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October 15, 2024

Navigating Buying and Adoption Journeys for AI Cybersecurity Tools

More and more security teams are adopting AI-powered cybersecurity solutions, but first-time buyers may not know how to evaluate new vendors and tools. This blog covers questions to consider at each stage of the AI adoption journey to ensure return on investment.
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
Nicole Carignan
SVP, Security & AI Strategy, Field CISO
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15
Oct 2024

Enterprise AI tools go mainstream

In this dawning Age of AI, CISOs are increasingly exploring investments in AI security tools to enhance their organizations’ capabilities. AI can help achieve productivity gains by saving time and resources, mining intelligence and insights from valuable data, and increasing knowledge sharing and collaboration.  

While investing in AI can bring immense benefits to your organization, first-time buyers of AI cybersecurity solutions may not know where to start. They will have to determine the type of tool they want, know the options available, and evaluate vendors. Research and understanding are critical to ensure purchases are worth the investment.  

Challenges of a muddied marketplace

Key challenges in AI purchasing come from consumer doubt and lack of vendor transparency. The AI software market is buzzing with hype and flashy promises, which are not necessarily going to be realized immediately. This has fostered uncertainty among potential buyers, especially in the AI cybersecurity space.  

As Gartner writes, “There is a general lack of transparency and understanding about how AI-enhanced security solutions leverage AI and the effectiveness of those solutions within real-world SecOps. This leads to trust issues among security leaders and practitioners, resulting in slower adoption of AI features” [1].  

Similarly, only 26% of security professionals report a full understanding of the different types of AI in use within security products.

Given this widespread uncertainty generated through vague hype, buyers must take extra care when considering new AI tools to adopt.  

Goals of AI adoption

Buyers should always start their journeys with objectives in mind, and a universal goal is to achieve return on investment. When organizations adopt AI, there are key aspects that will signal strong payoff. These include:  

  • Wide-ranging application across operations and areas of the business
  • Actual, enthusiastic adoption and application by the human security team  
  • Integration with the rest of the security stack and existing workflows
  • Business and operational benefits, including but not limited to:  
  • Reduced risk
  • Reduced time to response
  • Reduced potential downtime, damage, and disruption
  • Increased visibility and coverage
  • Improved SecOps workflows
  • Decreased burden on teams so they can take on more strategic tasks  

Ideally, most or all these measurements will be fulfilled. It is not enough for AI tools to benefit productivity and workflows in theory, but they must be practically implemented to provide return on investment.  

Investigation before investment

Before investing in AI tools, buyers should ask questions pertaining to each stage of the adoption journey. The answers to these questions will not only help buyers gauge if a tool could be worth the investment, but also plan how the new tool will practically fit into the organization’s existing technology and workflows.  

Figure 1: Initial questions to consider when starting to shop for AI [2].

These questions are good to imagine how a tool will fit into your organization and determine if a vendor is worth further evaluation. Once you decide a tool has potential use and feasibility in your organization, it is time to dive deeper and learn more.  

Ask vendors specific questions about their technology. This information will most likely not be on their websites, and since it involves intellectual property, it may require an NDA.  

Find a longer list of questions to ask vendors and what to look for in their responses in the white paper “CISO’s Guide to Buying AI.”

Committing to transparency amidst the AI hype

For security teams to make the most out of new AI tools, they must trust the AI. Especially in an AI marketplace full of hype and obfuscation, transparency should be baked into both the descriptions of the AI tool and the tool’s functionality itself. With that in mind, here are some specifics about what techniques make up Darktrace’s AI.  

Darktrace as an AI cybersecurity vendor

Darktrace has been using AI technology in cybersecurity for over 10 years. As a pioneer in the space, we have made innovation part of our process.  

The Darktrace ActiveAI Security Platform™ uses multi-layered AI that trains on your unique business operations data for tailored security across the enterprise. This approach ensures that the strengths of one AI technique make up for the shortcomings of another, providing well-rounded and reliable coverage. Our models are always on and always learning, allowing your team to stop attacks in real time.  

The machine learning techniques used in our solution include:

  • Unsupervised machine learning
  • Multiple Clustering Techniques
  • Multiple anomaly detection models in tandem analyzing data across hundreds of metrics
  • Bayesian probabilistic methods
  • Bayesian metaclassifier for autonomous fine-tuning of unsupervised machine learning models
  • Deep learning engines
  • Graph theory
  • Applied supervised machine learning for investigative AI  
  • Neural networks
  • Reinforcement Learning
  • Generative and applied AI
  • Natural Language Processing (NLP) and Large Language Models (LLMs)
  • Post-processing models

Additionally, since Darktrace focuses on using the customer’s data across its entire digital estate, it brings a range of advantages in data privacy, interpretability, and data transfer costs.  

