Windows Deployment Services (WDS) enables you to deploy Windows operating systems over the network, which means that you do not have to install each operating system directly from a CD or DVD. I have written some interesting guides on WDS, please take a look: ADK|WinPE|MDT: Deploy Windows with WDS, and how to set up and install the WDS role. Here are some more interesting articles: WDS and DHCP Deployment Scenarios: Configure DHCP Options 60, 66, and 67, and how to remove Windows Deployment Services role via the GUI and PowerShell. In this article, I will be showing you how to fix “OOBEZDP: Something went wrong during the Windows deployment. You can try again or skip it for now”.

Windows Out of Box Experience (OOBE)

Before proceeding to fix this issue, let us discuss what an OOBE is. When a user starts a new Windows-based computer, or after they install a new Windows operating system, the Out-Of-Box Experience (OOBE) guides the user through various setup operations. OOBE is a series of screens that require customers to accept license agreements, connect to the internet, log in with, or sign up for a Microsoft Account (MSA), and share information with the OEM. The choices you make in your hardware and software determine how much work customers must do to complete OOBE before they can enjoy their new devices.

Please see Fix macOS Apps opening on the wrong desktop, How to create AWS Flow logs Role, how to fix “The plugin filter file/etc/ansible/plugin_filters(yml) does not exist – Skipping, and how to fix “The logon attempt failed for the remote desktop connection“.

The OOBE flow is also designed to reduce cognitive load significantly by breaking up tasks into discrete chunks. Although there are several pages in the OOBE flow, each one requests a specific action or input from the user. This is helpful for our average customer (and even many power users) and has been shown to reduce fatigue significantly. Below is a typical example of the OOBE workflow.

The following is a non-exhaustive list of screens the user may see during OOBE. The order below is the generally expected order of pages, however, some pages may not appear or may appear in a different order than the flow below.
- Language selection
- Region selection
- Keyboard selection
- Connect to a network. Note that connecting to a network is required to complete OOBE on Home SKUs.
- Download of critical patches and driver updates. See Windows updates during OOBE for more details.
- End User License Agreement (EULA)
- Sign in to, or create, a local account or Microsoft account (MSA).
- Welcome back. This screen displays if a user logs in with a Microsoft account and has previously backed up a Windows device.
- Windows Hello setup
- Privacy settings. Users will see up to seven privacy settings on this screen. Not all users will see the same settings.
- Customize your device. See Device usage intent for more details
- Save files to OneDrive
- Microsoft 365 trial
- OEM Registration pages. See Design guidance for OEM registration pages for design guidance.
- Get the latest from Windows.

OOBEZDP Background

If you have looked at your WSUS (Windows Server Update Services) server lately should have seen a new “Product and Classification” named OOBEZDP! Should you want to read about ZDP, please visit this link.

Why was the “You can try again or skip it for now – OOBEZDP” Prompted?

When deploying Windows 11 VM on HyperV, you might be prompted with this window. All you need to do is click on Try again. The first attempt might fail but subsequent attempts will run and updates will be downloaded and applied to your VM. Here is a similar scenario relating to OOBE: Windows Out Of Box Experience: OOBESETTINGSMULTIPLEPAGE error on Windows 10.

The reason for this error is that "OOBEZDP was designed to allow “must have” updates to be installed during OOBE before the user reaches the Start Screen. These updates are meant to fix security holes and functional issues that block core experiences in Blue as early as possible"

Resolution

To resolve these issues, you will have to click on “Try again” at the bottom of the screen as shown in the above image. The OOBE process should continue as expected. If it fails on the first try, please try again. It should succeed…

Note: OOBE ZDP update should not require more than one reboot. The combined size of all available OOBE ZDP updates should be less than 5MB. The combined install time of all OOBE ZDP should be less than 4 minutes. A device will reboot during OOBE if one or more of the following occurs:

A customer chooses a language that isn’t the default language.
A device downloads a ZDP update during OOBE.
If an updated version of Windows is installed.

Note: After a reboot, a device will repeat one or more pages during OOBE if any of the following occurs.
- If a device didn't previously connect to a network or 
- If a device loses its network connection during the reboot.

I hope you found this blog post helpful on how to go about “OOBEZDP: Something went wrong during the Windows deployment”. If you have any questions, please let me know in the comment section.