What Happens If Your Organisation Doesn’t Upgrade to Windows 11? 

While systems won’t stop working immediately after Microsoft Windows 10 support ends, the downstream effects will be more severe than many organisations realise. 

From our experience with previous Windows transitions, companies that delay migrations face escalating problems that compound over time. The expenses and dangers of remaining on unsupported systems greatly outweigh the upfront cost of proactive upgrades.  

Here’s what to consider when evaluating your Windows 10 strategy: 

• Security exposure grows as updates and security patches end 
• Software vendor support will phase out over 12-24 months 
• Regulatory compliance is compromised 
• Increased Cost 

End of Support Timeline 

When Microsoft stops supporting Windows 10 on October 14, 2025 your infrastructure will keep working as normal. Files are accessible, applications work as expected and everything will look the same at first. 

But without security updates your risk profile changes. Each day without patches means more exposure to new threats. History shows that delayed transitions can be costly, the UK government spent £5.5 million on extended security updates for the Windows 7 transition to keep critical systems secure. 

Organisations in regulated environments have extra considerations: 

• Compliance frameworks require current security standards 
• Insurance policies often have clauses about supported systems 
• Data protection regulations like GDPR expect reasonable security 
• Audit requirements often demand up to date infrastructure 

Security Implications and Risk Assessment 

Post support Windows systems become a bigger target for cybercriminals. After Windows 7 ended support, security researchers saw a 125% increase in malware targeting those systems in the next 12 months. This shows that attackers are watching the support lifecycle and developing their attacks accordingly. 

The WannaCry ransomware attack in 2017 is a great example. Organisations running outdated Windows versions got hit the hardest, some even went down completely. The attack showed how vulnerabilities in old systems can cascade across the entire network. 

Modern attacks target the core of the operating system where traditional antivirus solutions don’t provide much protection. Windows 11’s new security architecture, including mandatory TPM 2.0 and secure boot, is a big step forward that can’t be retrofitted on older systems. 

A single compromised Windows 10 machine can be a pivot point for lateral movement across your entire infrastructure. In connected business environments, unsupported endpoints can compromise your entire network ecosystem. 

Software and Hardware Ecosystem Evolution 

Software vendors usually support Windows 10 for 12-24 months after Microsoft ends support. During the Windows 7 transition, major browsers supported it for about 18 months before dropping support altogether. 

Enterprise software follows a different pattern. Productivity suites, collaboration tools and business applications need to keep getting security updates to remain protected. Vendors have little incentive to support unsupported platforms especially when security vulnerabilities can’t be fixed at the OS level. 

New devices are shipping with drivers optimised for current OS only. Advanced features like USB4, PCIe 5.0 and modern graphics may not work on Windows 10. Printer manufacturers and network equipment vendors have always been quick to drop support for legacy OS. 

Regulatory Compliance and Legal Considerations 

If you’re under regulatory oversight you’re at greater risk when running unsupported systems. Data protection regulations like GDPR and sector specific ones like HIPAA require you to implement reasonable security. Running systems without updates does not meet those requirements. 

Cyber insurance policies often have clauses that require you to run supported, patched systems. Claims following a security incident on unsupported infrastructure may be denied or reduced. Several companies found this out during the Windows 7 transition when their insurers argued that continued use was negligent security. 

Professional certifications and compliance audits are getting more granular on technology infrastructure currency. Client contracts, especially in industries handling sensitive data often have technology requirements that explicitly state current security standards. 

Security incidents on outdated systems can damage stakeholder confidence and competitive positioning. Customers and partners will question your commitment to cybersecurity best practices and may impact long term business relationships. 

Financial Impact and Hidden Costs 

Without Microsoft support you lose access to official technical support, security advisories and troubleshooting resources. You must rely on third party support services which can cost 2-3 times more and don’t have full system knowledge. 

Incident response gets much more expensive. Malware infections, system instability and security breaches require more extensive remediation. Hardware replacement gets harder as components become obsolete and you may have to wait for extended periods to get compatible parts. 

The cumulative effect often makes delaying migration more expensive than upgrading proactively. Organisations that delay transitions often end up in crisis mode and must do emergency upgrades at premium cost with tight timelines. 

Strategic Alternatives and Migration Paths 

Extended Security Updates (ESU) is  available for enterprise customers but these are expensive and time limited. ESU gives you extra security patches but is a temporary solution not a long-term strategy. 

Windows 10 LTSC is for specific use cases like embedded systems or medical devices but requires special licensing and may not be suitable for general business use. 

Cloud based solutions like Windows 365 Cloud PCs or Azure Virtual Desktop give you access to the latest Windows versions regardless of local hardware limitations. These platforms give you managed security updates and application compatibility and extend the life of your existing hardware. 

Hybrid approaches allow you to transition between operating systems with dual boot configurations or virtualised environments. This gives you flexibility during extended migration periods and business continuity.  

Implementation Planning and Timeline Considerations 

Transitions require significant planning, and timescales vary depending on the size of the estate. . Start with infrastructure assessment using Microsoft’s PC Health Check tool to see which systems can run Windows 11 and which need to be replaced. Pay attention to TPM 2.0 requirements, UEFI firmware and memory specs. 

Budget planning needs to account for hardware upgrades, new equipment, software licensing, professional services and potential downtime. Consider phased implementations that prioritise critical systems and keep business running. 

Application compatibility testing is key. Legacy business applications, special software and custom integrations may need updates or alternatives. Identify these early to avoid implementation delays. 

Develop and test data migration strategies before starting system transitions. Plan for full backups, user profile migrations and application settings transfers. Use migration projects to implement better data management practices. 

Training and change management need to be taken seriously. User productivity will drop temporarily as staff get used to new interfaces and features. Plan for training programs and support resources to minimise downtime. 

The competitive landscape is favouring organisations on current technology platforms. Software vendors, hardware manufacturers and service providers will shift focus to supported systems and Windows 10 environments will become unsupported. 

Planning your migration now gives you control over timing, budget and implementation approach rather than being forced into emergency transitions with limited options and higher costs. 

If you’ve left it late to begin your upgrade, don’t panic. QuoStar can help you deploy Windows 11 quickly using Microsoft Intune, streamlining the process with minimal disruption. And if you’re out of time entirely, we can guide you through Microsoft’s Extended Security Update (ESU) options to keep your organisation protected. 

Ready or not, the clock is ticking. Whether you need a fast-track Windows 11 rollout or short-term protection through Extended Support, QuoStar is ready to help. Contact us today to get started.