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July 9, 2024

How Darktrace Detects NTLM Hash Theft

Explore Darktrace's innovative methods for detecting NTLM hash theft and safeguarding your organization from cyber threats.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Charlotte Thompson
Cyber Analyst
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09
Jul 2024

What is credential theft and how does it work?

What began as a method to achieve unauthorized access to an account, often driven by the curiosity of individual attackers, credentials theft become a key tactic for malicious actors and groups, as stolen login credentials can be abused to gain unauthorized access to accounts and systems. This access can be leveraged to carry out malicious activities such as data exfiltration, fraud, espionage and malware deployment.

It is therefore no surprise that the number of dark web marketplaces selling privileged credentials has increased in recent years, making it easier for malicious actors to monetize stolen credentials [1]. This, in turn, has created new opportunities for threat actors to use increasingly sophisticated tactics such as phishing, social engineering and credential stuffing in their attacks, targeting individuals, organizations and government entities alike [1].

Credential theft example

TA577 Threat Actor

TA577 is a threat actor known to leverage stolen credentials, also known as Hive0118 [2], an initial access broker (IAB) group that was previously known for delivering malicious payloads [2]. On March 4, 2024, Proofpoint reported evidence of TA577 using a new attack chain with a different aim in mind: stealing NT LAN Manager (NTLM) hashes that can be used to authenticate to systems without needing to know plaintext passwords [3].

How does TA577 steal credentials?

Proofpoint reported that this new attack chain, which was first observed on February 26 and 27, was made up of two distinct campaigns. The first campaign consisted of a phishing attack featuring tens of thousands of emails targeting hundreds of organizations globally [3]. These phishing emails often appeared as replies to previous messages (thread hijacking) and contained zipped HTML attachments that each contained a unique file hash, customized for each recipient [3]. These attached files also contained a HTTP Meta refresh function, which triggered an automatic connection to a text file hosted on external IP addresses running as SMB servers [3].

When attempting to access the text file, the server requires an SMB session authentication via NTLM. This session is initiated when a client sends an ‘SMB_COM_NEGOTIATE’ request to the server, which answers with a ‘SMB_COM_NEGOTIATE’ response.

The client then proceeds to send a ‘SMB_COM_SESSION_SETUP_ANDX’ request to start the SMB session setup process, which includes initiating the NTLM authentication process. The server responds with an ‘SMB_COM_SESSION_SETUP_ANDX’ response, which includes an NTLM challenge message [6].

The client can then use the challenge message and its own credentials to generate a response by hashing its password using an NTLM hash algorithm. The response is sent to the server in an ‘SMB_COM_SESSION_SETUP_ANDX’ request. The server validates the response and, if the authentication is successful, the server answers with a final ‘SMB_COM_SESSION_SETUP_ANDX’ response, which completes the session setup process and allows the client to access the file listed on the server [6].

What is the goal of threat actor TA577?

As no malware delivery was detected during these sessions, researchers have suggested that the aim of TA577 was not to deliver malware, but rather to take advantage of the NTLMV2 challenge/response to steal NTLM authentication hashes [3] [4]. Hashes stolen by attackers can be exploited in pass-the-hash attacks to authenticate to a remote server or service [4]. They can also be used for offline password cracking which, if successful, could be utilized to escalate privileges or perform lateral movement through a target network [4]. Under certain circumstances, these hashes could also permit malicious actors to hijack accounts, access sensitive information and evade security products [4].

The open-source toolkit Impacket, which includes modules for password cracking [5] and which can be identified by the default NTLM server challenge “aaaaaaaaaaaaaaaa”[3], was observed during the SMB sessions. This indicates that TA577 actor aim to use stolen credentials for password cracking and pass-the-hash attacks.

TA577 has previously been associated with Black Basta ransomware infections and Qbot, and has been observed delivering various payloads including IcedID, SystemBC, SmokeLoader, Ursnif, and Cobalt Strike [2].This change in tactic to follow the current trend of credential theft may indicate that not only are TA577 actors aware of which methods are most effective in the current threat landscape, but they also have monetary and time resources needed to create new methods to bypass existing detection tools [3].  

