Blog
/
Network
/
September 4, 2022

Steps of a BumbleBee Intrusion to a Cobalt Strike

Discover the steps of a Bumblebee intrusion, from initial detection to Cobalt Strike deployment. Learn how Darktrace defends against evolving threats with AI.
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
Sam Lister
Specialist Security Researcher
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
04
Sep 2022

Introduction

Throughout April 2022, Darktrace observed several cases in which threat actors used the loader known as ‘BumbleBee’ to install Cobalt Strike Beacon onto victim systems. The threat actors then leveraged Cobalt Strike Beacon to conduct network reconnaissance, obtain account password data, and write malicious payloads across the network. In this article, we will provide details of the actions threat actors took during their intrusions, as well as details of the network-based behaviours which served as evidence of the actors’ activities.  

BumbleBee 

In March 2022, Google’s Threat Analysis Group (TAG) provided details of the activities of an Initial Access Broker (IAB) group dubbed ‘Exotic Lily’ [1]. Before March 2022, Google’s TAG observed Exotic Lily leveraging sophisticated impersonation techniques to trick employees of targeted organisations into downloading ISO disc image files from legitimate file storage services such as WeTransfer. These ISO files contained a Windows shortcut LNK file and a BazarLoader Dynamic Link Library (i.e, DLL). BazarLoader is a member of the Bazar family — a family of malware (including both BazarLoader and BazarBackdoor) with strong ties to the Trickbot malware, the Anchor malware family, and Conti ransomware. BazarLoader, which is typically distributed via email campaigns or via fraudulent call campaigns, has been known to drop Cobalt Strike as a precursor to Conti ransomware deployment [2]. 

In March 2022, Google’s TAG observed Exotic Lily leveraging file storage services to distribute an ISO file containing a DLL which, when executed, caused the victim machine to make HTTP requests with the user-agent string ‘bumblebee’. Google’s TAG consequently called this DLL payload ‘BumbleBee’. Since Google’s discovery of BumbleBee back in March, several threat research teams have reported BumbleBee samples dropping Cobalt Strike [1]/[3]/[4]/[5]. It has also been reported by Proofpoint [3] that other threat actors such as TA578 and TA579 transitioned to BumbleBee in March 2022.  

Interestingly, BazarLoader’s replacement with BumbleBee seems to coincide with the leaking of the Conti ransomware gang’s Jabber chat logs at the end of February 2022. On February 25th, 2022, the Conti gang published a blog post announcing their full support for the Russian state’s invasion of Ukraine [6]. 

Figure 1: The Conti gang's public declaration of their support for Russia's invasion of Ukraine

Within days of sharing their support for Russia, logs from a server hosting the group’s Jabber communications began to be leaked on Twitter by @ContiLeaks [7]. The leaked logs included records of conversations among nearly 500 threat actors between Jan 2020 and March 2022 [8]. The Jabber logs were supposedly stolen and leaked by a Ukrainian security researcher [3]/[6].

Affiliates of the Conti ransomware group were known to use BazarLoader to deliver Conti ransomware [9]. BumbleBee has now also been linked to the Conti ransomware group by several threat research teams [1]/[10]/[11]. The fact that threat actors’ transition from BazarLoader to BumbleBee coincides with the leak of Conti’s Jabber chat logs may indicate that the transition occurred as a result of the leaks [3]. Since the transition, BumbleBee has become a significant tool in the cyber-crime ecosystem, with links to several ransomware operations such as Conti, Quantum, and Mountlocker [11]. The rising use of BumbleBee by threat actors, and particularly ransomware actors, makes the early detection of BumbleBee key to identifying the preparatory stages of ransomware attacks.  

Intrusion Kill Chain 

In April 2022, Darktrace observed the following pattern of threat actor activity within the networks of several Darktrace clients: 

1.     Threat actor socially engineers user via email into running a BumbleBee payload on their device

2.     BumbleBee establishes HTTPS communication with a BumbleBee C2 server

3.     Threat actor instructs BumbleBee to download and execute Cobalt Strike Beacon

4.     Cobalt Strike Beacon establishes HTTPS communication with a Cobalt Strike C2 server

5.     Threat actor instructs Cobalt Strike Beacon to scan for open ports and to enumerate network shares

6.     Threat actor instructs Cobalt Strike Beacon to use the DCSync technique to obtain password account data from an internal domain controller

