For many businesses, the impending migration from Windows 10 to Windows 11 represents a complex crossroads of technology, security, and financial strategy. As Microsoft approaches the end-of-support timeline for Windows 10, an increasing number of organizations are feeling mounting pressure to upgrade their fleets—but new research reveals that the transition is anything but straightforward. Instead, it's fraught with technical, operational, and budgetary headaches that continue to cause hesitation and, in some cases, outright resistance.
Recent research from Panasonic offers a sobering snapshot of just how pervasive the hardware challenge remains. According to their study, nearly two-thirds of current business devices (62%) are incompatible with Windows 11 out of the box and will need to be replaced or significantly upgraded. Among larger organizations—defined as those with over 5,000 employees—that figure climbs to a staggering 76%. These numbers are consistent with independent assessments by other IT consultancies, many of which report that the hardware requirements for Windows 11, especially the demand for TPM 2.0 and newer CPUs, are a major stumbling block.
Upgrading or replacing such a large swath of corporate endpoint devices isn't a trivial matter. It cascades quickly from IT concern to boardroom anxiety: hardware outlays compete with other critical investments, introducing difficult choices about whether to delay migration and accept growing security risks, or accelerate upgrades and face short-term financial and productivity pain.
Organizations delaying migration often hedge their bets by considering Microsoft’s Extended Security Updates (ESU) program for Windows 10. However, the cost is steep—Microsoft estimates ESU for 1,000 devices will run to about £320,000 (approximately $410,000) over three years. Multiplied across larger fleets, this expense becomes unsustainable, further eroding the viability of “waiting out” Windows 10.
Alongside software issues, 45% of respondents cited fears about productivity loss during migration downtime. For many, any period of sustained IT unavailability translates into tangible operational impact, from missed revenue to cascading inefficiencies that reverberate beyond the IT department.
Furthermore, for about a quarter of organizations, hardware upgrades are inextricably linked to software upgrade expenses. Each device replaced often necessitates licenses or subscriptions for complementary software applications, compounding what is already a costly overall transition.
This warning comes at a time when the threat landscape is evolving with relentless speed and sophistication. The consequences of a poorly managed transition—or one that is rushed simply to meet a looming support deadline—can range from accidental data loss and security gaps to extended periods of business interruption. Turner’s remarks echo similar statements from cybersecurity authorities and IT consultancies, which consistently urge organizations to adopt phased, carefully resourced migration strategies.
1. Device and Application Inventory:
Conduct a detailed hardware and software inventory early. Tools like Microsoft Endpoint Manager or third-party solutions can help organizations map which devices meet Windows 11 requirements and identify applications at risk of compatibility issues.
2. Pilot Testing:
Deploy Windows 11 to a small group of power users or non-mission-critical devices first. This allows organizations to catch issues early and develop mitigation plans before full rollout.
3. Staff Training and Change Management:
Prepare IT and end-users in advance. Training on Windows 11’s new interface and productivity features can help minimize resistance and disruption.
4. Leverage Cloud and Virtual Desktop Infrastructure:
Where hardware upgrades are impractical, consider cloud-based solutions such as Windows 365 or Azure Virtual Desktop. These enable legacy devices to run a supported OS environment virtually, reducing the urgency (though not eliminating the need) for immediate hardware replacement.
5. Engage with Partners:
Work closely with OEMs, software vendors, and managed service providers to ensure hardware procurement and application updates align with migration timelines.
6. Plan for Downtime:
Schedule migration windows outside of peak business hours and provide realistic timelines for downtime. Communicate clearly and often with stakeholders.
7. Consider Security-First Migration:
Prioritize security-critical systems for early migration. Audit existing security controls and ensure they align with Windows 11’s security model, which includes features like secure boot, hardware-based isolation, and enhanced credential protection.
One variable that exacerbates the cost challenge is the global supply chain for IT hardware. Lead times for some business laptops and desktops can still fluctuate due to raw materials shortages, shipping delays, or demand spikes. Organizations that wait too long may find themselves not only pressed by EOS deadlines but also unable to procure needed equipment in time, increasing reliance on temporary and more expensive solutions like virtual desktops or device leases.
IT leaders must weigh these factors carefully and build flexibility into their budgets. Some may opt for phased hardware refresh cycles, balancing immediate migration needs against longer-term planning. Others may look to as-a-service device models to spread costs over a multi-year horizon.
Real-world examples abound. Each major Windows EOS has been followed by a significant uptick in cyberattacks targeting lapsed systems. Notably, the WannaCry and NotPetya outbreaks attacked organizations still running outdated, unpatched versions of Windows, resulting in billions in cumulative damages worldwide. Insurance companies increasingly scrutinize patch and support status as part of business cyber-risk profiles, sometimes increasing premiums or excluding coverage in the case of neglected operating systems.
It bears repeating that simply running antivirus or endpoint detection solutions is not a panacea for the absence of core operating system patches. The risk calculus is further complicated by compliance obligations in industries like healthcare (HIPAA) and finance (PCI DSS), where running unsupported systems may lead to costly regulatory fines.