Darktrace’s Coverage of TA577 Activity

On February 26 and 27, coinciding with the campaign activity reported by Proofpoint, Darktrace/Email™ observed a surge of inbound emails from numerous suspicious domains targeting multiple customer environments. These emails consistently included zip files with seemingly randomly generated names, containing HTLM content and links to an unusual external IP address [3].

A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Figure 1: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.
Figure 2: Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.

The URL of these links contained an unusually named .txt file, which corresponds with Proofpoint reports of the automatic connection to a text file hosted on an external SMB server made when the attachment is opened [3].

A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.
Figure 3: A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.

Darktrace identified devices on multiple customer networks connecting to external SMB servers via the SMB protocol. It understood this activity was suspicious as the SMB protocol is typically reserved for internal connections and the endpoint in question had never previously been observed on the network.

The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
Figure 4: The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
External Sites Summary highlighting the rarity of the external SMB server.
Figure 5: External Sites Summary highlighting the rarity of the external SMB server.
External Sites Summary highlightin that the SMB server is geolocated in Moldova.
Figure 6: External Sites Summary highlightin that the SMB server is geolocated in Moldova.

During these connections, Darktrace observed multiple devices establishing an SMB session to this server via a NTLM challenge/response, representing the potential theft of the credentials used in this session. During this session, some devices also attempted to access an unusually named .txt file, further indicating that the affected devices were trying to access the .txt file hosted on external SMB servers [3].

Packet captures (PCAPs) of these sessions show the default NTLM server challenge, indicating the use of Impacket, suggesting that the captured NTLM hashes were to be used for password cracking or pass-the-hash-attacks [3]

PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.
Figure 7: PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.

Conclusions

Ultimately, Darktrace’s suite of products effectively detected and alerted for multiple aspects of the TA577 attack chain and NTLM hash data theft activity across its customer base. Darktrace/Email was able to uncover the inbound phishing emails that served as the initial access vector for TA577 actors, while Darktrace DETECT identified the subsequent external connections to unusual external locations and suspicious SMB sessions.

Furthermore, Darktrace’s anomaly-based approach enabled it to detect suspicious TA577 activity across the customer base on February 26 and 27, prior to Proofpoint’s report on their new attack chain. This showcases Darktrace’s ability to identify emerging threats based on the subtle deviations in a compromised device’s behavior, rather than relying on a static list of indicators of compromise (IoCs) or ‘known bads’.

This approach allows Darktrace to remain one step ahead of increasingly adaptive threat actors, providing organizations and their security teams with a robust AI-driven solution able to safeguard their networks in an ever-evolving threat landscape.

Credit to Charlotte Thompson, Cyber Analyst, Anna Gilbertson, Cyber Analyst.

References

1)    https://www.sentinelone.com/cybersecurity-101/what-is-credential-theft/

2)    https://malpedia.caad.fkie.fraunhofer.de/actor/ta577

3)    https://www.proofpoint.com/us/blog/threat-insight/ta577s-unusual-attack-chain-leads-ntlm-data-theft

4)    https://www.bleepingcomputer.com/news/security/hackers-steal-windows-ntlm-authentication-hashes-in-phishing-attacks/

5)    https://pawanjswal.medium.com/the-power-of-impacket-a-comprehensive-guide-with-examples-1288f3a4c674

6)    https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-nlmp/c083583f-1a8f-4afe-a742-6ee08ffeb8cf

7)    https://www.hivepro.com/threat-advisory/ta577-targeting-windows-ntlm-hashes-in-global-campaigns/

