Windows 10 vs Windows 11
Do You Still Have to Upgrade, and What Happens If You Do Not?
By The Bold & The Wise Editorial Team
Friday, May 22, 2026 · 9 min read
Categories: Technology, Friday
Editor’s note: Software support timelines, pricing for Extended Security Updates, and Windows 11 hardware requirements can change; the figures below reflect the most current information available and should be sense-checked against Microsoft’s published guidance before we publish.
Microsoft officially ended support for Windows 10 on October 14, 2025. If you are reading this on a Windows 10 computer — and statistically, many of you are — you have probably received a notification or two suggesting that you upgrade, ignored most of them, and quietly hoped the situation would resolve itself.
It will not. But it is also not as urgent or as complicated as Microsoft would like you to believe.
This article is going to walk you through what your actual options are, in plain language, with the honest answers to the questions you would not feel comfortable asking your tech-fluent grandchild.
First, What “End of Support” Actually Means
When Microsoft says it has ended support for Windows 10, the company is not saying your computer will stop working on a particular date. Your Windows 10 computer turned on yesterday. It will turn on tomorrow. It will turn on next year. The operating system itself is not being remotely disabled.
What end of support means is much narrower, and the distinction matters.
Microsoft is no longer releasing free security updates for Windows 10. New vulnerabilities discovered after October 14, 2025 — and there are always new vulnerabilities — will not be patched on your machine unless you enroll in the paid Extended Security Updates program described below.
This is a real risk, but it is a slow-acting one. A Windows 10 computer used carefully — for email, web browsing on trusted sites, document editing, video calls with family — is not in immediate danger. The risk grows month by month as unpatched vulnerabilities accumulate. By 2027 or 2028, that risk will be meaningful. Today, it is manageable but increasing.
The question is not whether to address this. It is which path makes the most sense for your specific computer and situation.
Your Five Options, Plainly
There are five paths forward. Each is appropriate for someone, and one of them is appropriate for you.
Option one: upgrade to Windows 11 for free.
If your computer meets Windows 11’s hardware requirements, Microsoft will let you upgrade at no cost through Windows Update. This is the best option for most readers whose computers qualify. Your programs and files are preserved during the upgrade. The process takes between one and three hours and requires no technical skill beyond clicking through prompts.
Option two: enroll in Extended Security Updates.
Microsoft offers a paid program that continues delivering security updates for Windows 10 through October 2028. The first year of coverage costs approximately thirty dollars for individual users (some users qualified for free first-year coverage through Microsoft account sync). Pricing for years two and three is higher. This is a reasonable option for someone whose computer cannot run Windows 11 but is otherwise functioning well.
Option three: buy a new computer with Windows 11 preinstalled.
A solid mid-range Windows 11 laptop costs between five hundred and seven hundred dollars new. If your current computer is old, slow, struggling with basic tasks, or simply due for replacement, this is the path that makes the most sense. The remaining useful life of the old machine has to be weighed against the cost of keeping it secure with ESU.
Option four: continue using Windows 10 without security updates.
This is not what Microsoft recommends and not what we recommend, but we want to be honest about it. A cautious user who avoids suspicious websites, does not download files from unknown sources, keeps their browser updated, and runs reputable antivirus software can continue using an unsupported Windows 10 machine for some time. The risk is real but not immediate. We mention this option only because the alternative — pressuring readers into purchases they cannot afford — is worse.
Option five: switch to a different operating system entirely.
If you are willing to consider it, this is the moment to think about whether a Mac or a Chromebook might serve you better going forward. We are not advocating for this — Windows works well for most people — but if you have been frustrated with Windows for years, this transition point is a reasonable moment to reconsider.
How to Check Whether Your Computer Can Run Windows 11
Microsoft publishes a free tool called PC Health Check that examines your computer and tells you definitively whether it qualifies for the free Windows 11 upgrade. Download it from Microsoft’s website by searching for “PC Health Check download” in any search engine and clicking the official Microsoft link.
Run the program. It will produce a clear yes or no answer in under a minute.
The general pattern: computers manufactured in 2018 or later usually qualify. Computers manufactured in 2017 sometimes qualify. Computers manufactured in 2016 or earlier usually do not, because they lack a specific security chip called TPM 2.0 that Windows 11 requires.
If your computer qualifies, the upgrade path is free and we would recommend taking it.
If your computer does not qualify, you are choosing among options two, three, four, or five from the list above.
What Is Actually Different About Windows 11?
