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June 23, 2023

How Darktrace Quickly Foiled An Information Stealer

Discover how Darktrace thwarted the CryptBot malware in just 2 seconds. Learn about this fast-moving threat and the defense strategies employed.
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
Alexandra Sentenac
Cyber Analyst
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23
Jun 2023

The recent trend of threat actors using information stealer malware, designed to gather and exfiltrate confidential data, shows no sign of slowing. With new or updated info-stealer strains appearing in the wild on a regular basis, it came as no surprise to see a surge in yet another prolific variant in late 2022, CryptBot.

What is CryptBot?

CryptBot is a Windows-based trojan malware that was first discovered in the wild in December 2019. It belongs to the prolific category of information stealers whose primary objective, as the name suggests, is to gather information from infected devices and send it to the threat actor.

ZeuS was reportedly the first info-stealer to be discovered, back in 2006. After its code was leaked, many other variants came to light and have been gaining popularity amongst cyber criminals [1] [2] [3]. Indeed, Inside the SOC has discussed multiple infections across its customer base associated with several types of stealers in the past months [4] [5] [6] [7]. 

The Darktrace Threat Research team investigated CryptBot infections on the digital environments of more than 40 different Darktrace customers between October 2022 and January 2023. Darktrace DETECT™ and its anomaly-based approach to threat detection allowed it to successfully identify the unusual activity surrounding these info-stealer infections on customer networks. Meanwhile, Darktrace RESPOND™, when enabled in autonomous response mode, was able to quickly intervene and prevent the exfiltration of sensitive company data.

Why is info-stealer malware popular?

It comes as no surprise that info-stealers have “become one of the most discussed malware types on the cybercriminal underground in 2022”, according to Accenture’s Cyber Threat Intelligence team [10]. This is likely in part due to the fact that:

More sensitive data on devices

Due to the digitization of many aspects of our lives, such as banking and social interactions, a trend accelerated by the COVID-19 pandemic.

Cost effective

Info-stealers provide a great return on investment (ROI) for threat actors looking to exfiltrate data without having to do the traditional internal reconnaissance and data transfer associated with data theft. Info-stealers are usually cheap to purchase and are available through Malware-as-a-Service (MaaS) offerings, allowing less technical and resourceful threat actors in on the stealing action. This makes them a prevalent threat in the malware landscape. 

How does CryptBot work?

The techniques employed by info-stealers to gather and exfiltrate data as well as the type of data targeted vary from malware to malware, but the data targeted typically includes login credentials for a variety of applications, financial information, cookies and global information about the infected computer [8]. Given its variety and sensitivity, threat actors can leverage the stolen data in several ways to make a profit. In the case of CryptBot, the data obtained is sold on forums or underground data marketplaces and can be later employed in higher profile attacks [9]. For example, stolen login information has previously been leveraged in credential-based attacks, which can successfully bypass authentication-based security measures, including multi-factor authentication (MFA). 

CryptBot functionalities

Like many information stealers, CryptBot is designed to steal a variety of sensitive personal and financial information such as browser credentials, cookies and history information and social media accounts login information, as well as cryptocurrency wallets and stored credit card information [11]. General information (e.g., OS, installed applications) about the infected computer is also retrieved. Browsers targeted by CryptBot include Chrome, Firefox, and Edge. In early 2022, CryptBot’s code was revamped in order to streamline its data extraction capabilities and improve its overall efficiency, an update that coincided with a rise in the number of infections [11] [12].

Some of CryptBot's functionalities were removed and its exfiltration process was streamlined, which resulted in a leaner payload, around half its original size and a quicker infection process [11]. Some of the features removed included sandbox detection and evasion functionalities, the collection of desktop text files and screen captures, which were deemed unnecessary. At the same time, the code was improved in order to include new Chrome versions released after CryptBot’s first appearance in 2019. Finally, its exfiltration process was simplified: prior to its 2022 update, the malware saved stolen data in two separate folders before sending it to two separate command and control (C2) domains. Post update, the data is only saved in one location and sent to one C2 domain, which is hardcoded in the C2 transmission function of the code. This makes the infection process much more streamlined, taking only a few minutes from start to finish. 