Darktrace Model Detections

Darktrace/Email

·       Attachment / Unsolicited Archive File

·       Attachment / Unsolicited Attachment

·       Link / New Correspondent Classified Link

·       Link / New Correspondent Rare Link

·       Spoof / Internal User Similarities

Darktrace DETECT

·       Compliance / External Windows Communications

Darktrace RESPOND

·       Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

IoCs

IoC - Type - Description

176.123.2[.]146 - IP address -Likely malicious SMB Server

89.117.2[.]33 - IP address - Likely malicious SMB Server

89.117.1[.]161 - IP address - Likely malicious SMB Server

104.129.20[.]167 - IP address - Likely malicious SMB Server

89.117.1[.]160 - IP address - Likely malicious SMB Server

85.239.33[.]149 - IP address - Likely malicious SMB Server

89.117.2[.]34 - IP address - Likely malicious SMB Server

146.19.213[.]36 - IP address - Likely malicious SMB Server

66.63.188[.]19 - IP address - Likely malicious SMB Server

103.124.104[.]76 - IP address - Likely malicious SMB Server

103.124.106[.]224 - IP address - Likely malicious SMB Server

\5aohv\9mn.txt - SMB Path and File - SMB Path and File

\hvwsuw\udrh.txt - SMB Path and File - SMB Path and File

\zkf2rj4\VmD.txt = SMB Path and File - SMB Path and File

\naams\p3aV.txt - SMB Path and File - SMB Path and File

\epxq\A.txt - SMB Path and File - SMB Path and File

\dbna\H.txt - SMB Path and File - SMB Path and File

MAGNAMSB.zip – Filename - Phishing Attachment

e751f9dddd24f7656459e1e3a13307bd03ae4e67 - SHA1 Hash - Phishing Attachment

OMNIS2C.zip  - Filename - Phishing Attachment

db982783b97555232e28d5a333525118f10942e1 - SHA1 Hash - Phishing Attachment

aaaaaaaaaaaaaaaa - NTLM Server Challenge -Impacket Default NTLM Challenge

MITRE ATT&CK Tactics, Techniques and Procedures (TTPs)

Tactic - Technique

TA0001            Initial Access

TA0002            Execution

TA0008            Lateral Movement

TA0003            Persistence

TA0005            Defense Evasion

TA0006            Credential Access

T1021.002       SMB/Windows Admin Shares

T1021  Remote Services

T1566.001       Spearfishing Attachment

T1566  Phishing

T1204.002       Malicious File

T1204  User Execution

T1021.002       SMB/Windows Admin Shares

T1574  Hijack Execution Flow

T1021  Remote Services

T1555.004       Windows Credential Manager

T1555  Credentials from Password Stores

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Charlotte Thompson
Cyber Analyst

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July 7, 2026

Securing AI: Analysis of the Complete Security Stack with Governance and Controls

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Why traditional cybersecurity approaches are not enough for AI

AI adoption outpaces most security programs’ ability to adapt.  That gap is now one of the most consequential sources of cyber risk facing enterprises. As organizations embed generative and agentic AI into development workflows, business operations, and security tooling itself, the question is no longer whether AI will introduce risk. The question is whether organizations understand where that risk actually lives and how to manage it operationally.  

Two recent pieces of guidance underscore this shift:

  1. The upcoming Cybersecurity Framework Profile for AI from NIST
  1. The Five Eyes government guidance on the careful adoption of agentic AI services

Taken together, they point to a critical conclusion. AI security cannot be reduced to model hardening or prompt filtering. It requires a defense in depth strategy that treats AI as both a new attack surface and a force multiplier for defense, while accounting for how AI fundamentally changes scale, speed, and autonomy.  

Recent threat research suggests that today's cyber risk is driven less by initial compromise and more by an adversary's ability to blend into normal operations over time. AI systems create the same exposure in a new form: more autonomy, more scale, and more opportunities for risky behavior to blend into normal operations.

How NIST defines the three core pillars of AI security

The NIST profile organizes AI risk across three inseparable focus areas that span all cybersecurity functions, Secure, Defend and Thwart. These areas are not sequential. They exist simultaneously and must be addressed together.

