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May 19, 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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19
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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September 17, 2026

The Problem of Re-defining Human Value in the Agentic Age

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Newsfeeds are constantly informing us about the rapid escalation of agentic AI systems. These systems move far beyond simple machine-based computations, and  the focused, defined and bounded assistance that most AI systems started out as.

The next evolution of AI will harness the agentic properties of orchestration, automation, and heightened value-chains in IT, taking on the burden of workflow management, not just workflow delivery.

In nearly all of these instances, promises are made such as ‘this will free up human time’ or ‘this will allow people to focus on higher-order strategy’. However that message is delivered, one thing is clear: in ceding the orchestration and management of work to increasingly sophisticated AI agents and agentic systems, human value will be elevated to a particular and specific layer: the ability to judge its outputs.  As AI takes on more tasks, humans should be able to focus on a higher level of governance; making sure the decisions that AI offers us are ethical, responsible and worthwhile.  

But there are two major problems with that approach.

This blog discusses the problem of how Agentic systems are re-shaping how we review information, where we fit in, and when we make decisions.  It also discusses the problem of how the increased flow of confident, generated information affects the way we make judgement.  This blog considers how human judgement needs to adapt, and how a behavioral defense approach – using techniques pioneered by Darktrace – can help us do that.

The challenge of knowing where human judgement belongs

As we confer more automated decision-making to agentic systems, it might look increasingly less like ‘granting permissions’, and more like ‘surrendering authority’.  

The judgement layer for AI-generated work is not a fixed boundary. We have become used to the idea of a ‘human in the loop’ (HITL) and, historically, relationships between humans and IT systems were reasonably clear and bounded.  Computer and software systems were programmed to carry out certain tasks or automated functions, and humans could control the gates and decision points where actions were undertaken. Even across highly complex computational workflows, human interaction was a controllable node within the process; we were able to configure and regulate. But in the agentic age, where that human interaction sits, and what it can influence shifts every time AI systems are granted autonomy.  

This leads us to the first problem: if humans are moving themselves (or are being moved) into the ‘judgement’ part of the value chain, exactly where and when do we exercise that judgement?  

Humans are no longer the sole shepherds of computer-based or software-controlled outputs.  We are at times at least one step further (and slower) behind the new agentic shepherds.  We might also be blind to what they are doing.  Not only might we be removed and blind to the actions of our AI shepherds, but with the challenge of unknown, unapproved AI systems operating beyond our control, humans might not even know that our work is being shepherded by an AI at all.  Simply put, with the advent of greater levels of autonomy and orchestration, humans are at risk of not even knowing where to apply our newly-extended powers of strategic judgement.

Shadow AI – the use of unapproved AI systems or processes – is a growing threat to the role of effective governance and oversight. Shadow AI isn't just the AI you can't see. Its the AI you already know about being used in an unapproved way. The ability to generate effective oversight of the AI systems you use (or that are used on your behalf) will be increasingly important to ensure that human judgement in the AI value chain is effective, and deliberately placed.

The problem of what makes good judgement

The second problem lies in how flawed human judgement can be.  Humans are historically, notoriously, and, sometimes dangerously, unreliable when it comes to exercising judgement.  Humans are prone to the worst kinds of bias, the seduction of malign influence, and the sometimes-overwhelming urge to succeed. AI has long had a known flaw of operating with sycophancy, providing outputs that tend to agree with or flatter the human user.  But as AI grows ever more effective, there is a risk of both hyper-enablement (where humans increasingly and knowingly enable AI despite potential harm), as well as the greater risk of suggestion. Both of these aspects could skew the newly-elevated input of human judgement.

Imagine a highly competent AI system that has just orchestrated and managed a dizzying array of processes and workflows.  The AI is designed to present the human decision-maker with recommendations; based on analysis, comparison and other programmed factors.  This is where the human judgement layer is enabled.  But what if that judgement is summarily diffused by an AI-based recommendation that emulates the decision, provides plausible but unattractive alternatives, then suggests (or, worse, directs) the human end-user to take a particular course of action.

The risk here is that you are given a recommendation, tailored to your preferences (which the AI has learned, or which you have divulged), and which appears to make perfect sense.  It appears to be a well-weighted recommendation, with sound arguments that tap into our inherent biases or inclinations so that a specific decision-path is followed. With the growth of agentic systems specifically designed to match user profiles (from Cowork agents to ‘digital twin’ models), the likelihood of agentic influence could badly skew human judgement or, at the least, devalue the proposition that humans are taking a higher-layer of strategic control over AI-based decisions.

If AI convincingly recommends something that may be problematic, it can be difficult to discern both accurate data, and the context required to make the right judgement.

Given the two problems described above, the job of exercising valuable human judgement in the agentic age can draw down to these two questions:

  • When should humans intervene in the agentic process?  
  • How can we make the best possible judgement calls?

What humans contribute that AI cannot

For all the flaws that make human judgement unreliable, people have the edge over even the most sophisticated and powerful AI systems when it comes to issues such as ethics and social context.  An AI system can, with startling granularity, rank the value of adopting a new business proposal: offering predictive metrics on costs, returns, market value, time-to-deliver operations, conformance with legal registers, etc.  But it can’t tell if the business proposal is ethically sound, or if the business venture will potentially affect groups outside of the analyzed proposal. It can’t tell you if the CEO has a ‘bad feeling’ about this effort.  It can’t tell you if this is the right thing to do.  

The ability to add social context, balance complex interpersonal dynamics, understand nuance, and to go beyond what seems economically reasonable is where human judgement can add value.  

Human judgement is difficult to encapsulate in metrics. And the way we train our development may need to adapt too. Rather than building up a gradual, experiential knowledge base, we should think about training the skill of judgement itself; especially for an agentic age.

