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Windows Server 2016 Jobs (NOW HIRING)

Encode, Inc.

VA · On-site

Experience supporting MS Windows server 2016/2019, Microsoft SQL 2014/2017, Windows 10. * Five (5)+ years of technical experience in integration and support of server and desktop technologies ...

Encode, Inc

Sr. Windows Administrator

Montgomery, VA · On-site

Experience supporting MS Windows server 2016/2019, Microsoft SQL 2014/2017, Windows 10. * Five (5)+ years of technical experience in integration and support of server and desktop technologies ...

Winaxis

Windows Systems Engineer

Lansing, MI · On-site

... Windows Server (2016+), RHEL 7.0+, Cloud platforms (Azure/AWS/GCP), Tomcat, IIS, MS SQL Management Studio, Dynatrace or similar monitoring tools, XML, PowerShell, Azure DevOps, Visio, and SSO ...

ASM Research

Windows Systems Administrator - Senior

Manage Windows Server infrastructure (2016/2019/2022) across all environments. * Perform system provisioning, configuration, patching, and hardening. * Administer Active Directory, Group Policy, and ...

Select Minds LLC

Senior Windows Engineer/Admin

Dallas, TX · On-site

$55 - $65/hr

Windows Server Management: Administer, maintain, and troubleshoot Windows Server 2016, 2019, and 2022 across large enterprise systems. Patch Management: Lead Microsoft's monthly patching cycles using ...

Jane Street

Windows Engineer

New York, NY

Advanced experience with the inner workings of Microsoft Windows 10/11 or Microsoft Windows Server 2016/2019/2022 * Experience with using PowerShell (or Python, C#) to automate deployment ...

Jane Street

Windows Engineer

New York, NY · On-site

Advanced experience with the inner workings of Microsoft Windows 10/11 or Microsoft Windows Server 2016/2019/2022 * Experience with using PowerShell (or Python, C#) to automate deployment ...

City of New York

Windows Support Engineer

Brooklyn, NY · On-site

... Server 2016, 2019, 2022, and 2025 environments. • Provide technical support, troubleshooting, diagnosis, and problem resolution; perform Windows Server maintenance activities. • Provide 24/7 ...

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Windows Server 2016 information

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$89.5K

$107.8K

$124.5K

How much do windows server 2016 jobs pay per year?

As of Jul 12, 2026, the average yearly pay for windows server 2016 in the United States is $107,814.00, according to ZipRecruiter salary data. Most workers in this role earn between $98,500.00 and $117,000.00 per year, depending on experience, location, and employer.

What is Windows Server 2016?

Windows Server 2016 is a server operating system developed by Microsoft as part of the Windows NT family. Released in October 2016, it provides a robust platform for running enterprise-level applications, managing network resources, and supporting cloud integration. Key features include enhanced security, support for containers, Nano Server deployment, and improved virtualization through Hyper-V. It is widely used by organizations to manage infrastructure, data storage, and application hosting. Windows Server 2016 is supported by a range of tools and services to help businesses achieve scalability and reliability.

What are some common challenges faced when managing a Windows Server 2016 environment, and how can I prepare for them?

Managing a Windows Server 2016 environment often involves challenges such as maintaining system security, ensuring regular updates, and troubleshooting compatibility issues with legacy applications. You may also encounter complexities in configuring roles like Active Directory, DNS, and file services, especially in larger or hybrid infrastructures. Preparing for these challenges involves staying current with Microsoft's best practices, regularly testing updates in a lab environment, and actively collaborating with network and security teams to maintain system integrity and minimize downtime.

What is the difference between Windows Server 2016 vs Windows System Administrator?

FeatureWindows Server 2016Windows System Administrator
Primary RoleServer OS deployment and managementManaging and maintaining Windows Server environments
CertificationsMicrosoft Certified: Windows Server 2016Microsoft Certified: Windows Server Fundamentals or equivalent
Work EnvironmentData centers, enterprise networksIT departments, server rooms, cloud environments
Skills FocusServer configuration, security, virtualizationTroubleshooting, deployment, user management

Windows Server 2016 is an operating system designed for server deployment, while a Windows System Administrator is a professional responsible for managing and maintaining Windows Server environments. The administrator's role involves applying skills and certifications related to Windows Server 2016, working in enterprise or data center settings. Understanding the OS features helps administrators optimize server performance and security.

