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January 31, 2024

How Darktrace Defeated SmokeLoader Malware

Read how Darktrace's AI identified and neutralized SmokeLoader malware. Gain insights into their proactive approach to cybersecurity.
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
Patrick Anjos
Senior Cyber Analyst
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31
Jan 2024

What is Loader Malware?

Loader malware is a type of malicious software designed primarily to infiltrate a system and then download and execute additional malicious payloads.

In recent years, loader malware has emerged as a significant threat for organizations worldwide. This trend is expected to continue given the widespread availability of many loader strains within the Malware-as-a-Service (MaaS) marketplace. The MaaS marketplace contains a wide variety of innovative strains which are both affordable, with toolkits ranging from USD 400 to USD 1,650 [1], and continuously improving, aiming to avoid traditional detection mechanisms.

SmokeLoader is one such example of a MaaS strain that has been observed in the wild since 2011 and continues to pose a significant threat to organizations and their security teams.

How does SmokeLoader Malware work?

SmokeLoader’s ability to drop an array of different malware strains onto infected systems, from backdoors, ransomware, cryptominers, password stealers, point-of-sale malware and banking trojans, means its a highly versatile loader that has remained consistently popular among threat actors.

In addition to its versatility, it also exhibits advanced evasion strategies that make it difficult for traditional security solutions to detect and remove, and it is easily distributed via methods like spam emails or malicious file downloads.

Between July and August 2023, Darktrace observed an increasing trend in SmokeLoader compromises across its customer base. The anomaly-based threat detection capabilities of Darktrace, coupled with the autonomous response technology, identified and contained the SmokeLoader infections in their initial stages, preventing attackers from causing further disruption by deploying other malicious software or ransomware.

SmokeLoader Malware Attack Details

PROPagate Injection Technique

SmokeLoader utilizes the PROPagate code injection technique, a less common method that inserts malicious code into existing processes in order to appear legitimate and bypass traditional signature-based security measures [2] [3]. In the case of SmokeLoader, this technique exploits the Windows SetWindowsSubclass function, which is typically used to add or change the behavior of Windows Operation System. By manipulating this function, SmokeLoader can inject its code into other running processes, such as the Internet Explorer. This not only helps to disguise  the malware's activity but also allows attackers to leverage the permissions and capabilities of the infected process.

Obfuscation Methods

SmokeLoader is known to employ several obfuscation techniques to evade the detection and analysis of security teams. The techniques include scrambling portable executable files, encrypting its malicious code, obfuscating API functions and packing, and are intended to make the malware’s code appear harmless or unremarkable to antivirus software. This allows attackers to slip past defenses and execute their malicious activities while remaining undetected.

Infection Vector and Communication

SmokeLoader typically spreads via phishing emails that employ social engineering tactics to convince users to unknowingly download malicious payloads and execute the malware. Once installed on target networks, SmokeLoader acts as a backdoor, allowing attackers to control infected systems and download further malicious payloads from command-and-control (C2) servers. SmokeLoader uses fast flux, a DNS technique utilized by botets whereby IP addresses associated with C2 domains are rapidly changed, making it difficult to trace the source of the attack. This technique also boosts the resilience of attack, as taking down one or two malicious IP addresses will not significantly impact the botnet's operation.

Continuous Evolution

As with many MaaS strains, SmokeLoader is continuously evolving, with its developers regularly adding new features and techniques to increase its effectiveness and evasiveness. This includes new obfuscation methods, injection techniques, and communication protocols. This constant evolution makes SmokeLoader a significant threat and underscores the importance of advanced threat detection and response capabilities solution.

Darktrace’s Coverage of SmokeLoader Attack

Between July and August 2023, Darktrace detected one particular SmokeLoader infection at multiple stages of its kill chain on a customer network. This detection was made possible by Darktrace DETECT’s anomaly-based approach and Self-Learning AI that allows it to identify subtle deviations in device behavior.

One of the key components of this process is the classification of endpoint rarity and determining whether an endpoint is new or unusual for any given network. This classification is applied to various aspects of observed endpoints, such as domains, IP addresses, or hostnames within the network. It thereby plays a vital role in identifying SmokeLoader activity, such as the initial infection vector or C2 communication, which typically involve a device contacting a malicious endpoint associated with SmokeLoader.

The First Signs of Infection SmokeLoader Infection

Beginning in July 2023, Darktrace observed a surge in suspicious activities that were assessed with moderate to high confidence to be associated with SmokeLoader malware.

For example on July 30, a device was observed making a successful HTTPS request to humman[.]art, a domain that had never been seen on the network, and therefore classified as 100% rare by DETECT. During this connection, the device in question received a total of 6.0 KiB of data from the unusual endpoint. Open-source intelligence (OSINT) sources reported with high confidence that this domain was associated with the SmokeLoader C2 botnet.

