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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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April 21, 2025

Why Asset Visibility and Signature-Based Threat Detection Fall Short in ICS Security

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In the realm of Industrial Control System (ICS) security, two concepts often dominate discussions:

  1. Asset visibility
  2. Signature-based threat detection

While these are undoubtedly important components of a cybersecurity strategy, many organizations focus on them as the primary means to enhance ICS security. However, this is more of a short-term approach and these organizations often realize too late that these efforts do not translate into actually securing their environment.

To truly secure your environment, organizations should focus their efforts on anomaly detection across core network segments. This shift enables enhanced threat detection, while also providing a more meaningful and dynamic view of asset communication.

By prioritizing anomaly detection, organizations can build a more resilient security posture, detecting and mitigating threats before they escalate into serious incidents.

The shortcomings of asset visibility and signature-based threat detection

Asset visibility is frequently touted as the foundation of ICS security. The idea is that you cannot protect what you cannot see.

However, organizations that invest heavily in asset discovery tools often end up with extensive inventories of connected devices but little actionable insight into their security posture or risk level, let alone any indication as to whether these assets have been compromised.

Simply knowing what assets exist does not equate to securing them.

Worse, asset discovery is often a time-consuming static process. By the time practitioners complete their inventory, not only is there likely to have been changes to their assets, but the threat landscape may have already evolved, introducing new vulnerabilities and attack vectors  that were not previously accounted for.

Signature-based detection is reactive, not proactive

Traditional signature-based threat detection relies on known attack patterns and predefined signatures to identify malicious activity. This approach is fundamentally reactive because it can only detect threats that have already been identified elsewhere.

In an ICS environment where cyber-attacks on OT systems have become more frequent, sophisticated, and destructive, signature-based detection provides a false sense of security while failing to detect sophisticated, previously unseen threats:

Additionally, adversaries often dwell within OT networks for extended periods, studying their specific conditions to identify the most effective way to cause disruption. This means that the likelihood of any attack within OT network looking the same as a previous attack is unlikely.

Implementation effort vs. actual security gains

Many organizations spend considerable time and resources implementing asset visibility solutions and signature-based detection systems only to be required to constantly tune and adjust the sensitivity of the solution.

Despite these efforts, these tools often fail to deliver the level of protection expected, leaving gaps in detection, an overwhelming amount of asset data, and a constant stream of false positives and false negatives from signature-based systems.

A more effective approach: Anomaly detection at core network segments

While it's important to understand the type of device involved during alert triage, organizations should shift their focus from static asset visibility and threat signatures to anomaly detection across critical network segments. This method provides a superior approach to ICS security for several reasons:

Proactive threat detection

Anomaly detection monitors network behavior in real time and identifies deviations . This means that even novel or previously unseen threats can be detected based on unusual network activity, rather than relying on predefined signatures.

Granular security insights

By analyzing traffic patterns across key network segments, organizations can gain deeper insights into how assets interact. This not only improves threat detection but also organically enhances asset visibility. Instead of simply cataloging devices, organizations gain meaningful visibility into how they behave within the network, understanding their unique pattern of life, and making it easier to detect malicious activity.

Efficiency and scalability

Implementing anomaly detection allows security teams to focus on real threats rather than sifting through massive inventories of assets or managing signature updates. It scales better with evolving threats and provides continuous monitoring without requiring constant manual intervention.

Enhanced threat detection for critical infrastructure

Unlike traditional security approaches that rely on static baselines or threat intelligence that doesn't reflect the unique behaviors of your OT environment, Darktrace / OT uses multiple AI techniques to continuously learn and adapt to your organization’s real-world activity across IT, OT, and IoT.

By building a dynamic understanding of each device’s pattern of life, it detects threats at every stage of the kill chain — from known malware to zero-days and insider attacks — without overwhelming your team with false positives or unnecessary alerts. This ensures scalable protection as your environment evolves, without a significant increase in operational overhead.

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About the author
Jeffrey Macre
Industrial Security Solutions Architect

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April 16, 2025

Introducing Version 2 of Darktrace’s Embedding Model for Investigation of Security Threats (DEMIST-2)

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DEMIST-2 is Darktrace’s latest embedding model, built to interpret and classify security data with precision. It performs highly specialized tasks and can be deployed in any environment. Unlike generative language models, DEMIST-2 focuses on providing reliable, high-accuracy detections for critical security use cases.

DEMIST-2 Core Capabilities:  

  • Enhances Cyber AI Analyst’s ability to triage and reason about security incidents by providing expert representation and classification of security data, and as a part of our broader multi-layered AI system
  • Classifies and interprets security data, in contrast to language models that generate unpredictable open-ended text responses  
  • Incorporates new innovations in language model development and architecture, optimized specifically for cybersecurity applications
  • Deployable across cloud, on-prem, and edge environments, DEMIST-2 delivers low-latency, high-accuracy results wherever it runs. It enables inference anywhere.