Secure

This treats AI as an attack surface. It includes models, prompts, agents, pipelines, training and inference data, retrieval augmented generation corpora, and the AI supply chain itself. AI systems are opaque, probabilistic, and non-deterministic by design. Some vulnerabilities are inherent in how models are trained or how data is sourced. Traditional patching does not fully mitigate these risks. This is also where many enterprises are weakest today and, critically, where many security programs stop.  

Defend

This is AI as a defensive force multiplier. AI can improve detection speed, scale, correlation, and response, but only if the right models are used and operationalized correctly. Machine-speed behavior-based detection, response and containment becomes critical in defending non-deterministic systems. Accuracy, explainability, governance, testing, validation, and integration into SOC workflows matter as much as capability. Without those controls, hallucination risk, over automation, and misplaced trust become security risks themselves.  

Thwart

This treats AI as an adversarial accelerant. Threat actors are already using AI to generate targeted social engineering attacks, deepfakes, malware, and autonomous attack agents. Asymmetric warfare is highlighting faster vulnerability discovery and exploitation with a lag on patch development, testing and deployment.  

How this looks in practice

Darktrace researchers observed scaled, automated exploitation of the React2Shell vulnerability within days of disclosure. A vulnerable cloud asset was exploited in under 120 seconds of being deployed. Darktrace research team observed an AI/LLM-generated malware sample used in exploitation activity tied to React2Shell. The significance isn't novelty. It is that AI lowers the barrier to producing usable offensive tooling and compresses the time between experimentation and deployment.  

Tactics are getting more and more creative in order to string together steps of an attack kill chain. This creates a dependency on behavior-based detection, autonomous investigation, autonomous containment, training, resilience investment, and recovery planning across the entire enterprise.

Why agentic AI fundamentally changes enterprise cyber risk

The Five Eyes guidance on agentic AI highlights material changes to the cyber risk profile of an organization. Unlike generative AI systems that produce content for human consumption, agentic AI systems reason, plan, and act autonomously across tools, data, and environments. That autonomy, combined with access to real systems, amplifies the impact of traditional cyber failures and introduces new system level risks that are difficult to predict, observe, and contain.  

Risk in agentic systems does not live in the model alone. It emerges from interactions between models, prompts, memory, tools, APIs, identities, privileges, inter-agent trust relationships, and human assumptions baked into design. Vulnerabilities are often introduced through data, connectors, natural language interfaces, protocols, and drift by design.

In supply-chain incidents, attackers did not need sophisticated exploits to scale impact. They abused trusted systems built for automation and implicit access. Agentic AI inherits that model. Once a system can act across tools, data, and workflows, compromise propagates through trust relationships that were never designed for machine autonomy.

The major agentic AI risk classes include the following:  

  • The identity control for non-human identities or autonomous agents makes it difficult to mitigate over-permissioning, limiting access, scope, and duration, as well as access hygiene
  • Agents are frequently over permissioned
  • Compromised tools inherit agent authority
  • Static secrets enable impersonation
  • Implicit trust between agents enables lateral movement

Design and configuration risks compound this, including privileges evaluated once at startup, poor segmentation, unvetted third party tools, reused authorization decisions outside their original context, and guardrail limitations.  

Behavioral risk  

Agents can optimize for goals in unsafe ways, misinterpret ambiguous intent, chain actions into unintended sequences, change behavior during evaluation, and exhibit deceptive or sycophantic responses.  

Structural risk  

Structural risk follows from agentic systems that are tightly coupled, multicomponent ecosystems. Failures can propagate across agents. Hallucinations cascade downstream. Resource exhaustion becomes systemic. Tool misuse enables indirect prompt injection and command execution. Rogue agents can poison peer agents through trust relationships.  

