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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
Analyst Content Lead
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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 Autonomous Response been enabled in fully autonomous 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
Analyst Content Lead

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May 1, 2026

How email-delivered prompt injection attacks can target enterprise AI – and why it matters

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What are email-delivered prompt injection attacks?

As organizations rapidly adopt AI assistants to improve productivity, a new class of cyber risk is emerging alongside them: email-delivered AI prompt injection. Unlike traditional attacks that target software vulnerabilities or rely on social engineering, this is the act of embedding malicious or manipulative instructions into content that an AI system will process as part of its normal workflow. Because modern AI tools are designed to ingest and reason over large volumes of data, including emails, documents, and chat histories, they can unintentionally treat hidden attacker-controlled text as legitimate input.  

At Darktrace, our analysis has shown an increase of 90% in the number of customer deployments showing signals associated with potential prompt injection attempts since we began monitoring for this type of activity in late 2025. While it is not always possible to definitively attribute each instance, internal scoring systems designed to identify characteristics consistent with prompt injection have recorded a growing number of high-confidence matches. The upward trend suggests that attackers are actively experimenting with these techniques.

Recent examples of prompt injection attacks

Two early examples of this evolving threat are HashJack and ShadowLeak, which illustrate prompt injection in practice.

HashJack is a novel prompt injection technique discovered in November 2025 that exploits AI-powered web browsers and agentic AI browser assistants. By hiding malicious instructions within the URL fragment (after the # symbol) of a legitimate, trusted website, attackers can trick AI web assistants into performing malicious actions – potentially inserting phishing links, fake contact details, or misleading guidance directly into what appears to be a trusted AI-generated output.

ShadowLeak is a prompt injection method to exfiltrate PII identified in September 2025. This was a flaw in ChatGPT (now patched by OpenAI) which worked via an agent connected to email. If attackers sent the target an email containing a hidden prompt, the agent was tricked into leaking sensitive information to the attacker with no user action or visible UI.

What’s the risk of email-delivered prompt injection attacks?

Enterprise AI assistants often have complete visibility across emails, documents, and internal platforms. This means an attacker does not need to compromise credentials or move laterally through an environment. If successful, they can influence the AI to retrieve relevant information seamlessly, without the labor of compromise and privilege escalation.

The first risk is data exfiltration. In a prompt injection scenario, malicious instructions may be embedded within an ordinary email. As in the ShadowLeak attack, when AI processes that content as part of a legitimate task, it may interpret the hidden text as an instruction. This could result in the AI disclosing sensitive data, summarizing confidential communications, or exposing internal context that would otherwise require significant effort to obtain.

The second risk is agentic workflow poisoning. As AI systems take on more active roles, prompt injection can influence how they behave over time. An attacker could embed instructions that persist across interactions, such as causing the AI to include malicious links in responses or redirect users to untrusted resources. In this way, the attacker inserts themselves into the workflow, effectively acting as a man-in-the-middle within the AI system.

Why can’t other solutions catch email-delivered prompt injection attacks?

AI prompt injection challenges many of the assumptions that traditional email security is built on. It does not fit the usual patterns of phishing, where the goal is to trick a user into clicking a link or opening an attachment.  

Most security solutions are designed to detect signals associated with user engagement: suspicious links, unusual attachments, or social engineering cues. Prompt injection avoids these indicators entirely, meaning there are fewer obvious red flags.

In this case, the intention is actually the opposite of user solicitation. The objective is simply for the email to be delivered and remain in the inbox, appearing benign and unremarkable. The malicious element is not something the recipient is expected to engage with, or even notice.

Detection is further complicated by the nature of the prompts themselves. Unlike known malware signatures or consistent phishing patterns, injected prompts can vary widely in structure and wording. This makes simple pattern-matching approaches, such as regex, unreliable. A broad rule set risks generating large numbers of false positives, while a narrow one is unlikely to capture the diversity of possible injections.

How does Darktrace catch these types of attacks?

The Darktrace approach to email security more generally is to look beyond individual indicators and assess context, which also applies here.  

For example, our prompt density score identifies clusters of prompt-like language within an email rather than just single occurrences. Instead of treating the presence of a phrase as a blocking signal, the focus is on whether there is an unusual concentration of these patterns in a way that suggests injection. Additional weighting can be applied where there are signs of obfuscation. For example, text that is hidden from the user – such as white font or font size zero – but still readable by AI systems can indicate an attempt to conceal malicious prompts.

This is combined with broader behavioral signals. The same communication context used to detect other threats remains relevant, such as whether the content is unusual for the recipient or deviates from normal patterns.

Ask your email provider about email-delivered AI prompt injection

Prompt injection targets not just employees, but the AI systems they rely on, so security approaches need to account for both.

Though there are clear indications of emerging activity, it remains to be seen how popular prompt injection will be with attackers going forward. Still, considering the potential impact of this attack type, it’s worth checking if this risk has been considered by your email security provider.

Questions to ask your email security provider

  • What safeguards are in place to prevent emails from influencing AI‑driven workflows over time?
  • How do you assess email content that’s benign for a human reader, but may carry hidden instructions intended for AI systems?
  • If an email contains no links, no attachments, and no social engineering cues, what signals would your platform use to identify malicious intent?

Visit the Darktrace / EMAIL product hub to discover how we detect and respond to advanced communication threats.  