What jobs can I get with Server+?

CompTIA Server+ certification qualifies individuals for roles such as server administrator, systems administrator, network technician, and IT support specialist. These jobs involve managing, troubleshooting, and maintaining server hardware and software in enterprise environments, often requiring knowledge of Windows Server 2016 and related technologies.

Is Windows Server 2016 no longer supported?

Windows Server 2016 reached its end of mainstream support on January 11, 2022, and extended support will end on October 14, 2027. As a Windows Server administrator, staying current with supported versions is important for security and compliance, so upgrading to newer versions is recommended before support ends.

Can you go from server 2016 to 2025?

Upgrading from Windows Server 2016 to Windows Server 2025 is not possible because Windows Server 2025 does not exist; Microsoft typically releases new server versions every few years, and the latest available is Windows Server 2022. To stay current, administrators should plan upgrades to supported versions as they are released and ensure compatibility with existing applications and infrastructure.

What are the key skills and qualifications needed to thrive as a Windows Server 2016 Administrator, and why are they important?

To thrive as a Windows Server 2016 Administrator, you need a solid understanding of Windows Server operating systems, networking fundamentals, and experience with Active Directory and system administration, often verified by a relevant IT degree or Microsoft certification (such as MCSA: Windows Server 2016). Familiarity with tools like PowerShell, Hyper-V, and server monitoring solutions is typically required to efficiently manage and troubleshoot server environments. Strong problem-solving skills, attention to detail, and effective communication help administrators collaborate with teams and address technical issues proactively. These competencies ensure secure, reliable, and optimal server performance, which is crucial for supporting organizational IT infrastructure.

Is the 2016 server end of life?

Windows Server 2016 reached its end of mainstream support on January 11, 2022, and extended support will end on October 14, 2027. As a Windows Server administrator or IT professional, it is important to plan for upgrades or migrations before the end of support to ensure security and compliance.
More about Windows Server 2016 jobs
What job categories do people searching Windows Server 2016 jobs look for? The top searched job categories for Windows Server 2016 jobs are:
Windows Server 2016 jobs near you
Infographic showing various Windows Server 2016 job openings in the United States as of July 2026, with employment types broken down into 74% Full Time, 24% Part Time, and 2% Contract. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution, with an average salary of $107,814 per year, or $51.8 per hour.

Technical Lead-Cloud & Infra Engg

Birlasoft

Alpharetta, GA • On-site

Full-time

Posted 12 days ago

Job description

Competencies
Area(s) of responsibility
Windows Vulnerability Remediation Engineer (Server Infrastructure - Windows Server 2016/2019/2022)
The Windows Vulnerability Remediation Engineer is responsible for accelerating vulnerability remediation and patching activities across server infrastructure.
o Chef (cookbooks/recipes, attributes, templates, policy files as applicable)
o Ansible (playbooks, roles, inventories, modules-Windows modules/WinRM-based execution as applicable)
o PowerShell and scripting (server-side automation and custom remediation logic)
o Ruby for maintaining/extending Chef-based remediation code and custom logic
Scope (In-Scope / Out-of-Scope)
In-Scope
• Server infrastructure running Windows Server 2016, 2019, 2022
• End-user computing (desktops/laptops)
• Network/security appliances, storage appliances, or specialized non-server devices
Required Qualifications
• 6-10 years of strong hands-on experience with Windows Server 2016/2019/2022 in enterprise environments.
• Proven experience driving vulnerability remediation and patch management for Windows servers.
• Expertise with Qualys (or equivalent vulnerability scanners) including interpreting findings, false-positive validation, and closure verification.
• Automation experience with Chef and/or Ansible in production Windows server environments.
• Strong scripting skills (PowerShell; plus ability to use/maintain shell scripting where applicable in the environment).
• Working proficiency in Ruby (or ability to maintain/extend existing Ruby codebases used for Chef remediation).
• Strong understanding of Windows security fundamentals (patching, services, permissions, registry, authentication, TLS/cipher considerations as applicable).
• Experience working with change management, incident/problem management, and coordinating across multiple support teams.
Preferred Qualifications
• Familiarity with compliance/security frameworks and server hardening concepts (e.g., Microsoft Security Baselines, CIS benchmarks, STIG concepts) as applied to Windows Server.
• Experience with CI/CD or automated testing for infrastructure code (linting, unit/integration testing where applicable).

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