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Dear @Jill Blain,
Thank you for the detailed explanation. I understand what you’re trying to achieve here.
Based on your description, this behavior is expected. When the user initially selects “No, this app only”, the device is not registered in your organization, and Windows will not automatically show the “Allow my organization to manage this device” prompt again
In this case, you’ll need to reconnect the work account through Windows so the registration process (and the popup you need) is triggered again. Please ask the user to follow the steps below:
Step 1: First, on the device, go to Windows Settings > Accounts > Access work or school. If the work account is listed, select it and click Disconnect.
Go to Settings > Accounts > Email & accounts and remove any connected work or school accounts if they are still listed. Then restart the device.
Step 2: Sign out of all Office applications (such as Outlook, Teams, or Word), close them.
Step 3: Type credential manager in the search box on the taskbar and select Credential Manager Control panel > Select Windows Credentials to access the credentials you want to manage. From there, remove any entries related to Microsoft accounts, Office, or work/school accounts (for example, entries containing “MicrosoftOffice”, “ADAL”, or “Token Broker”). For reference: Credential Manager in Windows
Step 4: After the restart, go back to Settings > Accounts > Access work or school, and click Connect. Enter the work account credentials and proceed with the sign-in.
During this process, the system should display the “Automatically sign in to all desktop apps and websites on this device” screen again, where they can tick “Allow my organization to manage my device” and select “Yes, all apps.”
However, if the issue still persists after clearing the Windows credentials and reconnecting the account, you can proceed with creating a new Windows user profile on the device. For more information and instruction, please follow this article: Manage User Accounts in Windows
This step helps because a new profile provides a completely clean environment with no cached sign-in data, which ensures the device registration process starts fresh. Once the new profile is created, please sign in with the work account again.
Note: Please understand that as a forum moderator, my role is to provide general guidance and troubleshooting support. I don’t have access to internal systems or backend tools, and I appreciate your understanding of these limits.
I hope the information shared helps point you in the right direction. Please try the steps above and let me know if they work. If not, we can continue working together to narrow this down.
The first response may not always resolve the issue right away, but with your help and more details, we can work toward a solution.
Thank you for your patience and understanding. I'm looking forward for your reply.
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