As a C-Suite leader, you’re tasked with making decisions that protect your business, its operations, and its bottom line. One decision you cannot afford to delay is upgrading your organisation from Windows 10 to Windows 11.

Microsoft has confirmed that Windows 10 will reach its official End of Life (EOL) on 14 October 2025. After this date, Microsoft will no longer provide security updates, patches, or technical support for the operating system.

For multi-site businesses—where endpoint management is already a complex challenge—the risks of running an unsupported OS multiply rapidly.

Why do Microsoft Retire Older Operating Systems?

It's not just to make more money...

Microsoft’s product lifecycle policy is designed to ensure security, compatibility, and innovation. Retiring older operating systems like Windows 10 allows Microsoft to:

• Focus resources on modern platforms with stronger security and performance capabilities.

• Address emerging cyber threats with advanced security features that older systems cannot support.

• Streamline development for software vendors who must maintain compatibility across fewer OS versions.

Put simply: technology moves fast, and the longer an OS is on the market, the harder it becomes to keep it secure and compatible with the latest hardware and software.

When Windows 10 Goes End of Life

On 14 October 2025, Windows 10 will officially reach EOL. From that date:

• No security patches will be released for new vulnerabilities.

• No bug fixes will be issued for performance or stability issues.

• No official Microsoft support will be available for troubleshooting.

While Microsoft may offer an Extended Security Updates (ESU) programme for a limited time, it comes at a high cost per device and only delays the inevitable.

The Real-World Risks of Staying on Windows 10 After EOL

For multi-site organisations, the decision to remain on Windows 10 beyond October 2025 is more than a technology choice—it’s a business risk.

1. Cybersecurity Vulnerabilities

Unsupported operating systems are prime targets for cybercriminals. Once EOL hits, any new exploit discovered will remain unpatched, leaving your endpoints open to ransomware, data breaches, and compliance violations.

2. Compliance Failures

In regulated industries (finance, healthcare, retail), using an unsupported OS can breach data protection requirements such as the UK GDPR or Cyber Essentials. This can result in fines, reputational damage, and loss of customer trust.

3. Software Incompatibility

Vendors will quickly drop support for Windows 10 in their applications. Business-critical software may stop receiving updates or fail to run entirely on outdated systems.

4. Higher Operational Costs

Running multiple OS versions across sites creates complexity in IT management, increases helpdesk demand, and raises the total cost of ownership. Downtime caused by unsupported systems can cost far more than a planned upgrade.

Why Businesses Need to Act Now

Upgrading a single office to Windows 11 is straightforward; upgrading dozens—or hundreds—of endpoints across multiple locations requires strategic planning, resource allocation, and coordination. Delaying action risks:

• Supply chain delays for compatible hardware.

• Compressed migration timelines, increasing the risk of errors.

• Budget shocks from unplanned emergency upgrades.

The longer you wait, the more disruptive and expensive the transition will become.

The Benefits of Moving to Windows 11 Now

Windows 11 brings enhanced security, modern productivity tools, and better performance. For multi-site businesses, the key advantages include:

• Stronger default security features such as TPM 2.0, Secure Boot, and enhanced phishing protection.

• Improved endpoint management via Microsoft Intune and other modern management tools.

• Better collaboration features for hybrid and remote teams.

Final Word for the C-Suite

The end of Windows 10 isn’t just an IT issue—it’s a strategic business priority. Ignoring the deadline exposes your organisation to cyber risk, operational disruption, and regulatory penalties.

By acting now, you can spread the cost of the upgrade, minimise disruption, and position your business to take advantage of Windows 11’s enhanced capabilities well before competitors who leave it too late.