Last month, we discussed the approaching Windows 10 End of Life deadline on October 14, 2025. With only four months remaining, businesses that haven’t started their migration planning are now entering a critical phase. In this follow-up, we’ll focus on practical next steps, address common questions we’ve received from clients, and provide more detailed guidance on overcoming migration obstacles.
Where Should You Be in Your Windows 10 Migration Journey?
If you’ve been following our recommended timeline from last month’s blog, you should now be wrapping up your assessment phase and moving into active planning and initial deployments. By mid-June, businesses should have:
- Completed a full inventory of Windows 10 devices and their hardware specifications
- Identified which devices can be upgraded to Windows 11 and which need replacement
- Tested Windows 11 compatibility with your critical business applications
- Developed a preliminary budget for the migration
- Selected pilot users or departments for initial deployment
If you haven’t reached these milestones yet, don’t panic—but you should prioritize these steps immediately. Our team can help accelerate this assessment phase to get your migration back on track.
Addressing the Top 5 Client Questions
Since our last blog post, we’ve received numerous questions from clients about their Windows 10 to Windows 11 migrations. Here are the most common concerns and our expert guidance:
1. “How disruptive will this migration from Windows 10 be to our daily operations?”
With proper planning, the disruption can be minimal. Most user data and settings can transfer seamlessly to Windows 11, and the learning curve for basic operations is modest. The key is a phased approach with adequate preparation:
For each department or team, we typically schedule migrations during off-hours or lower-activity periods. The actual upgrade process takes 1-2 hours per machine, but users can generally resume work immediately afterward with only minor adjustments to their workflow. We are available for guidance to smooth the transition.
2. “What about our legacy applications that won’t run on Windows 11?”
This is a legitimate concern for many businesses. We’ve found several effective solutions depending on your specific situation:
For truly incompatible applications with no available updates, virtualization offers a viable path forward. This can include setting up Windows 10 virtual machines that run on Windows 11 hosts, implementing Remote Desktop Services to centrally host these applications, or exploring application virtualization technologies that isolate the legacy software from the underlying operating system.
In some cases, it may be time to evaluate modern alternatives to legacy software. We can help identify replacement options that offer similar or enhanced functionality while ensuring Windows 11 compatibility.
3. “How much will this migration really cost our business?”
The cost varies significantly based on your current infrastructure, but it typically falls into three categories:
Hardware costs are often the largest expense, particularly for businesses with older equipment. However, these costs would eventually be incurred through normal refresh cycles regardless of Windows 11. The Windows 10 EOL deadline simply accelerates this timeline.
Software licensing costs may include Windows 11 upgrades (though many businesses qualify for free upgrades through existing Microsoft agreements) and potential costs for application updates or replacements.
Implementation costs include the technical work of deployment, potential downtime, and user training. These can be minimized through careful planning and phased implementation.
We find that most businesses can reduce the total cost by approximately 15-20% through strategic planning rather than last-minute migration. This includes optimizing hardware purchases, consolidating software licenses, and minimizing productivity disruption.
4. “Is Microsoft going to extend the deadline like they’ve done in the past?”
While Microsoft has occasionally extended support deadlines for previous operating systems, we strongly advise against banking on this possibility. Even if an extension is announced, it would likely come with significant costs for Extended Security Updates (ESUs), which typically increase each year.
For reference, when Windows 7 reached EOL, Microsoft’s ESU program cost $25-$50 per device in the first year, doubling each subsequent year. For a business with 100 computers, this could mean $2,500-$5,000 in the first year, $5,000-$10,000 in the second, and $10,000-$20,000 in the third—all for machines that would still be running increasingly outdated technology.
5. “What if we just can’t complete the migration by October?”
If full migration from Windows 10 by the deadline isn’t feasible due to unique business constraints, we recommend a risk mitigation strategy:
First, prioritize migrating internet-facing and data-sensitive systems, as these represent the highest security risk when running an unsupported operating system.
Second, implement enhanced security measures for any remaining Windows 10 systems, including network isolation, additional endpoint protection, and stricter access controls.
