Windows System Engineer

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Senior Windows Infrastructure Migration Engineer

6+ Month Contract (with potential extension)
Work Hours: Monday–Friday, 8:00 AM – 5:00 PM
Work Arrangement: Hybrid – minimum 2–3 days per week onsite
Benefits: Medical, dental, and vision benefits included

Please Note: Not open to Third-Party Firms and candidate must reside in the Charlotte, NC area.

We are seeking a senior‑level Windows Infrastructure Migration Engineer to support enterprise modernization efforts focused on upgrading legacy Windows Server environments. This role is hands‑on and execution‑driven, centered on migrating business‑critical applications and services from Windows Server 2008 to newer supported versions (2019 / 2022) within an IaaS environment.  This is not a software development role. The focus is on operating system upgrades, IIS‑hosted applications, Windows Services, and legacy infrastructure dependencies.

Key Responsibilities

  • Migrate applications and server workloads from Windows Server 2008 to Windows Server 2019/2022
  • Lead and execute IIS website migrations, including application pools, bindings, authentication, and certificates
  • Migrate and validate Windows Services, including service accounts, permissions, and startup dependencies
  • Assess and support SQL Server application dependencies such as connection strings, service accounts, and permissions
  • Evaluate and migrate message queues (MSMQ or equivalent technologies)
  • Identify migration risks, compatibility issues, and remediation pathsDocument existing environments, migration steps, and post‑migration configurations
  • Collaborate with infrastructure, DevOps, and application teams during planning and execution
  • Troubleshoot and resolve post‑migration issues in production and non‑production environments

Required Skills & Experience

  • 8+ years of hands‑on Windows infrastructure experience
  • Proven experience migrating Windows Server workloads from legacy to modern versions
  • Strong IIS administration and application migration experience
  • Solid experience with Windows Services configuration and troubleshooting
  • Practical SQL Server knowledge from an application dependency standpoint
  • Experience working with MSMQ or similar enterprise queuing technologies
  • Strong troubleshooting, root‑cause analysis, and documentation skills
  • Working knowledge of Microsoft technologies (.NET applications from a hosting perspective)
  • Familiarity with Active Directory and networking fundamentals

Nice‑to‑Have

  • PowerShell scripting for automation or configuration Exposure to CI/CD tools (e.g., TeamCity, Octopus Deploy)
  • Azure IaaS familiarity
  • Experience working in change‑controlled enterprise environments
  • Security awareness in regulated systems

Soft Skills

  • Clear and effective communication
  • Ability to work independently while collaborating across teams
  • Detail‑oriented and methodical approach to migration work
  • Strong troubleshooting mindset
  • Willingness to learn legacy environments and undocumented systems

Onboarding Requirements
Employment is contingent upon successful completion of a background check and drug screening.


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