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{URGENT}: Windows 10 Support ENDS on Oct. 14th. Extended Security Updates Available

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Windows 11

ACT NOW!  Support for Windows 10 officially ends on October 14, 2025. After this date, Microsoft will no longer provide software updates and technical assistance. If you are not upgrading to Windows 11, you must purchase Windows 10 Extended Security Updates to continue receiving critical and important security updates.

Without these extended security updates, continuing to use Windows 10 dramatically increases your exposure to significant risks. Your systems become prime targets for cyberattacks, ransomware, and data breaches. You risk costly downtime, loss of sensitive information, and severe compliance issues. 

Proactive planning and action are not just recommended, they are critical for your business continuity and security.

Know Your Windows 10 Options

We agree with Microsoft’s recommendation to upgrade all eligible systems to Windows 11. We also understand you may have budget constraints or compatibility issues with older software.

You can check if your PCs will run Windows 11 using Microsoft’s PC Health Check app. If your PC will not run Windows 11, you have options other than buying new devices.

Windows 10 Extended Security Updates (ESU): 

Microsoft has release pricing for ESU licenses.  The license are available as a one-time purchase for each year. You do not need to commit to multiple years up-front, you can purchase the licenses annually if needed.  The pricing is as follows:

  • Year 1 – from October 2025 to October 2026 – $61 each
  • Year 2 – from October 2026 to October 2027 – $122 each
  • Year 3 – from October 2027 to October 2028 – $244 each

Important Notes:

  • Not all systems are eligible to install the updates. To be eligible to install updates from the ESU program, devices must be running Windows 10, version 22H2. For more information on prerequisites and enabling ESU in commercial environments, see Enable Extended Security Updates (ESU).
  • ESU Program updates do NOT include: New features; Customer-requested non-security updates; Design change requests; or General support.
  • The Windows 10 ESU only includes support for the license activation, installation, and possible regressions of the ESU itself for organizations with a support plan in place.

Keep in mind, the Windows 10 Extended Security Update program serves as a temporary bridge and does not address underlying hardware or software compatibility issues related to upgrading to Windows 11.

Virtual Desktop Services: 
  • Using virtual desktop services, such as Azure Virtual Desktop, allow you to use your existing PCs to access a robust and secure Windows 11 environment. Virtual desktops work well for hybrid team members and to mitigate the cost of upgrading multiple devices.
  • Connect with one of our Cloud Advisors to explore this option.

Windows 11 Upgrade HelpPlan for Your Windows 11 Transition

Regardless of the strategy you choose, proactive planning is crucial for a smooth and secure transition. Follow these steps to ensure you’re ready:

Assess Your Current IT Environment
  • Use Microsoft’s PC Health Check app to determine which devices can run Windows 11, which can be upgraded, and which require replacement. If you use Windows 10 in embedded systems, check with your vendor.
  • Confirm which of your business-critical applications and tools are compatible with Windows 11. Identify necessary software upgrades or migrations.
Prepare Your Budget
  • Accurately map the cost of upgrading and/or replacing devices. Keep in mind that older systems, even if upgraded now, may soon require replacement.
  • Identify any software upgrade costs.
  • Keep in mind any fees for tech support or professional services. You may need or want help transferring applications and data to new devices or setting up virtual desktops.
Develop Your Transition Plan & Data Strategy
  • Plan your timing and procedures for upgrades, purchases, and migrations. Focus on preventing data loss during migration and consider staging your rollout in phases to minimize disruption.
  • Crucially, ensure all critical data is securely backed up before upgrading or migrating systems. 
  • Remember to allow time to test critical software on Windows 11 before upgrading.
Train Your Team
  • Provide resources and help your team become familiar with the Windows 11 interface and new features.
  • If you are upgrading your business software for compatibility, you may want to provide additional training on new functionalities and capabilities.
  • Stay Informed: Monitor Microsoft’s official updates and announcements. Keep current with regarding Windows 10 end of life and Windows 11 developments.

Cumulus Global Will Help

Plan and Act Now.  As with any major upgrade, we expect demand for PCs, laptops, and technical services will increase as the deadline nears. Waiting may result in delays and missed deadlines. Losing Windows 10 support can result in costly business disruptions.