For additional resources, best-practice guides, and migration support, Microsoft offers detailed Windows 11 migration toolkits and compatibility checks, while independent IT service firms can provide impartial advice tailored to each organization’s unique environment.
There may be pain in the process, but for most, the pain of standing still will be far greater. The clock is ticking, and the next move belongs to business leaders everywhere.
Source: TechRadar Windows 11 migration is still causing lots of headaches for some firms
The High Cost of Compatibility
Recent research from Panasonic offers a sobering snapshot of just how pervasive the hardware challenge remains. According to their study, nearly two-thirds of current business devices (62%) are incompatible with Windows 11 out of the box and will need to be replaced or significantly upgraded. Among larger organizations—defined as those with over 5,000 employees—that figure climbs to a staggering 76%. These numbers are consistent with independent assessments by other IT consultancies, many of which report that the hardware requirements for Windows 11, especially the demand for TPM 2.0 and newer CPUs, are a major stumbling block.Upgrading or replacing such a large swath of corporate endpoint devices isn't a trivial matter. It cascades quickly from IT concern to boardroom anxiety: hardware outlays compete with other critical investments, introducing difficult choices about whether to delay migration and accept growing security risks, or accelerate upgrades and face short-term financial and productivity pain.
Security Risks of Staying Behind
The risk calculation is pressing. Businesses overwhelmingly recognize that running unsupported operating systems introduces significant security vulnerabilities. Panasonic's report indicates that 94% of surveyed organizations express fears of elevated ransomware and malware risk if they remain on Windows 10 post-end-of-support, while 93% worry specifically about the potential for data breaches. These anxieties are far from theoretical: attackers exploit unpatched vulnerabilities, as demonstrated by the surge in exploits observed after Windows 7 and XP reached their respective end-of-support dates.Organizations delaying migration often hedge their bets by considering Microsoft’s Extended Security Updates (ESU) program for Windows 10. However, the cost is steep—Microsoft estimates ESU for 1,000 devices will run to about £320,000 (approximately $410,000) over three years. Multiplied across larger fleets, this expense becomes unsustainable, further eroding the viability of “waiting out” Windows 10.
The Unseen Pitfalls: Software Compatibility and Downtime
The transition to Windows 11 isn’t just about hardware and cost, it’s also riddled with software-related landmines. Nearly half of Panasonic's respondents noted concerns about software compatibility issues (47%), fearing that line-of-business applications—especially legacy or custom-built software—might break or require costly updates. Organizations in sectors such as healthcare, manufacturing, and logistics are particularly sensitive to even brief disruptions to specialized platform availability.Alongside software issues, 45% of respondents cited fears about productivity loss during migration downtime. For many, any period of sustained IT unavailability translates into tangible operational impact, from missed revenue to cascading inefficiencies that reverberate beyond the IT department.
Furthermore, for about a quarter of organizations, hardware upgrades are inextricably linked to software upgrade expenses. Each device replaced often necessitates licenses or subscriptions for complementary software applications, compounding what is already a costly overall transition.
A Glimpse of the Upside
Not all the feedback in the report is negative, and forward-thinking organizations see opportunities amid the challenges. Around a third of those surveyed acknowledge definite upside:- 36% expect improved device performance and processing power,
- 36% see value in a more future-proof ecosystem,
- 34% are eyeing Windows 11’s advanced features, such as built-in AI tools and Microsoft Copilot integration, as a differentiator.
“The Window Is Closing”: The Ticking Clock of Migration
Panasonic TOUGHBOOK Europe’s Head of Go-to-Market, Chris Turner, put it bluntly: “The window is closing for organisations to make a well-planned, measured and cost-effective transition to Windows 11 and start unlocking its benefits. Organisations that are still to undertake Windows 11 migration need support to ensure their deployment is not rushed and risky.”This warning comes at a time when the threat landscape is evolving with relentless speed and sophistication. The consequences of a poorly managed transition—or one that is rushed simply to meet a looming support deadline—can range from accidental data loss and security gaps to extended periods of business interruption. Turner’s remarks echo similar statements from cybersecurity authorities and IT consultancies, which consistently urge organizations to adopt phased, carefully resourced migration strategies.
Migration Best Practices: How to Avoid a Rushed, Risky Move
Industry experts recommend several best practices for a successful Windows 11 migration:1. Device and Application Inventory:
Conduct a detailed hardware and software inventory early. Tools like Microsoft Endpoint Manager or third-party solutions can help organizations map which devices meet Windows 11 requirements and identify applications at risk of compatibility issues.
2. Pilot Testing:
Deploy Windows 11 to a small group of power users or non-mission-critical devices first. This allows organizations to catch issues early and develop mitigation plans before full rollout.
3. Staff Training and Change Management:
Prepare IT and end-users in advance. Training on Windows 11’s new interface and productivity features can help minimize resistance and disruption.
4. Leverage Cloud and Virtual Desktop Infrastructure:
Where hardware upgrades are impractical, consider cloud-based solutions such as Windows 365 or Azure Virtual Desktop. These enable legacy devices to run a supported OS environment virtually, reducing the urgency (though not eliminating the need) for immediate hardware replacement.
5. Engage with Partners:
Work closely with OEMs, software vendors, and managed service providers to ensure hardware procurement and application updates align with migration timelines.
