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Windows 10 Upgrade Jobs (NOW HIRING)

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$20 - $35/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$20 - $35/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$17.50 - $22.25/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$20 - $35/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$17.50 - $22.25/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

MetroSys

Desktop Support Technician

Vincennes, IN · On-site

$17.50 - $22.25/hr

Provide brief end-user support and walk-throughs following upgrade completion. Required Qualifications * 2-5 years of hands-on desktop support experience. * Strong experience performing Windows 10/11 ...

Connection

IT Upgrade Technician, WIN11

Hudson, NH

$35/hr

Connection has a fantastic opportunity through our Technical Staffing division for a Windows 11 ... This will be a contract opportunity (8-10 weeks) The offering pay is $35/hr. Onsite: M-F ...

Connection

IT Upgrade Technician, WIN11

Hudson, NH · On-site

$35/hr

We are seeking experienced and professional Windows 11 Deployment Technicians to support a large ... This will be a contract opportunity (8-10 weeks) The offering pay is $35/hr. Onsite: M-F ...

CONNECTION

IT Upgrade Technician, WIN11

Hudson, NH · On-site

$35/hr

We are seeking experienced and professional Windows 11 Deployment Technicians to support a large ... This will be a contract opportunity (8-10 weeks) The offering pay is $35/hr. Onsite: M-F ...

CONNECTION

IT Upgrade Technician, WIN11

Hudson, NH

$35/hr

We are seeking experienced and professional Windows 11 Deployment Technicians to support a large ... This will be a contract opportunity (8-10 weeks) The offering pay is $35/hr. Onsite: M-F ...

Connection

IT Upgrade Technician, WIN11

Hudson, NH · On-site

$35/hr

We are seeking experienced and professional Windows 11 Deployment Technicians to support a large ... This will be a contract opportunity (8-10 weeks) The offering pay is $35/hr. Onsite: M-F ...

SEBENZA

Deskside Support Technician

Washington, DC

$60K - $80K/yr

Baseline desktop support (Windows 7 & Windows 10) and the Microsoft Office Suite. * Perform network ... Security patches and software upgrade surge support * Support technology upgrades - both hardware ...

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All JobsWindows 10 Upgrade Jobs

Windows 10 Upgrade information

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$10

$55

$67

How much do windows 10 upgrade jobs pay per hour?

As of Jul 11, 2026, the average hourly pay for windows 10 upgrade in the United States is $55.87, according to ZipRecruiter salary data. Most workers in this role earn between $48.08 and $61.54 per hour, depending on experience, location, and employer.

Can I still upgrade to Windows 11 for free?

Windows 10 users can upgrade to Windows 11 for free if their device meets the minimum hardware requirements, such as compatible processors, TPM 2.0, and Secure Boot capability. The upgrade is available through Windows Update and requires a compatible system with the latest updates installed. As a Windows 10 upgrade specialist, ensuring device compatibility is essential before initiating the upgrade process.

What is a Windows 10 Upgrade job?

A Windows 10 Upgrade job involves updating computers from an older version of Windows to Windows 10. This process includes preparing systems, backing up data, ensuring software compatibility, and installing the upgrade. IT professionals may also troubleshoot issues, configure settings, and provide user support post-upgrade. The goal is to ensure a smooth transition with minimal downtime and optimal performance.

How to get paid updates for Windows 10?

As a Windows 10 upgrade specialist, paid updates are typically provided through official Microsoft support plans or service agreements. These may include extended support or custom maintenance contracts that ensure timely updates and technical assistance for enterprise environments.

Can I still use Windows 10 after 2026?

Windows 10 will continue to receive support and security updates until October 14, 2025, after which it will no longer be officially supported. As a Windows 10 upgrade specialist, it is advisable to plan for a future upgrade to Windows 11 or newer operating systems to ensure ongoing security and compatibility.

Can I still upgrade to Windows 11 for free in 2026?

