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October 3, 2023

Unveiling ViperSoftX: A Darktrace Investigation

Read about the ViperSoftX threat and how Darktrace's innovative detection methods exposed this cyber intrusion and its potential impacts.
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
Zoe Tilsiter
Cyber Analyst
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03
Oct 2023

Fighting Info-Stealing Malware

The escalating threat posed by information-stealing malware designed to harvest and steal the sensitive data of individuals and organizations alike has become a paramount concern for security teams across the threat landscape. In direct response to security teams improving their threat detection and prevention capabilities, threat actors are forced to continually adapt and advance their techniques, striving for greater sophistication to ensure they can achieve the malicious goals.

What is ViperSoftX?

ViperSoftX is an information stealer and Remote Access Trojan (RAT) malware known to steal privileged information such as cryptocurrency wallet addresses and password information stored in browsers and password managers. It is commonly distributed via the download of cracked software from multiple sources such as suspicious domains, torrent downloads, and key generators (keygens) from third-party sites.

ViperSoftX was first observed in the wild in 2020 [1] but more recently, new strains were identified in 2022 and 2023 utilizing more sophisticated detection evasion techniques, making it more difficult for security teams to identify and analyze. This includes using more advanced encryption methods alongside monthly changes to command-and-control servers (C2) [2], using dynamic-link library (DLL) sideloading for execution techiques, and subsequently loading a malicious browser extension upon infection which works as an independent info-stealer named VenomSoftX [3].

Between February and June 2023, Darktrace detected activity related to the VipersoftX and VenomSoftX information stealers on the networks of more than 100 customers across its fleet. Darktrace DETECT™ was able to successfully identify the anomalous network activity surrounding these emerging information stealer infections and bring them to the attention of the customers, while Darktrace RESPOND™, when enabled in autonomous response mode, was able to quickly intervene and shut down malicious downloads and data exfiltration attempts.

ViperSoftX Attack & Darktrace Coverage

In cases of ViperSoftX information stealer activity observed by Darktrace, the initial infection was caused through the download of malicious files from multimedia sites, endpoints of cracked software like Adobe Illustrator, and torrent sites. Endpoint users typically unknowingly download the malware from these endpoints with a sideloaded DLL, posing as legitimate software executables.

Darktrace detected multiple downloads from such multimedia sites and endpoints related to cracked software and BitTorrent, which were likely representative of the initial source of ViperSoftX infection. Darktrace DETECT models such as ‘Anomalous File / Anomalous Octet Stream (No User Agent)’ breached in response to this activity and were brought to the immediate attention of customer security teams. In instances where Darktrace RESPOND was configured in autonomous response mode, Darktrace was able to enforce a pattern of life on offending devices, preventing them from downloading malicious files.  This ensures that devices are limited to conducting only their pre-established expected activit, minimizing disruption to the business whilst targetedly mitigating suspicious file downloads.

The downloads are then extracted, decrypted and begin to run on the device. The now compromised device will then proceed to make external connections to C2 servers to retrieve secondary PowerShell executable. Darktrace identified that infected devices using PowerShell user agents whilst making HTTP GET requests to domain generation algorithm (DGA) ViperSoftX domains represented new, and therefore unusual, activity in a large number of cases.

For example, Darktrace detected one customer device making an HTTP GET request to the endpoint ‘chatgigi2[.]com’, using the PowerShell user agent ‘Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.19041.2364’. This new activity triggered a number of DETECT models, including ‘Anomalous Connection / PowerShell to Rare External’ and ‘Device / New PowerShell User Agent’. Repeated connections to these endpoints also triggered C2 beaconing models including:  

  • Compromise / Agent Beacon (Short Period)
  • Compromise / Agent Beacon (Medium Period)
  • Compromise / Agent Beacon (Long Period)
  • Compromise / Quick and Regular Windows HTTP Beaconing
  • Compromise / SSL or HTTP Beacon

Although a large number of different DGA domains were detected, commonalities in URI formats were seen across affected customers which matched formats previously identified as ViperSoftX C2 communication by open-source intelligence (OSINT), and in other Darktrace investigations.  

URI paths for example, were always of the format /api/, /api/v1/, /v2/, or /v3/, appearing to detail version number, as can be seen in Figure 1.