For assistance, schedule a brief, free call with one of our Cloud Advisors to discuss your assessment, plan, and upgrade needs, priorities, and budget.

About the Author

Allen Falcon is the co-founder and CEO of Cumulus Global.  Allen co-founded Cumulus Global in 2006 to offer small businesses enterprise-grade email security and compliance using emerging cloud solutions. He has led the company’s growth into a managed cloud service provider with over 1,000 customers throughout North America.

Act Now! Windows 10 Support ENDS in 4 Months

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Windows 11

Don’t get caught off guard! Support for Windows 10 officially ends on October 14, 2025. After this date, Microsoft will no longer provide software updates, technical assistance, or critical security patches and fixes.

Continuing to use Windows 10 will dramatically increase your exposure to significant risks. Without security updates, your systems become prime targets for cyberattacks, ransomware, and data breaches. You risk costly downtime, loss of sensitive information, and severe compliance issues. 

Proactive planning and action are not just recommended, they are critical for your business continuity and security.

Know Your Windows 10 Options

We agree with Microsoft’s recommendation to upgrade all eligible systems to Windows 11. We also understand you may have budget constraints or compatibility issues with older software.

You can check if your PCs will run Windows 11 using Microsoft’s PC Health Check app. If your PC will not run Windows 11, you have options other than buying new devices.

Extended Security Updates (ESU): 
  • Microsoft will offer an ESU subscription providing critical security updates for Windows 10 for up to three years. While pricing details are not yet available, ESU programs for Windows 7 were more than $100 per device annually. We expect the Windows 10 ESU program will be more expensive. 
  • This option serves as a temporary bridge but doesn’t address underlying hardware or software compatibility.
Virtual Desktop Services: 
  • Using virtual desktop services, such as Azure Virtual Desktop, allow you to use your existing PCs to access a robust and secure Windows 11 environment. Virtual desktops work well for hybrid team members and to mitigate the cost of upgrading multiple devices.
  • Connect with one of our Cloud Advisors to explore this option.

Windows 11 Upgrade Help

Plan for Your Windows 11 Transition

Regardless of the strategy you choose, proactive planning is crucial for a smooth and secure transition. Follow these steps to ensure you’re ready:

Assess Your Current IT Environment
  • Use Microsoft’s PC Health Check app to determine which devices can run Windows 11, which can be upgraded, and which require replacement. If you use Windows 10 in embedded systems, check with your vendor.
  • Confirm which of your business-critical applications and tools are compatible with Windows 11. Identify necessary software upgrades or migrations.
Prepare Your Budget
  • Accurately map the cost of upgrading and/or replacing devices. Keep in mind that older systems, even if upgraded now, may soon require replacement.
  • Identify any software upgrade costs.
  • Keep in mind any fees for tech support or professional services. You may need or want help transferring applications and data to new devices or setting up virtual desktops.
Develop Your Transition Plan & Data Strategy
  • Plan your timing and procedures for upgrades, purchases, and migrations. Focus on preventing data loss during migration and consider staging your rollout in phases to minimize disruption.
  • Crucially, ensure all critical data is securely backed up before upgrading or migrating systems. 
  • Remember to allow time to test critical software on Windows 11 before upgrading.
Train Your Team
  • Provide resources and help your team become familiar with the Windows 11 interface and new features.
  • If you are upgrading your business software for compatibility, you may want to provide additional training on new functionalities and capabilities.
  • Stay Informed: Monitor Microsoft’s official updates and announcements. Keep current with regarding Windows 10 end of life and Windows 11 developments.

Cumulus Global Will Help

Plan Now; Act Soon.  As with any major upgrade, we expect demand for PCs, laptops, and technical services will increase as the deadline nears. Waiting may result in delays and missed deadlines. Losing Windows 10 support can result in costly business disruptions.

For assistance, schedule a brief, free call with one of our Cloud Advisors to discuss your assessment, plan, and upgrade needs, priorities, and budget.

About the Author

Allen Falcon is the co-founder and CEO of Cumulus Global.  Allen co-founded Cumulus Global in 2006 to offer small businesses enterprise-grade email security and compliance using emerging cloud solutions. He has led the company’s growth into a managed cloud service provider with over 1,000 customers throughout North America.

