RDP 'Please Wait' Black Screen? A Simple Fixeric

If you've ever tried to connect to a Windows machine via RDP only to be greeted by an endless black screen displaying "Please Wait," you know how frustrating this can be. The good news? It could be an easy fix.

In my case the target Windows machine has pending system updates that require installation or a restart to complete. Windows Update can interfere with the RDP service's ability to properly initialize the desktop environment, leaving users stranded at the "Please Wait" screen.

The Simple Solution: Windows Updates

No matter how much we don't want to, but we have to: update Windows.

Step-by-Step Fix

Option 1: Physical or Local Access

If you have physical access to the machine:

1. Log in locally to the Windows machine experiencing the RDP issue
2. Check for Windows Updates:
   • Press Windows + I to open Settings
   • Navigate to "Update & Security"
   • Click "Check for updates"
3. Install all available updates
4. Restart the machine when prompted
5. Test RDP connection after the restart completes

Option 2: Command Line Approach

If you have limited access but can run commands:

Copy # Check for updates using PowerShell
Get-WindowsUpdate

# Install updates (requires PSWindowsUpdate module)
Install-WindowsUpdate -AcceptAll -AutoReboot

# Alternative: Use Windows Update command line
UsoClient StartScan
UsoClient StartDownload
UsoClient StartInstall

Option 3: Group Policy Method

For domain environments:

Copy # Force Group Policy update
gpupdate /force

# Trigger Windows Update check
wuauclt /detectnow /updatenow

Verification Steps

After applying updates and restarting:

1. Test RDP connectivity:

   shell

   Copy # Test RDP port connectivity
   telnet target-machine-ip 3389
   

2. Check RDP service status:

   powershell

   Copy # Verify Remote Desktop Services are running
   Get-Service -Name "TermService"
   Get-Service -Name "UmRdpService"
   

3. Verify Windows Update status:

   powershell

   Copy # Check for pending updates
   Get-WindowsUpdate
   
   # Check update history
   Get-WUHistory | Select-Object Date, Title, Result