The device was then detected making an HTTP request to another 100% rare external IP, namely 85.208.139[.]35, using a new user agent. This request contained the URI ‘/DefenUpdate.exe’, suggesting a possible download of an executable (.exe) file. This was corroborated by the total amount of data received in this connection, 4.3 MB. Both the file name and its size suggest that the offending device may have downloaded additional malicious tooling from the SmokeLoader C2 endpoint, such as a trojan or information stealer, as reported on OSINT platforms [4].

Figure 1: Device event log showing the moment when a device made its first connection to a SmokeLoader associated domain, and the use of a new user agent. A few seconds later, the DETECT model “Anomalous Connection / New User Agent to IP Without Hostname” breached.

The observed new user agent, “Mozilla/5.0 (Windows NT 10.0; Win64; x64; Trident/7.0; rv:11.0) like Gecko” was identified as suspicious by Darktrace leading to the “Anomalous Connection / New User Agent to IP Without Hostname” DETECT model breach.

As this specific user agent was associated with the Internet Explorer browser running on Windows 10, it may not have appeared suspicious to traditional security tools. However, Darktrace’s anomaly-based detection allows it to identify and mitigate emerging threats, even those that utilize sophisticated evasion techniques.

This is particularly noteworthy in this case because, as discussed earlier, SmokeLoader is known to inject its malicious code into legitimate processes, like Internet Explorer.

Figure 2: Darktrace detecting the affected device leveraging a new user agent and establishing an anomalous HTTP connection with an external IP, which was 100% rare to the network.

C2 Communication

Darktrace continued to observe the device making repeated connections to the humman[.]art endpoint. Over the next few days. On August 7, the device was observed making unusual POST requests to the endpoint using port 80, breaching the ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’ DETECT model. These observed POST requests were observed over a period of around 10 days and consisted of a pattern of 8 requests, each with a ten-minute interval.

Figure 3: Model Breach Event Log highlighting the Darktrace DETECT model breach ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’.

Upon investigating the details of this activity identified by Darktrace DETECT, a particular pattern was observed in these requests: they used the same user-agent, “Mozilla/5.0 (Windows NT 10.0; Win64; x64; Trident/7.0; rv:11.0) like Gecko”, which was previously detected in the initial breach.

Additionally, they the requests had a constantly changing  eferrer header, possibly using randomly generated domain names for each request. Further examination of the packet capture (PCAP) from these requests revealed that the payload in these POST requests contained an RC4 encrypted string, strongly indicating SmokeLoader C2 activity.

Figure4: Advanced Search results display an unusual pattern in the requests made by the device to the hostname humman[.]art. This pattern shows a constant change in the referrer header for each request, indicating anomalous behavior.
Figure 5: The PCAP shows the payload seen in these POST requests contained an RC4 encrypted string strongly indicating SmokeLoader C2 activity.  

Unfortunately in this case, Darktrace RESPOND was not active on the network meaning that the attack was able to progress through its kill chain. Despite this, the timely alerts and detailed incident insights provided by Darktrace DETECT allowed the customer’s security team to begin their remediation process, implementing blocks on their firewall, thus preventing the SmokeLoader malware from continuing its communication with C2 infrastructure.

Darktrace RESPOND Halting Potential Threats from the Initial Stages of Detection

With Darktrace RESPOND, organizations can move beyond threat detection to proactive defense against emerging threats. RESPOND is designed to halt threats as soon as they are identified by DETECT, preventing them from escalating into full-blown compromises. This is achieved through advanced machine learning and Self-Learning AI that is able to understand  the normal ‘pattern of life’ of customer networks, allowing for swift and accurate threat detection and response.

One pertinent example was seen on July 6, when Darktrace detected a separate SmokeLoader case on a customer network with RESPOND enabled in autonomous response mode. Darktrace DETECT initially identified a string of anomalous activity associated with the download of suspicious executable files, triggering the ‘Anomalous File / Multiple EXE from Rare External Locations’ model to breach.

The device was observed downloading an executable file (‘6523.exe’ and ‘/g.exe’) via HTTP over port 80. These downloads originated from endpoints that had never been seen within the customer’s environment, namely ‘hugersi[.]com’ and ‘45.66.230[.]164’, both of which had strongly been linked to SmokeLoader by OSINT sources, likely indicating the initial infection stage of the attack [5].

Figure 6: This figure illustrates Darktrace DETECT observing a device downloading multiple .exe files from rare endpoints and the associated model breach, ‘Anomalous File / Multiple EXE from Rare External Locations’.

Around the same time, Darktrace also observed the same device downloading an unusual file with a numeric file name. Threat actors often employ this tactic in order to avoid using file name patterns that could easily be recognized and blocked by traditional security measures; by frequently changing file names, malicious executables are more likely to remain undetected.

Figure 7: Graph showing the unusually high number of executable files downloaded by the device during the initial infection stage of the attack. The orange and red circles represent the number of model breaches that the device made during the observed activity related to SmokeLoader infection.
Figure 8: This figure illustrates the moment when Darktrace DETECT identified a suspicious download with a numeric file name.

