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"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."
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Ian Harkess
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Discover why Windows 10 End-of-Life poses a serious security risk, how Microsoft’s latest licensing changes impact your business, and why upgrading to Windows 11 and Microsoft 365 E5 Security is crucial.
"This isn’t just about licensing changes or operating system updates - it’s about future-proofing your business against cyber threats."
When it comes to technology, standing still is the fastest way to fall behind; attackers are getting more sophisticated, leveraging AI-powered threats, credential theft, and supply chain vulnerabilities.
With Microsoft’s latest licensing changes and the upcoming Windows 10 End-of-Life, now is the time for IT leaders to reassess their security posture and ensure they’re not leaving critical gaps open to exploitation.
Two shifts from Microsoft should be flashing red flags for IT leaders:
The upcoming End-of-Life (EOL) for Windows 10 in October 2025
The availability of Microsoft 365 E5 Security as an add-on for Business Premium customers
Both represent changes in how businesses need to approach security and modernisation in the coming few months.
Let’s break down what this means for you and why proactive action today could save you from a security disaster tomorrow.
Windows 10 EOL: Why You Can’t Afford to Ignore This
Microsoft has confirmed that Windows 10 will officially reach End-of-Life on October 14, 2025. After this date, there will be:
No security updates – leaving systems exposed to zero-days, ransomware, and malware.
No technical support – making troubleshooting and maintenance a major risk.
No compliance guarantees – creating regulatory headaches for industries with security mandates.
“But Windows 10 will still work, right?”
Yes, technically. But the reality is that running an EOL operating system turns your business into a target. Cyber-criminals actively exploit unsupported software, and without security patches, you’re essentially leaving the doors to your business wide open for malicious actors.
What Should IT Leaders Do?
Start your Windows 11 migration strategy NOW – Don’t wait until Q4 2025 when you’ll be scrambling.
Assess hardware compatibility – Windows 11 has stricter system requirements, and some older machines may need to be replaced.
Plan for security & compliance – Unsupported operating systems violate many cyber security frameworks (ISO 27001, Cyber Essentials, NIST, etc.).
Consider Microsoft 365 cloud-first strategies – A Windows 11 upgrade is the perfect time to evaluate Microsoft’s security stack and ensure you’re leveraging best-in-class protection.
Microsoft 365 E5 Security: The Most Cost-Effective Upgrade You Can Make
At the same time, this month Microsoft has announced a game-changing licensing update that could significantly boost security, without breaking the budget.
The Microsoft 365 E5 Security add-on is now available to Business Premium customers, meaning mid-sized organisations can now access enterprise-grade security without the full E5 price tag.
Enables Risk-Based Conditional Access, ensuring only verified, low-risk users access your systems.
Microsoft Defender for Identity (ITDR)
Detects and stops identity-based attacks, including privilege escalation and credential compromise—two of the most common attack vectors today.
Microsoft 365 E5 Security: The Most Cost-Effective Upgrade You Can Make
80% of breaches involve compromised credentials. → Attackers aren’t just targeting devices; they’re targeting users. If you don’t have identity-based security, you’re a step behind.
AI-powered threats are evolving faster than traditional security. → Cybercriminals use AI to automate phishing, deepfake identities, and bypass MFA. If you’re not matching their sophistication, you’re at risk.
Hybrid Work & BYOD have killed the network perimeter. → Security must extend beyond endpoints and protect identities, cloud apps, and data flows.
What Should You Do Now?
Upgrade to Windows 11
Avoid security, compliance, and operational headaches from Windows 10 EOL.
Evaluate Your Microsoft Licensing
If you’re on Business Premium, the E5 Security add-on is your most cost-effective way to get enterprise-grade protection without a full E5 upgrade.
Identity-first security is the new standard. MFA alone isn’t enough—Defender XDR, Entra ID P2, and Defender for Identity should be core to your security strategy.
Get ahead of the curve now, or risk playing defence against attackers who never sleep.
Final Thoughts: Your Security Wake-Up Call
This isn’t just about licensing changes or operating system updates – it’s about future-proofing your business against cyber threats.
Windows 10 EOL will create a security and compliance nightmare for businesses that don’t act.
Failing to upgrade security licensing leaves your identity and cloud infrastructure wide open to attackers.
The businesses that thrive will be those that proactively modernise, adopt AI-driven security, and take identity protection seriously.
Realistically, for those that aren’t taking security seriously right now, The choice is simple… Upgrade now or become a target later.
If you need guidance navigating Microsoft’s security ecosystem, our team are here to help you maximize your Microsoft investment.
Book a free discovery session with us — we’ll help you identify quick wins and strengthen your security posture, before it starts causing you a problem.
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