7.     Threat actor instructs Cobalt Strike Beacon to distribute malicious payloads to other internal systems 

With limited visibility over affected clients’ email environments, Darktrace was unable to determine how the threat actors interacted with users to initiate the BumbleBee infection. However, based on open-source reporting on BumbleBee [3]/[4]/[10]/[11]/[12]/[13]/[14]/[15]/[16]/[17], it is likely that the actors tricked target users into running BumbleBee by sending them emails containing either a malicious zipped ISO file or a link to a file storage service hosting the malicious zipped ISO file. These ISO files typically contain a LNK file and a BumbleBee DLL payload. The properties of these LNK files are set in such a way that opening them causes the corresponding DLL payload to run. 

In several cases observed by Darktrace, devices contacted a file storage service such as Microsoft OneDrive or Google Cloud Storage immediately before they displayed signs of BumbleBee infection. In these cases, it is likely that BumbleBee was executed on the users’ devices as a result of the users interacting with an ISO file which they were tricked into downloading from a file storage service. 

Figure 2: The above figure, taken from the event log for an infected device, shows that the device contacted a OneDrive endpoint immediately before making HTTPS connections to the BumbleBee C2 server, 45.140.146[.]244
Figure 3: The above figure, taken from the event log for an infected device, shows that the device contacted a Google Cloud Storage endpoint and then the malicious endpoint ‘marebust[.]com’ before making HTTPS connections to the  BumbleBee C2 servers, 108.62.118[.]61 and 23.227.198[.]217

After users ran a BumbleBee payload, their devices immediately initiated communications with BumbleBee C2 servers. The BumbleBee samples used HTTPS for their C2 communication, and all presented a common JA3 client fingerprint, ‘0c9457ab6f0d6a14fc8a3d1d149547fb’. All analysed samples excluded domain names in their ‘client hello’ messages to the C2 servers, which is unusual for legitimate HTTPS communication. External SSL connections which do not specify a destination domain name and whose JA3 client fingerprint is ‘0c9457ab6f0d6a14fc8a3d1d149547fb’ are potential indicators of BumbleBee infection. 

Figure 4:The above figure, taken from Darktrace's Advanced Search interface, depicts an infected device's spike in HTTPS connections with the JA3 client fingerprint ‘0c9457ab6f0d6a14fc8a3d1d149547fb’

Once the threat actors had established HTTPS communication with the BumbleBee-infected systems, they instructed BumbleBee to download and execute Cobalt Strike Beacon. This behaviour resulted in the infected systems making HTTPS connections to Cobalt Strike C2 servers. The Cobalt Strike Beacon samples all had the same JA3 client fingerprint ‘a0e9f5d64349fb13191bc781f81f42e1’ — a fingerprint associated with previously seen Cobalt Strike samples [18]. The domain names ‘fuvataren[.]com’ and ‘cuhirito[.]com’ were observed in the samples’ HTTPS communications. 

Figure 5:The above figure, taken from Darktrace's Advanced Search interface, depicts the Cobalt Strike C2 communications which immediately followed a device's BumbleBee C2 activity

Cobalt Strike Beacon payloads call home to C2 servers for instructions. In the cases observed, threat actors first instructed the Beacon payloads to perform reconnaissance tasks, such as SMB port scanning and SMB enumeration. It is likely that the threat actors performed these steps to inform the next stages of their operations.  The SMB enumeration activity was evidenced by the infected devices making NetrShareEnum and NetrShareGetInfo requests to the srvsvc RPC interface on internal systems.

Figure 6: The above figure, taken from Darktrace’s Advanced Search interface, depicts a spike in srvsvc requests coinciding with the infected device's Cobalt Strike C2 activity

After providing Cobalt Strike Beacon with reconnaissance tasks, the threat actors set out to obtain account password data in preparation for the lateral movement phase of their operation. To obtain account password data, the actors instructed Cobalt Strike Beacon to use the DCSync technique to replicate account password data from an internal domain controller. This activity was evidenced by the infected devices making DRSGetNCChanges requests to the drsuapi RPC interface on internal domain controllers. 

