This study aims to evaluate the formative and reflective methodology--Thinkspace--which is aimed at teachers and based on Attachment Theory, allowing pedagogic strategies to be adjusted to the internal working models of attachment of students with challenging behaviours. The sample consisted of 28 teachers from the 5th to the 9th grade of schooling, belonging to schools in the Autonomous Region of Madeira, Portugal. We used a sociodemographic questionnaire, the Adult Attachment Scale, the Student-Teacher Relationship Scale and the Teacher Report Form for Teachers as evaluation instruments. Results show important changes in how teachers evaluate their students' behaviour and educational strategies, with higher use of Proximity and less use of Conflict within the relationship with challenging students. In conclusion, the "Thinkspace" methodology helped teachers adjust their strategies for improving the pedagogical relationship with the students that they considered challenging. Despite the small sample size, the study has significant ecological validity, providing clear indications that more research should focus on the applicability and benefits of educational practices informed by Attachment Theory and the "Thinkspace" model.