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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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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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July 1, 2026

5 Ways AI is changing traditional security models according to modern CISOs

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The Reality of Securing AI in Motion

Traditional security tools were built for environments defined by fixed rules and predictable workflows. But AI behavior is non-deterministic. The same prompt can produce different outcomes, and risk often emerges gradually as AI behavior adapts, and permissions drift over time. This creates a constantly shifting environment where security teams are working to define control in a system that resists stability. “In AI security, yesterday's priorities can become tomorrow's blind spots. The landscape shifts that fast,” warned the SVP and Head of Technology and Cybersecurity of a real estate investment trust. Conventional approaches, which rely on establishing and maintaining a steady baseline, struggle to keep up with that level of change.

At the same time, AI adoption is accelerating across organizations, often faster than security teams can implement the controls needed to manage it. “The car is being built while it’s already on the road,” explained the CISO of a global private fund administrator. “The threats we're securing against today won't be the threats we're facing tomorrow. What kept us up three months ago looks nothing like what we're dealing with today.”

As businesses move quickly to unlock value from AI, security teams are left closing gaps in real time, while also facing adversaries who are using AI to make their attacks more scalable, adaptive, and difficult to detect. In this recent roundtable discussion of CISOs and security leaders, five themes emerged around AI cyber risk.  

1. AI agents with human access but no human judgment

In Darktrace’s 2026 State of AI Cybersecurity report, 96% of the surveyed security professionals agree that AI significantly improves the speed and efficiency with which they work. Yet, 92% admitted that they’re concerned with the security implications of the use of AI agents across their workforce.

AI agents now operate with human-level permissions across systems, acting at machine speed, orchestrating actions across platforms, and making decisions without the judgment or caution a person would apply. Unlike human users, they cannot be expected to pause and question whether a given action is appropriate.

Their identities are also difficult to inventory, govern, and audit. As agents become easier to deploy than legacy IT systems ever were, organizations are quickly losing track of what is running, what it has access to, and what it is doing. This creates a growing class of highly privileged, autonomous actors operating without the visibility or oversight that traditional identity and access controls were designed to provide.“While AI adoption is critical to running a modern business, AI alone can’t solve all our cybersecurity challenges,” said a global financial sector CISO. “We still need think critically and use human judgement. Those are two things AI can’t do.”

This lack of human judgment becomes especially risky as new architectures, such as Model Context Protocol (MCP), can expand how agents connect to data, tools, and external systems. By design, MCP enables agents to dynamically discover and interact with new resources, increasing flexibility but also introducing new pathways for unintended access, data exposure, or abuse if not properly governed.

The CISO of a fund administrator highlighted one emerging vector as an example: rogue MCP servers. “Our developers want to move quickly and bring value to the business, but technologies like these can unintentionally expose sensitive data in ways that would never have happened before.”

2. Increased digital complexity and expanded attack surface

AI activity rarely stays contained. A single prompt can trigger a chain of actions across networks, email, cloud infrastructure, SaaS platforms, endpoints, identity systems, and development environments, spanning systems that were never designed to be secured as a single, connected flow. This expands both the scale and complexity of what security teams need to monitor and defend.

Yet no single control has visibility across that entire chain. “You can’t defend effectively what you can’t see,” cautioned the private fund administrator CISO. As AI-driven activity moves fluidly across environments, gaps in coverage become inevitable, creating blind spots that attackers can exploit.

Threat actors are already capitalizing on this lack of visibility. “Threat actors have advanced their use of generative AI to launch more convincing phishing campaigns, automate social engineering, and scale attacks with greater precision down to the individual level,” said the SVP of Technology and Cybersecurity for the real estate investment trust. What was once manual and targeted can now be automated and personalized at scale, making attacks harder to detect and easier to execute.

At the same time, the pace of exploitation is accelerating. As a global CISO operating across 40+ countries described it: “Zero-day vulnerabilities are no longer zero day; it’s minus one day. By the time you get to it and address it, it’s already a problem.” By the time risk is identified, it has often already been realized.

