Windows 10 reached its official end of life on October 14, 2025, which means Microsoft no longer provides free security patches, bug fixes, or technical support for the operating system. If your business is still running Windows 10 on any of its workstations, those machines are now exposed to unpatched vulnerabilities that attackers are actively targeting. The fix is straightforward but requires planning: you need to migrate to Windows 11 or adopt an extended support arrangement to stay protected.
Despite months of advance notice, a significant number of small and mid-sized businesses across New Jersey and the tri-state area are still running Windows 10 on at least some of their fleet. We see it regularly in our assessments. Sometimes it is a handful of older desktops in a back office; other times it is the majority of an organization's endpoints. Either way, the risk profile changed the moment Microsoft stopped issuing patches.
Why Running an Unsupported Operating System Is a Real Threat
This is not a theoretical concern. When an operating system goes end of life, every newly discovered vulnerability becomes a permanent, unfixable hole in your defenses. Attackers know this and deliberately target unsupported systems because they represent guaranteed entry points.
The consequences extend beyond just security exposure. Many compliance frameworks, including HIPAA, PCI DSS, CMMC, and the FTC Safeguards Rule, explicitly require that systems run supported software with current security patches. Running Windows 10 without extended support can put your organization out of compliance and expose you to regulatory penalties, failed audits, and cyber insurance claim denials.
Your cyber insurance carrier is paying attention too. Insurers are increasingly asking about operating system versions during renewals, and running end-of-life software can be grounds for a coverage denial if you experience a breach.
What Are Your Options Right Now?
You have three realistic paths forward, and the right choice depends on your hardware, budget, and timeline.
Upgrade to Windows 11. This is the recommended long-term solution. Windows 11 includes meaningful security improvements such as hardware-backed encryption through TPM 2.0, enhanced credential protection, and tighter integration with Microsoft's Zero Trust security model. If your hardware meets the requirements (TPM 2.0, Secure Boot capable, 8th gen Intel or newer), upgrading is the most cost-effective path. The upgrade itself is free if you have a valid Windows 10 license.
Purchase Extended Security Updates (ESU). Microsoft offers paid ESU for Windows 10 that provides critical and important security patches beyond the end-of-life date. For businesses, this runs approximately $61 per device for the first year, doubling each subsequent year. This is a bridge solution, not a permanent fix. It buys time while you plan your hardware refresh and migration, but the escalating cost makes it impractical beyond a year or two.
Replace aging hardware. Many businesses discover that their older workstations cannot run Windows 11 because they lack TPM 2.0 or have processors that do not meet the minimum requirements. In these cases, a hardware refresh is necessary. The upside is that new machines come with Windows 11 pre-installed, improved performance, better energy efficiency, and modern security features built in at the hardware level.
How to Plan a Smooth Migration
A rushed migration creates its own set of problems, from broken applications to frustrated employees. Here is how to approach it methodically.
Start with an inventory. Document every Windows 10 machine in your environment, including who uses it, what applications run on it, and whether the hardware can support Windows 11. This is the foundation for every decision that follows.
Test your critical applications. Most modern business software runs fine on Windows 11, but legacy line-of-business applications, specialized industry tools, and older hardware peripherals like label printers or scanners sometimes have compatibility issues. Test these before rolling out broadly.
Create a phased rollout plan. Do not try to upgrade every machine in a single weekend. Start with a pilot group of tech-comfortable users, collect feedback, resolve issues, then expand to the rest of the organization in planned waves.
Back up everything first. Before touching any machine, ensure you have verified, tested backups of all user data and system configurations. An upgrade failure without a backup turns a manageable project into a data loss incident.
Communicate with your team. Let employees know what is happening, when their machine will be affected, and what (if anything) they need to do. The Windows 11 interface is familiar enough that most users adapt quickly, but a heads-up prevents unnecessary helpdesk calls.
If you need support planning or executing your migration, our managed IT services team handles these rollouts regularly for businesses across New Jersey and can manage the entire process with minimal disruption to your operations.
What About Security in the Meantime?
If you are still running Windows 10 on some machines and cannot migrate immediately, take these steps to reduce your exposure while you plan:
Ensure your endpoint detection and response (EDR) solution is running and up to date on every Windows 10 machine. Layer your defenses with DNS filtering, email security, and network segmentation to limit what an attacker can reach if they do compromise an unpatched endpoint. Restrict administrative privileges on these machines and monitor them more closely for suspicious activity.
These measures do not eliminate the risk of running an unsupported OS, but they reduce the blast radius of a potential compromise while you work through your upgrade plan.
The Business Case for Acting Now
Every month you delay increases your risk and your eventual cost. Hardware prices are stable right now, and Microsoft licensing is straightforward. More importantly, the longer you wait, the more likely it is that a vulnerability in an unpatched Windows 10 machine becomes the entry point for a ransomware attack, a data breach, or a failed compliance audit.
We work with businesses across Morris County, Essex County, and the greater northern New Jersey area to plan and execute these migrations. Whether you need a full fleet assessment, a phased upgrade plan, or hands-on deployment support, we have done this hundreds of times and can get it done with minimal downtime.
How do I check if my PC can run Windows 11?
Open Settings, then System, then About. Look for a processor that is 8th gen Intel or newer and confirm TPM 2.0 is enabled in your BIOS. You can also download Microsoft's PC Health Check tool for a quick pass/fail answer.
Is Windows 10 Extended Security Updates worth the cost?
ESU is a reasonable short-term bridge if you need a few months to plan your migration, but at $61 per device per year (doubling annually), it becomes expensive quickly. For most businesses, that money is better invested in new hardware that will serve you for the next five to seven years.
What happens if I just keep running Windows 10 without updates?
Your machines will continue to work, but every newly discovered security vulnerability will remain permanently unpatched. This makes you a target for attackers, can void your cyber insurance coverage, and will likely cause compliance failures during your next audit. The risk compounds with every passing month.