On October 14th 2025, just weeks from now, Windows 10 will reach its end-of-life. While your computer won’t suddenly die, nor will you be locked out of your devices or programs, this deadline represents a world of risk for law firms.
“End-of-life" is a term used in the technology world to describe the end of manufacturer-provided security updates and support services for a program or product. You may also know this as “sunsetting” or “end-of-support.”
After this deadline, Windows 10 users will not receive free security updates, and Microsoft will cease user support services for this operating system. While some users are eligible to purchase continued security updates, these updates will only address critical security-related issues, and will not improve productivity or user experiences.
If an issue occurs with your Windows 10 instance, you will no longer be able to utilize Microsoft’s support services to get a solution. Neither will your IT provider—meaning that, if you can’t fix the issue in-house, you may not be able to get a solution at all.
Past a certain point in time and adoption rate, it is no longer profitable or feasible for a technology provider to continue servicing old hardware or software. Usually, the manufacturer has since released products that are too powerful or modern to support the old software, or is changing the focus of their products to a new objective—in this case, it’s the cloud.
Most modern businesses are utilizing cloud-based services, which are often more cost-effective, safe, and efficient for both users and the manufacturer to maintain. It’s a sign of technology progress and a way to ensure continued capability with the best solutions on the market today, like AI tools, most of which are cloud-based already—and besides, selling new products and devices is a huge incentive for manufacturers to move in a cloud-first direction.
Some of the most important technology objectives for your law firm are to remain safe, productive, and profitable. To do so throughout this time of transition, you’ll need to start the decision-making and action process ASAP.
If you’re still using Windows 10 today, now is the time to create a plan of action. Many important protocols exist for creating a smooth transition away from Windows 10 – here are five actionable steps you can begin taking now.
The first thing your law firm should do to prepare for Windows 10 end-of-life is to evaluate all of your technology devices to assess the scale of impact.
Roughly 45% of Windows users are still running Windows 10, and your law firm may be entirely reliant on this operating system today. It’s possible that you have started upgrading devices, but if that process is incomplete, any remaining Windows 10 devices will be impacted by the additional cybersecurity and productivity risks incurred after the deadline.
Regardless of how many of your PCs are still on Windows 10, it only takes one compromised device or system to create a massive cyber incident at your law firm. However, assessing your full tech stack can help you gain perspective on just how much your risk level will increase after the deadline.
Unfortunately, you may need to update your devices, not just your Windows subscription. Not all devices support operating systems newer than Windows 10- in fact, nearly 240M are ineligible for a system upgrade.
When developing your Windows 10 action plan, be sure to factor in potential device procurement and the time required to transition your operating systems—this will give you a rough idea of how long your firm will remain at risk. Experts recommend beginning your transition process as quickly as possible to mitigate these risks and ensure a smooth upgrade process.
Microsoft is offering an Extended Security Update (ESU) Program for businesses and individuals to prolong their exposure to major cybersecurity risks. But, it doesn’t come without a catch.
Personal PCs are eligible for $30 per year ESUs, while businesses will see a cost of $61 per device per year.
Your organization may be eligible, which you can determine by checking the ESU guide linked above. But, you should know:
Businesses can purchase up to 3 years’ worth of extended updates, but the price “doubles every consecutive year, for a maximum of three years,” per the latest guidance from Microsoft. Users will inevitably need to upgrade as their system degrades and incompatibilities arise. It’s better to begin this process before it becomes dire for your law firm.
Be forewarned -- extended updates are limited. Only “critical” and “important” security updates, as defined here, will be covered, and only for the duration of the ESU purchase coverage. No improvements, bug fixes, compatibility issues, or extended capabilities will be introduced, which will contribute to the degrading quality of Windows 10 over time. Chances are, if you are adopting any new technology this year, including AI, your needs will quickly outpace your capabilities with Windows 10.
If your law firm can’t complete your transition by the October 14th deadline, you’ll want to at least enroll in an ESU program if possible—this offers you some additional risk mitigation as you evaluate next steps and begin the process of moving away from Windows 10.
