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March 8, 2024

Malicious Use of Dropbox in Phishing Attacks

Understand the tactics of phishing attacks that exploit Dropbox and learn how to recognize and mitigate these emerging cybersecurity 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
Ryan Traill
Content Manager - Digital Customer Success
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08
Mar 2024

Evolving Phishing Attacks

While email has long been the vector of choice for carrying out phishing attacks, threat actors, and their tactics, techniques, and procedures (TTPs), are continually adapting and evolving to keep pace with the emergence of new technologies that represent new avenues to exploit. As previously discussed by the Darktrace analyst team, several novel threats relating to the abuse of commonly used services and platforms were observed throughout 2023, including the rise of QR Code Phishing and the use of Microsoft SharePoint and Teams in phishing campaigns.

Dropbox Phishing Attacks

It should, therefore, come as no surprise that the malicious use of other popular services has gained traction in recent years, including the cloud storage platform Dropbox.

With over 700 million registered users [1], Dropbox has established itself as a leading cloud storage service celebrated for its simplicity in file storage and sharing, but in doing so it has also inadvertently opened a new avenue for threat actors to exploit. By leveraging the legitimate infrastructure of Dropbox, threat actors are able to carry out a range of malicious activities, from convincing their targets to unknowingly download malware to revealing sensitive information like login credentials.

Darktrace Detection of Dropbox Phishing Attack

Darktrace detected a malicious attempt to use Dropbox in a phishing attack in January 2024, when employees of a Darktrace customer received a seemingly innocuous email from a legitimate Dropbox address. Unbeknownst to the employees, however, a malicious link had been embedded in the contents of the email that could have led to a widespread compromise of the customer’s Software-as-a-Service (SaaS) environment. Fortunately for this customer, Darktrace / EMAIL quickly identified the suspicious emails and took immediate actions to stop them from being opened. If an email was accessed by an employee, Darktrace / IDENTITY was able to recognize any suspicious activity on the customer’s SaaS platform and bring it to the immediate detection of their security team.

Attack overview

Initial infection  

On January 25, 2024, Darktrace / EMAIL observed an internal user on a customer’s SaaS environment receiving an inbound email from ‘no-reply@dropbox[.]com’, a legitimate email address used by the Dropbox file storage service.  Around the same time 15 other employees also received the same email.

The email itself contained a link that would lead a user to a PDF file hosted on Dropbox, that was seemingly named after a partner of the organization. Although the email and the Dropbox endpoint were both legitimate, Darktrace identified that the PDF file contained a suspicious link to a domain that had never previously been seen on the customer’s environment, ‘mmv-security[.]top’.  

Darktrace understood that despite being sent from a legitimate service, the email’s initiator had never previously corresponded with anyone at the organization and therefore treated it with suspicion. This tactic, whereby a legitimate service sends an automated email using a fixed address, such as ‘no-reply@dropbox[.]com’, is often employed by threat actors attempting to convince SaaS users to follow a malicious link.

As there is very little to distinguish between malicious or benign emails from these types of services, they can often evade the detection of traditional email security tools and lead to disruptive account takeovers.

As a result of this detection, Darktrace / EMAIL immediately held the email, stopping it from landing in the employee’s inbox and ensuring the suspicious domain could not be visited. Open-source intelligence (OSINT) sources revealed that this suspicious domain was, in fact, a newly created endpoint that had been reported for links to phishing by multiple security vendors [2].

A few days later on January 29, the user received another legitimate email from ‘no-reply@dropbox[.]com’ that served as a reminder to open the previously shared PDF file. This time, however, Darktrace / EMAIL moved the email to the user’s junk file and applied a lock link action to prevent the user from directly following a potentially malicious link.

Figure 1: Anomaly indicators associated with the suspicious emails sent by ’no.reply@dropbox[.]com’, and the corresponding actions performed by Darktrace / EMAIL

Unfortunately for the customer in this case, their employee went on to open the suspicious email and follow the link to the PDF file, despite Darktrace having previously locked it.

Figure 2: Confirmation that the SaaS user read the suspicious email and followed the link to the PDF file hosted on Dropbox, despite it being junked and link locked.

Darktrace / NETWORK subsequently identified that the internal device associated with this user connected to the malicious endpoint, ‘mmv-security[.]top’, a couple of days later.

Further investigation into this suspicious domain revealed that it led to a fake Microsoft 365 login page, designed to harvest the credentials of legitimate SaaS account holders. By masquerading as a trusted organization, like Microsoft, these credential harvesters are more likely to appear trustworthy to their targets, and therefore increase the likelihood of stealing privileged SaaS account credentials.  

Figure 3: The fake Microsoft login page that the user was directed to after clicking the link in the PDF file.

Suspicious SaaS activity

In the days following the initial infection, Darktrace / IDENTITY began to observe a string of suspicious SaaS activity being performed by the now compromised Microsoft 365 account.

Beginning on January 31, Darktrace observed a number of suspicious SaaS logins from multiple unusual locations that had never previously accessed the account, including 73.95.165[.]113. Then on February 1, Darktrace detected unusual logins from the endpoints 194.32.120[.]40 and 185.192.70[.]239, both of which were associated with ExpressVPN indicating that threat actors may have been using a virtual private network (VPN) to mask their true location.

FIgure 4: Graph Showing several unusual logins from different locations observed by Darktrace/Apps on the affected SaaS account.

