Windows 10 EoSL Is Coming: Now What?

For those operating Windows 10 based machines, the clock's running out. With Windows 10 EoSL (End of Service Life) set for October 14, 2025, technical support — including critical security patches — will come to an end. Running these machines after that End-of-Service Life adds significant cyber risk to the network. Over time, the risks associated with continuing to run Windows 10 will only grow as new vulnerabilities are discovered and hackers will develop new attack methods.

Replacing those machines would obviously be incredibly expensive and impractical for organizations with large fleets. Thankfully, Windows is offering an "Extended Security" package for up to 3 more years. But it won't be free and it's really just a bandaid — passing today's headaches to tomorrow.

Extended support packages are priced on a per device basis — increasing each year — and can be purchased via the Microsoft M365 admin center or from qualified Cloud Solution Providers. And while it's great to have as a backup, good businesses tend to avoid these sorts of stopgap solutions — understanding that they risk inviting operationally insurmountable challenges as they accumulate and come due.

So where does that leave you?

Upgrading to newer Windows versions is the obvious path forward, but it's not always easy. There can, for example, be consequential interdependencies at play that come into conflict with Windows 11's stringent hardware compatibility requirements. For some devices, upgrading the OS may even require a full device upgrade cycle — affecting the motherboard, the processor, and other core components.

At scale, this is guaranteed to pose a challenge — with migration constituting a massive undertaking and consuming considerable resources. 

This combined with the challenges of proper inventory management, budgetary restrictions, and limited available man-hours — can make it difficult to comprehensively oversee upgrades.

Windows 10 EoSL Risk & Process Management

It's with these challenges in mind that GYTPOL is proud to offer comprehensive support for a smooth and simplified migration from Windows 10 to Windows 11. With our assistance, you'll be able to set your business up for security and success in 2025 and beyond.

Leveraging our unique endpoint security technology, we will accelerate and harden the upgrade process, adding value and security across the estate. Here's what that entails...

Comprehensive Visibility

Through the GYTPOL platform, you will receive detailed insights into configurations and compliance statuses for both Windows 10 and Windows 11 devices.

Granular and context-aware monitoring ensures all systems are tracked and subject to available controls — reducing the chance that key risks are overlooked in the course of migration.

Device Incompatibility Auditing

GYTPOL automatically identifies devices that do not meet Windows 11 requirements. This includes cross-referencing compatibility requirements with core functionality and essential components such as the processor, RAM, storage, graphics car, and security features.

Pinpointing devices unable to support the new operating system allows for informed decision-making and risk management. Identifying these devices as early as possible is vital to avoiding both disruption and exposure.

For those devices, managers will need to carefully weigh their options. These include (from most to least secure):

• Replacing those devices with more modern machines
• De-networking those devices
• Placing those devices in their own VLANs, subject to constant oversight, with strict security and access policies.

Migration Support

Detecting and analyzing OS-specific configurations, GYTPOL empowers operators to effectively filter and concentrate on Windows 10 or Windows 11 settings as needed. By delivering bulk remediation capabilities at the local device level, GYTPOL empowers IT administrators to systematically and efficiently eliminate configuration risks.

At the same time, up-to-date compliance data ensures that each device is fully prepared and migration ready. This makes it possible to preemptively flag and finagle any issues capable of putting a spoke in the wheels of the migration.  

Risk Management

Itemizing risks according to exposed devices, severity, and fixability, GYTPOL provides a structured approach to managing potential threats — supporting smart prioritization and streamlined task execution. 

By ensuring that the most critical issues are addressed first, GYTPOL reduces the overall risk to the network — addressing immediate security concerns AND establishing a robust security baseline for the new Windows 11 environment. This goes a long way to ensuring a smooth and secure transition.

Golden Image Guidance

Conducting a thorough analysis of your Windows 11 images, GYTPOL points out any configuration flaws or vulnerabilities that could compromise system integrity.

Based on that analysis, GYTPOL provides image modification recommendations to enhance security, compliance, and performance. By defining and refactoring your golden image in this manner, you can perfect it before you roll it out organization-wide. 

CIS Benchmarking & Enablement

Evaluating system settings against Center for Internet Security (CIS) benchmarks, GYTPOL highlights where current states are out of step with best practices — paving the way for the organization to fortify their security posture. 

In this way, operators can streamline their migration to Windows 11 by aligning system configurations with industry standards. This will help prevent unwelcome surprises and harden security leading up to and beyond Windows 10 EoSL.

Device Drift Detection & Policy Enforcement

GYTPOL's "Devices" view enables direct and detailed monitoring of individual devices within the network. This gives users a comprehensive and real-time view of all open alerts associated with each device — allowing for a more precise and controlled approach to device management.

This empowers IT administrators to swiftly identify and address any problems that may arise — ensuring that each endpoint is duly secure and prepared for Windows 11; making the migration as seamless and efficient as possible.

The Bottom Line On Windows 10 EoSL

The bottom line is this: without proper support, you face a difficult transition ahead. But the absolute worst thing you can do is bury your head in the sand and ignore it. Regardless of the particulars, you're no without options when it comes to managing Windows 10 EoSL. And it's important that you weigh those options carefully and with a clear view of the costs and risks associated.

But don't drag your feet. It's important to get in front of any potential problems by planning ahead to ensure a smooth, disruption-free migration. Don't wait until it's too late!

As always, we're here to help. We  can streamline the transition while tackling misconfigurations and enhancing security. And most importantly, we can do that while ensuring zero business disruptions.

By identifying incompatible devices, refining Windows 11 images, ensuring best practice adoption & enforcement, and proactively addressing configuration risks, GYTPOL can help enhance the security and efficiency of your migration to Windows 11.