BOE Appoints Pupil Services Director, Looking to Move Past Controversy
- Philip Thibodeau
- 2 days ago
- 4 min read
The first order of business for the Board of Education at its February 5 special meeting was to vote on the appointment of a permanent Director of Pupil Services for the Southington school system.
All nine members of the Board voted in favor of appointing interim director Amy Aresco to the position. Once the votes were cast, the Board stood up to applaud Aresco, who was present on the dais, followed by members of the public. During the brief recess that followed, friends and a large contingent of Aresco’s family came up to congratulate her.
It has been a long journey for Aresco, who took on the role of interim director in September of 2025. Before that she had served as Special Education Coordinator for the district, with additional responsibilities for handling Title IX and VI staff training and claims. She began her career as a special education specialist in Meriden, where she still resides. She has a B.S. in education from Keene State College, an M.A. from SCSU, and a certificate in School Superintendency from CCSU.
Pupil Services is a department in the school system that offers support for the education of students who has been officially classified as having special needs. The students in question range from 3 to 22 years old and confront a variety of specific challenges that impact their ability to read, communicate, or interact with other people. The department is staffed by psychologists, social workers, nurses and other specialists, and serves roughly 1,000 students.
In a press release Aresco wrote:
“Thank you to the Board of Education for its confidence in my ability to lead the Pupil Services Department. I have had the privilege of working in Southington for the past ten years as part of the Special Education Coordinator Team, and I am excited for the opportunity to implement my vision to promote excellence in services for students with special needs while strengthening partnerships with families and school teams. I look forward to connecting with Southington families and continuing to collaborate with our dedicated staff.”
“As we move forward, my focus will remain on keeping students at the center of our work, supporting staff in their vital roles, and strengthening our practices while meeting all state and federal responsibilities. I value open communication, collaboration, and shared problem-solving, and I look forward to building strong relationships across our department, schools, and community.”
Trying to Move on from a Troubled Chapter
The task that confront her now is a formidable one. Aresco came on as a replacement for Rebecca Cavallaro, who left the district last year after a tenure as Pupil Services Director that was marked by controversy.
Cavallaro was originally hired by Southington School System in 2020, just as the most disruptive effects of the COVID-19 pandemic were being felt. The superintendent at the time, Timothy Connollan, asked and received permission from the Board of Education to exercise his own best judgment in making an offer for a new Pupil Services Director. Connollan then brought on Cavallaro, who he knew from their time together in the Oxford school system, a district Connollan headed from 2012 to 2018.
Cavallaro began her tenure as Southington’s Pupil Services director in July of 2020. Just a few months earlier, she had left Oxford under a separation agreement that paid her $105,000 in return for her resignation.
The exact reasons for the separation are not a matter of public record. However, her management of Oxford’s special education program had become the object of public criticism. As reported by the Connecticut Post, the parents of special education students in that town felt frustrated with virtually every aspect of the program – from the initial diagnosis of student needs to adherence to protocols and record-keeping. The Oxford parents group was a large one, boasting 100 members in a district that has about 1,600 students in total.
Eventually, parents complaints led to an audit that was designed to identify failings in the program and recommend improvements. The firm Cavallaro chose to conduct the audit, Cooperative Education Services, was headed by one Michael Regan - Cavallaro’s uncle. The seeming conflict of interest drew additional criticism.
After Cavallaro arrived in Southington, a similar pattern emerged. Once again, many parents of special needs students grew concerned that their children were not being screened properly, and that the services they were receiving failed to adhere to state standards. Parents shared their complaints with her and other members of the school administration, but not all felt that their concerns were being addressed.
While this was happening, Cavallaro once again sought help from a firm headed by Regan, this time paying it for a variety of consulting services. The firm, Incompliance LLC, was incorporated in August of 2021 from a Southington PO Box. From then until January of 2025 it was a vendor for the district. During that time it received over $128,045 for what are listed on budget documents as ‘purchased services’.
Eventually, district parents broached their concerns with members of the Board of Education and the Town Attorney. In March of 2025, Cavallaro was placed on administrative leave; an investigation was conducted in May, and she left the district last August.
The preceding account of Cavallaro’s tenure in Southington was based on documents obtained through FOIA from Oxford and Southington as well as conversations with parents and district officials. One parent, Jillian Carlson, has repeatedly spoken up at meetings of the Board of Education, calling for more transparency in its handling of the Pupil Services issue. She has also pleaded that the district taking parent input more seriously when screening special needs students.
Aresco is now the permanent director of a department that has had to endure this controversy. Part of the challenge she faces is how to move forward in a way that offers staff, parents and above all the students the support they require.