Windows 10 upgrade offers ended in 2023, and Microsoft no longer provides free upgrades to Windows 11 for new devices or existing Windows 10 PCs. Upgrading to Windows 11 typically requires compatible hardware and a valid license, which may involve purchasing a new license if your device is not eligible for a free upgrade. As of 2026, free upgrades are unlikely unless specific promotional offers are announced by Microsoft.

What are some common challenges faced during a Windows 10 upgrade project?

One of the most common challenges in a Windows 10 upgrade project is ensuring compatibility with legacy applications and hardware throughout the organization. IT professionals in this role must manage potential disruptions to end users, address unexpected errors, and maintain data integrity during migration. Working closely with multiple departments, upgrade specialists also coordinate schedules and provide user training to ensure a seamless transition. Addressing these challenges requires thorough planning, clear communication, and adaptability to troubleshoot issues as they arise.

What are the key skills and qualifications needed to thrive in the Windows 10 Upgrade position, and why are they important?

To excel in a Windows 10 Upgrade role, you should have strong technical knowledge of Windows operating systems, experience in system administration, and a background in IT support or related fields. Familiarity with deployment tools such as Microsoft Deployment Toolkit (MDT), System Center Configuration Manager (SCCM), and relevant certifications like CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate are commonly required. Excellent problem-solving abilities, communication skills, and attention to detail are crucial soft skills for success. These qualifications ensure smooth upgrade processes, minimal downtime, and effective user support in dynamic enterprise environments.

More about Windows 10 Upgrade jobs
What are the most commonly searched types of Windows 10 Upgrade jobs? The most popular types of Windows 10 Upgrade jobs are:
What states have the most Windows 10 Upgrade jobs? States with the most job openings for Windows 10 Upgrade jobs include:
What job categories do people searching Windows 10 Upgrade jobs look for? The top searched job categories for Windows 10 Upgrade jobs are:
Windows 10 Upgrade jobs near you
Infographic showing various Windows 10 Upgrade job openings in the United States as of July 2026, with employment types broken down into 1% As Needed, 78% Full Time, 15% Part Time, and 6% Contract. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution, with an average salary of $116,200 per year, or $55.9 per hour.
Desktop Support Technician

Desktop Support Technician

MetroSys

Vincennes, IN • On-site

$20 - $35/hr

Contractor

Re-posted 14 days ago

Job description

Position Overview

MetroSys is seeking experienced Desktop Support Technicians to support a large-scale Windows upgrade initiative within a hospital environment. This role will focus on upgrading, imaging, deploying, and validating approximately 1,400 Windows devices while minimizing disruption to clinical and administrative operations.

Candidates must be comfortable working onsite in a healthcare setting and adhering to strict security, compliance, and operational standards.

Key Responsibilities

  • Perform Windows OS upgrades and re-imaging on desktops and laptops across multiple hospital departments.

  • Backup and migrate user data, profiles, and settings as required.

  • Install and validate required applications, security tools, and updates post-upgrade.

  • Coordinate device swaps and ensure minimal downtime for clinical and administrative staff.

  • Troubleshoot hardware, software, and driver issues during deployment.

  • Document completed upgrades and update asset management systems.

  • Follow hospital compliance, privacy, and infection-control protocols.

  • Provide brief end-user support and walk-throughs following upgrade completion.

Required Qualifications

  • 2–5 years of hands-on desktop support experience.

  • Strong experience performing Windows 10/11 upgrades and system imaging.

  • Familiarity with enterprise deployment tools (SCCM, Intune, or similar).

  • Experience backing up and restoring user data.

  • Ability to work onsite in a hospital or regulated environment.

  • Strong customer service and communication skills.

  • Ability to lift and move equipment as needed.

Preferred Qualifications

  • Prior healthcare or hospital IT support experience.

  • Experience supporting clinical workstations or shared device environments.

  • Familiarity with Active Directory and user account troubleshooting.

Project Details

  • Fully onsite role.

  • Project-based engagement (timeline dependent on deployment schedule).

  • May require flexibility for early morning, evening, or weekend upgrade windows to minimize operational disruption.

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