NTLM Relay over SMB is typically impeded by SMB signing, which prevents relayed requests unless the signing is disabled. Attackers overcome this challenge by either finding systems with SMB signing turned off or exploiting vulnerabilities like CVE-2019-1040, enabling them to relay NTLM authentication over protocols that bypass signing requirements, such as LDAP .

NTLM's challenge-response model and lack of a network protocol stack layer make it susceptible to relay attacks, where attackers intercept authentication messages to impersonate clients. By using tools like Responder to poison networks and ntlmrelayx to relay intercepted communications, attackers can leverage NTLM's inherent weaknesses to gain unauthorized access or execute commands on target machines .

The NTLM authentication process involves three main messages: The NEGOTIATE_MESSAGE is sent by the client to indicate the desire to authenticate and specify supported NTLM options. The CHALLENGE_MESSAGE is sent by the server to state the options it can support and challenge the client to prove its identity. Finally, the AUTHENTICATE_MESSAGE is sent by the client to prove possession of the shared secret key, effectively completing the authentication process .

Despite its known vulnerabilities, the NTLM protocol continues to be used because of its seamless integration capabilities with Windows-based applications through the SSPI. This integration offers a unified security mechanism across many applications, outweighing alternatives that may require significant changes to infrastructure. However, its vulnerabilities present severe risks, as attackers can exploit relay attacks through NTLM's challenge-response model, underscoring the necessity for organizations to implement more secure protocols or adequately mitigate NTLM's security flaws .

The NegotiateFlags field, present in all NTLM messages, is significant because it enables the communicating parties to indicate which NTLM capabilities are supported or requested. This 32-bit flag structure ensures that both client and server can agree on the NTLM options to utilize, such as NTLM version and encryption methods, which is crucial for a successful authentication exchange .

Session security in NTLM plays a role in providing message integrity and confidentiality if negotiated between the client and server. It is facilitated by options specified in the NegotiateFlags during the authentication process, which allow for the activation of message signing and sealing to protect the data exchanged during authenticated connections .

NTLM's design as a function library allows it to be implemented across different application protocols without needing a dedicated network protocol stack layer. This flexibility enables it to be easily integrated into various Windows-based applications through the Security Support Provider Interface (SSPI), facilitating seamless authentication and session security across the network despite its vulnerabilities .

NTLM Relay Attacks exploit authenticated sessions gained by a tool like ntlmrelayx's SOCKS server, allowing attackers to tunnel other tools through these sessions for further exploitation. This method of leveraging authenticated sessions enables attackers to bypass normal security controls and directly impact target systems by injecting malicious commands or capturing sensitive information, highlighting the critical nature of these vulnerabilities in NTLM .

Understanding how NTLM works internally is crucial to effectively attack it during Active Directory engagements due to its known vulnerabilities and cryptographic weaknesses. Knowing the protocol's structure and operations, such as its challenge-response mechanism using nonces and pseudo-random numbers, allows attackers to increase their chances of successfully compromising network security through methods like NTLM relay attacks .

NTLM hash farming involves capturing and relaying authentication hashes from users on a network. This is achieved by targeting shared folders that allow anonymous access or by using techniques such as Responder to poison the network. The purpose is to obtain hashes that can be relayed using tools like ntlmrelayx, enabling unauthorized access and actions on target systems, demonstrating the critical need to protect against NTLM vulnerabilities .