Accountability

Accountability becomes unclear as autonomy increases. Autonomous agents assume human identity permissions, and humans should have clear ownership of these agents, but they don’t, and this model is flawed. Decision paths are opaque and non-deterministic. Logs are fragmented and difficult to interpret. Reproducing an incident will be impossible without explicit design for observability and forensics. An agent compromise is functionally an insider threat, often with better access and fewer behavioral constraints than a human.  

What does defense in depth look like for AI?

Agentic AI runs on software, networks, identities, and data. It must be governed using the same foundational principles that have proven resilient under uncertainty, including secure by design, defense in depth, zero trust, least privilege, continuous monitoring, behavior-based advanced threat detection and containment, and incident response and recovery.

Core components to a Defense in depth Strategy for Securing the use of AI:

  • Strong, precise identity control plane to include an identity per agent (cryptographic, non‑shared)
    • Privilege monitoring and just‑in‑time access
  • Data Governance
  • Secure‑by‑default configurations
    • Security Posture Management  
    • Zero Trust principles  
  • Strong guardrails, deny‑by‑default policies, and isolation
  • Explicit instruction hierarchies and controlled context
  • Behavioral-based detection across entire enterprise to include inputs, tools, and outputs as well as AI used on the endpoint, across the network, cloud, SaaS, email, and OT
    • Runtime anomaly detection and goal‑drift detection
    • Autonomous containment to mitigate risk and minimize damage
  • Hard boundaries on autonomy and delegation
  • Testing, Evaluation, Validation and Verification  
    • Determine when autonomous action and when human in the loop
    • Adversarial training and agent‑specific testing
    • Simulation, red teaming, and chaos testing
  • Kill‑switches, rollback, and containment mechanisms
    • Forensics data captures, interpretability, autonomous containment, and remediation/recovery plans  

Until standards, tooling, and assurance methods mature, organizations should assume agentic AI systems will behave unexpectedly and design deployments around resilience, behavior-based detection, reversibility, and containment, not efficiency.

How security leaders should prepare for enterprise AI adoption

AI security is not model security alone. Data, pipelines, identities, and agents are first class assets. Many AI attacks succeed through standard cyber failures amplified by AI. Identity, data, and supply chain risk dominate. Behavior-based detection and response are critical, not optional. Logging, provenance, versioning, and forensics data capture of detections are mandatory because you cannot investigate or recover from AI incidents without them.  

Risk will often be visible in behavior before it is clearly defined in policy or guidance. The same pattern has been seen in pre-CVE disclosure detection, where abnormal activity appears before the industry has named or described the vulnerability. AI systems introduce that uncertainty by design.

Security leaders should prioritize controls before AI is fully deployed, avoid generic AI security checklists, integrate AI risk into existing cyber programs, and mitigate the risk of non-deterministic technology with continuous oversight, monitoring, behavior analytics, anomaly detection, autonomous investigation, and autonomous containment.

Visibility has a different connotation with AI. Previously, audit logging worked for software/people, but with Generative AI-based systems, interpretability and explainability is difficult to understand, you cannot "undo" what has been done, or see the logic or control a chain of events. This is why behavioral-based detections and containment becomes critical.  

What capabilities should every AI security program include?

If an organization asked “what must be in place before scaling AI?”:

  1. AI Risk board and approval workflow
  1. IAM + PAM for all AI services and agents
  1. AI asset inventory
  1. Prompt/output DLP with sanctioned AI access – This is not just pre- and post- filters, but behavior-based detections of semantic interface as well as behavior-based analysis of output with associated risk context.  
  1. Shadow AI identification
  1. Secure MLOps – This is an entire paper itself
  1. Runtime guardrails and tool restrictions
    • Including AI Gateway/SASE/Zero trust/
  1. Runtime security with behavior-based detections
    • Complete visibility, monitoring, behavior analytics, anomaly detection, risk/intent/context evaluation of anomalies, autonomous investigation and autonomous containment of all AI assets across endpoint, network, SaaS, SASE, cloud, OT, email, and messaging platforms
  1. Secure data pipelines and data governance
  1. SOC workflow changes from malicious classification workflows to behavior-based detection workflows
  1. Remediation plans for AI-related incidents  

Layered Governance and Security Stack for Securing AI  

The following outline considers governance and security tools that should be considered, well-integrated, deployed, tested, operationalized and embedded within security workflows. These tools and controls map to NIST’s CMF for AI.  

