Many Windows administrators are familiar with the traditional control userpasswords2 method to enable automatic login. While this worked perfectly in earlier Windows Server versions, Server 2016 implements stricter security policies that override this setting.

The most reliable method involves directly modifying the Windows Registry:

Windows Registry Editor Version 5.00

[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Winlogon]
"DefaultUserName"="YourUsername"
"DefaultPassword"="YourPassword"
"DefaultDomainName"="YourDomain"
"AutoAdminLogon"="1"

Save this as a .reg file and import it, or modify these values manually through regedit.

Before implementing auto-login, consider these security implications:

• Encrypt the registry keys containing credentials
• Use a dedicated service account with minimal privileges
• Implement additional physical security measures

For environments where registry modification isn't possible, create a scheduled task that runs at startup:

$action = New-ScheduledTaskAction -Execute "explorer.exe"
$trigger = New-ScheduledTaskTrigger -AtStartup
$settings = New-ScheduledTaskSettingsSet -AllowStartIfOnBatteries -DontStopIfGoingOnBatteries
$task = Register-ScheduledTask -Action $action -Trigger $trigger -Settings $settings -TaskName "AutoLogin" -User "DOMAIN\user" -Password "password"

If auto-login fails, check:

1. Account lockout policies
2. Password expiration settings
3. Group Policy conflicts (especially Computer Configuration\Windows Settings\Security Settings\Local Policies\Security Options)

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Many Windows administrators are familiar with the legacy control userpasswords2 method that worked perfectly in Windows Server 2012 and earlier versions. However, in Windows Server 2016, unchecking "Users must enter a user name and password to use this computer" doesn't enable automatic login as expected.

The most reliable method involves modifying the Windows Registry. Here's the step-by-step process:

Windows Registry Editor Version 5.00

[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Winlogon]
"AutoAdminLogon"="1"
"DefaultUserName"="YourUsername"
"DefaultPassword"="YourPassword"
"DefaultDomainName"="YourDomain"  # Omit if not domain-joined
"ForceAutoLogon"="1"  # Optional for reboots

To implement this quickly:

1. Open Notepad and paste the above content
2. Replace the placeholder values with your credentials
3. Save as autologin.reg
4. Right-click and select "Merge"

While convenient, automatic login stores credentials in plaintext. Mitigate risks by:

• Restricting physical access to the server
• Using a dedicated service account with minimal privileges
• Setting appropriate NTFS permissions on the registry keys (e.g., SYSTEM-only access)

For deployment across multiple servers, use this PowerShell script:

# Configure AutoLogin
$regPath = "HKLM:\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Winlogon"
Set-ItemProperty -Path $regPath -Name "AutoAdminLogon" -Value "1" -Type String
Set-ItemProperty -Path $regPath -Name "DefaultUserName" -Value "svc_autologin" -Type String
Set-ItemProperty -Path $regPath -Name "DefaultPassword" -Value "P@ssw0rd123!" -Type String

# Optional: Secure the registry entry
$acl = Get-Acl $regPath
$rule = New-Object System.Security.AccessControl.RegistryAccessRule ("SYSTEM","FullControl","Allow")
$acl.SetAccessRule($rule)
Set-Acl -Path $regPath -AclObject $acl

For domain environments, consider these GPO settings:

1. Computer Configuration → Administrative Templates → System → Logon
2. Enable "Always use classic logon"
3. Configure "Do not display the Getting Started welcome screen at logon"

If automatic login fails:

• Verify the account has "Log on as a batch job" rights (gpedit.msc → Computer Configuration → Windows Settings → Security Settings → Local Policies → User Rights Assignment)
• Check for lingering Ctrl+Alt+Del requirements: HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\Policies\System\disablecad
• Confirm password hasn't expired or changed