Cybersecurity is constantly evolving, but the need to build precise and reliable detections remains constant in the face of new and emerging threats. Darktrace’s Embedding Model for Investigation of Security Threats (DEMIST-2) addresses these critical needs and is designed to create stable, high-fidelity representations of security data while also serving as a powerful classifier. For security teams, this means faster, more accurate threat detection with reduced manual investigation. DEMIST-2's efficiency also reduces the need to invest in massive computational resources, enabling effective protection at scale without added complexity.  

As an embedding language model, DEMIST-2 classifies and creates meaning out of complex security data. This equips our Self-Learning AI with the insights to compare, correlate, and reason with consistency and precision. Classifications and embeddings power core capabilities across our products where accuracy is not optional, as a part of our multi-layered approach to AI architecture.

Perhaps most importantly, DEMIST-2 features a compact architecture that delivers analyst-level insights while meeting diverse deployment needs across cloud, on-prem, and edge environments. Trained on a mixture of general and domain-specific data and designed to support task specialization, DEMIST-2 provides privacy-preserving inference anywhere, while outperforming larger general-purpose models in key cybersecurity tasks.

This proprietary language model reflects Darktrace's ongoing commitment to continually innovate our AI solutions to meet the unique challenges of the security industry. We approach AI differently, integrating diverse insights to solve complex cybersecurity problems. DEMIST-2 shows that a refined, optimized, domain-specific language model can deliver outsized results in an efficient package. We are redefining possibilities for cybersecurity, but our methods transfer readily to other domains. We are eager to share our findings to accelerate innovation in the field.  

The evolution of DEMIST-2

Key concepts:  

  • Tokens: The smallest units processed by language models. Text is split into fragments based on frequency patterns allowing models to handle unfamiliar words efficiently
  • Low-Rank Adaptors (LoRA): Small, trainable components added to a model that allow it to specialize in new tasks without retraining the full system. These components learn task-specific behavior while the original foundation model remains unchanged. This approach enables multiple specializations to coexist, and work simultaneously, without drastically increasing processing and memory requirements.

Darktrace began using large language models in our products in 2022. DEMIST-2 reflects significant advancements in our continuous experimentation and adoption of innovations in the field to address the unique needs of the security industry.  

It is important to note that Darktrace uses a range of language models throughout its products, but each one is chosen for the task at hand. Many others in the artificial intelligence (AI) industry are focused on broad application of large language models (LLMs) for open-ended text generation tasks. Our research shows that using LLMs for classification and embedding offers better, more reliable, results for core security use cases. We’ve found that using LLMs for open-ended outputs can introduce uncertainty through inaccurate and unreliable responses, which is detrimental for environments where precision matters. Generative AI should not be applied to use cases, such as investigation and threat detection, where the results can deeply matter. Thoughtful application of generative AI capabilities, such as drafting decoy phishing emails or crafting non-consequential summaries are helpful but still require careful oversight.

Data is perhaps the most important factor for building language models. The data used to train DEMIST-2 balanced the need for general language understanding with security expertise. We used both publicly available and proprietary datasets.  Our proprietary dataset included privacy-preserving data such as URIs observed in customer alerts, anonymized at source to remove PII and gathered via the Call Home and aianalyst.darktrace.com services. For additional details, read our Technical Paper.  

DEMIST-2 is our way of addressing the unique challenges posed by security data. It recognizes that security data follows its own patterns that are distinct from natural language. For example, hostnames, HTTP headers, and certificate fields often appear in predictable ways, but not necessarily in a way that mirrors natural language. General-purpose LLMs tend to break down when used in these types of highly specialized domains. They struggle to interpret structure and context, fragmenting important patterns during tokenization in ways that can have a negative impact on performance.  

DEMIST-2 was built to understand the language and structure of security data using a custom tokenizer built around a security-specific vocabulary of over 16,000 words. This tokenizer allows the model to process inputs more accurately like encoded payloads, file paths, subdomain chains, and command-line arguments. These types of data are often misinterpreted by general-purpose models.  

When the tokenizer encounters unfamiliar or irregular input, it breaks the data into smaller pieces so it can still be processed. The ability to fall back to individual bytes is critical in cybersecurity contexts where novel or obfuscated content is common. This approach combines precision with flexibility, supporting specialized understanding with resilience in the face of unpredictable data.  

