"Moving to E5 has been really good from a security point of view... Now we can get a holistic view of what’s going on, which helps us to make changes and recommendations for future plans."
IT Service Manager
Ian Harkess
Trusted by industry leaders
Kickstart Your FastTrack Journey
Fill out the short form below to express your interest in our FastTrack programme, and we’ll be in touch soon.
Please note: A minimum of 150 enterprise licenses is required for FastTrack eligibility.
“We needed to find solutions to a variety of issues whilst being a complex business, operating in a 24/7 environment. Stripe OLT listened and understood immediately the challenges we faced.”
IT Operations Manager
Simon Darley
Trusted by industry leaders
Let's Talk
Call us on one of the numbers below, we cover the whole of the UK, so call the nearest office.
“We needed to find solutions to a variety of issues whilst being a complex business, operating in a 24/7 environment. Stripe OLT listened and understood immediately the challenges we faced.”
2025 is the end of life for Windows 10 - no more patches, no more support. This guide gets to the point to help you plan a smooth Windows 11 upgrade. Discover, the biggest rollout risks, how to not break legacy apps and our downloadable checklist
“Windows 11 isn’t an optional upgrade, its a business requirement for maintaining a secure and compliant environment.”
Jump to…
Windows 10 End-of-Life
If you haven’t heard by now, Windows 10 reaches end-of-life on October 14, 2025. After that, it’s no more security updates, no support, and no safety net.
For most businesses, that means upgrading to Windows 11. But here’s the thing, an OS migration isn’t just a tick-box IT task – it’s a complex project with real risks, dependencies, and long-term consequences if mishandled.
This isn’t a deep dive into every Windows 11 feature and why you need to upgrade. It’s a straight-talking guide to help you assess your next steps.
Why Windows 10 End of Life Matters
First some quick context, if you’re still running Windows 10 after the deadline, here’s what you’re exposing your business to:
No security patches – leaving you wide open to zero-days and malware
Compliance risks – particularly in regulated sectors like legal, finance or healthcare
Third-party tool issues – vendors may stop supporting Windows 10
Cyber insurance complications – outdated software could void or reduce coverage
“Threat actors love unsupported systems. Our SOC still sees legacy OS attacks years after EOL.”
Soon to be relegated to the history books – Windows 10
What IT Teams Miss During a Windows 11 Rollout
Upgrading to Windows 11 can seem straightforward – until you hit real-world complexities. Even vendors like CrowdStrike have recently shown us how one misstep in a deployment can cause serious disruption…
These are the most common rollout pitfalls we see:
Hardware Compatibility Gaps TPM 2.0 and Secure Boot are mandatory, but many older devices fall short. Without a proper audit, you’re flying blind.
Application Breakage Legacy or bespoke tools may behave unpredictably (or stop working entirely) if not tested in a Windows 11 environment.
Deployment Disruption Uncontrolled rollouts can eat bandwidth, interrupt users mid-task, and flood your IT helpdesk with avoidable tickets.
Endpoint Drift Rolling out without modern endpoint management (like Intune or Autopilot) can lead to configuration inconsistencies and patching failures.
What You Gain with Windows 11(That Actually Matters)
Yes, we all know the OS looks nicer, but here’s what’s genuinely useful for your business (from my perspective anyway) :
Feature
Why it matters
Snap Layouts & Virtual Desktops
Simplifies multitasking, improves productivity
TPM 2.0 & Secure Boot
Helps block firmware-level attacks
Modern Device Management
Intune/Autopilot-ready for secure, remote deployments
Streamlined UI
Easier onboarding for new users & hybrid teams
Future Support
Windows 11 is Microsoft’s primary OS – support, features, and patches will all focus here
“Windows 11 isn’t an optional upgrade, its a business requirement for maintaining a secure and compliant environment.”
The Essential Windows 11 Migration Checklist
So you don’t risk missing something crucial during your upgrade process, I’ve created a free, Windows 11 readiness checklist covering:
This is Not Just an Upgrade. It’s Risk Mitigation.
Whether you’re managing 30 or 3,000 devices, this isn’t something to leave to the last minute. A secure, staged upgrade takes time – but it’s far better than trying to fix it after the fact.
Crucially, rolling out a new OS without thinking about security, user disruption, and operational risk can create more problems than it solves.
If you’re looking for someone to support you with your Windows 11 project, get in touch here.
This website uses cookies. By using this site you agree to our use of cookies. We use cookies to enhance your experience. To understand the specific cookies we use and how we handle your data, see out Cookie Policy, Privacy Policy and Terms & Conditions. Mange your preferences at any time by clicking the 'View Preferences' button.
Functional
Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes.The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.