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Remote Windows Administrator Jobs in Boston, MA (NOW HIRING)

Performix

System Administrator

Boston, MA · Remote

While this position is primarily remote, you will serve our Boston\-based team and must live within ... Provision, image, and ship laptops (Windows\/Mac) and peripherals for onboarding employees ...

Eliassen Group

System Administrator - Mid

Cambridge, MA · Remote

$28 - $32/hr

The role will manage day-to-day administration of Windows-centric infrastructure across on-prem and ... and remote desktop technologies (VPN, RDP). * Ability to attain a Position of Public Trust and ...

CarGurus

Systems Administrator II

Boston, MA · Remote

You will work across identity, collaboration tools, office networking, and remote access ... Support and administer core enterprise systems and collaboration platforms across the business

RL Recruiting

Tech Support Engineer III (473)

Boston, MA · Remote

$35 - $45/hr

Systems Admin (Microsoft 365 Tech Support) Contract: 3 months Location: Remote Boston, MA - will ... Provision, image, and ship laptops (Windows/Mac) and peripherals for onboarding employees ...

Nadia Care

IT Support Specialist

Boston, MA · Remote

Administer Microsoft Intune (MDM) and O365 for a remote, multi-OS device fleet * Enforce security ... Experience supporting both Windows and macOS environments * Experience with IAM / access management ...

Arctiq

Senior Systems Engineer

Boston, MA · Remote

$107K - $146K/yr

... remote access/mobility solutions. * Administer and support cloud-based platforms and services such ... Advanced knowledge of VMware, Windows Server, TCP/IP, DNS, and related protocols. * Strong ...

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All JobsWindows Administrator JobsRemote Windows Administrator JobsRemote Windows Administrator Jobs in Boston, MA

Remote Windows Administrator information

See Boston, MA salary details

$11

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$71

How much do remote windows administrator jobs pay per hour?

As of Aug 30, 2026, the average hourly pay for remote windows administrator in Boston, MA is $50.99, according to ZipRecruiter salary data. Most workers in this role earn between $45.72 and $57.21 per hour, depending on experience, location, and employer.

What is a remote Windows administrator?

Remote Windows Administrators are IT professionals who manage and maintain Windows-based servers, desktops, and networks from a remote location. Their responsibilities include installing and configuring Windows operating systems, troubleshooting technical issues, performing system updates, and ensuring security policies are enforced. They use remote management tools to monitor system performance, apply patches, and resolve user problems without being physically present at the office or data center. This role is essential for organizations that operate distributed environments or have a need for offsite IT support.

What does a remote Windows administrator do?

The job duties of a remote Windows administrator involve working on the customization, configuration, maintenance, and updates of a Windows computer system. Your responsibilities in this work from home position involve performing updates and providing support for the company and organization that uses the Windows system, software, and apps that you install. You take steps to monitor the Windows network from your remote location and troubleshoot when problems arise. As an administrator, you often train staff to use Windows software and also communicate with vendors to ensure that your network has the latest software, cybersecurity, and compatibility updates.

What are the key skills and qualifications needed to thrive as a remote Windows administrator, and why are they important?

To thrive as a Remote Windows Administrator, you need a solid understanding of Windows Server operating systems, network protocols, and system security, typically backed by a degree in IT or relevant certifications like Microsoft Certified: Windows Server Fundamentals. Familiarity with remote management tools (such as Remote Desktop Services, PowerShell, and Active Directory) and ticketing systems is crucial for day-to-day operations. Strong problem-solving abilities, communication skills, and the ability to work independently help distinguish top professionals in this role. These skills ensure effective system administration, rapid issue resolution, and secure, reliable IT environments even when working remotely.

What are some common challenges faced by remote Windows administrators and how can they be managed?

Remote Windows Administrators often encounter challenges such as troubleshooting issues without physical access to the hardware, managing security updates across distributed systems, and coordinating with on-site staff for tasks that require hands-on intervention. Effective communication, leveraging remote management tools, and maintaining clear documentation are key strategies to address these challenges. Regular training on new remote technologies and cybersecurity best practices also helps ensure smooth system administration and reduces downtime.

