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May 20, 2020

Understanding a SaaS Attack and How AI Can Investigate

The Cyber AI Platform recently detected and investigated two incidents of SaaS account takeover in real-time. Learn about the importance of cyber security here!
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
Max Heinemeyer
Global Field CISO
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20
May 2020

Executive summary

  • Darktrace has observed a significant increase in attacks against SaaS platforms, including file storage, collaborative work, and email solutions.
  • This blog post details two example threats that are representative of the current threat landscape: an Office 365 business email compromise and a Box.com file sharing account compromise.
  • Organizations are recommended to enable multi-factor authentication to combat credential stuffing attacks and the re-use of stolen credentials from data dumps. It is further advised to actively monitor SaaS environments for in-progress cyber-attacks.
  • SaaS exacerbates the skill gap in security – identifying and investigating threats in SaaS environments is a different skill to traditional security operations skill-sets.

Introduction

The digital transformation – whether planned naturally or forced by the global pandemic – has increased the use of Software-as-a-Service (SaaS) solutions in modern organizations. The annual growth rate of the SaaS market is currently 18%, and as the workforce becomes increasingly remote throughout 2020, this is set to skyrocket.

Attackers have been targeting SaaS solutions for a long time – but almost nobody talks about how the Techniques, Tools & Procedures (TTPs) in SaaS attacks differ significantly from traditional TTPs seen in networks and endpoint attacks.

How do you create meaningful detections in SaaS environments that don’t have endpoint or network data? How can you investigate threats in a SaaS environment as an analyst? What does a ‘good’ SaaS event look like, and what does a threat look like? Finding skilled security analysts that can work in traditional IT environments is already hard – it gets even harder when trying to hire security people with SaaS domain knowledge.

SaaS consumers are left with only a few choices: either use the native SaaS security controls provided in each SaaS solution – and rely on the (non-)maturity of the SaaS provider – or go with a third party SaaS security solution, often in the form of Cloud Access Security Brokers (CASBs). Both cases are often not ideal.

This blog outlines two attacks we have recently observed in SaaS environments that are representative for the broader SaaS threat landscape: a Microsoft (Office) 365 business email compromise (BEC) and the compromise of a corporate Box.com account. The analysis serves to illuminate the sharp distinction between a traditional network attack and a SaaS compromise – demonstrating how using machine learning to detect anomalies in behavior offers crucial hope for defenders as SaaS applications define this new era of work.

Anonymized SaaS Threat 1: Office 365 Business Email Compromise

Figure 1: The timeline of attack for the Microsoft 365 Compromise

In this case of a classic BEC attack, a threat-actor infiltrated an employee’s Microsoft 365 account to access sensitive financial documents hosted in SharePoint, including pay slip and banking details. The attacker went on to make configuration changes to the hacked inbox, deleting items and making updates that may have allowed them to cover their tracks.

Darktrace first observed the employee’s account log in from unusual IP ranges. The particular account had never logged in from Bulgaria before, and the peer accounts belonging to those from the same department had not exhibited similar behavioral traits. This in itself was a low-level anomaly and not necessarily indicative of malicious activity – employees might change locations after all.

The unusual login location was then accompanied by an unusual login time and a new user-agent. All of these anomalies triggered Cyber AI Analyst – Darktrace’s automated threat investigation technology – to launch a deeper analysis.

Darktrace then identified that the account was starting to access highly sensitive information, including payroll information on a Sharepoint. Two examples that were highlighted by AI Analyst are shown below:

  • hxxps://anonymised[.]sharepoint[.]com/anonymised/pages/Understanding-my-payslip[.]aspx
  • hxxps:// anonymised [.]sharepoint[.]com/anonymised /pages/Changing-my-bank-details[.]aspx

The attacker tried to gain insights about payment information and credit card details, with the likely intention of changing the payroll details to an attacker-controlled bank account. But with its ability to automatically analyze events to piece together attack narratives, Cyber AI Analyst was able to put together these weak signals of a threat and illuminate the likely account compromise. The security team was then able to lock the account and alert the user, who subsequently changed their credentials.

Anonymized SaaS Threat 2: Box.com Compromise

Figure 2: The timeline of attack for the Box.com Compromise

Darktrace observed a case of unauthorized access to a corporate Box.com file storage account belonging to an employee of a global supply company. The Box.com account login took place in the US – the same country that this organization operates in – but from an unusual IP space and ASN. Made suspicious by this low-level anomaly, Cyber AI Analyst did further, ongoing investigations into the user’s activity.

The actor behind the account logged in to Box.com successfully, and then proceeded to download expense reports, invoices, and other financial documents. It became evident that the account started accessing files that were highly unusual for the account to access. Darktrace recognized that neither the account itself, nor its peer group were usually accessing the file called ‘PASSWORD SHEET.xlsx’.

With Cyber AI’s bespoke knowledge of ‘self’ for every member of the organization’s workforce, the technology was able to identify the threat immediately. The Darktrace Cyber AI Platform detected that the activity occurred at a highly unusual time for the legitimate user, and that the location of the actor’s IP address was also anomalous compared to the employee’s previous access locations for this particular SaaS service.

While accessing these documents may have been normal for the employee in another context, Darktrace Cyber AI’s deep understanding of user behavior and granular visibility within the Box.com application allowed it to spot the subtle signs of account compromise. Moreover, when Darktrace’s Cyber AI Analyst automatically investigated the threat, it was able to illuminate the wider narrative, understanding that each unauthorized file exposure was part of a connected incident and highlighted the breach as a key concern for the security team.

Conclusion

Traditional detection approaches like ‘more than X failed logins from Y’ are not enough to ensure sufficient security across SaaS applications. Keeping threat intelligence lists up to date is even more difficult, as most SaaS attacks don’t involve any Command & Control – just indiscriminate logins from remote devices. Attackers may use VPN, Tor, other compromised devices, dynamic DNS, or virtual private servers to further mask their tracks.

A more intricate and effective approach to SaaS security requires understanding the dynamic individual behind the account. SaaS applications are fundamentally platforms for humans to communicate – allowing them to exchange and store ideas and information. Abnormal, threatening behavior is therefore impossible to detect without a nuanced understanding of those unique individuals: where and when do they typically access a SaaS account, which files are they like to access, who do they typically connect with?

Cyber AI asks these questions, continuously analyzing data not only across SaaS platforms, but from the unique ‘patterns of life’ of every user and device in the organization as a whole. With this context, it can chain together seemingly disparate anomalies – unusual login times, login locations, access of new or unusual files, and hundreds of other indicators of threat. These anomalies then act as a trigger for more in-depth investigations via Cyber AI Analyst that can link the anomalies together and create a coherent attack narrative.

Both of the above SaaS attacks were comprehensively but succinctly investigated and fully reported on by the Darktrace’s Cyber AI Analyst, which then surfaced an easy-to-understand incident report, ready for executive review. For a more in-depth look at how Cyber AI Analyst investigated an emerging APT threat in the wild, read: Catching APT41 exploiting a zero-day vulnerability.

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
Max Heinemeyer
Global Field CISO

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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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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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