December 15, 2023

How Darktrace Halted A DarkGate in MS Teams

Discover how Darktrace thwarted DarkGate malware in Microsoft Teams. Stay informed on the latest cybersecurity measures and protect your business.

Written by

Natalia Sánchez Rocafort

Cyber Security Analyst

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

Natalia Sánchez Rocafort

Cyber Security Analyst

Dec 2023

Securing Microsoft Teams and SharePoint

Given the prevalence of the Microsoft Teams and Microsoft SharePoint platforms in the workplace in recent years, it is essential that organizations stay vigilant to the threat posed by applications vital to hybrid and remote work and prioritize the security and cyber hygiene of these services. For just as the use of these platforms has increased exponentially with the rise of remote and hybrid working, so too has the malicious use of them to deliver malware to unassuming users.

Researchers across the threat landscape have begun to observe these legitimate services being leveraged by malicious actors as an initial access method. Microsoft Teams can easily be exploited to send targeted phishing messages to individuals within an organization, while appearing legitimate and safe. Although the exact contents of these messages may vary, the messages frequently use social engineering techniques to lure users to click on a SharePoint link embedded into the message. Interacting with the malicious link will then download a payload [1].

Darktrace observed one such malicious attempt to use Microsoft Teams and SharePoint in September 2023, when a device was observed downloading DarkGate, a commercial trojan that is known to deploy other strains of malware, also referred to as a commodity loader [2], after clicking on SharePoint link. Fortunately for the customer, Darktrace’s suite of products was perfectly poised to identify the initial signs of suspicious activity and Darktrace RESPOND™ was able to immediately halt the advancement of the attack.

DarkGate Attack Overview

On September 8, 2023, Darktrace DETECT™ observed around 30 internal devices on a customer network making unusual SSL connections to an external SharePoint site which contained the name of a person, 'XXXXXXXX-my.sharepoint[.]com' (107.136[.]8, 13.107.138[.]8). The organization did not have any employees who went by this name and prior to this activity, no internal devices had been seen contacting the endpoint.

At first glance, this initial attack vector would have appeared subtle and seemingly trustworthy to users. Malicious actors likely sent various users a phishing message via Microsoft Teams that contained the spoofed SharePoint link to the personalized SharePoint link ''XXXXXXXX-my.sharepoint[.]com'.

Figure 1: Advanced Search query showing a sudden spike in connections to ''XXXXXXXX -my.sharepoint[.]com'.

Darktrace observed around 10 devices downloading approximately 1 MB of data during their connections to the Sharepoint endpoint. Darktrace DETECT observed some of the devices making subsequent HTTP GET requests to a range of anomalous URIs. The devices utilized multiple user-agents for these connections, including ‘curl’, a command line tool that allows individuals to request and transfer data from a specific URL. The connections were made to the IP 5.188.87[.]58, an endpoint that has been flagged as an indicator of compromise (IoC) for DarkGate malware by multiple open-source intelligence (OSINT) sources [3], commonly associated with HTTP GET requests:

GET request over port 2351 with the User-Agent header 'Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5)' and the target URI '/bfyxraav' to 5.188.87[.]58
GET request over port 2351 with the user-agent header 'curl' and the target URI '/' to 5.188.87[.]58
GET request over port 2351 with the user-agent header 'curl/8.0.1' and the target URI '/msibfyxraav' to 5.188.87[.]58

The HTTP GET requests made with the user-agent header 'curl' and the target URI '/' to 5.188.87[.]58 were responded to with a filename called 'Autoit3.exe'. The other requests received script files with names ending in '.au3, such as 'xkwtvq.au3', 'otxynh.au3', and 'dcthbq.au3'. DarkGate malware has been known to make use of legitimate AutoIt files, and typically runs multiple AutoIt scripts (‘.au3’) [4].

Following these unusual file downloads, the devices proceeded to make hundreds of HTTP POST requests to the target URI '/' using the user-agent header 'Mozilla/4.0 (compatible; Synapse)' to 5.188.87[.]58. The contents of these requests, along with the contents of the responses, appear to be heavily obfuscated.

Figure 2: Example of obfuscated response, as shown in a packet capture downloaded from Darktrace.

While Microsoft’s Safe Attachments and Safe Links settings were unable to detect this camouflaged malicious activity, Darktrace DETECT observed the unusual over-the-network connectivity that occurred. While Darktrace DETECT identified multiple internal devices engaging in this anomalous behavior throughout the course of the compromise, the activity observed on one device in particular best showcases the overall kill chain of this attack.

The device in question was observed using two different user agents (curl/8.0.1 and Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5)) when connecting to the endpoint 5.188.87[.]58 and target URI ‘/bfyxraav’. Additionally, Darktrace DETECT recognized that it was unusual for this device to be making these HTTP connections via destination port 2351.

