Agenda Report
Fullerton City Council
MEETING DATE: October 21, 2025
TO: CITY COUNCIL
SUBMITTED BY: EDDIE MANFRO, INTERIM CITY MANAGER
PREPARED BY: AARON FRY, CHIEF TECHNOLOGY OFFICER
Kim Chaudhry, Senior administrative analyst
SUBJECT: $197,857 AGREEMENT WITH GLASS BOX TECHNOLOGY FOR WINDOWS 11 UPGRADE PROJECT
SUMMARY
Staff requests approval to contract with Glass Box Technology to upgrade all City of Fullerton workstations from Windows 10 to Windows 11 to enhance security, improve system performance and ensure continued support from Microsoft as Windows 10 approaches end-of-support in October 2025.
PROPOSED MOTION
Authorize City Manager, or designee, to execute $197,857 Agreement with Glass Box Technology for Windows 11 Upgrade project implementation, in a form approved by the City Attorney.
ALTERNATIVE OPTIONS
Approve the Proposed Motion
Continue using Windows 10 until support ends, risking security vulnerabilities and compliance issues Adopt a hybrid OS strategy and upgrade only critical departments to Windows 11 while others remain on Windows 10 temporarily Explore using alternative operating systems, such as Linux or other platforms, which would require extensive retraining and software compatibility assessments Other options brought by City Council.
STAFF RECOMMENDATION
Staff recommends the Proposed Motion.
CITY MANAGER REMARKS
None.
PRIORITY POLICY STATEMENT
This item matches the following Priority Policy Statement:
Fiscal and Organizational Stability.
FISCAL IMPACT
The estimated cost for the Windows 11 Upgrade project implementation with Glass Box Technology totals $197,857. The Fiscal Year 25-26 Adopted Budget includes this project within the Information Technology Fund (Fund 68). The Enterprise Agreement with Microsoft includes Windows 11 licenses. The licenses do not require separate purchase or additional appropriations.
BACKGROUND AND DISCUSSION
Microsoft announced Windows 10 will reach end of support in October 2025. After this date, Microsoft will no longer provide:
Security updates or patches (which increases vulnerability to cyber threats) Bug fixes or performance enhancements (which may affect system reliability) Technical support, including troubleshooting or issue resolution assistance.
Continuing to use unsupported software poses serious risks for municipal operations, including:
Non-compliance with federal cybersecurity standards, such as the National Institute of Standards and Technology (NIST) Cybersecurity Framework, which emphasizes the importance of maintaining secure and up-to-date systems Violation of Criminal Justice Information Services (CJIS) Security Policy, which requires agencies handling criminal justice data to implement robust security controls, including timely software updates and patch management.
Failure to upgrade may increase exposure to malware, ransomware and data breaches which could disrupt public services and compromise sensitive information. Transitioning to Windows 11 ensures continued compliance with these standards, access to critical security updates and aligns with government IT operations best practices.
The City operates approximately 550 workstations on Windows 10. IT conducted Windows 11 pilot testing in several departments with positive results. The upgrade would occur in multiple phases, allowing sufficient time between phases to resolve issues. This approach minimizes impacts to regular business operations.
Glass Box Technology (Glass Box) currently provides managed IT services to the City and staff recommends as the vendor to perform the Windows 11 upgrade. Glass Box has an in-depth understanding of the City technology environment, departmental workflows and operational priorities. Their proven expertise in managing and configuring Microsoft products in complex enterprise settings, combined with familiarity with City infrastructure and security requirements, makes them the most qualified and efficient partner to lead this critical upgrade initiative.
The project would include the following activities:
design, build and test a new standard Windows 11 operating system image compatible with devices and applications used at the City of Fullerton identify users and devices for upgrade
develop a phased migration strategy based on device readiness and user roles assess and resolve application compatibility through testing and packaging pilot testing to validate performance, stability and user experience align rollout with cybersecurity policies, including patching and compliance integrate deployment with existing cloud management tools establish change control processes and project communications update IT support documentation and train Help Desk on new procedures maintain oversight of schedule, budget, risks and issues throughout the project lifecycle contingency for unexpected technical issues.
Glass Box implementation for the Windows 11 Upgrade project costs an estimated $197,857. The FY 2025-26 Adopted Budget includes this approved project.
Attachments:
Attachment 1 – Glass Box Technology Statement of Work
cc: Interim City Manager Eddie Manfro
Glass Box Agreement for Windows 11 Upgrade Project
October 21, 2025 - Page 2