Building trust with Darktrace AI

Darktrace further supports the human security team’s adoption of our technology by building trust. To do that, we designed our platform to give your team visibility and control over the AI.  

Instead of functioning as a black box, our products focus on interpretability and sharing confidence levels. This includes specifying the threshold of what triggered a certain alert and the details of the AI Analyst’s investigations to see how it reached its conclusions. The interpretability of our AI uplevels and upskills the human security team with more information to drive investigations and remediation actions.  

For complete control, the human security team can modify all the detection and response thresholds for our model alerts to customize them to fit specific business preferences.  

Conclusion

CISO’s are increasingly considering investing in AI cybersecurity tools, but in this rapidly growing field, it’s not always clear what to look for.  

Buyers should first determine their goals for a new AI tool, then research possible vendors by reviewing validation and asking deeper questions. This will reveal if a tool is a good match for the organization to move forward with investment and adoption.  

As leaders in the AI cybersecurity industry, Darktrace is always ready to help you on your AI journey.  

CISOs guide to buying AI white paper cover

How to evaluate an AI cybersecurity vendor

Download the white paper to learn how buyers should approach purchasing AI-based solutions. It includes:

  • Key steps for selecting AI cybersecurity tools
  • Questions to ask and responses to expect from vendors
  • Understand tools available and find the right fit
  • Ensure AI investments align with security goals and needs

References

  1. Gartner, April 17, 2024, “Emerging Tech: Navigating the Impact of AI on SecOps Solution Development.”  
  1. Inspired by Gartner, May 14, 2024, “Presentation Slides: AI Survey Reveals AI Security and Privacy Leads to Improved ROI” and NHS England, September, 18, 2020, “A Buyer’s Guide to AI in Health and Care,” Available at: https://transform.england.nhs.uk/ai-lab/explore-all-resources/adopt-ai/a-buyers-guide-to-ai-in-health-and-care/  
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
Nicole Carignan
SVP, Security & AI Strategy, Field CISO

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April 16, 2025

Why Data Classification Isn’t Enough to Prevent Data Loss

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Why today’s data is fundamentally difficult to protect

Data isn’t what it used to be. It’s no longer confined to neat rows in a database, or tucked away in a secure on-prem server. Today, sensitive information moves freely between cloud platforms, SaaS applications, endpoints, and a globally distributed workforce – often in real time. The sheer volume and diversity of modern data make it inherently harder to monitor, classify, and secure. And the numbers reflect this challenge – 63% of breaches stem from malicious insiders or human error.

This complexity is compounded by an outdated reliance on manual data management. While data classification remains critical – particularly to ensure compliance with regulations like GDPR or HIPAA – the burden of managing this data often falls on overstretched security teams. Security teams are expected to identify, label, and track data across sprawling ecosystems, which can be time-consuming and error-prone. Even with automation, rigid policies that depend on pre-defined data classification miss the mark.

From a data protection perspective, if manual or basic automated classification is the sole methodology for preventing data loss, critical data will likely slip through the cracks. Security teams are left scrambling to fill the gaps, facing compliance risks and increasing operational overhead. Over time, the hidden costs of these inefficiencies pile up, draining resources and reducing the effectiveness of your entire security posture.

What traditional data classification can’t cover

Data classification plays an important role in data loss prevention, but it's only half the puzzle. It’s designed to spot known patterns and apply labels, yet the most common causes of data breaches don’t follow rules. They stem from something far harder to define: human behavior.

When Darktrace began developing its data loss detection capabilities, the question wasn’t what data to protect — it was how to understand the people using it. The numbers pointed clearly to where AI could make the biggest difference: 22% of email data breaches stem directly from user error, while malicious insider threats remain the most expensive, costing organizations an average of $4.99 million per incident.

Data classification is blind to nuance – it can’t grasp intent, context, or the subtle red flags that often precede a breach. And no amount of labeling, policy, or training can fully account for the reality that humans make mistakes. These problems require a system that sees beyond the data itself — one that understands how it’s being used, by whom, and in what context. That’s why Darktrace leans into its core strength: detecting the subtle symptoms of data loss by interpreting human behavior, not just file labels.

Achieving autonomous data protection with behavioral AI

Rather than relying on manual processes to understand what’s important, Darktrace uses its industry-leading AI to learn how your organization uses data — and spot when something looks wrong.

Its understanding of business operations allows it to detect subtle anomalies around data movement for your use cases, whether that’s a misdirected email, an insecure cloud storage link, or suspicious activity from an insider. Crucially, this detection is entirely autonomous, with no need for predefined rules or static labels.

