Automate Windows 11 Upgrade

by | Apr 1, 2025 | Deployments, Information Technology, PowerShell | 0 comments

Upgrading Windows 11 across multiple machines is one of those tasks that sounds simple—until you realize you need to manually download the ISO, mount it, and run the upgrade for every single computer. If you’re managing a fleet of devices, that’s a lot of clicking and waiting. Thankfully, PowerShell can help automate this process, saving IT admins from hours of repetitive work. So today, we will Automate Windows 11 Upgrade with PowerShell.

But before we jump in, there’s one crucial step: Microsoft requires you to manually generate the download link for the Windows 11 ISO. That’s right—no direct API calls or magic URLs here. You’ll need to visit the Microsoft website and grab the link yourself. Don’t worry, we’ll walk you through that part.

And hey, if you’re wondering why Microsoft makes you do this manually… well, let’s just say it’s like trying to convince a cat to use the expensive bed you bought instead of the random cardboard box it found in the corner. Some things just don’t make sense, but we roll with it anyway.

Alright, let’s dive in! First up: generating that all-important download link.

The Script

Write-Host "Go to: https://www.microsoft.com/en-us/software-download/windows11"
Write-Host "Select Windows 11 (multi-edition ISO for x64 devices)"
Write-Host "Click Download"
Write-Host "Select English (United States)"
Write-Host "Click Confirm"
Write-Host "Right Click '64-bit Download' and click 'Copy link'"

$DownloadURL = Read-Host "Enter the Windows 11 ISO download link (in quotes)"
$ComputerName = Read-Host "Enter the target Computer Name"

# Check if the computer is online
if ($null -ne (Test-Connection -ComputerName $ComputerName -Count 1 -Quiet)) {  
    
    # Start a remote PowerShell session
    Enter-PSSession -ComputerName $ComputerName  
    
    # Ensure C:\temp exists
    if (!(Test-Path C:\temp)) {New-Item -Path C:\ -Name temp -ItemType Directory -Force}  

    # Set download path
    $DownloadPath = "C:\temp\win11.iso"

    # Download Windows 11 ISO
    Invoke-WebRequest -Uri $DownloadURL -OutFile $DownloadPath  

    # Mount the ISO
    $DiskImage = Mount-DiskImage -ImagePath $DownloadPath -StorageType ISO -NoDriveLetter -PassThru  
    $ISOPath = (Get-Volume -DiskImage $DiskImage).UniqueId

    # Create a PSDrive for the mounted ISO
    New-PSDrive -Name ISOFile -PSProvider FileSystem -Root $ISOPath  
    Push-Location ISOFile:

    # Find and run Setup.exe with upgrade parameters
    $SetupExe = (Get-ChildItem | Where-Object {$_.Name -like "*Setup.exe*"}).FullName  
    $Arguments = "/auto upgrade /DynamicUpdate Disable /quiet /eula accept /noreboot"  
    Start-Process -Wait -FilePath $SetupExe -ArgumentList "$Arguments" -PassThru  

    # Clean up: Unmount ISO and remove PSDrive  
    Pop-Location  
    Remove-PSDrive ISOFile  
    Dismount-DiskImage -DevicePath $DiskImage.DevicePath  

    # Ask for a restart decision  
    $YN = Read-Host "Do you want to restart? (Y/N)"  
    if ($YN -like "*Y*") {Restart-Computer -Force}  
    elseif ($YN -like "*N*") {Write-Host "Ask the user to restart."}  
    else {Write-Host "Ok, whatever, ask the user to restart."}  

} else {  
    Write-Host "The target computer is not reachable. Check the network or hostname and try again."  
}

Step 1: Generate the Windows 11 ISO Download Link

Before we can automate the upgrade, we need the direct download link for the Windows 11 ISO. Microsoft doesn’t make this easy—there’s no simple API to fetch it. Instead, you have to manually grab the link from their website.

This step is non-negotiable because Microsoft generates a unique download link each time, which expires after 24 hours. So if you’re thinking, “Can’t I just reuse an old link?”—nope, Microsoft shut that door. But don’t worry, it’s a quick process:

How to Get the Windows 11 Download Link

  1. Go to the official Microsoft download page:
  2. Scroll down to ‘Download Windows 11 Disk Image (ISO)’
    • Select Windows 11 (multi-edition ISO for x64 devices) from the dropdown.
  3. Click ‘Download’ and select English (United States) as the language.
  4. Click ‘Confirm’—Microsoft will generate a download button.
  5. Right-click ‘64-bit Download’ and select ‘Copy link’ (This is the direct ISO link).