Interestingly, the threat actors observed during these logins appeared to use a valid multi-factor authentication (MFA) token, indicating that they had successfully bypassed the customer’s MFA policy. In this case, it appears likely that the employee had unknowingly provided the attackers with an MFA token or unintentionally approved a login verification request. By using valid tokens and meeting the necessary MFA requirements, threat actors are often able to remain undetected by traditional security tools that view MFA as the silver bullet. However, Darktrace’s anomaly-based approach to threat detection allows it to quickly identify unexpected activity on a device or SaaS account, even if it occurs with legitimate credentials and successfully passed authentication requirements, and bring it to the attention of the customer’s security team.

Shortly after, Darktrace observed an additional login to the SaaS account from another unusual location, 87.117.225[.]155, this time seemingly using the HideMyAss (HMA) VPN service. Following this unusual login, the actor was seen creating a new email rule on the compromised Outlook account. The new rule, named ‘….’, was intended to immediately move any emails from the organization’s accounts team directly to the ‘Conversation History’ mailbox folder. This is a tactic often employed by threat actors during phishing campaigns to ensure that their malicious emails (and potential responses to them) are automatically moved to less commonly visited mailbox folders in order to remain undetected on target networks. Furthermore, by giving this new email rule a generic name, like ‘….’ it is less likely to draw the attention of the legitimate account holder or the organizations security team.

Following this, Darktrace / EMAIL observed the actor sending updated versions of emails that had previously been sent by the legitimate account holder, with subject lines containing language like “Incorrect contract” and “Requires Urgent Review”, likely in an attempt to illicit some kind of follow-up action from the intended recipient.  This likely represented threat actors using the compromised account to send further malicious emails to the organization’s accounts team in order to infect additional accounts across the customer’s SaaS environment.

Unfortunately, Darktrace's Autonomous Response was not deployed in the customer’s SaaS environment in this instance, meaning that the aforementioned malicious activity did not lead to any mitigative actions to contain the compromise. Had RESPOND been enabled in autonomous response mode at the time of the attack, it would have quickly moved to log out and disable the suspicious actor as soon as they had logged into the SaaS environment from an unusual location, effectively shutting down this account takeover attempt at the earliest opportunity.

Nevertheless, Darktrace / EMAIL's swift identification and response to the suspicious phishing emails, coupled with Darktrace / IDENTITY's detection of the unusual SaaS activity, allowed the customer’s security team to quickly identify the offending SaaS actor and take the account offline before the attack could escalate further

Conclusion

As organizations across the world continue to adopt third-party solutions like Dropbox into their day-to-day business operations, threat actors will, in turn, continue to seek ways to exploit these and add them to their arsenal. As illustrated in this example, it is relatively simple for attackers to abuse these legitimate services for malicious purposes, all while evading detection by endpoint users and security teams alike.

By leveraging these commonly used platforms, malicious actors are able to carry out disruptive cyber-attacks, like phishing campaigns, by taking advantage of legitimate, and seemingly trustworthy, infrastructure to host malicious files or links, rather than relying on their own infrastructure. While this tactic may bypass traditional security measures, Darktrace’s Self-Learning AI enables it to recognize unusual senders within an organization’s email environment, even if the email itself seems to have come from a legitimate source, and prevent them from landing in the target inbox. In the event that a SaaS account does become compromised, Darktrace is able to identify unusual login locations and suspicious SaaS activities and bring them to the attention of the customer for remediation.

In addition to the prompt identification of emerging threats, Darktrace's Autonomous Response is uniquely placed to take swift autonomous action against any suspicious activity detected within a customer’s SaaS environment, effectively containing any account takeover attempts in the first instance.

Credit to Ryan Traill, Threat Content Lead, Emily Megan Lim, Cyber Security Analyst

Appendices

Darktrace Model Detections  

- Model Breach: SaaS / Access::Unusual External Source for SaaS Credential Use

- Model Breach: SaaS / Unusual Activity::Multiple Unusual External Sources For SaaS Credential

- Model Breach: SaaS / Access::Unusual External Source for SaaS Credential Use

- Model Breach: SaaS / Access::Unusual External Source for SaaS Credential Use

- Model Breach: SaaS / Unusual Activity::Multiple Unusual SaaS Activities

- Model Breach: SaaS / Unusual Activity::Unusual MFA Auth and SaaS Activity

- Model Breach: SaaS / Compromise::Unusual Login and New Email Rule

- Model Breach: SaaS / Compliance::Anomalous New Email Rule

- Model Breach: SaaS / Compliance::New Email Rule

- Model Breach: SaaS / Compromise::SaaS Anomaly Following Anomalous Login

- Model Breach: Device / Suspicious Domain

List of Indicators of Compromise (IoCs)

Domain IoC

mmv-security[.]top’ - Credential Harvesting Endpoint

IP Address

73.95.165[.]113 - Unusual Login Endpoint

194.32.120[.]40 - Unusual Login Endpoint

87.117.225[.]155 - Unusual Login Endpoint

MITRE ATT&CK Mapping

DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS

T1078.004 - Cloud Accounts

DISCOVERY

T1538 - Cloud Service Dashboard

RESOURCE DEVELOPMENT

T1586 - Compromise Accounts

CREDENTIAL ACCESS

T1539 - Steal Web Session Cookie

PERSISTENCE

T1137 - Outlook Rules

INITIAL ACCESS

T156.002 Spearphishing Link

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
Ryan Traill
Content Manager - Digital Customer Success

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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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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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