Along with our custom tokenizer, we made changes to support task specialization without increasing model size. To do this, DEMIST-2 uses LoRA . LoRA is a technique that integrates lightweight components with the base model to allow it to perform specific tasks while keeping memory requirements low. By using LoRA, our proprietary representation of security knowledge can be shared and reused as a starting point for more highly specialized models, for example, it takes a different type of specialization to understand hostnames versus to understand sensitive filenames. DEMIST-2 dynamically adapts to these needs and performs them with purpose.  

The result is that DEMIST-2 is like having a room of specialists working on difficult problems together, while sharing a basic core set of knowledge that does not need to be repeated or reintroduced to every situation. Sharing a consistent base model also improves its maintainability and allows efficient deployment across diverse environments without compromising speed or accuracy.  

Tokenization and task specialization represent only a portion of the updates we have made to our embedding model. In conjunction with the changes described above, DEMIST-2 integrates several updated modeling techniques that reduce latency and improve detections. To learn more about these details, our training data and methods, and a full write-up of our results, please read our scientific whitepaper.

DEMIST-2 in action

In this section, we highlight DEMIST-2's embeddings and performance. First, we show a visualization of how DEMIST-2 classifies and interprets hostnames, and second, we present its performance in a hostname classification task in comparison to other language models.  

Embeddings can often feel abstract, so let’s make them real. Figure 1 below is a 2D visualization of how DEMIST-2 classifies and understands hostnames. In reality, these hostnames exist across many more dimensions, capturing details like their relationships with other hostnames, usage patterns, and contextual data. The colors and positions in the diagram represent a simplified view of how DEMIST-2 organizes and interprets these hostnames, providing insights into their meaning and connections. Just like an experienced human analyst can quickly identify and group hostnames based on patterns and context, DEMIST-2 does the same at scale.  

DEMIST-2 visualization of hostname relationships from a large web dataset.
Figure 1: DEMIST-2 visualization of hostname relationships from a large web dataset.

Next, let’s zoom in on two distinct clusters that DEMIST-2 recognizes. One cluster represents small businesses (Figure 2) and the other, Russian and Polish sites with similar numerical formats (Figure 3). These clusters demonstrate how DEMIST-2 can identify specific groupings based on real-world attributes such as regional patterns in website structures, common formats used by small businesses, and other properties such as its understanding of how websites relate to each other on the internet.

Cluster of small businesses
Figure 2: Cluster of small businesses
Figure 3: Cluster of Russian and Polish sites with a similar numerical format

The previous figures provided a view of how DEMIST-2 works. Figure 4 highlights DEMIST-2’s performance in a security-related classification task. The chart shows how DEMIST-2, with just 95 million parameters, achieves nearly 94% accuracy—making it the highest-performing model in the chart, despite being the smallest. In comparison, the larger model with 2.78 billion parameters achieves only about 89% accuracy, showing that size doesn’t always mean better performance. Small models don’t mean poor performance. For many security-related tasks, DEMIST-2 outperforms much larger models.

Hostname classification task performance comparison against comparable open source foundation models
Figure 4: Hostname classification task performance comparison against comparable open source foundation models

With these examples of DEMIST-2 in action, we’ve shown how it excels in embedding and classifying security data while delivering high performance on specialized security tasks.  

The DEMIST-2 advantage

DEMIST-2 was built for precision and reliability. Our primary goal was to create a high-performance model capable of tackling complex cybersecurity tasks. Optimizing for efficiency and scalability came second, but it is a natural outcome of our commitment to building a strong, effective solution that is available to security teams working across diverse environments. It is an enormous benefit that DEMIST-2 is orders of magnitude smaller than many general-purpose models. However, and much more importantly, it significantly outperforms models in its capabilities and accuracy on security tasks.  

Finding a product that fits into an environment’s unique constraints used to mean that some teams had to settle for less powerful or less performant products. With DEMIST-2, data can remain local to the environment, is entirely separate from the data of other customers, and can even operate in environments without network connectivity. The size of our model allows for flexible deployment options while at the same time providing measurable performance advantages for security-related tasks.  

As security threats continue to evolve, we believe that purpose-built AI systems like DEMIST-2 will be essential tools for defenders, combining the power of modern language modeling with the specificity and reliability that builds trust and partnership between security practitioners and AI systems.

Conclusion

DEMIST-2 has additional architectural and deployment updates that improve performance and stability. These innovations contribute to our ability to minimize model size and memory constraints and reflect our dedication to meeting the data handling and privacy needs of security environments. In addition, these choices reflect our dedication to responsible AI practices.

DEMIST-2 is available in Darktrace 6.3, along with a new DIGEST model that uses GNNs and RNNs to score and prioritize threats with expert-level precision.

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About the author
Margaret Cunningham, PhD
Director, Security & AI Strategy, Field CISO
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