What is the difference between Remote Windows Administrator vs Remote Network Administrator?

AspectRemote Windows AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and system updatesManaging network infrastructure, routers, switches, and firewalls
Industry UsageIT support, data centers, enterprise environmentsNetwork service providers, large organizations, IT departments
Common Search/ComparisonYesYes

The Remote Windows Administrator primarily focuses on managing Windows-based servers, Active Directory, and system configurations, while the Remote Network Administrator handles network infrastructure, including routers, switches, and firewalls. Both roles require similar certifications and are essential in IT environments, but they specialize in different aspects of IT infrastructure management.

More about Remote Windows Administrator jobs

What are the most commonly searched types of Windows Administrator jobs in Boston, MA?

The most popular types of Windows Administrator jobs in Boston, MA are:

What are popular job titles related to Remote Windows Administrator jobs in Boston, MA?

For Remote Windows Administrator jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Remote Windows Administrator jobs in Boston, MA look for?

The top searched job categories for Remote Windows Administrator jobs in Boston, MA are:

What cities near Boston, MA are hiring for Remote Windows Administrator jobs?

Cities near Boston, MA with the most Remote Windows Administrator job openings:

Remote Windows Administrator jobs near you
Infographic showing various Remote Windows Administrator job openings in Boston, MA as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 18% Part Time, and 8% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $106,062 per year, or $51 per hour.

System Administrator

Performix

Boston, MA • Remote

Contractor

Posted 4 days ago

Job description

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Job Overview<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>We are seeking a skilled and proactive Helpdesk Specialist \/ Junior Systems Administrator for a 3\-month contract.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>In this dual\-focus role, you will provide top\-tier end\-user support while handling foundational systems administration tasks, with a heavy emphasis on Microsoft 365 environments.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>While this position is primarily remote, you will serve our Boston\-based team and must live within 30 minutes of Boston to assist with occasional hands\-on hardware deployments, equipment imaging, or urgent on\-site troubleshooting.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Will need to be able to reach office in 30 minutes to support any tech emergencies if needed.<\/span><\/span><\/span>
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Key Responsibilities:<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>End\-User Support & Helpdesk<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Serve as the primary point of contact for remote and local employees experiencing technical issues (hardware, software, network, and access).<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Diagnose, troubleshoot, and resolve Tier 1 and Tier 2 helpdesk tickets with a high level of customer service and responsiveness.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Provision, image, and ship laptops (Windows\/Mac) and peripherals for onboarding employees; coordinate the return of equipment for offboarding.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Junior Systems Administration & M365<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Handle end\-to\-end Microsoft 365 (Office 365) setups, including creating user accounts, configuring mailboxes, assigning licenses, and setting up distribution groups\/shared mailboxes.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Manage user permissions and access control via Microsoft Entra ID (formerly Azure Active Directory) and\/or local Active Directory.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Configure and troubleshoot M365 applications (Teams, SharePoint, OneDrive, Outlook) for end\-users.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Assist with basic network troubleshooting (VPN connectivity, Wi\-Fi, home internet configurations for remote workers).<\/span><\/span>
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Required Experience:<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>2+ years of experience in an IT Helpdesk, Technical Support, or Junior SysAdmin role.<\/span><\/span>
<\/p>

        <\/span><\/span><\/span><\/span><\/span>Strong M365 Experience: Proven track record of configuring Office 365 accounts, provisioning mailboxes, and managing basic tenant settings.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Proficient with Active Directory \/ Microsoft Entra ID user administration.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Strong troubleshooting skills across Windows 10\/11 and macOS environments.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Experience utilizing MDM tools (e.g., Intune, Jamf) for device deployment is a major plus.<\/span><\/span>
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Location & Contract Requirements:<\/span><\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>Must be physically located within a 30\-minute radius of Boston, MA.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Must have a reliable home internet connection and a dedicated quiet workspace.<\/span><\/span>
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