Overcoming OneDrive Sign-In Hurdles: AD Domain, Azure AD, and MFA Insights


My PC is connected to an on-premise AD domain, and it utilizes Azure AD Connect with Password Hash Sync and writeback capabilities. Single Sign-On (SSO) is operational for my Office 365 applications. I’ve established Test OUs for experimentation, and my group policies seem to be enforcing correctly, in line with the GPOs mentioned in a prior discussion.

OneDrive was installed on my test PC with the ‘/allusers /silent’ parameters.

Our setup includes Multi-Factor Authentication (MFA) and conditional access, with policies in place to exempt MFA within our corporate network.

Attempts to modify the EnableADAL registry setting to either ‘1’ or ‘2’ haven’t yielded the desired outcome.

Given that all configurations appear correct, is there a possibility that OneDrive may not support the functionality I’m envisioning? If so, could you suggest a method to script the automatic login process?”


In a well-integrated Active Directory (AD) environment, seamless user experiences are expected, especially when it comes to applications like OneDrive. The scenario you’ve described—where OneDrive requires manual sign-in despite the presence of Single Sign-On (SSO) for Office 365 apps—can indeed be perplexing. Let’s delve into the potential reasons and explore scripting solutions that might address this issue.

Understanding the Configuration

Your setup involves a PC joined to an on-premise AD domain, leveraging Azure AD Connect with Password Hash Sync and writeback capabilities. This is a robust configuration that should, in theory, facilitate a smooth SSO experience across Office 365 applications, including OneDrive.

The use of Group Policy Objects (GPOs) to enforce settings and the deployment of OneDrive with ‘/allusers /silent’ switches are also in line with best practices for enterprise environments. Moreover, the exemption of MFA within corporate IPs through conditional access policies is a common approach to balancing security with usability.

Potential Causes for Sign-In Issues

Despite the correct configurations, the EnableADAL registry setting’s modification not leading to automatic sign-in suggests that there might be other underlying issues. Here are some potential causes:

  • Group Policy Conflicts: Ensure there are no conflicting GPOs that might override the desired auto sign-in behavior.
  • Version Compatibility: Verify that the OneDrive client version is compatible with the latest updates and patches from Microsoft.
  • Network Restrictions: Sometimes, network policies or firewall settings can interfere with the authentication process.
  • Scripting the Solution

    If OneDrive’s native functionality doesn’t support the envisioned auto sign-in process, scripting could be a viable workaround. Here’s a conceptual approach using PowerShell:


    PowerShell Script to Automate OneDrive Sign-In

    $UserCredential = Get-Credential -Message “Enter your Office 365 credentials”

    Start-Process “OneDrive.exe” -ArgumentList “/background”

    Start-Sleep -Seconds 5

    Wait for OneDrive to start

    $wshell = New-Object -ComObject wscript.shell

    foreach ($char in $UserCredential.GetNetworkCredential().Password.ToCharArray()) {

    $wshell.SendKeys($char) Start-Sleep -Milliseconds 500 } $wshell.SendKeys(“{ENTER}”) “`

    This script prompts for Office 365 credentials, launches OneDrive in the background, and simulates keystrokes to input the password and press Enter. Note that this is a simplified example and would need to be adapted to fit into your security framework and comply with your organization’s policies.


    While scripting can provide a temporary fix, it’s essential to investigate the root cause of the sign-in issue. Engaging with Microsoft support or consulting with IT professionals specializing in Azure AD and Office 365 integrations may yield a more permanent solution. Remember, any scripted solution should be thoroughly tested and reviewed for security implications before deployment in a production environment.

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