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product

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April 30, 2026

Mythos vs Ethos: Defending in an Era of AI‑Accelerated Vulnerability Discovery

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Anthropic’s Mythos and what it means for security teams

Recent attention on systems such as Anthropic Mythos highlights a notable problem for defenders. Namely that disclosure’s role in coordinating defensive action is eroding.

As AI systems gain stronger reasoning and coding capability, their usefulness in analyzing complex software environments and identifying weaknesses naturally increases. What has changed is not attacker motivation, but the conditions under which defenders learn about and organize around risk. Vulnerability discovery and exploitation increasingly unfold in ways that turn disclosure into a retrospective signal rather than a reliable starting point for defense.

Faster discovery was inevitable and is already visible

The acceleration of vulnerability discovery was already observable across the ecosystem. Publicly disclosed vulnerabilities (CVEs) have grown at double-digit rates for the past two years, including a 32% increase in 2024 according to NIST, driven in part by AI even prior to Anthropic’s Mythos model. Most notably XBOW topped the HackerOne US bug bounty leaderboard, marking the first time an autonomous penetration tester had done so.  

The technical frontier for AI capabilities has been described elsewhere as jagged, and the implication is that Mythos is exceptional but not unique in this capability. While Mythos appears to make significant progress in complex vulnerability analysis, many other models are already able to find and exploit weaknesses to varying degrees.  

What matters here is not which model performs best, but the fact that vulnerability discovery is no longer a scarce or tightly bounded capability.

The consequence of this shift is not simply earlier discovery. It is a change in the defender-attacker race condition. Disclosure once acted as a rough synchronization point. While attackers sometimes had earlier knowledge, disclosure generally marked the moment when risk became visible and defensive action could be broadly coordinated. Increasingly, that coordination will no longer exist. Exploitation may be underway well before a CVE is published, if it is published at all.

Why patch velocity alone is not the answer

The instinctive response to this shift is to focus on patching faster, but treating patch velocity as the primary solution misunderstands the problem. Most organizations are already constrained in how quickly they can remediate vulnerabilities. Asset sprawl, operational risk, testing requirements, uptime commitments, and unclear ownership all limit response speed, even when vulnerabilities are well understood.

If discovery and exploitation now routinely precede disclosure, then patching cannot be the first line of defense. It becomes one necessary control applied within a timeline that has already shifted. This does not imply that organizations should patch less. It means that patching cannot serve as the organizing principle for defense.

Defense needs a more stable anchor

If disclosure no longer defines when defense begins, then defense needs a reference point that does not depend on knowing the vulnerability in advance.  

Every digital environment has a behavioral character. Systems authenticate, communicate, execute processes, and access resources in relatively consistent ways over time. These patterns are not static rules or signatures. They are learned behaviors that reflect how an organization operates.

When exploitation occurs, even via previously unknown vulnerabilities, those behavioral patterns change.

Attackers may use novel techniques, but they still need to gain access, create processes, move laterally, and will ultimately interact with systems in ways that diverge from what is expected. That deviation is observable regardless of whether the underlying weakness has been formally named.

In an environment where disclosure can no longer be relied on for timing or coordination, behavioral understanding is no longer an optional enhancement; it becomes the only consistently available defensive signal.

Detecting risk before disclosure

Darktrace’s threat research has consistently shown that malicious activity often becomes visible before public disclosure.

In multiple cases, including exploitation of Ivanti, SAP NetWeaver, and Trimble Cityworks, Darktrace detected anomalous behavior days or weeks ahead of CVE publication. These detections did not rely on signatures, threat intelligence feeds, or awareness of the vulnerability itself. They emerged because systems began behaving in ways that did not align with their established patterns.

This reflects a defensive approach grounded in ‘Ethos’, in contrast to the unbounded exploration represented by ‘Mythos’. Here, Mythos describes continuous vulnerability discovery at speed and scale. Ethos reflects an understanding of what is normal and expected within a specific environment, grounded in observed behavior.

Revisiting assume breach

These conditions reinforce a principle long embedded in Zero Trust thinking: assume breach.

If exploitation can occur before disclosure, patching vulnerabilities can no longer act as the organizing principle for defense. Instead, effective defense must focus on monitoring for misuse and constraining attacker activity once access is achieved. Behavioral monitoring allows organizations to identify early‑stage compromise and respond while uncertainty remains, rather than waiting for formal verification.

AI plays a critical role here, not by predicting every exploit, but by continuously learning what normal looks like within a specific environment and identifying meaningful deviation at machine speed. Identifying that deviation enables defenders to respond by constraining activity back towards normal patterns of behavior.

Not an arms race, but an asymmetry

AI is often framed as fueling an arms race between attackers and defenders. In practice, the more important dynamic is asymmetry.

Attackers operate broadly, scanning many environments for opportunities. Defenders operate deeply within their own systems, and it’s this business context which is so significant. Behavioral understanding gives defenders a durable advantage. Attackers may automate discovery, but they cannot easily reproduce what belonging looks like inside a particular organization.

A changed defensive model

AI‑accelerated vulnerability discovery does not mean defenders have lost. It does mean that disclosure‑driven, patch‑centric models no longer provide a sufficient foundation for resilience.

As vulnerability volumes grow and exploitation timelines compress, effective defense increasingly depends on continuous behavioral understanding, detection that does not rely on prior disclosure, and rapid containment to limit impact. In this model, CVEs confirm risk rather than define when defense begins.

The industry has already seen this approach work in practice. As AI continues to reshape both offense and defense, behavioral detection will move from being complementary to being essential.

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About the author
Andrew Hollister
Principal Solutions Engineer, Cyber Technician
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