This is the question that quietly worries people more than any other. The honest answer is: less than you fear, but not nothing.
The visual differences are immediate. The taskbar icons are centered rather than left-aligned. The Start menu is simpler and looks more like a phone screen. The corners of windows are rounded. The overall appearance is cleaner and somewhat more spare than Windows 10’s busier look.
The functional differences are smaller. All of your existing programs continue to work. Microsoft Office runs identically. Your files open the same way. The web browser, email program, photo viewer, and printer connections all behave the way they did before. If you had to perform a task in Windows 10, the same task is available in Windows 11, in roughly the same place.
There are a few small adjustments that take getting used to. The right-click menu was simplified, though the full menu remains accessible via a “Show more options” link. Moving the taskbar to the top or sides of the screen is no longer possible without special software. The Settings app has been reorganized.
For most users, two or three days of normal use is enough to feel comfortable with the new layout. The differences are real, but they are not the differences between learning a new language and using your familiar one. They are closer to walking into a furniture-rearranged version of your own kitchen.
How to Actually Upgrade, If You Are Going To
Before beginning, back up your computer. This is non-negotiable. The upgrade process is generally smooth, but in the small percentage of cases where something goes wrong, the difference between an inconvenience and a catastrophe is whether your photos, documents, and tax records exist somewhere other than the computer being upgraded.
The cheapest backup is an external hard drive — a one-terabyte external drive costs around fifty dollars and will hold the entire contents of most home computers with room to spare. Plug it in, copy your important folders to it, and disconnect it before starting the upgrade.
Once the backup is complete:
- Click the Start button.
- Click Settings (the gear icon).
- Click Windows Update.
- Click Check for Updates.
If your computer qualifies for the free upgrade, Windows 11 will appear as an available update. Click Download and Install. The process will take between one and three hours depending on your computer’s speed and internet connection. Your computer will restart several times. Do not interrupt the process.
When it is complete, your familiar files, programs, and settings will all be present, in their new Windows 11 surroundings.
A Brief Word on the Extended Security Updates Program
If your computer cannot run Windows 11 and you do not want to replace it, the Extended Security Updates program is the practical answer. Enroll through Windows Update on a current Windows 10 machine — the option appears as a small link in the Update settings.
Microsoft offered free first-year coverage to certain consumers through 2026 if they synced their settings to a Microsoft account. The second year of coverage is priced more aggressively, in the range of sixty dollars. The third year, ending October 2028, costs more again. The program ends in October 2028, and at that point the decision becomes binary: replace the machine or accept the security risk.
For many readers, ESU is a way to buy a year or two to plan a thoughtful computer replacement rather than rushing one.
Our Honest Recommendation
If your computer can run Windows 11, upgrade now. It is free. Get it done. The disruption is real but small, and the alternative paths are all more expensive.
If your computer cannot run Windows 11 and is otherwise functioning well — fast enough, large enough hard drive, comfortable to use — enroll in Extended Security Updates and plan a thoughtful computer replacement over the next one to two years. There is no need to panic-buy a new machine this month.
If your computer cannot run Windows 11 and has been frustrating you for a year or more, this is the moment to replace it. The cost of a solid mid-range Windows 11 laptop is reasonable, and the difference in daily comfort between a sluggish old machine and a competent new one is substantial.
In all cases, back up your data this week regardless of which path you are on. Your photos and documents are the irreplaceable thing in your computer. Everything else can be re-bought.
The Thing No One Mentions
Microsoft’s communication around the end of Windows 10 support has been, charitably, alarming. The notifications imply urgency. The articles online imply you are taking serious risks. The salespeople in electronics stores imply you must buy something now.
The truth is calmer. You have options. The decision is not urgent in the panic sense; it is urgent in the do-not-let-it-slip-another-year sense. Pick a path from the five above. Set aside an afternoon next week to act on it. Then return to using your computer the way you always have, with the quiet satisfaction of knowing the decision is behind you.
Next Monday on The Bold & The Wise: Resistance Training After 55 — The Single Most Important Practice You Are Probably Not Doing, and How to Start Without a Gym, a Trainer, or a Tolerance for Pain.
Products That Make the Transition Easier
- A one-terabyte external hard drive for backing up before any upgrade
- A reliable cloud backup service that runs automatically in the background
- A mid-range Windows 11 laptop for readers who decide to replace
- A reputable antivirus program if you are running Windows 10 without ESU
- A USB drive for keeping Windows installation media on hand
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