You’ll need this URL when running the PowerShell script, so paste it somewhere handy.

Now that we have the link, let’s move on to running the script!

Step 2: Running the PowerShell Script

Alright, you’ve got your Windows 11 ISO download link. Now it’s time to run the PowerShell script and start the upgrade. But before we do that, let’s talk about remote execution. This is part of the process to Automate Windows 11 Upgrade with PowerShell.

PowerShell remoting (aka WinRM) needs to be enabled on the target machine. If you’ve never set it up before, it’s kind of like getting a cat to sit still for a vet visit—it might resist at first, but once it’s done, life is easier.

Prerequisites for Running the Script

Make sure the following are true before running the script:

  • Your user account has admin privileges on both the local and remote machine.
  • WinRM (Windows Remote Management) is enabled on the target machine. Run this command on the remote PC to check:
winrm quickconfig

If WinRM isn’t enabled, you’ll need to set it up first.

  • PowerShell Execution Policy allows scripts to run. If needed, you can temporarily bypass restrictions with:
Set-ExecutionPolicy Bypass -Scope Process -Force

Running the Script

Once the prerequisites are in place, open PowerShell as Administrator on your local machine and run the script. When prompted:

  1. Paste the Windows 11 ISO download link (from Step 1).
  2. Enter the target computer’s name (the one you want to upgrade).

If all goes well, PowerShell will initiate a remote session, create a C:\temp folder, and start downloading the ISO to the remote machine.

Just like how a cat will eventually use the new bed if you keep putting treats in it, the script will do its job—as long as everything is set up correctly.

Next up: Downloading and Mounting the ISO!

Step 3: Downloading and Mounting the ISO

At this point, the PowerShell script is running, and the target computer is ready. Now comes the fun part—actually downloading and mounting the Windows 11 ISO.

If you’ve ever tried downloading a large file over a shaky network, you know it can be as frustrating as a cat deciding to sprint across the house at 3 AM for no reason. But don’t worry, the script handles it all automatically.

How the Script Handles the Download

Once you enter the download link and the computer name, the script:

  1. Creates a C:\temp folder (if it doesn’t already exist).
  2. Uses Invoke-WebRequest to download the ISO to C:\temp\win11.iso.

Here’s the key part of the script doing the work:

if (!(Test-Path C:\temp)) {New-Item -Path c:\ -Name temp -ItemType Directory -Force}  
$DownloadPath = "C:\temp\win11.iso"  
Invoke-WebRequest -Uri $DownloadURL -OutFile $DownloadPath

Mounting the ISO

Once the ISO is downloaded, PowerShell mounts it like a virtual disk, allowing access to the installation files.

$DiskImage = Mount-DiskImage -ImagePath $DownloadPath -StorageType ISO -NoDriveLetter -PassThru  
New-PSDrive -Name ISOFile -PSProvider FileSystem -Root (Get-Volume -DiskImage $DiskImage).UniqueId  
Push-Location ISOFile:

At this point, the Windows 11 setup files are accessible.

If you check File Explorer on the target computer, you should see a new virtual drive containing the ISO contents—like when a cat suddenly appears on your keyboard, except this time, it’s actually doing something useful.

Now that we have the ISO mounted, it’s time for the real action: starting the upgrade!

Step 4: Starting the Upgrade Process

Alright, the ISO is mounted, and we’re at the final stretch—actually running the Windows 11 upgrade. If everything has gone smoothly so far, congratulations! You’re officially ahead of the game.

Now, instead of manually clicking through the Windows setup (which is about as exciting as watching a cat stare at a wall for hours), PowerShell will automate the upgrade process using Setup.exe and a few command-line arguments.

Finding and Running Setup.exe

Since we mounted the ISO in the previous step, we now need to:

  1. Find Setup.exe inside the mounted ISO
  2. Run it with automation flags to start the upgrade silently

The script takes care of that with:

$FileList = Get-ChildItem  
$SetupExe = ($FileList | Where-Object {$_.name -like "*Setup.exe*"}).FullName  
$Arguments = "/auto upgrade /DynamicUpdate Disable /quiet /eula accept /noreboot"  
Start-Process -Wait -FilePath $SetupExe -ArgumentList "$Arguments" -PassThru

Breaking Down the Command-Line Arguments

Here’s what each flag does when running Setup.exe:

  • /auto upgrade → Tells Windows to start an upgrade instead of a fresh install.
  • /DynamicUpdate Disable → Skips downloading the latest updates during the install (useful for speeding things up).
  • /quiet → Runs the installer in the background, so no annoying pop-ups.
  • /eula accept → Automatically accepts Microsoft’s End User License Agreement (because let’s be real, no one reads it).
  • /noreboot → Prevents an automatic restart so we can control when it happens.