Darktrace uses its contextual understanding of each user to stop all types of sensitive or misdirected data from leaving the organization
Fig 1: Darktrace uses its contextual understanding of each user to stop all types of sensitive or misdirected data from leaving the organization

Darktrace / EMAIL’s DLP add-on continuously learns in real time, enabling:

  • Automatic detection: Identifies risky data behavior to catch threats that traditional approaches miss – from human error to sophisticated insider threats.
  • A dynamic range of actions: Darktrace always aims to avoid business disruption in its blocking actions, but this can be adjusted according to the unique risk appetite of each customer – taking the most appropriate response for that business from a whole scale of possibilities.
  • Enhanced context: While Darktrace doesn’t require sensitivity data labeling, it integrates with Microsoft Purview to ingest sensitivity labels and enrich its understanding of the data – for even more accurate decision-making.

Beyond preventing data loss, Darktrace uses DLP activity to enhance its contextual understanding of the user itself. In other words, outbound activity can be a useful symptom in identifying a potential account compromise, or can be used to give context to that user’s inbound activity. Because Darktrace sees the whole picture of a user across their inbound, outbound, and lateral mail, as well as messaging (and into collaboration tools with Darktrace / IDENTITY), every interaction informs its continuous learning of normal.

With Darktrace, you can achieve dynamic data loss prevention for the most challenging human-related use cases – from accidental misdirected recipients to malicious insiders – that evade detection from manual classification. So don’t stand still on data protection – make the switch to autonomous, adaptive DLP that understands your business, data, and people.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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April 14, 2025

Email bombing exposed: Darktrace’s email defense in action

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What is email bombing?

An email bomb attack, also known as a "spam bomb," is a cyberattack where a large volume of emails—ranging from as few as 100 to as many as several thousand—are sent to victims within a short period.

How does email bombing work?

Email bombing is a tactic that typically aims to disrupt operations and conceal malicious emails, potentially setting the stage for further social engineering attacks. Parallels can be drawn to the use of Domain Generation Algorithm (DGA) endpoints in Command-and-Control (C2) communications, where an attacker generates new and seemingly random domains in order to mask their malicious connections and evade detection.

In an email bomb attack, threat actors typically sign up their targeted recipients to a large number of email subscription services, flooding their inboxes with indirectly subscribed content [1].

Multiple threat actors have been observed utilizing this tactic, including the Ransomware-as-a-Service (RaaS) group Black Basta, also known as Storm-1811 [1] [2].

Darktrace detection of email bombing attack

In early 2025, Darktrace detected an email bomb attack where malicious actors flooded a customer's inbox while also employing social engineering techniques, specifically voice phishing (vishing). The end goal appeared to be infiltrating the customer's network by exploiting legitimate administrative tools for malicious purposes.

The emails in these attacks often bypass traditional email security tools because they are not technically classified as spam, due to the assumption that the recipient has subscribed to the service. Darktrace / EMAIL's behavioral analysis identified the mass of unusual, albeit not inherently malicious, emails that were sent to this user as part of this email bombing attack.

Email bombing attack overview

In February 2025, Darktrace observed an email bombing attack where a user received over 150 emails from 107 unique domains in under five minutes. Each of these emails bypassed a widely used and reputable Security Email Gateway (SEG) but were detected by Darktrace / EMAIL.

Graph showing the unusual spike in unusual emails observed by Darktrace / EMAIL.
Figure 1: Graph showing the unusual spike in unusual emails observed by Darktrace / EMAIL.

The emails varied in senders, topics, and even languages, with several identified as being in German and Spanish. The most common theme in the subject line of these emails was account registration, indicating that the attacker used the victim’s address to sign up to various newsletters and subscriptions, prompting confirmation emails. Such confirmation emails are generally considered both important and low risk by email filters, meaning most traditional security tools would allow them without hesitation.

Additionally, many of the emails were sent using reputable marketing tools, such as Mailchimp’s Mandrill platform, which was used to send almost half of the observed emails, further adding to their legitimacy.

 Darktrace / EMAIL’s detection of an email being sent using the Mandrill platform.
Figure 2: Darktrace / EMAIL’s detection of an email being sent using the Mandrill platform.
Darktrace / EMAIL’s detection of a large number of unusual emails sent during a short period of time.
Figure 3: Darktrace / EMAIL’s detection of a large number of unusual emails sent during a short period of time.

While the individual emails detected were typically benign, such as the newsletter from a legitimate UK airport shown in Figure 3, the harmful aspect was the swarm effect caused by receiving many emails within a short period of time.

