaching in secondary-level mathematics classes.