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NTLMv1 SSP DES Mechanics Explained

Dustin EvilMog Heywood

Red TeamTalks10 minAdvancedOpen on YouTube ↗

Where

Talks
ShmooCon 2024

Duration

10 min

Explains how NTLMv1 challenge responses are built from DES keys and shows them cracked into domain controller hashes.

Summary

The talk opens with coercion. The speaker starts from a low-privilege domain account and makes a domain controller authenticate to his machine, which is running Responder to catch the hash. The capture is an NTLMv1 challenge response, and the speaker points out that older rainbow-table approaches stop working once the client challenge is modified by the extended session security setting. He then uses his own Python tool to split the response into its parts.

The middle of the talk covers the mechanics. The NT hash is divided into three seven-byte chunks, each padded and used as a DES key to encrypt the client challenge. The three ciphertexts are concatenated to form the response. Because of this structure, the attacker cracks three DES keys separately with hashcat mode 14000 and then reassembles them into the original NT hash. In the live demo, the recovered hash is validated against the domain controller machine account and used to dump credentials.

The closing section is about defense and cost. The speaker says the risk comes from the LAN Manager compatibility level being set to 0, 1 or 2, which permits NTLMv1 and leaves no real defense once it is allowed. He estimates the cracking cost at several thousand dollars of GPU time for a few hours of work. Administrators should find the setting in the domain controller security policy and raise it so that NTLMv1 is refused. The talk is mostly a live demonstration.

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