The Technical Support Specialist plays a key role in supporting desktop, mobile, endpoint management, and automotive diagnostic technologies used by Department of Fleet Services (DFS) staff. The position provides first- and second-level technical support for hardware, software, connectivity, user access, and device-related issues. Responsibilities also include supporting Microsoft Intune, Active Directory, Entra ID (Azure AD), Group Policy, Microsoft 365, Windows devices, and specialized Fleet diagnostic technologies, while assisting with device deployments, basic scripting, technical documentation, IT projects, and implementation of reliable technology solutions.   Essential Functions Must be resourceful, self-motivated, and able to take initiative while working independently or as part of a team. Diagnose and resolve advanced hardware, software, networking, mobile device, and vehicle diagnostic hardware/software issues. Support and administer Windows endpoints using Microsoft Intune, including device enrollment, application deployment, configuration, compliance, and troubleshooting. Perform user, computer, group, and device administration within Active Directory and Microsoft Entra ID (Azure AD). Assist with Group Policy (GPO) troubleshooting, testing, and implementation for Fleet devices and users. Utilize basic PowerShell scripting and command-line tools for user/device management, reporting, troubleshooting, and repetitive administrative tasks. Support Windows 10/11 deployments, updates, patching, device replacements, and technology lifecycle management. Follow DFS IT practices, including TDX – Team Dynamix, technical documentation, asset tracking, software licensing, and established IT procedures. Support specialized Fleet technology, including vehicle diagnostic laptops, tablets, diagnostic applications, and related hardware. Analyze and troubleshoot system/application, authentication, connectivity, and access-related issues and coordinate with Citywide IT when necessary. Assist with IT projects, technology deployments, system upgrades, and coordination with outside vendors. Maintain effective communication with DFS staff, management, vendors, and Citywide IT professionals and respond promptly to customer and operational needs. Maintain effective communication with DFS staff, management, vendors, and Citywide IT professionals and respond promptly to customer and operational needs.