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MD-102 Practice Question: A Microsoft 365 Endpoint Administrator for a…
You are a Microsoft 365 Endpoint Administrator for a mid-sized company with 5,000 Windows 10 devices. The company is planning to migrate to Windows 11. You are tasked with deploying Windows 11 using a phased approach with Windows Autopilot. You have configured an Autopilot deployment profile for self-deploying mode targeting all Windows 10 devices in a dynamic device group. However, during the first wave of deployment, you notice that devices that have been upgraded to Windows 11 via an in-place upgrade are not automatically transitioning to the Autopilot experience. Instead, they boot directly to the existing Windows 10 desktop without any Autopilot enrollment. You verify that the devices are registered in Autopilot and that the deployment profile is assigned correctly. What is the most likely cause of this issue?
⚠ Common exam trap
It's easy for candidates to assume Autopilot enrollment will automatically trigger after any upgrade or reboot on a registered device, but they overlook the critical requirement that the device must be in OOBE state to initiate the Autopilot process.
Answer choices
Why each option matters
Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
✓
The devices have not been reset to OOBE state after the in-place upgrade
Windows Autopilot requires the device to be in an Out-of-Box Experience (OOBE) state to trigger the enrollment process. An in-place upgrade to Windows 11 preserves the existing user state and settings, so the device boots directly to the desktop without entering OOBE. Even though the device is registered in Autopilot and the profile is assigned, the Autopilot experience only initiates when the device is reset to OOBE (e.g., via a Windows reset or a fresh start). Therefore, the most likely cause is that the devices have not been reset to OOBE state after the in-place upgrade.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
- ✗
The Autopilot profile has a pre-provisioning policy that blocks self-deploying mode
Why it's wrong here
Pre-provisioning is not related.
- ✓
The devices have not been reset to OOBE state after the in-place upgrade
Why this is correct
Autopilot requires OOBE; upgrade doesn't trigger OOBE.
- ✗
The Autopilot profile is configured for user-driven mode instead of self-deploying mode
Why it's wrong here
The mode does not affect enrollment after upgrade.
- ✗
The devices are not connected to the internet during the first boot after upgrade
Why it's wrong here
Internet connection is needed but not the root cause.
Go deeper
Related to this question
Learn chapter
Introduction to Endpoint Management in Microsoft 365
Key term
Fresh Start
Fresh Start is a Windows deployment and recovery feature that reinstalls Windows while removing all pre-installed manufacturer applications, aiming to restore the operating system to a clean, original state.
Key term
Dynamic device group
A Dynamic device group is an Azure AD / Microsoft Entra ID feature that automatically adds or removes devices based on membership rules you define.
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Written by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
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