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IT warns of cyber risks, seeks regular server and license upgrades and penetration tests
Summary
The town's IT director told the Finance Committee that cybersecurity remains a high priority, requested recurring capital for server replacement and workstation refresh, and asked for penetration testing and license upgrades to meet insurance requirements and support growing user counts.
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Michael (last name not specified), the town's IT director, briefed the Finance Committee on FY2026 IT and cybersecurity needs and requested operational and capital funding to support server replacement, device refresh and penetration testing.
He said the town has integrated Tyler content manager and OpenGov procurement and budgeting systems, rolled out Cartograph for GIS mapping for water, sewer and DPW, and is working on ADA compliance for websites ahead of new April regulations. Michael highlighted cybersecurity training for all town email users and warned that user compromise remains the leading risk vector despite technical protections.
IT requested funds for recurring workstation replacement (replacing COVID-era machines that are now end-of-life), a virtual server environment upgrade in its eighth year, annual licensing increases (Microsoft 365 and Adobe), and a penetration test required by the town's cyber-insurance policy. Michael said the penetration testing will cover municipal, airport, public safety and school systems and that the town has an insurance panel of vendors it can access quickly in the event of an incident.
Committee members asked about cyber-insurance mechanics, contingency funding and phone policy. Michael and Finance Director Brian said the town coordinates notification and response with insurers and can use panel vendors under insurance arrangements without seeking separate approvals to expedite remediation. The committee also discussed future IT staffing needs for additional application and GIS specialists.