These considerations do not need to be implemented in order. Runtime Detect and Respond will help mitigate risk while Governance, Visibility, and Identity mature.

Category Tooling Controls
Governance & Visibility
  • AI asset inventory / AI CMDB
  • Shadow AI discovery
  • SaaS discovery
  • AI usage on non-endpoint managed systems via network or cloud telemetry
  • MCP server/client usage via protocols
  • Browser telemetry
  • Gateway or SASE telemetry
  • Establish a risk board to set up controls
  • Mandatory registration of AI systems
  • Owner, data classification, intended use, and risk tier
  • Supplier disclosure requirements
  • Risk mitigation plan for AI adoption, innovation, or development
Identity, Access & Agent Control

Non-human autonomous agents should not have the full permissions associated with a human user.

  • IAM with workload identities
  • PAM for AI service accounts
  • Secrets management with short-lived tokens
  • Zero Trust principles
  • Identity, permission, and token hygiene
  • Unique identities per model, agent, and pipeline
  • Least privilege for tools, data, and APIs
  • Explicit approval for autonomous actions
Data Security & Privacy
  • Data classification and labeling
  • Enterprise DLP across endpoint, email, network, cloud, and SaaS
  • Forensics data capture after risky detections
  • Prompt-level DLP through behavior-based semantic analysis with risk and intent context
  • Input/interface analysis for risky data requests
  • Output analysis for sensitive data
  • Data integrity evaluation
  • Retention and redaction policies for prompts and responses
Secure MLOps / LLMOps
  • Secure CI/CD with AI-specific gates
  • Model registries with approval workflows
  • Dependency, container, and artifact scanning
  • SBOM/AIBOM generation
  • IaC security scanning
  • Security posture management
  • Misconfiguration identification
  • Hardening recommendations
  • Signed models and prompts
  • Versioned datasets, configurations, logging, and controls
  • Securing data pipelines
  • Controlled promotion
  • Quality assurance
  • Adversarial testing
Runtime Security

Securing runtime goes beyond guardrails and model firewalls to include behavior-based detections, response, and containment.

  • Detection, monitoring, and SOC integration
  • Centralized visibility into prompts, outputs, and tool calls
  • AI-specific detections
  • Behavior-based detection for AI usage patterns
  • Model drift and behavior monitoring
  • Autonomous containment
  • Behavior-based detection of model inputs and outputs
  • Prompt injection detection
  • Model manipulation, including jailbreaking, poisoning, and related attacks
  • Sensitive data access attempts
  • Behavior-based detection across low-code agents, high-code agents, MCP clients and servers, endpoint, network, cloud, email, SaaS, SASE, IoT, and OT
  • Policy enforcement between users, models, tools, agents, SaaS models/tools, and MCP servers/clients
  • Risk, intent, and context evaluation for detections and response actions
Response & Recovery
  • Autonomous containment
  • AI-assisted playbooks
  • Forensics data capture for AI-related events
  • Model rollback mechanisms
  • Backup and restore for models and datasets
  • Kill switch for agents
  • Autonomous response to agents performing risky behaviors
  • Model and dataset rollback
  • Remediation plans
  • Tabletop exercises
  • Supplier coordination plans
  • Post-incident AI performance validation

AI security requires continuous visibility and behavioral detection

AI changes how fast systems move, how decisions are made, and how risk propagates. It does not change the fundamentals of security. Organizations that succeed will be the ones that apply those fundamentals rigorously, assume failure, and build systems that can detect, contain, and recover when AI behaves in ways they did not anticipate. Security is not what AI is allowed to do. It is whether the organization can understand, trust, and control what AI actually does in practice.  

