Windows Office Hours: February 20, 2025

Autopilot Pre-prov and Web Sign-in not working

Has anyone else encountered a problem or have success with setting up Web Sign-in with Autopilot Pre-provision where it doesn't appear as an option on the first Windows logon? I'm trying to get this to work on the initial Windows sign-on, but only see two "Key" icons instead of an additional "Globe" icon indicating Web Sign-in is an available option. I've followed the instructions, and there's no mention of this being out of scope or unsupported.   System requirements which I am using - e.g., Windows 11 Enterprise 23h2 ( Feb 2025), Entra Joined device.

After logging into Windows for the first time, logging out or restarting makes the Web Sign-in option appear on subsequent logons. I confirmed that the device configuration to enable Web Sign-in is deployed during OOBE and checked the registry to ensure the value is present before the first Windows logon.

When setting up the device normally (without pre-provisioning), the Web Sign-in "Globe" icon appears on the initial Windows logon. I've searched other team channels and found references related to Windows 365 but nothing specific to Autopilot and pre-provisioning issues with Web Sign-in.

Has anyone else noticed this or had success configuring Web Sign-in with Autopilot pre-provisioning?