Town staff presented a proposal to migrate town email and systems to a .gov domain with Overwatch as the implementation partner under a grant-like program; staff said Overwatch would manage migration, training and initial support and that some costs and setup activities are covered by the program. Board members raised questions about account counts, recurring Microsoft 365 licensing costs, and the town's capacity to maintain the environment after Overwatch's implementation period ends.
After discussion the board authorized pursuing the Overwatch .gov migration and noted two parallel items: (1) execute the grant-covered migration steps and (2) develop or contract for an in‑town IT capability (staff or hourly contractor) to maintain security, document version control, and administration after the migration. One board member asked the town administrator to produce recent IT spending numbers and to scope potential ongoing IT support options in follow-up materials to the board.