Aside from the update to its malware code, CryptBot regularly updates and refreshes its C2 domains and dropper websites, making it a highly fluctuating malware with constantly new indicators of compromise and distribution sites. 

Even though CryptBot is less known than other info-stealers, it was reportedly infecting thousands of devices daily in the first months of 2020 [13] and its continued prevalence resulted in Google taking legal action against its distribution infrastructure at the end of April 2023 [14].  

How is CryptBot obtained?

CryptBot is primarily distributed through malicious websites offering free and illegally modified software (i.e., cracked software) for common commercial programs (e.g., Microsoft Windows and Office, Adobe Photoshop, Google Chrome, Nitro PDF Pro) and video games. From these ‘malvertising’ pages, the user is redirected through multiple sites to the actual payload dropper page [15]. This distribution method has seen a gain in popularity amongst info-stealers in recent months and is also used by other malware families such as Raccoon Stealer and Vidar [16] [17].

A same network of cracked software websites can be used to download different malware strains, which can result in multiple simultaneous infections. Additionally, these networks often use search engine optimization (SEO) in order to make adverts for their malware distributing sites appear at the top of the Google search results page, thus increasing the chances of the malicious payloads being downloaded.

Furthermore, CryptBot leverages Pay-Per-Install (PPI) services such as 360Installer and PrivateLoader, a downloader malware family used to deliver payloads of multiple malware families operated by different threat actors [18] [19] [20]. The use of this distribution method for CryptBot payloads appears to have stemmed from its 2022 update. According to Google, 161 active domains were associated with 360Installer, of which 90 were associated with malware delivery activities and 29 with the delivery of CryptBot malware specifically. Google further identified hundreds of domains used by CryptBot as C2 sites, all of which appear to be hosted on the .top top-level domain [21].

This simple yet effective distribution tactic, combined with the MaaS model and the lucrative prospects of selling the stolen data resulted in numerous infections. Indeed, CryptBot was estimated to have infected over 670,000 computers in 2022 [14]. Even though the distribution method chosen means that most of the infected devices are likely to be personal computers, bring your own device (BYOD) policies and users’ tendency to reuse passwords means that corporate environments are also at risk. 

CryptBot Attack Overview

In some cases observed by Darktrace, after connecting to malvertising websites, devices were seen making encrypted SSL connections to file hosting services such as MediaFire or Mega, while in others devices were observed connecting to an endpoint associated with a content delivery network. This is likely the location from where the malware payload was downloaded alongside cracked software, which is executed by the unsuspecting user. As the user expects to run an executable file to install their desired software, the malware installation often happens without the user noticing.

Some of the malvertising sites observed by Darktrace on customer deployments were crackful[.]com, modcrack[.]net, windows-7-activator[.]com and office-activator[.]com. However, in many cases detected by Darktrace, CryptBot was propagated via websites offering trojanized KMSPico software (e.g., official-kmspico[.]com, kmspicoofficial[.]com). KMSPico is a popular Microsoft Windows and Office product activator that emulates a Windows Key Management Services (KMS) server to activate licenses fraudulently. 

Once it has been downloaded and executed, CryptBot will search the system for confidential information and create a folder with a seemingly randomly generated name, matching the regex [a-zA-Z]{10}, to store the gathered sensitive data, ready for exfiltration. 

Figure 1: Packet capture (PCAP) of an HTTP POST request showing the file with the stolen data being sent over the connection.
Figure 1: Packet capture (PCAP) of an HTTP POST request showing the file with the stolen data being sent over the connection.