What Happens Next?

Once this runs, the Windows 11 upgrade process kicks off in the background. There won’t be any flashy UI—just PowerShell doing its thing. You can check progress by looking at Task Manager on the target machine.

At this point, it’s like when a cat finally decides to nap on that expensive bed instead of the cardboard box—you’ve done all the hard work, and now it just has to finish on its own.

But there’s one last decision to make: When do we restart?

How are we feeling about Automate Windows 11 Upgrade with PowerShell so far?

Step 5: Restarting the Machine

At this point, the Windows 11 upgrade is in motion, but the installation won’t complete until the target machine restarts. Now, we could just force a reboot, but let’s be real—no one likes unexpected restarts (especially end users in the middle of something important).

So, instead of pulling the plug immediately, the script politely asks whether to restart now or later. Here’s how that works:

$YN = Read-Host "Do you want to restart"  

if ($YN -like "*Y*") {  
    Restart-Computer -Force  
} elseif ($YN -like "*N*") {  
    Write-Host "Ask the user to restart"  
} else {  
    Write-Host "Ok, whatever, ask the user to restart."  
}

Breaking It Down

  • If the admin enters Y → The system restarts immediately.
  • If the admin enters N → A message reminds them to tell the user to restart manually.
  • If they enter anything else → The script shrugs and tells them to figure it out.

This gives IT teams a bit of flexibility, which is crucial in environments where timing matters—like avoiding a forced reboot during an important meeting (unless it’s for that one guy who never restarts his PC… then maybe it’s justified).

What Happens After Restart?

Once the machine reboots, Windows 11 will finish the upgrade process. The whole thing usually takes 30-90 minutes depending on the hardware. During this time, users will see the “Working on updates” screen—so if they call asking why their PC is taking forever, just tell them “It’s optimizing performance” (it sounds fancier than “it’s just installing”).

Final Thoughts

And that’s it! With this script, you can automate Windows 11 upgrades remotely with minimal effort. No more manual downloads, no more sitting through setup screens—just a smooth, scripted process. To Automate Windows 11 Upgrade with PowerShell makes life much easier.

Recap of the key steps:

  • Generate the ISO link manually from Microsoft’s website (because they make us).
  • Run the PowerShell script and provide the ISO link + target computer name.
  • Download and mount the ISO automatically.
  • Start the Windows 11 upgrade silently using Setup.exe.
  • Decide when to restart—now or later.

Now, go forth and upgrade with confidence! And if anything goes wrong, well… let’s just say this script is less stubborn than a cat, so it’s probably not the script’s fault.

What can we learn as a person?

Upgrading an operating system is a big change, but it’s the small steps that make it happen. You don’t just magically jump to Windows 11—first, you grab the ISO, then you run the script, then you mount the image, and finally, the upgrade takes place. One step at a time.

Turns out, our mental health works the same way.

A lot of us get caught up in the idea that improving our mood or reducing stress requires some huge effort—taking a long vacation, completely overhauling our routines, or mastering meditation overnight. But that’s just not how it works. Big upgrades don’t happen all at once.

Instead, try small upgrades for yourself, just like how we upgrade Windows in steps:

  • Clear out junk files → Declutter one small space
    • Just like a clean drive helps performance, tidying up one small area can help clear your mind.
  • Run a quick system check → Check in with yourself
    • Pause for a moment and ask: How am I feeling today? Just acknowledging your emotions can help.
  • Disable unnecessary background processes → Say “no” to one unnecessary thing
    • Reduce mental load by cutting out one thing that’s draining you—whether it’s skipping an unimportant meeting or ignoring a toxic group chat.
  • Reboot when needed → Take a short break
    • A quick restart helps a computer, and sometimes, five minutes away from your screen can work wonders for you too.

No Need for a Full Reinstall

You don’t need a full personality reboot or a total life upgrade to feel better. Small tweaks, small wins—they add up.

So while you’re waiting for that Windows 11 install to finish, maybe take just one small action for yourself. It doesn’t have to be big. Just enough to upgrade your mood one step at a time.

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