With the International Classification of Functioning, Disability and Health (ICF), the term disability is consolidated in its dynamic meaning as a condition that is defined by the interaction between personal factors and the environment in which one lives (WHO, 2001). The characteristics of the reference context that can be an obstacle or facilitation are evaluated with greater emphasis, including the perception of disability by teachers as a factor that will mediate the implementation of different behaviors and methodologies stemming from it. The purpose of the present survey, which includes 422 teachers attending a specialization course for support activities and was conducted through the administration of a questionnaire, was precisely to evaluate this perception. In particular, it evaluated the following: the differences in starting and finishing the specialization course for the achievement of the teaching qualification in support, the impact of previous experience with the disability, and the motivation to teach. Outcomes display a progressive normalization in the characteristics of a person with disabilities. The teaching strategies undergo a change between the beginning and the end of the course, with a focus from the general to the particular, becoming more targeted and detailed. In terms of opinions, emotions, and concerns, familiarity with disability seems to produce a less prejudicial and stereotyped representation, as does the teaching experience with a disabled pupil. The importance of active previous experience is confirmed in order to develop a better representation with a consequent reduction in prejudice. Further data emerge in terms of increased ability, at the end of the course, to verbally discriminate the concepts of inclusion and integration, with probable differences in approaches. The motivation for teaching is confirmed to be connected to job placement and therefore should be further investigated with scales that control the social desirability of the response. The present study shows the importance of both the perception of familiarity with disability and specialized education in supporting disabled students. We hope that future research might further investigate this area in order to improve the quality of life of disabled people through better relations with teachers and better academic outcomes.