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Remote Windows 10 Upgrade Jobs in Boston, MA (NOW HIRING)

RL Recruiting

Tech Support Engineer III (473)

Boston, MA · Remote

$35 - $45/hr

Remote Boston, MA - will need to be able to reach office in 30 minutes to support any tech ... Strong troubleshooting skills across Windows 10/11 and macOS environments. Experience utilizing MDM ...

Performix

System Administrator

Boston, MA · Remote

While this position is primarily remote, you will serve our Boston\-based team and must live within ... Strong troubleshooting skills across Windows 10\/11 and macOS environments. Experience utilizing ...

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Remote Windows 10 Upgrade information

See Boston, MA salary details

$11

$60

$73

How much do remote windows 10 upgrade jobs pay per hour?

As of Aug 30, 2026, the average hourly pay for remote windows 10 upgrade in Boston, MA is $60.69, according to ZipRecruiter salary data. Most workers in this role earn between $52.21 and $66.88 per hour, depending on experience, location, and employer.

What is the difference between Remote Windows 10 Upgrade vs Remote Desktop Support Specialist?

AspectRemote Windows 10 UpgradeRemote Desktop Support Specialist
Primary RoleUpgrading and installing Windows 10 on user devices remotelyProviding remote technical support and troubleshooting for desktop issues
Required SkillsOS installation, system configuration, troubleshootingRemote support tools, troubleshooting, user assistance
Work EnvironmentIT support teams, client sites, remote setupsHelp desks, IT support centers, remote assistance
CertificationsCompTIA A+, Microsoft certificationsCompTIA A+, Microsoft certifications

While both roles involve remote technical work and require similar certifications, a Remote Windows 10 Upgrade focuses on deploying and updating Windows operating systems, whereas a Remote Desktop Support Specialist provides ongoing support and troubleshooting for various desktop issues. Understanding these differences helps in choosing the right career path or service.

What are the most commonly searched types of Windows 10 Upgrade jobs in Boston, MA?

The most popular types of Windows 10 Upgrade jobs in Boston, MA are:

What are popular job titles related to Remote Windows 10 Upgrade jobs in Boston, MA?

For Remote Windows 10 Upgrade jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Remote Windows 10 Upgrade jobs in Boston, MA look for?

The top searched job categories for Remote Windows 10 Upgrade jobs in Boston, MA are:

Remote Windows 10 Upgrade jobs near you
Infographic showing various Remote Windows 10 Upgrade job openings in Boston, MA as of June 2026, with employment types broken down into 97% Full Time, 1% Part Time, and 2% Contract. Highlights an 91% Physical, 3% Hybrid, and 6% Remote job distribution, with an average salary of $126,240 per year, or $60.7 per hour.

Tech Support Engineer III (473)

RL Recruiting

Boston, MA • Remote

$35 - $45/hr

Contractor

Posted 17 days ago

Job description

Title: Systems Admin (Microsoft 365 Tech Support)
Contract: 3 months
Location: Remote Boston, MA - will need to be able to reach office in 30 minutes to support any tech emergencies if needed.
Certification: Office 365 Cert (Highly Preferred)
Pay Rate: $35-45 an hour
Job Overview
We are seeking a skilled and proactive Helpdesk Specialist / Junior Systems Administrator for a 3-month contract. 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.
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.


Key Responsibilities
End-User Support & Helpdesk
Serve as the primary point of contact for remote and local employees experiencing technical issues (hardware, software, network, and access).
Diagnose, troubleshoot, and resolve Tier 1 and Tier 2 helpdesk tickets with a high level of customer service and responsiveness.
Provision, image, and ship laptops (Windows/Mac) and peripherals for onboarding employees; coordinate the return of equipment for offboarding.
Junior Systems Administration & M365
Handle end-to-end Microsoft 365 (Office 365) setups, including creating user accounts, configuring mailboxes, assigning licenses, and setting up distribution groups/shared mailboxes.
Manage user permissions and access control via Microsoft Entra ID (formerly Azure Active Directory) and/or local Active Directory.
Configure and troubleshoot M365 applications (Teams, SharePoint, OneDrive, Outlook) for end-users.
Assist with basic network troubleshooting (VPN connectivity, Wi-Fi, home internet configurations for remote workers).


Qualifications & Skills
Required Experience:
2+ years of experience in an IT Helpdesk, Technical Support, or Junior SysAdmin role.
Strong M365 Experience: Proven track record of configuring Office 365 accounts, provisioning mailboxes, and managing basic tenant settings.
Proficient with Active Directory / Microsoft Entra ID user administration.
Strong troubleshooting skills across Windows 10/11 and macOS environments.
Experience utilizing MDM tools (e.g., Intune, Jamf) for device deployment is a major plus.
Location & Contract Requirements:
Must be physically located within a 30-minute radius of Boston, MA.
Must have a reliable home internet connection and a dedicated quiet workspace.