Windows 10 is set to reach its official end-of-support (EOS) on October 14, 2025, after which Microsoft will no longer provide security patches, bug fixes, or technical support for the OS. Yet many small and mid-sized businesses (SMBs) in the United States have slowly migrated off Windows 10. A recent poll found that over one-third of SMB customers either have no plans to upgrade or are unaware of the impending deadline (14% were completely unaware) techradar.com. This lag in transitioning to Windows 11 (or other supported systems) is driven by several key factors – from tight budgets and compatibility worries to resource constraints and a simple lack of awareness. Below, we examine why SMBs are delaying the move from Windows 10 and the business risks of not upgrading in time (including cybersecurity, compliance, cost, support, and productivity impacts).
The Reasons for Hesitation
1. Sticker Shock
For many SMBs, upgrading to Windows 11 is not just a software refresh—it is a hardware replacement plan. Windows 11 has higher hardware requirements that older systems cannot meet, and replacing a handful of PCs can implode a tightly managed budget.
Windows 11 has higher hardware requirements (such as mandatory TPM 2.0 support and newer CPUs), meaning some existing PCs cannot be upgraded in place. In an SMB with dozens of PCs, replacing even 10–15% of them can strain budgets. For resource-constrained small businesses, that percentage represents a significant capital expense.
As a result, some SMBs intentionally postpone upgrades across multiple budget cycles, hoping to defer costs. However, this strategy can backfire when waiting until Windows 10 expires leads to higher costs (e.g., emer agency break-fix expenses or breach remediation).
2. Fear of Breaking Things
Another primary reason for the delay is concern over software compatibility. Small businesses often rely on a handful of critical applications (i.e., accounting systems, inventory or point-of-sale software, and industry-specific tools), which may be older or custom-built. There is a genuine fear that these legacy applications might not work smoothly on a new operating system. The business could be severely disrupted if an essential program breaks or data is lost during the OS migration.
In some cases, software vendors may not yet fully certify their products on Windows 11, or the SMB may be using an old version of software that needs an expensive update to support the new OS. There may also be hardware peripherals (scanners, specialized printers, machinery interfaces) that lack updated drivers for Windows 11. All these compatibility questions lead to a “wait and see” approach. This cautious approach minimizes short-term disruption but risks leaving the business on an increasingly outdated platform.
3. Too Much on the Plate
Most SMBs do not have a deep IT bench. The person managing your systems might also handle payroll, answer phones, or have multiple responsibilities in your company. Skill and resources play a significant role in the upgrade process.
With such limited IT resources, even if management knows an upgrade is needed, they may be unable to plan and execute it. Deploying a new operating system across an organization, testing applications, backing up data, scheduling installations, and training users on any changes can be complex. In SMB environments, IT projects often take a back seat to daily operations.
Many SMBs also lack structured asset management and do not have a precise inventory of all machines running Windows 10, making migration more daunting. In some cases, tiny businesses might not be sure how to approach the upgrade technically. Engaging third-party IT support (like managed service providers) is an option to ensure the Windows 10 status quo is not the ult.
4. It Still Works
Some businesses simply are not aware of the end-of-support deadline. Others assume Microsoft will extend it or think Windows 10 will keep chugging along without consequence. Business owners may not grasp how quickly security and compliance issues could escalate once patches stop, or they mentally discount those risks, thinking their company is too small to be targeted.
Talk of a Windows 12 or future OS might make some business owners think skipping Windows 11 is an option to avoid two migrations in quick succession. In reality, pinning hopes on an unknown future OS is risky for any business and should not factor into the decision to delay any upgrade.
The Real Business Consequences of Waiting to Upgrade to Windows 11
Cybersecurity Risks Multiply
Once Microsoft stops releasing patches, every vulnerability that surfaces becomes an open invitation for attackers. And it will not take long; bad actors target unsupported systems precisely because they know they are unprotected. If you are still running Windows 10 in late 2025, you might as well hang a “Welcome” sign for ransomware.
Compliance Takes a Hit
If your business handles sensitive data or operates in a regulated industry, staying on Windows 10 could put you out of compliance. Think HIPAA, PCI DSS, or your clients’ vendor security questionnaires. Outdated systems can lead to fines, lost contracts, or failed audits.
Cyber Insurance Could Say No
Cyber insurers are tightening their underwriting. Many already require businesses to demonstrate they are running supported, up-to-date systems. Your claim could be denied if you suffer a breach tied to an unsupported OS. That is a brutal way to find out your policy had an asterisk.
Costs Creep Up Fast
Waiting often means paying more later. Emergency upgrades, overpriced last-minute hardware, and Microsoft’s Extended Security Updates (which get more expensive yearly) can rack up costs quickly. Delaying the inevitable usually makes it more expensive.
Vendor and App Support Fades
As software developers move on, apps you rely on may stop working on Windows 10. Your AV vendor, your accounting software, and your browser will all stop supporting it, one by one. You will either lose features or face unexpected downtime.
Productivity Takes a Hit
Every time your team is interrupted by a crash, an unsupported app, or a sluggish PC, your business pays for it in lost time. Multiply that across a team and a year, and the drag on your company becomes very real.
What SMBs Can Do Now
If you are not ready to rip the Band-Aid off all at once, you are not alone. But do not let that stop you from starting. Here is what you can do now:
- Inventory your devices: Know which machines can handle Windows 11 and which can not.
- Test your software: Make sure the tools you depend on are compatible with Windows 11.
- Create a phased plan: Upgrade in waves. Spread the cost across quarters.
- Lean on IT partners: Do not have an in-house team? A trusted managed service provider can help.
In the SMB sector, the slow migration away from Windows 10 is understandable – small businesses face tight budgets, potential compatibility landmines, limited IT staffing, and often have an “if it works, why change it?” outlook. However, with the Windows 10 end-of-support date rapidly approaching, the cost of inaction is rising daily. The very real threats of cyberattacks, non-compliance, financial penalties, loss of support, and operational turmoil loom for those who do not transition in time. Many SMBs treat end-of-life IT management as a one-time event rather than an ongoing responsibility, but this mindset needs to shift.
The good news is that with proper planning, even resource-strapped businesses can navigate the upgrade: spreading hardware upgrades over fiscal quarters, testing critical applications for Windows 11 compatibility early, training staff on the new system, or leveraging external IT partners for help. Microsoft and industry advisors strongly encourage starting migrations now rather than waiting for the October 2025 deadline, a sentiment echoed by channel partners who warn that nearly two-thirds of SMB customers are still passive or uncertain about their upgrade plans.
Need help planning your upgrade? Talk to our team about a Windows 11 readiness assessment and phased migration plan tailored to your business.
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