Finally, create a concrete timeline for completing the migration as soon as possible after the deadline, with clearly defined milestones and accountability.
Three Critical Next Steps for June and July
With the deadline approaching quickly, here are the four most important actions to take over the next two months:
1. Finalize Your Hardware Strategy
By the end of June, you should have firm decisions made about your hardware approach:
For Windows 11-compatible devices, schedule specific deployment dates and prepare the necessary upgrade tools and processes. For incompatible hardware, place orders now for replacement systems, as supply chain delays can still impact delivery timeframes.
Consider whether a hardware refresh cycle makes sense for systems that are technically compatible but nearing the end of their useful life. In many cases, it’s more efficient to replace aging hardware now rather than upgrading the operating system only to replace the device next year.
2. Begin Pilot Deployments
If you haven’t already, immediately identify a diverse group of users across different departments to participate in pilot deployments. This group should include:
- Both technically savvy and less technical users
- Representatives from each department or functional area
- Users of your most critical business applications
The pilot period should last 2-3 weeks, with regular feedback collection and issue tracking. This provides valuable insights before wider deployment and helps identify any application-specific issues that weren’t caught during compatibility testing.
3. Create Your Contingency Plans
While optimism is important, pragmatic planning requires preparing for potential complications:
Document rollback procedures for any deployment that encounters critical issues. Identify alternative work methods for each key business process in case of application compatibility problems. Establish clear criteria for when to implement contingency measures versus working through minor issues.
Special Considerations for Regulated Industries
Organizations in healthcare, finance, legal, and other regulated sectors face additional compliance considerations with the Windows 10 EOL transition. These include:
Documentation requirements: Regulated businesses should maintain detailed records of their migration planning, risk assessments, and implementation to demonstrate due diligence to auditors and regulatory bodies.
Data protection during migration: Ensuring that patient, client, or financial data remains protected throughout the transition process requires additional safeguards and verification procedures.
Validation processes: In some industries, systems must be revalidated after significant changes like operating system upgrades, requiring additional testing and documentation.
Our team has extensive experience working with businesses in regulated environments and can provide industry-specific guidance to ensure your migration maintains compliance throughout the process.
Making the Most of Your Windows 11 Migration
Beyond simply avoiding security risks, a well-planned Windows 11 migration presents opportunities to enhance your overall technology environment:
Standardization: Use this transition to standardize your technology environment, reducing variations that complicate management and support.
Security enhancements: Windows 11’s improved security architecture can be supplemented with additional measures during deployment, creating a substantially more secure environment.
Process improvements: The migration provides an excellent opportunity to review and optimize your technology-dependent business processes.
Digital transformation acceleration: Consider how Windows 11’s improved features could enable new digital capabilities or workflow enhancements for your organization.
Next Steps with Our MSP
As your technology partner, we’re prepared to support your Windows 10 to Windows 11 migration at any stage. Whether you’re just beginning your assessment or ready to accelerate deployment, our team can provide the expertise and resources needed to ensure success.
For businesses that haven’t yet begun their migration planning, we offer an expedited assessment program that can quickly determine your readiness status and develop a compressed migration timeline.
For those who have started but are facing challenges, our technical specialists can help overcome obstacles related to hardware compatibility, application issues, or deployment logistics.
Conclusion: The Time for Action Is Now
With just four months remaining until Windows 10 reaches end of life, businesses must move from planning to action. The steps taken in June and July will largely determine whether your migration is completed successfully before the October deadline.
By focusing on hardware decisions, pilot deployments, user preparation, and contingency planning over the next 60 days, you can establish the momentum needed to complete this critical transition on time and with minimal business disruption.
Contact our team today to schedule a migration readiness review and ensure your business remains secure and productive throughout this technology transition. You can reach our award-winning MSP here (or 504.454.6373).
Note that the image at the top of this blog was created using Microsoft Copilot. Here’s our blog on Copilot, which we wrote about a few months ago. Are you using generative AI?