6. Plan for Downtime:
Schedule migration windows outside of peak business hours and provide realistic timelines for downtime. Communicate clearly and often with stakeholders.
7. Consider Security-First Migration:
Prioritize security-critical systems for early migration. Audit existing security controls and ensure they align with Windows 11’s security model, which includes features like secure boot, hardware-based isolation, and enhanced credential protection.
The Financial Elephant in the Room
Financial concerns regarding Windows 11 migration are well-established and multifaceted. On one hand, the cost of ESUs for Windows 10 quickly escalates, providing a strong financial incentive to move to a supported OS. On the other, the massive outlay required for new hardware, application license updates, and the knock-on effects on productivity can lead to serious sticker shock.One variable that exacerbates the cost challenge is the global supply chain for IT hardware. Lead times for some business laptops and desktops can still fluctuate due to raw materials shortages, shipping delays, or demand spikes. Organizations that wait too long may find themselves not only pressed by EOS deadlines but also unable to procure needed equipment in time, increasing reliance on temporary and more expensive solutions like virtual desktops or device leases.
IT leaders must weigh these factors carefully and build flexibility into their budgets. Some may opt for phased hardware refresh cycles, balancing immediate migration needs against longer-term planning. Others may look to as-a-service device models to spread costs over a multi-year horizon.
The Risks of Kicking the Can Down the Road
A segment of organizations is hoping to delay as long as possible—either banking on an extension to the EOS deadline or on discounted ESU licenses. However, as security incidents involving outdated operating systems multiply, the risks of delay become harder and harder to justify.Real-world examples abound. Each major Windows EOS has been followed by a significant uptick in cyberattacks targeting lapsed systems. Notably, the WannaCry and NotPetya outbreaks attacked organizations still running outdated, unpatched versions of Windows, resulting in billions in cumulative damages worldwide. Insurance companies increasingly scrutinize patch and support status as part of business cyber-risk profiles, sometimes increasing premiums or excluding coverage in the case of neglected operating systems.
It bears repeating that simply running antivirus or endpoint detection solutions is not a panacea for the absence of core operating system patches. The risk calculus is further complicated by compliance obligations in industries like healthcare (HIPAA) and finance (PCI DSS), where running unsupported systems may lead to costly regulatory fines.
The Potential Upsides of Moving Early
Companies that act early to start or complete their Windows 11 migrations stand to gain several strategic and operational advantages:- Early adopter benefits: Gaining familiarity with Windows 11’s workflow enhancements and AI-powered features before competitors do.
- Improved security posture: Leveraging new OS-level protections, including hardware-based isolation, VBS (Virtualization-Based Security), and better credential safeguards.
- Reduced disruption: Organizations that phase in migration can avoid the “big bang” scenarios that often lead to downtime, rushed training, or unforeseen bugs.
- Enhanced support: Microsoft and OEM partners are allocating significant resources to early migration support, meaning organizations benefit from well-staffed help desks and the attention of vendor engineering teams.
Critical Analysis: Weighing Strengths and Weaknesses of the Migration Mandate
Strengths
- Security-Driven Change: Migrating to Windows 11 aligns with modern security best practices, helping to insulate organizations from the worst effects of ransomware, malware, and zero-day exploits.
- Operational Improvements: New productivity and AI tools built into Windows 11, especially Copilot, can drive real gains in efficiency—provided organizations are prepared to leverage them.
- Futureproofing: By refreshing hardware and software stacks, organizations position themselves for the next generation of cloud-native, AI-augmented business solutions, improving their long-term agility and digital readiness.
Weaknesses and Risks
- Substantial Upfront and Hidden Costs: Device and software upgrades rarely come at sticker price alone; hidden costs from licensing, downtime, and unanticipated compatibility issues can balloon migration budgets.
- Change Fatigue: After years of remote and hybrid work accelerations, another major IT transition can generate employee pushback and lower engagement unless handled with strong change management.
- Supply Chain Uncertainty: Hardware procurement remains subject to global uncertainties, creating the risk of missed deadlines or forced compromises in device choice.
- Application Fragmentation: Older, customized applications often resist quick or easy migration, potentially forcing companies to maintain parallel environments or split support resources.
Recommendations and Looking Ahead
The evidence is clear: delaying Windows 11 migration comes with escalating risks, both from a security and financial perspective. Organizations should act now with careful planning:- Begin inventory and compatibility assessments immediately.
- Budget realistically for both direct and indirect costs, factoring in contingencies.
- Leverage external partners and vendor support where possible, especially for complex environments.
- Prioritize mission-critical workloads and security-sensitive endpoints for early migration.
- Communicate clearly with stakeholders about the plan, its rationale, and its benefits.
For additional resources, best-practice guides, and migration support, Microsoft offers detailed Windows 11 migration toolkits and compatibility checks, while independent IT service firms can provide impartial advice tailored to each organization’s unique environment.
There may be pain in the process, but for most, the pain of standing still will be far greater. The clock is ticking, and the next move belongs to business leaders everywhere.
Source: TechRadar Windows 11 migration is still causing lots of headaches for some firms
