Based on the study entitled “National Observatory for Special Education: Network Studies on Multifunctional Resource Rooms" (Mendes, 2010), this article aims at discussing the assessment processes that took place in these rooms for multifunctional resources. The Greek mythology metaphor “Achilles’ Heel” in the title above is justified by the vulnerability of assessment in the process of inclusion. The main strategy for gathering data in this study was the adoption of focus groups led by the researchers. We sought to understand the meaning of initial assessment in the routines of the teachers involved in this study. Based on data analysis, we verified that the initial assessment procedures strongly resemble medical records issued by clinical professionals. The specialist teacher, together with the regular teacher, is in charge of identifying only students’ initial “learning inability”. Specialist teachers are not aware of the fact that they are responsible for this assessment, including for school census purposes. The data point to an unclear view of assessment, with poor interaction between these identification processes and the intervention procedures. The data also show the poor interaction between the relevant public services, which makes the family responsible for obtaining the student’s report. The results point to the need of more significant investments to restructure schools, providing them with collective spaces for discussing such serious issues and allowing us to develop more inclusive pedagogical practices regarding students' assessment.