Windows MDM setup

To control OS settings, updates, and more on Windows hosts follow the manual enrollment instructions.

To use automatic enrollment (aka zero-touch) features on Windows, follow instructions to connect Fleet to Microsoft Entra ID. You can further customize zero-touch with Windows Autopilot.

To migrate Windows hosts from your current MDM solution to Fleet, follow the instructions here.

Manual enrollment

Step 1: Generate your certificate and key

Fleet uses a certificate and key pair to authenticate and manage interactions between the Fleet server and a Windows host.

How to generate a certificate and key:

1. With OpenSSL installed, open your Terminal (macOS) or PowerShell (Windows) and run the following command to create a key: openssl genrsa --traditional -out fleet-mdm-win-wstep.key 4096.

2. Create a certificate: openssl req -x509 -new -nodes -key fleet-mdm-win-wstep.key -sha256 -days 3652 -out fleet-mdm-win-wstep.crt -subj '/CN=Fleet Root CA/C=US/O=Fleet.'.

Note: The default openssl binary installed on macOS is actually LibreSSL, which doesn't support the --traditional flag. To successfully generate these files, make sure you're using OpenSSL and not LibreSSL. You can check what your openssl command points to by running openssl version.

Step 2: Configure Fleet with your certificate and key

In your Fleet server configuration, set the contents of the certificate and key in the following environment variables:

Note: Any environment variable that ends in _BYTES expects the file's actual content to be passed in, not a path to the file. If you want to pass in a file path, remove the _BYTES suffix from the environment variable.

• FLEET_MDM_WINDOWS_WSTEP_IDENTITY_CERT_BYTES
• FLEET_MDM_WINDOWS_WSTEP_IDENTITY_KEY_BYTES

Restart the Fleet server.

Step 3: Turn on Windows MDM

1. Head to the Settings > Integrations > Mobile device management (MDM) page.

2. Next to Turn on Windows MDM select Turn on to navigate to the Manage Windows MDM page.

3. Select Turn on.

Step 4: Test manual enrollment

With Windows MDM turned on, enroll a Windows host to Fleet by installing Fleet's agent (fleetd).

Automatic enrollment

Available in Fleet Premium

To automatically enroll Windows workstations when they’re first unboxed and set up by your end users, we will connect Fleet to Microsoft Entra ID.

After you connect Fleet to Microsoft Entra ID, you can customize the Windows setup experience with Windows Autopilot.

In order to connect Fleet to Microsoft Entra ID, the IT admin (you) needs a Microsoft Enterprise Mobility + Security E3 license.

Each end user who automatically enrolls needs a Microsoft license

Step 1: Buy Microsoft licenses

1. Sign in to Microsoft 365 admin center.

2. In the left-side bar select Marketplace.

3. On the Marketplace page, select All products and in the search bar below All products enter "Enterprise Mobility + Security E3".

4. Find Enterprise Mobility + Security E3 and select Details

5. On the Enterprise Mobility + Security E3 page, select Buy and follow instructions to purchase the license.

6. Find and buy a license.

7. Sign in to Microsoft Entra ID portal.

8. At the top of the page search "Users" and select Users.

9. Select or create a test user and select Licenses.

10. Select + Assignments and assign yourself the Enterprise Mobility + Security E3. Assign the test user the Intune licnese.

Step 2: Connect Fleet to Microsoft Entra ID

For instructions on how to connect Fleet to Microsoft Entra ID, in the Fleet UI, select the avatar on the right side of the top navigation and select Settings > Integrations > Mobile device management (MDM). Then, next to Windows automatic enrollment select Details.

Step 3: Test automatic enrollment

Testing automatic enrollment requires creating a test user in Microsoft Entra ID and a freshly wiped or new Windows workstation.

1. Sign in to Microsoft Entra ID portal.

2. At the top of the page search "Users" and select Users.

3. Select + New user > Create new user, fill out the details for your test user, and select Review + Create > Create.

4. Go back to Users and refresh the page to confirm that your test user was created.

5. Open your Windows workstation and follow the setup steps. When you reach the How would you like to set up? screen, select Set up for an organization. If your workstations has Windows 11, select Set up for work or school.

6. Sign in with your test user's credentials and finish the setup steps.

7. When you reach the desktop on your Windows workstation, confirm that your workstation was automatically enrolled to Fleet by selecting the carrot (^) in your taskbar and then selecting the Fleet icon. This will navigate you to this workstation's My device page.

8. On the My device page, below My device confirm that your workstation has a Status of "Online."

Windows Autopilot

Step 1: Create an Autopilot profile

1. Sign in to Microsoft Intune using the Intune admin user from step 1.

2. In the left-side bar select Devices > Enroll devices. Under Windows Autopilot Deployment Program select Deployment Profiles to navigate to the Windows Autopilot deployment profiles page.

3. Select + Create profile > Windows PC and follow steps to create an Autopilot profile. On the Assignments step, select + Add all devices.

Step 2: Register a test workstation

1. Open your test workstation and follow these Microsoft instructions to export your workstations's device hash as a CSV. The CSV should look something like DeviceHash_DESKTOP-2V08FUI.csv

2. In Intune, in the left-side bar, select Devices > Enroll devices. Under Windows Autopilot Deployment Program select Devices to navigate to the Windows Autopilot devices page.

3. Select Import and import your CSV.

4. After Intune finishes the import, refresh the Windows Autopilot devices page several times to confirm that your workstation is registered with Autopilot.

Step 3: Upload your organization's logo

1. Navigate to Microsoft Entra ID portal.

2. At the top of the page, search for "Microsoft Entra ID", select Microsoft Entra ID, and then select Company branding.

3. On the Company Branding page, select Configure or Edit under Default sign-in experience.

4. Select the Sign-in form tab and upload your logo to the Square logo (light theme) and Square logo (dark theme) fields.

5. In the bottom bar, select Review + Save and then Save.

Step 4: Test Autopilot

1. Wipe your test workstation.

2. After it's been wiped, open your workstation and follow the setup steps. At screen in which you're asked to sign in, you should see the title "Welcome to [your organziation]!" next to the logo you uploaded in step 4.

Automatic Windows MDM Migration

Fleet can automatically migrate your Windows hosts from another MDM solution to Fleet without end user interaction.

Step 1: set up Windows MDM in Fleet

Follow the steps above to turn on Windows MDM in Fleet.

Step 2: install Fleet's agent on the hosts

1. Enroll the Windows hosts you want to migrate to Fleet.

2. Navigate to the Hosts tab in the main navigation bar and wait until your hosts are visible in the hosts list.

Step 3: enable automatic migration

1. Head back to the Settings > Integrations > Mobile device management (MDM) page.

2. Next to Windows MDM turned on (servers excluded) select Edit to navigate to the Manage Windows MDM page.

3. On the Manage Windows MDM page, select Automatically migrate hosts connected to another MDM solution. Click Save to save the change.

Step 4: monitor your hosts as they migrate to Fleet MDM

Once the automatic migration is enabled, Fleet sends a notification to each host to tell it to migrate. This process usually takes a few minutes at most.

You can track migration progress in Fleet. Learn how here.