Many law firms have a low tolerance for cyber risk. After all, legal professionals are frequently targeted by hackers, and the stakes are extremely high due to the sensitive and confidential information stored in their technology systems.
It’s important to evaluate your cybersecurity posture to gain a clear understanding of the risks introduced by using an outdated system. Continuing usage of Windows 10, especially without purchasing or enrolling in an ESU program, will introduce new cybersecurity vulnerabilities and exacerbate existing ones.
If your law firm is like many businesses, you’re likely enrolled in a cyber insurance policy. Using Windows 10 past the deadline could put your coverage at risk.
Your insurer, like many, may require updated software, as this is a critical facet of your cybersecurity risk. End-of-life or out of date software incurs a high volume of additional risk, and insurers may deny your coverage if you’re still using Windows 10 past the deadline—especially if you cannot or choose not to enroll in the ESU program.
Insurers often require regular security updates, and may deny your claim if any of your systems are not up-to-date at the time an incident occurs. Be sure to check with your insurance provider when making decisions about your Windows 10 plan of action.
For most Windows 10 customers, the two most popular options for upgrading after the deadline will be where their work environment lives - Windows 11 or Windows 365. Let’s break down the differences.
Windows 11 is the next comparable operating system released after Windows 10. Like Windows 10, it requires a one-time license purchase that remains yours forever or comes bundled with your Microsoft Office professional subscription. This operating system can be installed on any compatible device.
When Windows 11 was introduced, it impressed users with a suite of new features, such as:
Windows 11 is solely an operating system, meaning that you will need to couple it with non-Microsoft solutions such as security tools.
Windows 365 is a cloud-based desktop that your law firm may license on a subscription basis to run Windows 11 via the cloud. 365 offers seamless updates and easier management for organizations and their IT partners.
Windows 11 requires a certain level of hardware compatibility to draw its power from your device, whereas 365 is a virtual desktop compatible with a wider group of devices because it is powered by the cloud, lessening the demand on your hardware’s power.
Windows 365 offers additional features perfect for law firms, including:
Where each option fits into your tech stack can depend greatly on your use case—and your law firm may even need to utilize both alternatives in order to stay safe and functional. It’s best to consult your IT partner or in-house team before making any sudden purchases.
It can be extremely difficult to transition your workforce to new technology on your own—especially if you have a very small or perhaps no in-house IT department.
When transitioning from an end-of-life technology to an alternative, inherent risks and vulnerabilities open up your law firm to attacks. Hackers can impersonate vendors, slip a convincing phishing email in while staff receives legitimate emails relating to the transition, enter through new holes in your security posture as you commission and decommission devices and solutions, and exploit vulnerabilities in your new solutions that you may be unaware of.
Even getting rid of your devices is tricky—if you need to upgrade your hardware due to compatibility issues with Windows 11, for example, it can be extremely dangerous not to have a professional turn down the device.
Hackers use “e-waste hacking” methods to comb through discarded devices for data and access keys, and can easily restore deleted data if the device is not properly turned down.
All data and access portals must be thoroughly wiped prior to placing your device in potentially risky hands by disposing of the device, donating it, or sending it to a recycling company. The average non-IT expert cannot properly ensure that data isn’t still embedded in your hardware or software, even if they’re extremely careful—it takes truly expert eyes and vendor vetting to ensure your devices don’t end up in bad hands.
Most law firms avoid technology transitions for as long as possible due to the potential downtime and training time that takes away from their workflows and productivity. A professional IT partner helps you avoid this in many ways, including:
When approaching an end-of-life deadline, getting started quickly is crucial to your success. You’ll want to begin making decisions and starting the process today to prevent potential security risks, downtime, and additional headaches.
We’re proud to be a Microsoft Partner, and have helped law firms like yours migrate hundreds of users to Windows 11, Microsoft 365, and other Microsoft products with minimal impact to their business continuity and maximum value to their law firm. Our legal industry expertise helps us cater the transition process to the unique needs of your law firm and users.
Get in touch today for help, guidance, and services to support your transition process. Just click the button below to get started.