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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.

You Win in Microsoft’s $129 Billion Give-Away

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Windows 10 Logo
At this summer’s Worldwide Partner Conference, several Microsoft executives mentioned that they expect 1 billion users to download the Windows 10 for free.  With a “street price” of about $129, this equates to $129 billion give-away. The cynics among us might argue that this is a great strategic play for Microsoft as a way to maintain its customers base amid increasing competition from other operating platforms, including Chrome, Linux, Android, and iOS.

You, however, are the real winner in this give-away. And here is why …

  • Windows 10 is the first Microsoft operating system that is truly a single environment across all hardware platforms, from servers to smartphones. For software developers, it means that apps written for Windows 10 easily run across mobile and traditional (desktop and server) platforms.

    • You win: Expect better functional and operational equivalence for applications; no more waiting for phone and tablet versions to catch up to the desktop version.

  • Windows 10 is the first Microsoft operating system that is truly network-first. Microsoft has made a huge shift to a cloud-first, mobile-first strategy, and Windows 10 is part of this shift. Network services now launch with the core operating system, not as a service later in the boot cycle.

    • You win: Expect faster boot times as your networked and cloud apps will no longer ‘sit and spin’ while waiting for the network to come online.

  • Windows 10 is the first Microsoft operating system designed to evolve. The age of the monthly updated and periodic service packs is coming to an end. Microsoft will update, patch, and enhance Windows 10 as part of a continuous process. While domain system managers can still control when different types of updates propagate, updates will now happen “when ready and when needed”.

    • You win: Expect more feature and capability enhancements and a more secure/robust environment, as Windows 10 will more nimbly adapt to changing needs.

  • Windows 10 is the first Microsoft operating system with a user interface that matches user preferences. Let’s face it, Windows 8.x was a great experiment in a mobile-friendly user interface that was welcomed with mixed results. Windows 10, however, gives users the option of creating the environment that is most effective from them. Yes, you still have live tiles. But you also have desktops (yes, more than one if you want).

    • You win: Expect to create efficient workspaces for your different roles and tasks.  Separate desktop environments (including settings and apps) for personal versus work activity on your laptop. Customize desktops for different roles you may fill — manager, finance, marketing, operations — throughout your workday. In short, create environments that make life easier for you, and switch between them as y0u see fit.

With these firsts, and others, Microsoft is demonstrating that it “gets” the new cloud and mobile centric world order and  that Microsoft is ready to be a significant player. Microsoft’s Office 365 and Azure services, and many others from many vendors, are already moving to leverage the new capabilities of Windows 10. Regardless of your overall strategy, you should be prepping to move your Windows ecosystem to Windows 10.

Interested in discussing your go to strategy for Windows 10 and the cloud? Drop us a note; we are happy to listen, learn, and share.