How behavioral security strengthens AI governance

If this all feels like a vicious circle (‘I need AI help to make good judgements’ / ‘AI can twist what I need to judge’) it needn’t be. The key to this is having a defense-in-depth approach, with tools that can actually help.

This is precisely where behavioral security becomes important. The complex and nuanced way that humans exercise judgement is often rooted in our ability to recognize behavior that doesn't look right. We may not always be able to articulate it immediately, but we can often identify when an action, recommendation, or outcome feels inconsistent with the context around it. As AI systems take on more responsibility across the decision chain, preserving that ability to recognize meaningful deviations becomes increasingly important.

Darktrace’s / SECURE AI is designed to do exactly that. It applies behavioral security to AI ecosystems, helping organizations understand how people, AI tools, identities, and agents interact across the business. By learning the patterns of normal AI usage and surfacing activity that deviates from those patterns, it provides security teams with the context needed to investigate risk, understand unusual behavior, and make informed governance decisions. Rather than relying solely on predefined rules or assumptions, this behavioral understanding helps organizations distinguish between expected AI activity and behavior that warrants closer scrutiny.

This matters because we are already in an era of information overload. If humans are expected to elevate their value through strategic judgement, the ability to do this without being overwhelmed by data (good or bad) will be critical.  

We need the ability to discern when we're being misled by AI, and whether our judgement calls are being made on the basis of accurate, contextual information. Darktrace / SECURE AI provides that additional layer of defensive security for activity we cannot easily see. Whether it is suspected Shadow AI or skewed recommendations, the net result is a protected organization, where users can more effectively use AI to make positive judgements.

For those where that judgement is a critical skill (both individuals, as well as those working in security teams), improving our metacognition - the ability to understand information in a broader context - will supercharge the value of human judgement. When those judgements are grounded in context rather than assumptions we have better information to make sound decisions.

Conclusion

Human judgement is a skill that is honed over time and experience.  Darktrace’s / SECURE AI employs the same principles, but at machine-speed. Rather than influencing or directing, Darktrace / SECURE AI offers AI-enabled assurance; providing human-based judgement with the right context to make a balanced decision.  

What we judge can be valued by the legitimacy of its outputs. For AI, those outputs are valued on the speed and accuracy of the information provided.  Increasingly for humans, the value of our outputs will be based on the validity of our judgement, and how we justify our decisions in ways that engineer confidence.  

Humans often know more than we can express, while AI is prone to expressing more than it truly understands. Humans can bridge the context AI often fails to appreciate. When that judgement is supported by relevant, impartial AI systems, this is the future space where good AI governance will be exercised.

Discover Darktrace / SECURE AI.

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About the author
Jason Lusted
AI Governance Advisor

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September 4, 2026

Darktrace Advances Incident Investigation and AI-Agent Security with OpenAI Daybreak Models

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Earlier this year, Darktrace joined OpenAI’s Daybreak Defense Network to explore how their cyber capabilities can be integrated within Darktrace products and services to transform how security teams move from signal to action.

At the heart of this work is Darktrace's behavioral understanding of customer environments and identification of complex security incidents, combined with OpenAI models that can add context to help explain why an incident matters and its potential impact on the business. By bringing these capabilities into defensive workflows security teams already use, the goal is to give defenders not just greater visibility, but the context and guidance they need to act with confidence.

Since joining the program, we've been working with OpenAI to explore how these capabilities can address specific security challenges for defenders.

The problem we're solving

Attackers continue to change how they operate, including by using AI to increase the speed and scale of some techniques. Security teams are already managing a large volume of alerts, and the question isn't just what's happening, but how it could affect the organization. Even when an incident is fully investigated and correlated, technical severity alone doesn't tell a security team how much it actually matters to the business. That same challenge extends to internal AI adoption. As organizations adopt more AI systems and agents, security teams need visibility into their behavior, access and activity, along with the broader business context needed to identify and investigate potential risk.

Darktrace's Adaptive AI™ builds a detailed, organization-specific picture of what's normal for each environment, and uses that picture to investigate threats and identify complex security activity across domains. OpenAI's models can build on Darktrace's correlated, technically prioritized incidents by adding context that can help defenders understand what may be at stake.

What we're building

Our work is focused on two areas: supporting security investigation and response, and helping defenders identify risky behavior across enterprise AI systems and agents.

The first aligns Darktrace's behavioral understanding with OpenAI models to support  security investigation and prioritization. Darktrace's Adaptive AI continuously learns the unique patterns of normal behavior within each customer it protects, creating a deep, organization-specific understanding of its digital estate. When unusual activity emerges, OpenAI's models can draw on that context to help analysts investigate the incident, understand its significance and assess potential business consequences — reducing the need to manually assemble context from fragmented signals.

Second, we are exploring how these capabilities can support AI-agent and runtime security through Darktrace / SECURE AI™. OpenAI’s Daybreak models can build on the detections and visibility Darktrace / SECURE AI provides, connecting signals across a customer's environment and help defenders identify potentially risky behavior involving AI systems and agents. Activity that might appear isolated can instead be connected with related signals, helping defenders investigate the broader context and determine appropriate remediation.

Darktrace brings deep cybersecurity expertise, an evolving understanding of each customer's environment, and AI-driven identification of threats across the digital estate. Through the Daybreak Defense Network, Darktrace is exploring how OpenAI models can augment those capabilities in defensive security workflows — supporting incident investigation and response and improving visibility into AI-agent and runtime risk.

These capabilities are still in development, and we're excited to continue building on this work.

To learn more about how Darktrace continues to innovate to meet today's most pressing security challenges, register for our upcoming launch broadcast here.

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About the author
Dr. Tim Bazalgette
Chief AI Officer, Darktrace
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