Should You Upgrade to Windows 11 in 2026?

If your computer is popping up messages about Windows 11, you're not alone. Thousands of Connecticut families are getting these notices, and many are confused about what to do. With Windows 10 support ending in October 2025, you're probably wondering if you should upgrade now, wait, or just keep using what works.

Here's the reality: after October 2025, Microsoft will stop sending security updates to Windows 10 computers. For folks across Litchfield County and western Connecticut, this matters more than you might think. Without those updates, your computer becomes more vulnerable to viruses and hackers. But upgrading isn't always straightforward, and not every computer can even run Windows 11.

In this guide, I'll walk you through how to check if your computer can upgrade, whether you should upgrade right now, and what your other options are. No tech jargon, just straight answers.

Should You Upgrade to Windows 11 Right Now?

The short answer: it depends on your computer and how you use it.

Windows 11 has been out since 2021, so most of the early bugs are fixed. It's generally stable now. But here's what most people don't tell you: many older computers can't run Windows 11 at all, even if they run Windows 10 just fine. Microsoft added strict hardware requirements that lock out computers more than 4-5 years old.

If your computer can run Windows 11, and you're comfortable with change, upgrading before the October 2025 deadline makes sense. You'll keep getting security updates and new features. If your computer can't run it, you'll need to decide whether to buy a new computer or explore other options.

How to Check If Your Computer Can Run Windows 11

Before you make any decisions, let's find out if Windows 11 is even an option for you. Here are the steps to check:

1. Open the PC Health Check app. Microsoft created a free tool for this. Go to your Start menu and search for "PC Health Check." If it's not installed, go to Microsoft's website and download it (search "PC Health Check Microsoft" in your web browser). This tool does all the technical checking for you so you don't have to guess.
2. Run the compatibility check. Open the PC Health Check app and click the button that says "Check now" under Windows 11. The app will scan your computer for about 30 seconds. Why this works: the app checks for specific chips and security features that Windows 11 requires, like TPM 2.0 and Secure Boot, which sound complicated but are just security components built into newer computers.
3. Read the results carefully. You'll see one of two messages: either "This PC can run Windows 11" or "This PC doesn't currently meet Windows 11 system requirements." If you get the second message, click "See all results" to find out exactly what's missing.
4. Understand what the results mean. If your computer passes, you're good to upgrade whenever you're ready. If it fails because of TPM or Secure Boot, sometimes these features just need to be turned on in your computer's BIOS settings (this is technical and probably needs professional help). If it fails because your processor is too old, there's usually no way around it. Why this matters: Microsoft won't let you install Windows 11 on incompatible computers through normal methods.
5. Check your current Windows 10 version. Click the Start button, go to Settings (the gear icon), then System, then About. Look for "Version" under Windows specifications. If you see Version 21H2 or newer, your Windows 10 is relatively current. Older versions might mean your computer is too old for Windows 11 anyway.
6. Write down your results. Grab a piece of paper and note whether your computer passed or failed, and if it failed, write down what it said was missing. You'll want this information if you call a repair shop or need to make a decision later.
7. Check your computer's age. Look for a sticker on your computer (usually on the bottom of laptops or back of desktops) that shows the manufacture date or model number. Generally, computers from 2018 or newer have a better chance of running Windows 11. Those from 2017 or earlier usually can't. This gives you context for your decision: if your computer is 7-8 years old and can't run Windows 11, it might be time for a new one anyway.

Honest assessment: These steps will tell you definitively whether you can upgrade about 90% of the time. The other 10% involves BIOS settings that are too risky for most people to change on their own.

What to Do If Your Computer Can Run Windows 11

If you got the green light, here's my recommendation: upgrade sometime in 2025, but don't rush. Windows 11 is stable, but every computer is different. Waiting until spring or summer 2025 gives you a cushion before the October deadline while ensuring any remaining quirks are worked out.

Before you upgrade, back up your important files to an external hard drive or cloud storage. The upgrade usually keeps everything, but it's better to be safe. Also, write down any passwords you have saved, especially for your email and important websites.

When you're ready, Windows will likely offer you the upgrade through Windows Update. Go to Settings, Update & Security, then Windows Update. If you see an option to upgrade to Windows 11, you can click it and follow the prompts.