Traditional security tools, which analyze emails individually, often struggle to identify email bombing incidents. However, Darktrace / EMAIL recognized the unusual volume of new domain communication as suspicious. Had Darktrace / EMAIL been enabled in Autonomous Response mode, it would have automatically held any suspicious emails, preventing them from landing in the recipient’s inbox.

Example of Darktrace / EMAIL’s response to an email bombing attack taken from another customer environment.
Figure 4: Example of Darktrace / EMAIL’s response to an email bombing attack taken from another customer environment.

Following the initial email bombing, the malicious actor made multiple attempts to engage the recipient in a call using Microsoft Teams, while spoofing the organizations IT department in order to establish a sense of trust and urgency – following the spike in unusual emails the user accepted the Teams call. It was later confirmed by the customer that the attacker had also targeted over 10 additional internal users with email bombing attacks and fake IT calls.

The customer also confirmed that malicious actor successfully convinced the user to divulge their credentials with them using the Microsoft Quick Assist remote management tool. While such remote management tools are typically used for legitimate administrative purposes, malicious actors can exploit them to move laterally between systems or maintain access on target networks. When these tools have been previously observed in the network, attackers may use them to pursue their goals while evading detection, commonly known as Living-off-the-Land (LOTL).

Subsequent investigation by Darktrace’s Security Operations Centre (SOC) revealed that the recipient's device began scanning and performing reconnaissance activities shortly following the Teams call, suggesting that the user inadvertently exposed their credentials, leading to the device's compromise.

Darktrace’s Cyber AI Analyst was able to identify these activities and group them together into one incident, while also highlighting the most important stages of the attack.

Figure 5: Cyber AI Analyst investigation showing the initiation of the reconnaissance/scanning activities.

The first network-level activity observed on this device was unusual LDAP reconnaissance of the wider network environment, seemingly attempting to bind to the local directory services. Following successful authentication, the device began querying the LDAP directory for information about user and root entries. Darktrace then observed the attacker performing network reconnaissance, initiating a scan of the customer’s environment and attempting to connect to other internal devices. Finally, the malicious actor proceeded to make several SMB sessions and NTLM authentication attempts to internal devices, all of which failed.

Device event log in Darktrace / NETWORK, showing the large volume of connections attempts over port 445.
Figure 6: Device event log in Darktrace / NETWORK, showing the large volume of connections attempts over port 445.
Darktrace / NETWORK’s detection of the number of the login attempts via SMB/NTLM.
Figure 7: Darktrace / NETWORK’s detection of the number of the login attempts via SMB/NTLM.

While Darktrace’s Autonomous Response capability suggested actions to shut down this suspicious internal connectivity, the deployment was configured in Human Confirmation Mode. This meant any actions required human approval, allowing the activities to continue until the customer’s security team intervened. If Darktrace had been set to respond autonomously, it would have blocked connections to port 445 and enforced a “pattern of life” to prevent the device from deviating from expected activities, thus shutting down the suspicious scanning.

Conclusion

Email bombing attacks can pose a serious threat to individuals and organizations by overwhelming inboxes with emails in an attempt to obfuscate potentially malicious activities, like account takeovers or credential theft. While many traditional gateways struggle to keep pace with the volume of these attacks—analyzing individual emails rather than connecting them and often failing to distinguish between legitimate and malicious activity—Darktrace is able to identify and stop these sophisticated attacks without latency.

Thanks to its Self-Learning AI and Autonomous Response capabilities, Darktrace ensures that even seemingly benign email activity is not lost in the noise.

Credit to Maria Geronikolou (Cyber Analyst and SOC Shift Supervisor) and Cameron Boyd (Cyber Security Analyst), Steven Haworth (Senior Director of Threat Modeling), Ryan Traill (Analyst Content Lead)

Appendices

[1] https://www.microsoft.com/en-us/security/blog/2024/05/15/threat-actors-misusing-quick-assist-in-social-engineering-attacks-leading-to-ransomware/

[2] https://thehackernews.com/2024/12/black-basta-ransomware-evolves-with.html

Darktrace Models Alerts

Internal Reconnaissance

·      Device / Suspicious SMB Scanning Activity

·      Device / Anonymous NTLM Logins

·      Device / Network Scan

·      Device / Network Range Scan

·      Device / Suspicious Network Scan Activity

·      Device / ICMP Address Scan

·      Anomalous Connection / Large Volume of LDAP Download

·      Device / Suspicious LDAP Search Operation

·      Device / Large Number of Model Alerts

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About the author
Maria Geronikolou
Cyber Analyst
Your data. Our AI.
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