Figure 1: A Packet Capture (PCAP) taken from Darktrace showing a connection made to a ViperSoftX C2 endpoint containing versioning information, consistent with ViperSoftX pattern of communication.  

Before the secondary PowerShell executables are loaded, ViperSoftX takes a digital fingerprint of the infected machine to gather its configuration details, and exfiltrates them to the C2 server. These include the computer name, username, Operating System (OS), and ensures there are no anti-virus or montoring tools on the device. If no security tool are detected, ViperSoftX then downloads, decrypts and executes the PowerShell file.

Following the GET requests Darktrace observed numerous devices performing HTTP POST requests and beaconing connections to ViperSoftX endpoints with varying globally unique identifiers (GUIDs) within the URIs. These connections represented the exfiltration of device configuration details, such as “anti-virus detected”, “app used”, and “device name”. As seen on another customer’s deployment, this caused the model ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’ to breach, which was also detected by Cyber AI Analyst as seen in Figure 2.

Figure 2: Cyber AI Analyst’s detection of HTTP POSTs being made to apibiling[.]com, a ViperSoftX C2 endpoint.

The malicious PowerShell download then crawls the infected device’s systems and directories looking for any cryptocurrency wallet information and password managers, and exfiltrates harvest data to the C2 infrastructure. The C2 server then provides further browser extensions to Chromium browsers to be downloaded and act as a separate stand-alone information stealer, also known as VenomSoftX.

Similar to the initial download of ViperSoftX, these malicious extensions are disguised as legitimate browser extensions to evade the detection of security teams. VenomSoft X, in turn, searches through and attempts to gather sensitive data from password managers and crypto wallets stored in user browsers. Using this information, VenomSoftX is able to redirect crypocurrency transactions by intercepting and manipulating API requests between the sender and the intended recipient, directing the cryptocurrency to the attacker instead [3].

Following investigation into VipersoftX activity across the customer base, Darktrace notified all affected customers and opened Ask the Expert (ATE) tickets through which customer’s could directly contact the analyst team for support and guidance in the face on the information stealer infection.

How did the attack bypass the rest of the security stack?

As previously mentioned, both the initial download of ViperSoftX and the subsequent download of the VenomX browser extension are disguised as legitimate software or browser downloads. This is a common technique employed by threat actors to infect target devices with malicious software, while going unnoticed by security teams traditional security measures. Furthermore, by masquerading as a legitimate piece of software endpoint users are more likely to trust and therefore download the malware, increasing the likelihood of threat actor’s successfully carrying out their objectives. Additionally, post-infection analysis of shellcode, the executable code used as the payload, is made significantly more difficult by VenomSoftX’s use of bytemapping. Bytemapping prevents the encryption of shellcodes without its corresponding byte map, meaning that the payloads cannot easily be decrypted and analysed by security researchers. [3]

ViperSoftX also takes numerous attempts to prevent their C2 infrastructure from being identified by blocking access to it on browsers, and using multiple DGA domains, thus renderring defunct traditional security measures that rely on threat intelligence and static lists of indicators of compromise (IoCs).

Fortunately for Darktrace customers, Darktrace’s anomaly-based approach to threat detection means that it was able to detect and alert customers to this suspicious activity that may have gone unnoticed by other security tools.

Insights/Conclusion

Faced with the challenge of increasingly competent and capable security teams, malicious actors are having to adopt more sophisticated techniques to successfully compromise target systems and achieve their nefarious goals.

ViperSoftX information stealer makes use of numerous tactics, techniques and procedures (TTPs) designed to fly under the radar and carry out their objectives without being detected. ViperSoftX does not rely on just one information stealing malware, but two with the subsequent injection of the VenomSoftX browser extension, adding an additional layer of sophistication to the informational stealing operation and increasing the potential yield of sensitive data. Furthermore, the use of evasion techniques like disguising malicious file downloads as legitimate software and frequently changing DGA domains means that ViperSoftX is well equipped to infiltrate target systems and exfiltrate confidential information without being detected.

However, the anomaly-based detection capabilities of Darktrace DETECT allows it to identify subtle changes in a device’s behavior, that could be indicative of an emerging compromise, and bring it to the customer’s security team. Darktrace RESPOND is then autonomously able to take action against suspicious activity and shut it down without latency, minimizing disruption to the business and preventing potentially significant financial losses.

Credit to: Zoe Tilsiter, Senior Cyber Analyst, Nathan Lorenzo, Cyber Analyst.