What to Do If Your Computer Can't Run Windows 11

This is where it gets tricky, and you have several options:

Option 1: Keep using Windows 10 past October 2025. Your computer won't suddenly stop working. It just won't get security updates. If you mainly use your computer for basic tasks, don't store sensitive information, and are careful about what you click on, this might be okay for a year or two. But understand the risks: you're more vulnerable to viruses and security problems.

Option 2: Buy a new computer. If your computer is 6+ years old, this might make the most sense. New computers aren't as expensive as they used to be. A decent laptop for email, web browsing, and basic tasks runs $400-$600. Desktop computers can be even cheaper. Any new computer you buy today will come with Windows 11 already installed.

Option 3: Extended Security Updates. Microsoft announced they'll offer paid security updates for Windows 10 for one additional year (until October 2026). The price hasn't been announced yet, but for previous versions of Windows, this cost around $50-$100 per year for home users. This buys you time if you're not ready to upgrade or replace your computer.

Option 4: Switch to a different operating system. Some people switch to Linux (a free alternative to Windows) or buy a Chromebook. This only makes sense if you're comfortable learning something completely different or if you mainly use your computer for web browsing and email.

Common Problems People Run Into

Even when computers are compatible, the upgrade doesn't always go smoothly. Here are issues I see regularly:

Printers stop working. Older printers sometimes don't have Windows 11 drivers (the software that lets your computer talk to your printer). Before upgrading, check your printer manufacturer's website to see if Windows 11 drivers are available for your model.

Software compatibility issues. Old programs, especially business software or specialized applications, might not work on Windows 11. If you rely on specific software for work or hobbies, check with the software company first.

The upgrade gets stuck or fails. Sometimes the upgrade process freezes or gives error messages. This can happen for dozens of reasons, from not enough hard drive space to conflicting software running in the background.

Still Not Working?

Some problems are beyond basic troubleshooting:

• BIOS settings need adjustment: If your computer has the right hardware but the PC Health Check says it's not compatible, the issue might be in your BIOS settings. Changing these settings requires technical knowledge, and one wrong setting can prevent your computer from starting.
• The upgrade fails repeatedly: If you've tried upgrading and it keeps failing with error codes, there's usually an underlying problem with your hard drive, drivers, or Windows installation that needs professional diagnosis.
• You need to save data from an old computer: If you've decided to buy a new computer, you'll want to transfer your files, settings, email accounts, and bookmarks from the old one. This is straightforward for tech-savvy people but can be confusing if you're not sure where everything is stored.

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STILL HAVING PROBLEMS?

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Frequently Asked Questions

Will my files be deleted if I upgrade to Windows 11?

No, the upgrade process is designed to keep all your files, programs, and settings. However, you should always back up important files before any major computer change, just in case something goes wrong. Think of it like wearing a seatbelt: you probably won't need it, but you'll be glad it's there if you do.

How long does the Windows 11 upgrade take?

Plan on 1-3 hours depending on your computer's speed and how much stuff you have installed. Your computer will restart several times during the process. Don't turn it off or unplug it while it's upgrading, even if it seems stuck.

Can I go back to Windows 10 if I don't like Windows 11?

Yes, but only for 10 days after you upgrade. Windows keeps a copy of your old system for that period. After 10 days, that backup is automatically deleted to free up space, and going back becomes much more complicated.

Is Windows 11 really that different from Windows 10?

The Start menu moved to the center of the taskbar (you can move it back to the left), and some settings are in different places. The overall look is more rounded and colorful. But most of what you do day-to-day, like opening programs and browsing files, works basically the same way. Most people adjust within a week or two.

The Bottom Line

With Windows 10 support ending in October 2025, you have about a year to make a decision. If your computer can run Windows 11 and you're comfortable upgrading, plan to do it sometime in 2025. If your computer can't run it, start thinking about whether you want to buy a new computer or explore other options like extended security updates.

The worst thing you can do is nothing. Come November 2025, if you're still running Windows 10 without a plan, you're leaving yourself vulnerable to security problems. Take some time now to check your computer's compatibility and decide what makes sense for your situation.

And remember, you don't have to figure this out alone. Whether you need help checking compatibility, backing up your files, or making the upgrade happen smoothly, professional help is available right here in Connecticut.