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June 21, 2024

Elevating Network Security: Confronting Trust, Ransomware, & Novel Attacks

Ensuring trust, battling ransomware, and detecting novel attacks pose critical challenges in network security. This blog explores these challenges and shows how leveraging AI-driven security solutions helps security teams stay informed and effectively safeguard their network.
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
Mikey Anderson
Product Marketing Manager, Network Detection & Response
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21
Jun 2024

Understanding the Network Security Market

Old tools blind to new threats

With the rise of GenAI and novel attacks, organizations can no longer rely solely on traditional network security solutions that depend on historical attack data, such as signatures and detection rules, to identify threats. However, in many cases network security vendors and traditional solutions like IDS/IPS focus on detecting known attacks using historical data. What happens is organizations are left vulnerable to unknown and novel threats, as these approaches only detect known malicious behavior and cannot keep up with unknown threats or zero-day attacks.

Advanced threats

Darktrace's End of Year Threat Report for 2023 highlights significant changes in the cyber threat landscape, particularly due to advancements in technology such as generative AI. The report notes a substantial increase in sophisticated attacks, including those utilizing generative AI, which have made it more challenging for traditional security measures to keep up. The report also details the rise of multi-functional malware, like Black Basta ransomware, which not only encrypts data for ransom but also spreads other types of malware such as the Qbot banking trojan. These complex attacks are increasingly being deployed by advanced cybercriminal groups, underscoring the need for organizations to adopt advanced security measures that can detect and respond to novel threats in real-time.

Defenders need a solution that can level the playing field, especially when they are operating with limited resources and getting overloaded with endless alerts. Most network security tools on the market have a siloed approach and do not integrate with the rest of an organization’s digital estate, but attackers don’t operate in a single domain.

Disparate workforce

With so many organizations continuing to support a remote or hybrid working environment, the need to secure devices that are outside the corporate network or off-VPN is increasingly important. While endpoint protection or endpoint detection and response (EDR) tools are a fundamental part of any security stack, it’s not possible to install an agent on every device, which can leave blind spots in an organization’s attack surface. Managing trust and access policies is also necessary to protect identities, however this comes with its own set of challenges in terms of implementation and minimizing business disruption.

This blog will dive into these challenges and show examples of how Darktrace has helped mitigate risk and stop novel and never-before-seen threats.

Network Security Challenge 1: Managing trust

What is trust in cybersecurity?

Trust in cybersecurity means that an entity can be relied upon. This can involve a person, organization, or system to be authorized or authenticated by proving their identity is legitimate and can be trusted to have access to the network or sensitive information.

Why is trust important in cybersecurity?

Granting access and privileges to your workforce and select affiliates has profound implications for cybersecurity, brand reputation, regulatory compliance, and financial liability. In a traditional network security model, traffic gets divided into two categories — trusted and untrusted — with some entities and segments of the network deemed more creditable than others.

How do you manage trust in cybersecurity?

Zero trust is too little, but any is too much.

Modern network security challenges point to an urgent need for organizations to review and update their approaches to managing trust. External pressure to adopt zero trust security postures literally suggests trusting no one, but that impedes your freedom
to do business. IT leaders need a proven but practical process for deciding who should be allowed to use your network and how.

Questions to ask in updating Trusted User policies include:

  • What process should you follow to place trust in third
    parties and applications?
  • Do you subject trusted entities to testing and other due
    diligence first?
  • How often do you review this process — and trusted
    relationships themselves — after making initial decisions?
  • How do you tell when trusted users should no longer be
    trusted?

Once trust has been established, security teams need new and better ways to autonomously verify that those transacting within your network are indeed those trusted users that they claim to be, taking only the authorized actions you’ve allowed them to take.

Exploiting trust in the network

Insider threats have a major head start. The opposite of attacks launched by nameless, faceless strangers, insider threats originate through parties once deemed trustworthy. That might mean a current or former member of your workforce or a partner, vendor, investor, or service provider authorized by IT to access corporate systems and data. Threats also arise when a “pawn” gets unwittingly tricked into disclosing credentials or downloading malware.

Common motives for insider attacks include revenge, stealing or leaking sensitive data, taking down IT systems, stealing assets or IP, compromising your organization’s credibility, and simply harassing your workforce. Put simply, rules and signatures based security solutions won’t flag insider threats because an insider does not immediately present themselves as an intruder. Insider threats can only be stopped by an evolving understanding of ‘normal’ for every user that immediately alerts your team when trusted users do something strange.

“By 2026, 10% of large enterprises will have a comprehensive, mature and measurable zero-trust program in place, up from less than 1% today.” [1]

Use Case: Darktrace spots an insider threat

Darktrace / OT detected a subtle deviation from normal behavior when a reprogram command was sent by an engineering workstation to a PLC controlling a pump, an action an insider threat with legitimized access to OT systems would take to alter the physical process without any malware involved. In this instance, AI Analyst, Darktrace’s investigation tool that triages events to reveal the full security incident, detected the event as unusual based on multiple metrics including the source of the command, the destination device, the time of the activity, and the command itself.  

As a result, AI Analyst created a complete security incident, with a natural language summary, the technical details of the activity, and an investigation process explaining how it came to its conclusion. By leveraging Explainable AI, a security team can quickly triage and escalate Darktrace incidents in real time before it becomes disruptive, and even when performed by a trusted insider.

Read more about insider threats here

Network Security Challenge 2: Stopping Ransomware at every stage    

What is Ransomware?