This data is then sent to the C2 domain via HTTP POST requests on port 80 to the URI /gate.php. As previously stated, CryptBot C2 infrastructure is changed frequently and many of the domains seen by Darktrace had been registered within the previous 30 days. The domain names detected appeared to have been generated by an algorithm, following the regex patterns [a-z]{6}[0-9]{2,3}.top or [a-z]{6}[0-9]{2,3}.cfd. In several cases, the C2 domain had not been flagged as malicious by other security vendors or had just one detection. This is likely because of the frequent changes in the C2 infrastructure operated by the threat actors behind CryptBot, with new malicious domains being created periodically to avoid detection. This makes signature-based security solutions much less efficient to detect and block connections to malicious domains. Additionally, the fact that the stolen data is sent over regular HTTP POST requests, which are used daily as part of a multitude of legitimate processes such as file uploads or web form submissions, allows the exfiltration connections to blend in with normal and legitimate traffic making it difficult to isolate and detect as malicious activity. 

In this context, anomaly-based security detections such as Darktrace DETECT are the best way to pick out these anomalous connections amidst legitimate Internet traffic. In the case of CryptBot, two DETECT models were seen consistently breaching for CryptBot-related activity: ‘Device / Suspicious Domain’, breaching for connections to 100% rare C2 .top domains, and ‘Anomalous Connection / POST to PHP on New External Host’, breaching on the data exfiltration HTTP POST request. 

In deployments where Darktrace RESPOND was deployed, a RESPOND model breached within two seconds of the first HTTP POST request. If enabled in autonomous mode, RESPOND would block the data exfiltration connections, thus preventing the data safe from being sold in underground forums to other threat actors. In one of the cases investigated by Darktrace’s Threat Research team, DETECT was able to successfully identify and alert the customer about CryptBot-related malicious activity on a device that Darktrace had only begun to monitor one day before, showcasing how fast Darktrace’s Self-Learning AI learns every nuance of customer networks and the devices within it.

In most cases investigated by Darktrace, fewer than 5 minutes elapsed between the first connection to the endpoint offering free cracked software and the data being exfiltrated to the C2 domain. For example, in one of the attack chains observed in a university’s network, a device was seen connecting to the 100% rare endpoint official-kmspico[.]com at 16:53:47 (UTC).

Device Event Log showing SSL connections to the official-kmspico[.]com malvertising website.
Figure 2: Device Event Log showing SSL connections to the official-kmspico[.]com malvertising website.

One minute later, at 16:54:19 (UTC), the same device was seen connecting to two mega[.]co[.]nz subdomains and downloading around 13 MB of data from them. As mentioned previously, these connections likely represent the CryptBot payload and cracked software download.

Device Event Log showing SSL connections to mega[.]com endpoints following the connection to the malvertising site.
Figure 3: Device Event Log showing SSL connections to mega[.]com endpoints following the connection to the malvertising site.

At 16:56:01 (UTC), Darktrace detected the device making a first HTTP POST request to the 100% rare endpoint, avomyj24[.]top, which has been associated with CryptBot’s C2 infrastructure [22]. This initial HTTP POST connection likely represents the transfer of confidential data to the attacker’s infrastructure.

Device Event Log showing HTTP connections made by the infected device to the C2 domain. 
Figure 4: Device Event Log showing HTTP connections made by the infected device to the C2 domain. 

The full attack chain, from visiting the malvertising website to the malicious data egress, took less than three minutes to complete. In this circumstance, the machine-speed detection and response capabilities offered by Darktrace DETECT and RESPOND are paramount in order to stop CryptBot before it can successfully exfiltrates sensitive data. This is an incredibly quick infection timeline, with no lateral movement nor privilege escalation required to carry out the malware’s objective. 

Device Event Log showing the DETECT and RESPOND models breached during the attack. 
Figure 5: Device Event Log showing the DETECT and RESPOND models breached during the attack. 

Darktrace Cyber AI Analyst incidents were also generated as a result of this activity, displaying all relevant information in one panel for easy review by customer security teams.

Cyber AI Analyst event log showing the HTTP connections made by the breach device to the C2 endpoint.
Figure 6: Cyber AI Analyst event log showing the HTTP connections made by the breach device to the C2 endpoint.

