How to Programmatically Paste Clipboard Password into Windows Server 2008 R2 RDP Login Screen


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Many sysadmins and developers frequently connect to multiple Windows Server 2008 R2 instances via Remote Desktop. The inability to paste passwords directly into the RDP login screen creates significant workflow inefficiencies, especially when using clipboard managers like ClipMate to store credentials.

Microsoft intentionally disabled clipboard pasting in RDP login screens as a security measure. The credential input field is designed to only accept keyboard input to prevent potential malware from stealing passwords via clipboard monitoring.

While no native solution exists, we can create a workaround using AutoHotkey or PowerShell remoting. Here's a practical implementation:


; AutoHotkey script to simulate keyboard input from clipboard
#IfWinActive, Remote Desktop Connection
^v::
    SendInput, {Raw}%clipboard%
    return
#IfWinActive

For servers where you have admin access, consider setting up PowerShell remoting:


# Enable PSRemoting on target server
Enable-PSRemoting -Force

# Create credential object from clipboard
$password = ConvertTo-SecureString -String (Get-Clipboard) -AsPlainText -Force
$credential = New-Object -TypeName System.Management.Automation.PSCredential -ArgumentList "username", $password

# Establish remote session
Enter-PSSession -ComputerName server01 -Credential $credential

Several utilities can help bypass this limitation:

  • Remote Desktop Manager (Devolutions)
  • mRemoteNG
  • Terminals (open source)

When implementing any workaround:

  • Never store plaintext passwords
  • Use encrypted credential stores
  • Rotate passwords regularly
  • Enable two-factor authentication where possible

For testing environments only, you can modify the following registry key:


Windows Registry Editor Version 5.00

[HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Windows NT\Terminal Services]
"DisablePasswordSaving"=dword:00000000

Note: This may expose your system to security risks and isn't recommended for production environments.

Windows Server 2008 R2's Remote Desktop Protocol (RDP) client intentionally blocks clipboard pasting on the password field for security reasons. This becomes problematic when managing multiple servers with complex credentials stored in clipboard managers like ClipMate.

While direct pasting isn't natively supported, these technical solutions can simulate keyboard input:

// AutoHotkey script example for password simulation
#IfWinActive, Remote Desktop Connection
^v::
    Clipboard := ""  ; Clear clipboard
    Send ^c         ; Copy from source (ClipMate)
    ClipWait, 1     ; Wait for clipboard
    SendInput %Clipboard%
return

For more secure automation:

cmdkey /generic:TERMSRV/your.server.com /user:domain\username /pass:yourpassword
mstsc /v:your.server.com

Any automation solution should:

  • Use Windows DPAPI for credential encryption
  • Implement proper ACLs on credential storage
  • Consider using temporary credentials

For professional environments:

// PowerShell snippet using CredSSP
$securePass = ConvertTo-SecureString "P@ssw0rd" -AsPlainText -Force
$cred = New-Object System.Management.Automation.PSCredential ("domain\user", $securePass)
Enter-PSSession -ComputerName server01 -Credential $cred -Authentication CredSSP