Support is ending for yet another version of Windows, so I thought it’d be a good idea to go over how to prepare your organization’s devices for a new version of your primary operating system (OS).
In this case, I’ll be covering the end of Windows 10 support, but this advice is pretty versatile no matter which version of Windows you’re upgrading to.
I’ll go over how you might be able to gain access to extended support, what to consider before you migrate to a new OS, and how to ensure your migration goes over smoothly.
Why Upgrade to Windows 11?
As soon as the most current version of Windows becomes the only version Microsoft supports, upgrading to it is no longer a matter of preference. Instead, it becomes a matter of security.
Support for Windows 10 is due to end on October 14, 2025. After that, your PC will not receive any updates for Windows 10, including security updates, quality-of-life updates, and feature updates.
Here’s a direct quote from Microsoft:
“Microsoft will no longer provide free software updates from Windows Update, technical assistance, or security fixes for 10. Your PC will still work, but we recommend moving to Windows 11.”
Software applications will follow suit, so you’ll start to see more and more of the apps you use become inaccessible as your system will no longer be compliant with modern standards.
All of these issues will lead to increased maintenance costs and downtime as security threats and compliancy issues rise.
Can You Extend Support?
Yes, you can extend support until October 13, 2026 by opting into the Extended Security Updates (ESU) program.
It costs $30 and is only available for personal devices in select markets, but it will allow you to continue receiving “critical and important updates” until the program expires on October 13, 2026.
It does not include technical support. The only support you’ll continue receiving from Microsoft is help with activating your license for the ESU program and installing ESU-specific updates.
If you have an eligible device that’s running version 22H2 of Windows 10, you can purchase an ESU license from the Microsoft Store through a built-in tool located in Settings.
What Does Windows 11 Offer?
Microsoft has a page with a full side-by-side comparison you can view to see exactly how Windows 10 and Windows 11 differ and how they relate.
These are the main features Windows 11 offers that Windows 10 does not:
- New user interface (UI)
- The ability to sync your iPhone with your device
- Windows 10 only works with Android phones
- Backup and restore
- Windows 11 allows you to restore files from backups
- More features for Paint
- Smart recommendations in File Explorer and the Start menu
- Smart recommendations will appear as you type in the search bar
- Includes the ability to mark files as favorites and use File Explorer tabs
- Passkeys integrated with Windows Hello
- Apps that support passkeys will allow you to set up passkeys for your accounts instead of passwords. It makes easier to sign in using your phone or Windows Hello
- Passkeys are available for apps and websites in various browsers, not just Edge
- Automatic response
- You can set your device to wake when you approach or lock when you leave
- Smart App Control
- Provides an extra layer of security by only allowing apps with good reputations to be installed on your device
- Seamless docking
- Remembers your settings when you plug in and out of external displays
- Live Captions
- Enables instant captions for Teams calls
- Windows Studio Effects features for live calls
- Auto HDR for more color control
- Several new features targeted toward gamers
Step 1: Choose a Migration Path
Take the time to review the state of your organization’s IT stack. This will help you choose a migration path.
There are two ways to upgrade to Windows 11:
- Upgrade current devices
- Purchase new devices that already have Windows 11 preinstalled
Related: Don’t Let Outdated Tech Slow You Down: Build a Smart IT Refresh Plan
If your devices are more than five years old, replace them, especially if they’re mostly laptops that are harder to upgrade (CPUs are often soldered to motherboards and cannot be replaced, for example).
If they’re more than three years old, consider if you can get away with upgrading hardware instead by investing in faster CPUs, more RAM, better GPUs, and more storage space.
Have a meeting with your staff, and ask them if they ever experience any issues with their devices. This will make it easier for you to decide which course of action to take.
There’s also a possibility that your current devices aren’t compatible with Windows 11 at all. Use Microsoft’s PC Health Check tool to confirm.
If they aren’t compatible, you’ll need to replace them or upgrade incompatible hardware.
Windows 11 Home vs Pro vs Enterprise
Depending on which edition of Windows 10 you’re running, you might also need to consider which edition of Windows 11 you need.