With Darktrace RESPOND active and enabled in autonomous response mode, the SmokeLoader infection was thwarted in the first instance. RESPOND took swift autonomous action by blocking connections to the suspicious endpoints identified by DETECT, blocking all outgoing traffic, and enforcing a pre-established “pattern of life” on offending devices. By enforcing a patten of life on a device, Darktrace RESPOND ensures that it cannot deviate from its ‘normal’ activity to carry out potentially malicious activity, while allowing the device to continue expected business operations.

Figure 9:  A total of 8 RESPOND actions were applied, including blocking connections to suspicious endpoints and domains associated with SmokeLoader.

In addition to the autonomous mitigative actions taken by RESPOND, this customer also received a Proactive Threat Notification (PTN) informing them of potentially malicious activity on their network. This prompted the Darktrace Security Operations Center (SOC) to investigate and document the incident, allowing the customer’s security team to shift their focus to remediating and removing the threat of SmokeLoader.

Conclusion

Ultimately, Darktrace showcased its ability to detect and contain versatile and evasive strains of loader malware, like SmokeLoader. Despite its adeptness at bypassing conventional security tools by frequently changing its C2 infrastructure, utilizing existing processes to infect malicious code, and obfuscating malicious file and domain names, Darktrace’s anomaly-based approach allowed it to recognize such activity as deviations from expected network behavior, regardless of their apparent legitimacy.

Considering SmokeLoader’s wide array of functions, including C2 communication that could be used to facilitate additional attacks like exfiltration, or even the deployment of information-stealers or ransomware, Darktrace proved to be crucial in safeguarding customer networks. By identifying and mitigating SmokeLoader at the earliest possible stage, Darktrace effectively prevented the compromises from escalating into more damaging and disruptive compromises.

With the threat of loader malware expected to continue growing alongside the boom of the MaaS industry, it is paramount for organizations to adopt proactive security solutions, like Darktrace DETECT+RESPOND, that are able to make intelligent decisions to identify and neutralize sophisticated attacks.

Credit to Patrick Anjos, Senior Cyber Analyst, Justin Torres, Cyber Analyst

Appendices

Darktrace DETECT Model Detections

- Anomalous Connection / New User Agent to IP Without Hostname

- Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

- Anomalous File / Multiple EXE from Rare External Locations

- Anomalous File / Numeric File Download

List of IOCs (IOC / Type / Description + Confidence)

- 85.208.139[.]35 / IP / SmokeLoader C2 Endpoint

- 185.174.137[.]109 / IP / SmokeLoader C2 Endpoint

- 45.66.230[.]164 / IP / SmokeLoader C2 Endpoint

- 91.215.85[.]147 / IP / SmokeLoader C2 Endpoint

- tolilolihul[.]net / Hostname / SmokeLoader C2 Endpoint

- bulimu55t[.]net / Hostname / SmokeLoader C2 Endpoint

- potunulit[.]org / Hostname / SmokeLoader C2 Endpoint

- hugersi[.]com / Hostname / SmokeLoader C2 Endpoint

- human[.]art / Hostname / SmokeLoader C2 Endpoint

- 371b0d5c867c2f33ae270faa14946c77f4b0953 / SHA1 / SmokeLoader Executable

References:

[1] https://bazaar.abuse.ch/sample/d7c395ab2b6ef69210221337ea292e204b0f73fef8840b6e64ab88595eda45b3/#intel

[2] https://malpedia.caad.fkie.fraunhofer.de/details/win.smokeloader

[3] https://www.darkreading.com/cyber-risk/breaking-down-the-propagate-code-injection-attack

[4] https://n1ght-w0lf.github.io/malware%20analysis/smokeloader/

[5] https://therecord.media/surge-in-smokeloader-malware-attacks-targeting-ukrainian-financial-gov-orgs

MITRE ATT&CK Mapping

Model: Anomalous Connection / New User Agent to IP Without Hostname

ID: T1071.001

Sub technique: T1071

Tactic: COMMAND AND CONTROL

Technique Name: Web Protocols

Model: Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

ID: T1185

Sub technique: -

Tactic: COLLECTION

Technique Name: Man in the Browser

ID: T1071.001

Sub technique: T1071

Tactic: COMMAND AND CONTROL

Technique Name: Web Protocols

Model: Anomalous File / Multiple EXE from Rare External Locations

ID: T1189

Sub technique: -

Tactic: INITIAL ACCESS

Technique Name: Drive-by Compromise

ID: T1588.001

Sub technique: - T1588

Tactic: RESOURCE DEVELOPMENT

Technique Name: Malware

Model: Anomalous File / Numeric File Download

ID: T1189

Sub technique: -

Tactic: INITIAL ACCESS

Technique Name: Drive-by Compromise

ID: T1588.001

Sub technique: - T1588

Tactic: RESOURCE DEVELOPMENT

Technique Name: Malware

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
Patrick Anjos
Senior Cyber Analyst

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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.

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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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