Appendices

References

[1] https://www.fortinet.com/blog/threat-research/vipersoftx-new-javascript-threat

[2] https://www.trendmicro.com/en_us/research/23/d/vipersoftx-updates-encryption-steals-data.html

[3] https://decoded.avast.io/janrubin/vipersoftx-hiding-in-system-logs-and-spreading-venomsoftx/

Darktrace DETECT Model Detections

·       Anomalous File / Anomalous Octet Stream (No User Agent)

·       Anomalous Connection / PowerShell to Rare External

·       Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

·       Anomalous Connection / Lots of New Connections

·       Anomalous Connection / Multiple Failed Connections to Rare Endpoint

·       Anomalous Server Activity / Outgoing from Server

·       Compromise / Large DNS Volume for Suspicious Domain

·       Compromise / Quick and Regular Windows HTTP Beaconing

·       Compromise / Beacon for 4 Days

·       Compromise / Suspicious Beaconing Behaviour

·       Compromise / Large Number of Suspicious Failed Connections

·       Compromise / Large Number of Suspicious Successful Connections

·       Compromise / POST and Beacon to Rare External

·       Compromise / DGA Beacon

·       Compromise / Agent Beacon (Long Period)

·       Compromise / Agent Beacon (Medium Period)

·       Compromise / Agent Beacon (Short Period)

·       Compromise / Fast Beaconing to DGA

·       Compromise / SSL or HTTP Beacon

·       Compromise / Slow Beaconing Activity To External Rare

·       Compromise / Beaconing Activity To External Rare

·       Compromise / Excessive Posts to Root

·       Compromise / Connections with Suspicious DNS

·       Compromise / HTTP Beaconing to Rare Destination

·       Compromise / High Volume of Connections with Beacon Score

·       Compromise / Sustained SSL or HTTP Increase

·       Device / New PowerShell User Agent

·       Device / New User Agent and New IP

Darktrace RESPOND Model Detections

·       Antigena / Network / External Threat / Antigena Suspicious File Block

·       Antigena / Network / External Threat / Antigena File then New Outbound Block

·       Antigena / Network / External Threat / Antigena Watched Domain Block

·       Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

·       Antigena / Network / External Threat / Antigena Suspicious Activity Block

·       Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

·       Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

·       Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

·       Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach

List of IoCs

Indicator - Type - Description

ahoravideo-blog[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-cdn[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-chat[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

apibilng[.]com - Hostname - ViperSoftX C2 endpoint

arrowlchat[.]com - Hostname - ViperSoftX C2 endpoint

bideo-blog[.]com - Hostname - ViperSoftX C2 endpoint

bideo-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-cdn[.]com - Hostname - ViperSoftX C2 endpoint

bideo-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-chat[.]com - Hostname - ViperSoftX C2 endpoint

bideo-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-endpoint[.]com - Hostname - ViperSoftX C2 endpoint

bideo-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

chatgigi2[.]com - Hostname - ViperSoftX C2 endpoint

counter[.]wmail-service[.]com - Hostname - ViperSoftX C2 endpoint

fairu-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

fairu-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

fairu-endpoint[.]com - Hostname - ViperSoftX C2 endpoint

fairu-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

fairu-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-blog[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-cdn[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

static-cdn-349[.]net - Hostname - ViperSoftX C2 endpoint

wmail-blog[.]com - Hostname - ViperSoftX C2 endpoint

wmail-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

wmail-chat[.]com - Hostname - ViperSoftX C2 endpoint

wmail-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

wmail-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.19041.2364 - User Agent -PowerShell User Agent

MITRE ATT&CK Mapping

Tactic - Technique - Notes

Command and Control - T1568.002 Dynamic Resolution: Domain Generation Algorithms

Command and Control - T1321 Data Encoding

Credential Access - T1555.005 Credentials from Password Stores: Password Managers

Defense Evasion - T1027 Obfuscated Files or Information

Execution - T1059.001 Command and Scripting Interpreter: PowerShell

Execution - T1204 User Execution T1204.002 Malicious File

Persistence - T1176 Browser Extensions - VenomSoftX specific

Persistence, Privilege Escalation, Defense Evasion - T1574.002 Hijack Execution Flow: DLL Side-Loading

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
Zoe Tilsiter
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.

[related-resource]

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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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