For small businesses, Windows 11 Pro is all you need.
It allows you to lock down your device and manage systems from a remote location with BitLocker Device Encryption and Windows Information Protection, which are features that do not come with Windows 11 Home.
Related: Essential Security Practices for Remote Workers
If you’re a larger organization operating enough devices to justify the need for Windows 11 Enterprise, you’re better off hiring an IT company to manage your IT stack and having them migrate your organization to Windows 11 or whatever OS they recommend for your organization.
If you’re already running Windows 10 Pro, you can upgrade to Windows 11 directly.
If you’re running Windows 10 Home, you have two migration paths you can take:
- Upgrade to Windows 11, then upgrade to Windows 11 Pro
- Upgrade to Windows 10 Pro, then upgrade to Windows 11
Step 2: Create Backups
If you’re upgrading from Windows 10 to Windows 11 on the same device, your files will transfer automatically.
Even so, create backups of your most important files just to be safe.
Theoretically, your organization already has a process for backing up files, so you should already have backups of your most important files.
If not, use this time to develop a backup process. It should include onsite backups and cloud backups. This ensures you always have a backup available should something happen to one or the other.
This is another task you can ask an IT company to manage, especially if your files are sensitive and require more security.
For small businesses, backing up files to OneDrive is more than enough.
Do this by going to Settings → Update & Security → Files Backup → Back up files to OneDrive.
OneDrive storage is free for up to 5GB. Your organization will have access to more storage if you subscribe to Microsoft 365.
Related: 10 Tips to Get the Most Out of Your Microsoft 365 Apps
If you’re upgrading your organization to new devices, you can transfer files between an old device and a new device by connecting an ethernet cable between the two.
Step 3: Test Your Migration Path
Choose a small group of employees, and upgrade their systems first.
Ideally, these will be employees whose devices are not critical to your business’ infrastructure, such as a secretary who can perform their work by logging into another device.
Create your backups, and upgrade to Windows 11 using whatever migration path you chose.
If you’re upgrading to Windows 11 directly, you can download and install it from the Windows Update screen in Settings.
Alternatively, you can download Microsoft’s Windows Installation Assistance tool.
As you upgrade each device one by one, you’ll be able to see how they handle the upgrade and if your files transfer over correctly.
You can tackle any hiccups that occur in a controlled environment, allowing you to work out any kinks before you migrate the rest of your organization.
Step 4: Complete Your Migration to Windows 11
Migrate the rest of your organization in groups. Make sure each device performs as intended and that files get transferred over properly.
If a process your organization uses is changed by Windows 11, train your staff on how to perform that same process in Windows 11.
While no changes will be made to the apps they use, give your team time to adjust to Windows 11.
Ideally, you should perform this upgrade during a period when your organization’s workload is light. That way, your team’s productivity won’t be interrupted by learning new processes.
All in all, this process is a fantastic way to audit the way your organization handles IT.
Plan for the future by making sure you at least have these systems set up by the time you’re done with this process:
- Backups – Make sure your organization has a secure process for backing up files. You should at least back up files to the cloud so you can still access them if your original files get destroyed. You can also create onsite backups with external hard drives, flash drives, and a NAS (Network Attached Storage) server
- Device lifecycle – Choose a timeframe for when your employees’ devices should be replaced or upgraded
Related: Simple Backup and Recovery Plans Every Small Business Needs
Alternative Step: Hire an IT Company
I know I mentioned this a few times, but once your organization gets to a point where your day-to-day operations are dependent on multiple devices, you’re better off hiring an IT company.
Our organization, Digital Technology Solutions, offers the following services:
- Helpdesk support
- Network management
- Endpoint management
- Cloud services management
- Cybersecurity
- Backup and recovery
Get in touch for a custom quote.
Regardless if you hire us or another IT company, outsourcing migration and similar IT tasks to a specialist is highly recommended, especially if your organization is still too small to justify hiring a specialist full time.
It’ll prevent downtime, reduce the duration of outages when they do occur, and strengthen security overall.