Ransomware is a type of malware that encrypts valuable files on a victim’s device, denying the account holder access, and demanding money in exchange for the encryption key. Ransomware has been increasingly difficult to deal with, especially with ransom payments being made in crypto currency which is untraceable. Ransomware can enter a system by clicking a link dangerous or downloading malicious files.

Avoiding ransomware attacks ranks at the top of most CISOs’ and risk managers’ priority lists, and with good reason. Extortion was involved in 25% of all breaches in 2022, with front-page attacks wreaking havoc across healthcare, gas pipelines, food processing plants, and other global supply chains. [2]

What else is new?

The availability of “DIY” toolkits and subscription-based ransom- ware-as-a-service (RaaS) on the dark web equips novice threat actors to launch highly sophisticated attacks at machine speed. For less than $500, virtually anyone can acquire and tweak RaaS offerings such as Philadelphia that come with accessible customer interfaces, reviews, discounts, and feature updates — all the signature features of commercial SaaS offerings.                  

Darktrace Cyber AI breaks the ransomware cycle

The preeminence of ransomware keeps security teams on high alert for indicators of attack but hypervigilance — and too many tools churning out too many alerts — quickly exhausts analysts’ bandwidth. To reverse this trend, AI needs to help prioritize and resolve versus merely detect risk.

Darktrace uses AI to recognize and contextualize possible signs of ransomware attacks as they appear in your network and across multiple domains. Viewing behaviors in the context of your organization’s normal ‘pattern of life’ updates and enhances detection that watches for a repeat of previous techniques.

Darktrace's AI brings the added advantage of continuously analyzing behavior in your environment at machine speed.

Darktrace AI also performs Autonomous Response, shutting down attacks at every stage of the ransomware cycle, including the first telltale signs of exfiltration and encryption of data for extortion purposes.

Use Case: Stopping Hive Ransomware attack

Hive is distributed via a RaaS model where its developers update and maintain the code, in return for a percentage of the eventual ransom payment, while users (or affiliates) are given the tools to carry out attacks using a highly sophisticated and complex malware they would otherwise be unable to use.

In early 2022, Darktrace / NETWORK identified several instances of Hive ransomware on the networks of multiple customers. Using its anomaly-based detection, Darktrace was able to successfully detect the attacks and multiple stages of the kill chain, including command and control (C2) activity, lateral movement, data exfiltration, and ultimately data encryption and the writing of ransom notes.

Darktrace’s AI understands customer networks and learns the expected patterns of behavior across an organization’s digital estate. Using its anomaly-based detection Darktrace is able to identify emerging threats through the detection of unusual or unexpected behavior, without relying on rules and signatures, or known IoCs.

Read the full story here

Network Security Challenge 3: Spotting Novel Attacks

You can’t predict tomorrow’s weather by reading yesterday’s forecast, yet that’s essentially what happens when network security tools only look for known attacks.

What are novel attacks?

“Novel attacks” include unknown or previously unseen exploits such as zero-days, or new variations of known threats that evade existing detection rules.

Depending on how threats get executed, the term “novel” can refer to brand new tactics, techniques, and procedures (TTPs), or to subtle new twists on perennial threats like DoS, DDoS, and Domain Name Server (DNS) attacks.

Old tools may be blind to new threats

Stopping novel threats is less about deciding whom to trust than it is about learning to spot something brand new. As we’ve seen with ransomware, the growing “aaS” attack market creates a profound paradigm shift by allowing non-technical perpetrators to tweak, customize, and coin never-before-seen threats that elude traditional network, email, VPN, and cloud security.

Tools based on traditional rules and signatures lack a frame of reference. This is where AI’s ability to spot and analyze abnormalities in the context of normal patterns of life comes into play.                        

Darktrace AI spots what other tools miss                                      

Instead of training in cloud data lakes that pool data from unrelated attacks worldwide, Darktrace AI learns about your unique environment from your environment. By flagging and analyzing everything unusual — instead of only known signs of compromise — Darktrace’s Self-Learning AI keeps security stacks from missing less obvious but potentially more dangerous events.

The real challenge here is achieving faster “time to meaning” and contextualizing behavior that might — or might not — be part of a novel attack. Darktrace/Network does not require a “patient zero” to identify a novel attack, or one exploiting a zero-day vulnerability.

Use Case: Stopping Novel Ransomware Attack

In late May 2023, Darktrace observed multiple instances of Akira ransomware affecting networks across its customer base. Thanks to its anomaly-based approach to threat detection Darktrace successfully identified the novel ransomware attacks and provided full visibility over the cyber kill chain, from the initial compromise to the eventual file encryptions and ransom notes. Darktrace identified Akira ransomware on multiple customer networks, even when threat actors were utilizing seemingly legitimate services (or spoofed versions of them) to carry out malicious activity. While this may have gone unnoticed by traditional security tools, Darktrace’s anomaly-based detection enabled it to recognize malicious activity for what it was. In cases where Darktrace’s autonomous response was enabled these attacks were mitigated in their early stages, thus minimizing any disruption or damage to customer networks.

Read the full story here

References

[1] Gartner, “Gartner Unveils Top Eight Cybersecurity Predictions for 2023-2024,” 28 March 2023.                    

[2] TechTarget, “Ransomware trends, statistics and facts in 2023,” Sean Michael Kerner, 26 January 2023.

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
Mikey Anderson
Product Marketing Manager, Network Detection & Response

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

[related-resource]

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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