Conclusion 

CryptBot info-stealer is fast, efficient, and apt at evading detection given its small size and swift process of data gathering and exfiltration via legitimate channels. Its constantly changing C2 infrastructure further makes it difficult for traditional security tools that really on rules and signatures or known indicators of compromise (IoCs) to detect these infections. 

In the face of such a threat, Darktrace’s anomaly-based detection allows it to recognize subtle deviations in a device’s pattern of behavior that may signal an evolving threat and instantly bring it to the attention of security teams. Darktrace DETECT is able to distinguish between benign activity and malicious behavior, even from newly monitored devices, while Darktrace RESPOND can move at machine-speed to prevent even the fastest moving threat actors from stealing confidential company data, as it demonstrated here by stopping CryptBot infections in as little as 2 seconds.

Credit to Alexandra Sentenac, Cyber Analyst, Roberto Romeu, Senior SOC Analyst

Darktrace Model Detections  

AI Analyst Coverage 

  • Possible HTTP Command and Control  

DETECT Model Breaches  

  • Device / Suspicious Domain 
  • Anomalous Connection / POST to PHP on New External Host 
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname 
  • Compromise / Multiple SSL to Rare DGA Domains

List of IOCs

Indicator Type Description
luaigz34[.]top Hostname CryptBot C2 endpoint
watibt04[.]top Hostname CryptBot C2 endpoint
avolsq14[.]top Hostname CryptBot C2 endpoint

MITRE ATT&CK Mapping

Category Technique Tactic
INITIAL ACCESS Drive-by Compromise - T1189 N/A
COMMAND AND CONTROL Web Protocols - T1071.001 N/A
COMMAND AND CONTROL Domain Generation Algorithm - T1568.002 N/A

References

[1] https://www.malwarebytes.com/blog/threats/info-stealers

[2] https://cybelangel.com/what-are-infostealers/

[3] https://ke-la.com/information-stealers-a-new-landscape/

[4] https://darktrace.com/blog/vidar-info-stealer-malware-distributed-via-malvertising-on-google

[5] https://darktrace.com/blog/a-surge-of-vidar-network-based-details-of-a-prolific-info-stealer 

[6] https://darktrace.com/blog/laplas-clipper-defending-against-crypto-currency-thieves-with-detect-respond

[7] https://darktrace.com/blog/amadey-info-stealer-exploiting-n-day-vulnerabilities 

[8] https://cybelangel.com/what-are-infostealers/

[9] https://webz.io/dwp/the-top-10-dark-web-marketplaces-in-2022/

[10] https://www.accenture.com/us-en/blogs/security/information-stealer-malware-on-dark-web

[11] https://www.bleepingcomputer.com/news/security/revamped-cryptbot-malware-spread-by-pirated-software-sites/

[12] https://blogs.blackberry.com/en/2022/03/threat-thursday-cryptbot-infostealer

[13] https://www.deepinstinct.com/blog/cryptbot-how-free-becomes-a-high-price-to-pay

[14] https://blog.google/technology/safety-security/continuing-our-work-to-hold-cybercriminal-ecosystems-accountable/

[15] https://asec.ahnlab.com/en/31802/

[16] https://darktrace.com/blog/the-last-of-its-kind-analysis-of-a-raccoon-stealer-v1-infection-part-1

[17] https://www.trendmicro.com/pt_br/research/21/c/websites-hosting-cracks-spread-malware-adware.html

[18] https://intel471.com/blog/privateloader-malware

[19] https://cyware.com/news/watch-out-pay-per-install-privateloader-malware-distribution-service-is-flourishing-888273be 

[20] https://regmedia.co.uk/2023/04/28/handout_google_cryptbot_complaint.pdf

[21] https://www.bankinfosecurity.com/google-wins-court-order-to-block-cryptbot-infrastructure-a-21905

[22] https://github.com/stamparm/maltrail/blob/master/trails/static/malware/cryptbot.txt

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
Alexandra Sentenac
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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