Prepare for Windows 10 End of Life and Windows 11

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Windows 11A Guide: From Windows 10 End of Life to Windows 11

Support for Windows 10 ends on October 14, 2025. After this date, Microsoft will no longer provide:

  • Free software updates, including updated or new features
  • Security patches and fixes
  • Technical assistance

Although you can continue to use Windows 10, doing so dramatically increases your risks of cyberattacks, security breaches, and other issues.

Know Your Windows 10 Options

Microsoft recommends that you upgrade all systems to Windows 11 before the deadline. While we generally agree, we understand that challenges such as software dependencies and costs may complicate this transition. Your current software may not function properly on Windows 11, and older PCs or laptops might not meet its requirements, potentially leading to significant expenses for hardware replacement.

You will need to assess whether your devices can run Windows 11 as-is or with upgrades. If they cannot, there are alternatives to purchasing new devices.

Plan your move to Windows 11 Free Consultation Schedule a free, no-obligation meeting with one of our Cloud Advisors.  

Microsoft recommends that you upgrade all systems to Windows 11 before the deadline. While we generally agree, we understand that challenges such as software dependencies and costs may complicate this transition. Your current software may not function properly on Windows 11, and older PCs or laptops might not meet its requirements, potentially leading to significant expenses for hardware replacement.

You will need to assess whether your devices can run Windows 11 as-is or with upgrades. If they cannot, there are alternatives to purchasing new devices.

  • Extended Security Updates (ESU): Microsoft will offer an ESU subscription providing critical security updates for Windows 10. While pricing details are not yet available, ESU programs for Windows 7 were more than $100 per device annually. We expect the ESU program for Windows 10 will be more expensive.
  • Virtual Desktop Services: You can also mitigate the cost of upgrading by moving to virtual desktop services. This option is best if you are facing multiple system replacements.

Determining the right path forward depends on your unique IT environment, budget, and business needs. 

Plan for Windows 11

Regardless of the strategy you choose, proactive planning is crucial. Follow these steps to ensure a smooth transition to Windows 11:

  1. Assess Your Current IT Environment:
    • Review your inventory of all devices running Windows 10. This includes computers, laptops, servers, and any embedded systems.
    • Identify which devices can run Windows 11, which can be upgraded, and which devices you should replace.
    • Identify the business-critical applications and tools you currently use and whether they are compatible with Windows 11. You may need to upgrade some of your software.
  2. Create Your Budget:
    • Budget the cost of upgrading and/or replacing devices that cannot run Windows 11. Keep in mind that older systems may require replacement soon, even if upgraded now.
    • Include the cost of any tech support or professional services you may need to transfer applications and data to the new devices.
  3. Develop a Transition Plan:
    • Plan on the timing for upgrades, purchases, and migrations.
    • Remember that you may need to test some of your software on Windows 11 before upgrading or replacing devices.
  4. Train Your Team:
    • Provide learning resources to help your team learn and become familiar with Windows 11.
    • If you need to upgrade any of your business software, consider providing training on new features and capabilities.
  5. Stay Informed:
    • Monitor Microsoft’s official updates and announcements to ensure you have the latest information about Windows 10 end of life.

Your Next Step

As with any major operating system upgrade, we expect demand for PCs and laptops to increase during 2025. Prices will likely increase and availability may become an issue. Plan now and execute soon.

For assistance, schedule a brief, free call with one of our Cloud Advisors to discuss your assessment, plan, and upgrade needs, priorities, and budget.

About the Author

Allen Falcon is the co-founder and CEO of Cumulus Global.  Allen co-founded Cumulus Global in 2006 to offer small businesses enterprise-grade email security and compliance using emerging cloud solutions. He has led the company’s growth into a managed cloud service provider with over 1,000 customers throughout North America. Starting his first business at age 12, Allen is a serial entrepreneur. He has launched strategic IT consulting, software, and service companies. An advocate for small and midsize businesses, Allen served on the board of the former Smaller Business Association of New England, local economic development committees, and industry advisory boards.