Take this guidance to understand different initiatives that organizations should be considering. Securing AI is the most critical component to AI safety. As organizations invest more in AI adoption, they should be investing in security in order to mitigate the risk of AI adoption. Organizations should be evaluating their governance and security stack to include well-integrated tools that are deployed, tested, operationalized and embedded within security workflows. While organizations mature in governance, visibility and identity access management, they should be investing in behavior-based detection and autonomous containment to mitigate AI risk.  

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About the author
Nicole Carignan
SVP, Security & AI Strategy, Field CISO

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July 6, 2026

NIST Just Proved It: AI Security Can’t Be Solved With Rules

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Static AI guardrails are inherently limited

As organizations adopt generative AI, many still assume that the right set of guardrails will be enough. The problem is you can’t anticipate every way these systems might be misused, abused or attacked. What NIST has done is put a mathematical foundation under that intuition.

In recent research building on Gödel’s incompleteness theorems, which showed that any system built on a fixed set of rules will always have gaps, NIST demonstrates that there is no finite set of guardrails that can be universally robust against adversarial prompts. In plain terms, if your defense is based on a fixed set of rules, there will always be inputs that bypass them. Not because the rules are badly written, but because the problem space is bigger than static rules can ever cover.

This is not new in cybersecurity - detection rules have always had to live with this trade-off. What is different with GenAI is the scale and shape of that problem. These systems are built on human language, and human language is not bounded. It is fluid, contextual and deliberately ambiguous. The number of ways intent can be hidden is effectively limitless. You are not defending against a defined protocol or a fixed exploit chain. You are defending against the entire expressive capacity of people.

So attempting to create a complete set of rules is the wrong starting point. It assumes the problem can be deterministically described. NIST’s work shows that it cannot. Organizations still need a way to manage AI risk, but the traditional approach of defining allowed and disallowed patterns is always going to lag behind what is actually happening. The same input can be benign in one context and risky in another, and static rules struggle to capture that distinction.

The question then is what fills that gap?

AI security must shift from rules to behavior

What's required is a shift in what you are trying to understand. Rules try to describe what should and shouldn't happen. Behavior shows you what is happening. Or to put it another way, if inputs are unbounded and adversaries adapt, the only stable signal is behavior.

In a GenAI context, that means analyzing how an AI model is being used, how prompts evolve over time, how outputs are shaped, and where AI agent interactions start to drift from what is expected. It means moving from static definitions of bad to a more dynamic understanding of intent.

Instead of trying to predict every bad prompt, you focus on identifying when behavior starts to move outside expected norms. Instead of asking whether a single input matches a rule, you ask whether the overall pattern of activity makes sense for the system and how it’s being used.

Guardrails remain important but they are only one layer

This does not eliminate the need for guardrails. They still play a role. But they will never address the entire problem space and are simply one part of your defense in depth approach.

NIST’s proof is useful because it makes this explicit. It removes the assumption that with enough effort, a complete rule set is achievable. It isn’t.

Once you accept that, the shift becomes unavoidable. This is no longer a problem of writing better rules, but of understanding behavior in a space where the possible inputs are effectively unbounded.

For security leaders, that changes the nature of the problem. It is less about defining what should be allowed, and more about recognizing when something is no longer consistent with expected behavior.

That does not remove the need for guardrails, but it does change their role. They set boundaries, but they do not define understanding. The gap between the two is where risk now sits.

In the end, this is what “can’t be solved with rules” really means. Rules will always leave gaps, and those gaps are not theoretical. They show up in how systems actually behave Not what we expect them to do, or what we intended them to do, but what they are doing in practice. That is where the signal is, and increasingly, that is where the security problem sits.

References:

https://www.nist.gov/news-events/news/2026/06/nist-mathematical-proof-supports-transition-continuous-monitor-and-update

https://ieeexplore.ieee.org/document/11475847

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About the author
Andrew Hollister
Principal Solutions Engineer, Cyber Technician
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