Figure 7: The above figure, taken from Darktrace’s Advanced Search interface, depicts a spike in DRSGetNCChanges requests coinciding with the infected device’s Cobalt Strike C2 activity

After leveraging the DCSync technique, the threat actors sought to broaden their presence within the targeted networks.  To achieve this, they instructed Cobalt Strike Beacon to get several specially selected internal systems to run a suspiciously named DLL (‘f.dll’). Cobalt Strike first established SMB sessions with target systems using compromised account credentials. During these sessions, Cobalt Strike uploaded the malicious DLL to a hidden network share. To execute the DLL, Cobalt Strike abused the Windows Service Control Manager (SCM) to remotely control and manipulate running services on the targeted internal hosts. Cobalt Strike first opened a binding handle to the svcctl interface on the targeted destination systems. It then went on to make an OpenSCManagerW request, a CreateServiceA request, and a StartServiceA request to the svcctl interface on the targeted hosts: 

·      Bind request – opens a binding handle to the relevant RPC interface (in this case, the svcctl interface) on the destination device

·      OpenSCManagerW request – establishes a connection to the Service Control Manager (SCM) on the destination device and opens a specified SCM database

·      CreateServiceA request – creates a service object and adds it to the specified SCM database 

·      StartServiceA request – starts a specified service

Figure 8: The above figure, taken from Darktrace’s Advanced Search interface, outlines an infected system’s lateral movement activities. After writing a file named ‘f.dll’ to the C$ share on an internal server, the infected device made several RPC requests to the svcctl interface on the targeted server

It is likely that the DLL file which the threat actors distributed was a Cobalt Strike payload. In one case, however, the threat actor was also seen distributing and executing a payload named ‘procdump64.exe’. This may suggest that the threat actor was seeking to use ProcDump to obtain authentication material stored in the process memory of the Local Security Authority Subsystem Service (LSASS). Given that ProcDump is a legitimate Windows Sysinternals tool primarily used for diagnostics and troubleshooting, it is likely that threat actors leveraged it in order to evade detection. 

In all the cases which Darktrace observed, threat actors’ attempts to conduct follow-up activities after moving laterally were thwarted with the help of Darktrace’s SOC team. It is likely that the threat actors responsible for the reported activities were seeking to deploy ransomware within the targeted networks. The steps which the threat actors took to make progress towards achieving this objective resulted in highly unusual patterns of network traffic. Darktrace’s detection of these unusual network activities allowed security teams to prevent these threat actors from achieving their disruptive objectives. 

Darktrace Coverage

Once threat actors succeeded in tricking users into running BumbleBee on their devices, Darktrace’s Self-Learning AI immediately detected the command-and-control (C2) activity generated by the loader. BumbleBee’s C2 activity caused the following Darktrace models to breach:

·      Anomalous Connection / Anomalous SSL without SNI to New External

·      Anomalous Connection / Suspicious Self-Signed SSL

·      Anomalous Connection / Rare External SSL Self-Signed

·      Compromise / Suspicious TLS Beaconing To Rare External

·      Compromise / Beacon to Young Endpoint

·      Compromise / Beaconing Activity To External Rare

·      Compromise / Sustained SSL or HTTP Increase

·      Compromise / Suspicious TLS Beaconing To Rare External

·      Compromise / SSL Beaconing to Rare Destination

·      Compromise / Large Number of Suspicious Successful Connections

·      Device / Multiple C2 Model Breaches 

BumbleBee’s delivery of Cobalt Strike Beacon onto target systems resulted in those systems communicating with Cobalt Strike C2 servers. Cobalt Strike Beacon’s C2 communications resulted in breaches of the following models: 

·      Compromise / Beaconing Activity To External Rare

·      Compromise / High Volume of Connections with Beacon Score

·      Compromise / Large Number of Suspicious Successful Connections

·      Compromise / Sustained SSL or HTTP Increase

·      Compromise / SSL or HTTP Beacon

·      Compromise / Slow Beaconing Activity To External Rare

·      Compromise / SSL Beaconing to Rare Destination 

The threat actors’ subsequent port scanning and SMB enumeration activities caused the following models to breach:

·      Device / Network Scan

·      Anomalous Connection / SMB Enumeration

·      Device / Possible SMB/NTLM Reconnaissance

·      Device / Suspicious Network Scan Activity  

The threat actors’ attempts to obtain account password data from domain controllers using the DCSync technique resulted in breaches of the following models: 

·      Compromise / Unusual SMB Session and DRS

·      Anomalous Connection / Anomalous DRSGetNCChanges Operation

Finally, the threat actors’ attempts to internally distribute and execute payloads resulted in breaches of the following models:

·      Compliance / SMB Drive Write

·      Device / Lateral Movement and C2 Activity

·      Device / SMB Lateral Movement

·      Device / Multiple Lateral Movement Model Breaches

·      Anomalous File / Internal / Unusual SMB Script Write

·      Anomalous File / Internal / Unusual Internal EXE File Transfer

·      Anomalous Connection / High Volume of New or Uncommon Service Control

If Darktrace/Network had been configured in the targeted environments, then it would have blocked BumbleBee’s C2 communications, which would have likely prevented the threat actors from delivering Cobalt Strike Beacon into the target networks. 