The result is a rapidly expanding and increasingly interconnected attack surface that challenges security teams to maintain visibility, context, and control across AI-driven activity.

3. Shadow AI is already everywhere

76% of organizations now cite shadow AI as a problem, one that is spreading through organizations in ways that are hard to track and even harder to control.

Employees are experimenting with publicly available Gen AI tools. Teams are spinning up low-code automations on their own. SaaS providers are quietly embedding AI into existing products. Developers are plugging AI services directly into workflows, often without pausing to consider what that exposure means.

The result is a lack of visibility into:

  • What AI tools are being used
  • What data those tools can access
  • Where prompts and outputs are going
  • Which AI agents are interacting with enterprise systems

The SVP of Cybersecurity at a real estate investment trust described the shift: “Before, I was worried about someone sending data erroneously to their personal email. Now we have all these agents online that people are utilizing, and we’re looking at those vectors as well.” For security teams, this means operating without a complete view of how AI is being used, what it can access, and where risk may already be emerging.

4. Built-in guardrails are not enough

Organizations often assume that native AI guardrails or provider-level controls are sufficient to manage AI risk. But securing AI requires ongoing visibility, oversight, and governance, not just controls configured at deployment. "It’s a misconception that adopting AI is going to solve all your problems,” warns a global financial services CISO.

Security leaders are increasingly recognizing the limitations of these controls as:

  • Fragmented and difficult to enforce consistently across multiple AI systems, workflows, and environments
  • Ambiguous in terms of accountability due to shared responsibility for AI governance between IT, security, developers, business teams, and third-party providers
  • Limited in end-to-end oversight, leaving gaps that stretch from the initial prompt all the way through to the downstream impact of an agent's actions

Securing AI demands more than simple prompt filtering or static policy enforcement. It requires understanding intent, behavior, and context across both human and AI activity.

The next phase of cybersecurity: securing AI

To safely and responsibly adopt AI at scale, organizations need a new operational model for cybersecurity that’s capable of:

• Understanding AI behavior

• Identifying risk in real time

• Maintaining governance without slowing innovation

The CSO of a $10 billion municipal utility organization described the challenge with precision: “We have to move at the speed of innovation and risk, because both are accelerating faster than ever.”

Embrace AI with confidence with Darktrace / SECURE AI

Darktrace has introduced Darktrace / SECURE AI™, a new product within the Darktrace ActiveAI Security Platform™  ,designed to provide enterprise-wide security for AI by applying industry leading behavioral analysis to how prompts, agents, and AI systems are used.

Darktrace / SECURE AITM delivers real-time visibility and control across Enterprise and SaaS GenAI prompts, AI agent identities, development and production environments, and Shadow AI - detecting even subtle misuse, misconfiguration, and drift that traditional, rule-based controls simply do not understand. By interpreting context and intent across humans and machines, Darktrace enables organizations to adopt AI at scale without introducing unmanaged risk

What makes this possible is Darktrace’s decade-long maturity and expertise in behavioral understanding and AI-native cybersecurity. Achieved with Self-Learning AI that has been proven across more than 10,000 organizations, Darktrace understands what “normal” looks like for a business, across its users, systems, and now AI, so that meaningful deviations can be detected and acted on before they become incidents.

With one CISO describing Darktrace’s Self-Learning AI as “a leap forward compared to other tools” and another as a “force multiplier,” the technology can interpret ambiguous interactions, understand how access accumulates over time, and recognize when behavior, human or machine, begins to drift.

“Strategically, we’re looking to gain more visibility into how AI is operating across the environment and achieve greater control over what AI should be allowed to access and do,” shared the CISO at a private fund administrator.  

“What I’ve seen from Darktrace / SECURE AI is extremely promising. I have tremendous confidence in Darktrace’s vision for where this is headed and its ability to execute on this new solution.”

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