Recently while deploying Windows Server 2008 R2 instances on VMware, I encountered a peculiar RDP behavior where connections would hang for 20-30 seconds at the "Securing Remote Connection" phase. Unlike typical network latency issues, this delay occurs before authentication and persists across failed login attempts.

Affected configuration:

Host: VMware ESXi 6.7
Guest OS: Windows Server 2008 R2 SP1 (fully patched)
RDP Client: Windows 7 Professional
Network: 1Gbps LAN

The temporary resolution after successful login suggests this might relate to credential caching or security negotiation. Let's examine the cryptographic components:

# Check RDP security settings via PowerShell:
Get-ItemProperty -Path "HKLM:\\SYSTEM\\CurrentControlSet\\Control\\Terminal Server\\WinStations\\RDP-Tcp" -Name "SecurityLayer"

Packet captures revealed excessive time spent during TLS handshake. Try this Wireshark filter for diagnosis:

tls.handshake.type == 1 or tcp.port == 3389

The root cause appears to be certificate validation against an unavailable CRL (Certificate Revocation List). To verify:

# Check certificate store behavior:
certutil -urlcache * delete
certutil -setreg chain\\ChainCacheResyncFiletime @now

Two approaches worked consistently:

1. Disable CRL checking (not recommended for production):

   reg add "HKLM\\SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\WinTrust\\Trust Providers\\Software Publishing" /v State /t REG_DWORD /d 0x00023e00 /f

2. Proper certificate management:

   # Reissue terminal server certificate with proper CRL distribution points
   $cert = New-SelfSignedCertificate -DnsName $env:COMPUTERNAME -CertStoreLocation Cert:\LocalMachine\My
   Set-RDCertificate -Role RDGateway -ImportPath $cert.PSPath -Force

For VMware VMs, ensure VMXNET3 adapter with these settings:

ethernet0.virtualDev = "vmxnet3"
ethernet0.uptCompatibility = "TRUE"
monitor_control.restrict_backdoor = "TRUE"

For environments where certificate changes aren't possible, adjust the RDP security layer:

reg add "HKLM\\SYSTEM\\CurrentControlSet\\Control\\Terminal Server\\WinStations\\RDP-Tcp" /v SecurityLayer /t REG_DWORD /d 1 /f

This forces RDP to use native encryption rather than negotiating TLS.

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Many administrators encounter this frustrating scenario: When establishing a Remote Desktop Protocol (RDP) connection to a Windows Server 2008 R2 instance (physical or virtual), the connection hangs at the "Securing Remote Connection" message for 20-30 seconds before proceeding. The delay occurs consistently for failed authentication attempts but improves after successful logins.

Common environmental factors reported with this issue include:

• VMware virtualization platforms (though not exclusively)
• Mixed Windows 7/Server 2008 R2 environments
• Networks with strict security policies
• Servers with multiple network interfaces

First, verify basic network functionality with these PowerShell commands:

# Check basic connectivity
Test-NetConnection -ComputerName SERVERNAME -Port 3389

# Trace route analysis
Test-NetConnection -ComputerName SERVERNAME -TraceRoute

# Check TLS handshake timing
$TCPClient = New-Object Net.Sockets.TcpClient
$StopWatch = [System.Diagnostics.Stopwatch]::StartNew()
$TCPClient.Connect('SERVERNAME', 3389)
$StopWatch.Stop()
Write-Output "Connection established in $($StopWatch.ElapsedMilliseconds)ms"

The delay often relates to certificate validation. Examine the RDP certificate with:

Get-ChildItem -Path Cert:\LocalMachine\Remote Desktop -Recurse | 
Where-Object { $_.Subject -match "SERVERNAME" } | 
Select-Object Subject, Thumbprint, NotBefore, NotAfter

Try these registry modifications on the client machine:

Windows Registry Editor Version 5.00

[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings]
"SecureProtocols"=dword:00000AA0

[HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Terminal Server\WinStations\RDP-Tcp]
"SecurityLayer"=dword:00000001
"UserAuthentication"=dword:00000000

On the Windows 2008 R2 server, ensure proper TLS configuration:

# Disable legacy protocols
New-ItemProperty -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 2.0\Server" -Name Enabled -Value 0 -PropertyType DWORD
New-ItemProperty -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 3.0\Server" -Name Enabled -Value 0 -PropertyType DWORD

# Enable modern protocols
New-ItemProperty -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Server" -Name Enabled -Value 1 -PropertyType DWORD
New-ItemProperty -Path "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server" -Name Enabled -Value 1 -PropertyType DWORD

For immediate relief while troubleshooting, consider:

mstsc /v:SERVERNAME /admin /f /public

Or create a customized RDP file with these parameters:

enablecredsspsupport:i:0
authentication level:i:2
negotiate security layer:i:1

When analyzing network traffic during the delay period, watch for:

• Multiple TLS handshake attempts
• CRL (Certificate Revocation List) check timeouts
• OCSP (Online Certificate Status Protocol) verification delays
• Network interface switching