ALL INSIGHTS

Countdown to the End of Windows 10: October 2025

Zach Jones,
Engineering Manager & Lead Architect

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February 4, 2025
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As organizations scramble to get PCs upgraded to Windows 11, the chosen upgrade path may have long term implications on both business productivity and future endpoint management capabilities. For organizations not leveraging modern endpoint management tools the death of Windows 10 can be a tedious, manual struggle. Whether an endpoint management tool exists within your organization or not, here are the top considerations to successfully migrate to Windows 11 before end of support on October 14th of 2025.

In-Place Upgrade vs Re-Image: Traditional methods of OS version upgrades usually result in a PC being re-imaged. This measure is a drastic step to achieve desired results and has major costs associated with the process from end user downtime to increased frontline IT support costs. If modern management solutions are in place, it is easiest to do an in-place upgrade. This will reduce complexity, end-user impact and the financial burden required before Microsoft support ends.

Mitigate End User Impact & Loss of Business Data: Beyond an in-place upgrade to Windows 11, several other modern management policies can be enabled. This will increase the overall success of an initiative at this scale for an organization. As an example, policies should ensure data is automatically backed up from your end user PCs to OneDrive. Data loss can have major impacts on business operations as well as an organization’s reputation. IT leaders should anticipate that they will have incompatible hardware or complete hardware failures with this type of upgrade. Putting in place OneDrive known folder management policies ahead of any migration activity will aid in data retention by automatically backing up user data to OneDrive.

Training for a New Look and Feel: Although Windows 11 may not seem different to savvy end users, the bulk of end users are often intimidated by any change to the user interface such as this. Be proactive by communicating this change to end users in advance, provide training through workshops, user groups, and KBAs. It is best to start with a pilot group of early adopters who will act as champions of change, helping to promote the benefits of Windows 11 to the larger organization.

Opportunities to Modernize with Unified Endpoint Mgmt. Tooling: End of life announcements are fantastic opportunities to promote new UEM solutions. Quite often, modern UEM tools can pay for themselves through the automation benefits they provide. By enabling end-user self-service and automated provisioning, organizations can dramatically reduce the manual effort by end-user computing support teams.

Does my organization really need to upgrade? Yes!! Do not underestimate or deprioritize the need to be compliant with your organization’s security polices and controls. As part of Microsoft depreciating Windows 10; Office 365 applications will also no longer receive updates after October 2025. This simply compounds the likelihood a security vulnerability will be exploited with your end users PCs. Now is the time to act! If your organization does not have the technology, talent or simply needs temporary augmentation reach out to an experienced IT managed service provider to aid in this extremely critical migration to Windows 11.

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