Figure 9: Attack timeline

Conclusion

Threat actors use loaders to smuggle more harmful payloads into target networks. Prior to March 2022, it was common to see threat actors using the BazarLoader loader to transfer their payloads into target environments. However, since the public disclosure of the Conti gang’s Jabber chat logs at the end of February, the cybersecurity world has witnessed a shift in tradecraft. Threat actors have seemingly transitioned from using BazarLoader to using a novel loader known as ‘BumbleBee’. Since BumbleBee first made an appearance in March 2022, a growing number of threat actors, in particular ransomware actors, have been observed using it.

It is likely that this trend will continue, which makes the detection of BumbleBee activity vital for the prevention of ransomware deployment within organisations’ networks. During April, Darktrace’s SOC team observed a particular pattern of threat actor activity involving the BumbleBee loader. After tricking users into running BumbleBee on their devices, threat actors were seen instructing BumbleBee to drop Cobalt Strike Beacon. Threat actors then leveraged Cobalt Strike Beacon to conduct network reconnaissance, obtain account password data from internal domain controllers, and distribute malicious payloads internally.  Darktrace’s detection of these activities prevented the threat actors from achieving their likely harmful objectives.  

Thanks to Ross Ellis for his contributions to this blog.

Appendices 

References 

[1] https://blog.google/threat-analysis-group/exposing-initial-access-broker-ties-conti/ 

[2] https://securityintelligence.com/posts/trickbot-gang-doubles-down-enterprise-infection/ 

[3] https://www.proofpoint.com/us/blog/threat-insight/bumblebee-is-still-transforming

[4] https://www.cynet.com/orion-threat-alert-flight-of-the-bumblebee/ 

[5] https://research.nccgroup.com/2022/04/29/adventures-in-the-land-of-bumblebee-a-new-malicious-loader/ 

[6] https://www.bleepingcomputer.com/news/security/conti-ransomwares-internal-chats-leaked-after-siding-with-russia/ 

[7] https://therecord.media/conti-leaks-the-panama-papers-of-ransomware/ 

[8] https://www.secureworks.com/blog/gold-ulrick-leaks-reveal-organizational-structure-and-relationships 

[9] https://www.prodaft.com/m/reports/Conti_TLPWHITE_v1.6_WVcSEtc.pdf 

[10] https://www.kroll.com/en/insights/publications/cyber/bumblebee-loader-linked-conti-used-in-quantum-locker-attacks 

[11] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/bumblebee-loader-cybercrime 

[12] https://isc.sans.edu/diary/TA578+using+thread-hijacked+emails+to+push+ISO+files+for+Bumblebee+malware/28636 

[13] https://isc.sans.edu/diary/rss/28664 

[14] https://www.logpoint.com/wp-content/uploads/2022/05/buzz-of-the-bumblebee-a-new-malicious-loader-threat-report-no-3.pdf 

[15] https://ghoulsec.medium.com/mal-series-23-malware-loader-bumblebee-6ab3cf69d601 

[16]  https://blog.cyble.com/2022/06/07/bumblebee-loader-on-the-rise/  

[17]  https://asec.ahnlab.com/en/35460/ 

[18] https://thedfirreport.com/2021/07/19/icedid-and-cobalt-strike-vs-antivirus/

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
Sam Lister
Specialist Security Researcher

More in this series

No items found.

Blog

/

Email

/

December 18, 2025

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

Man at laptopDefault blog imageDefault blog image

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]

Continue reading
About the author
Carlos Gray
Senior Product Marketing Manager, Email

Blog

/

Email

/

December 17, 2025

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

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with DarktraceDefault blog imageDefault blog image

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

Continue reading
About the author
David Ison
Cyber Analyst
Your data. Our AI.
Elevate your network security with Darktrace AI