As a result, Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the suspicious activity and was able to connect the unusual external connections together, viewing them as one beaconing incident as opposed to isolated series of connections.

Figure 3: Cyber AI Analyst investigation summarizing the unusual repeated connections made to 5.188.87[.]58 via destination port 2351.

Darktrace then observed the device downloading the ‘Autoit3.exe’ file. Darktrace RESPOND took swift mitigative action by blocking similar connections to this endpoint, preventing the device from downloading any additional suspicious files.

Figure 4: Suspicious ‘Autoit3.exe’ downloaded by the source device from the malicious external endpoint.

Just one millisecond later, Darktrace observed the device making suspicious HTTP GET requests to URIs including ‘/msibfyxraav’. Darktrace recognized that the device had carried out several suspicious actions within a relatively short period of time, breaching multiple DETECT models, indicating that it may have been compromised. As a result, RESPOND took action against the offending device by preventing it from communicating externally [blocking all outbound connections] for a period of one hour, allowing the customer’s security team precious time to address the issue.

It should be noted that, at this point, had the customer subscribed to Darktrace’s Proactive Threat Notification (PTN) service, the Darktrace Security Operations Center (SOC) would have investigated these incidents in greater detail, and likely would have sent a notification directly to the customer to inform them of the suspicious activity.

Additionally, AI Analyst collated various distinct events and suggested that these stages were linked as part of an attack. This type of augmented understanding of events calculated at machine speed is extremely valuable since it likely would have taken a human analyst hours to link all the facets of the incident together.

Figure 5: AI Analyst investigation showcasing the use of the ‘curl’ user agent to connect to the target URI ‘/msibfyxraav’.

Figure 6: Darktrace RESPOND moved to mitigate any following connections by blocking all outgoing traffic for 1 hour.

Following this, an automated investigation was launched by Microsoft Defender for Endpoint. Darktrace is designed to coordinate with multiple third-party security tools, allowing for information on ongoing incidents to be seamlessly exchanged between Darktrace and other security tools. In this instance, Microsoft Defender identified a ‘low severity’ incident on the device, this automatically triggered a corresponding alert within DETECT, presented on the Darktrace Threat Visuallizer.

The described activity occurred within milliseconds. At each step of the attack, Darktrace RESPOND took action either by enforcing expected patterns of life [normality] on the affected device, blocking connections to suspicious endpoints for a specified amount of time, and/or blocking all outgoing traffic from the device. All the relevant activity was detected and promptly stopped for this device, and other compromised devices, thus containing the compromise and providing the security team invaluable remediation time.

Figure 7: Overview of the compromise activity, all of which took place within a matter of miliseconds.

Darktrace identified similar activity on other devices in this customer’s network, as well as across Darktrace’s fleet around the same time in early September.

On a different customer environment, Darktrace DETECT observed more than 25 ‘.au3’ files being downloaded; this activity can be seen in Figure 9.

Figure 8: High volume of file downloads following GET request and 'curl' commands.

Figure 9 provides more details of this activity, including the source and destination IP addresses (5.188.87[.]58), the destination port, the HTTP method used and the MIME/content-type of the file

Figure 9: Additional information of the anomalous connections.

A compromised server in another customer deployment was seen establishing unusual connections to the external IP address 80.66.88[.]145 – an endpoint that has been associated with DarkGate by OSINT sources [5]. This activity was identified by Darktrace/DETECT as a new connection for the device via an unusual destination port, 2840. As the device in question was a critical server, Darktrace DETECT treated it with suspicion and generated an ‘Anomalous External Activity from Critical Network Device’ model breach.

Figure 10: Model breach and model breach event log for suspicious connections to additional endpoint.

Conclusion

While Microsoft Teams and SharePoint are extremely prominent tools that are essential to the business operations of many organizations, they can also be used to compromise via living off the land, even at initial intrusion. Any Microsoft Teams user within a corporate setting could be targeted by a malicious actor, as such SharePoint links from unknown senders should always be treated with caution and should not automatically be considered as secure or legitimate, even when operating within legitimate Microsoft infrastructure.

Malicious actors can leverage these commonly used platforms as a means to carry out their cyber-attacks, therefore organizations must take appropriate measures to protect and secure their digital environments. As demonstrated here, threat actors can attempt to deploy malware, like DarkGate, by targeting users with spoofed Microsoft Teams messages. By masking malicious links as legitimate SharePoint links, these attempts can easily convince targets and bypass traditional security tools and even Microsoft’s own Safe Links and Safe Attachments security capabilities.

When the chain of events of an attack escalates within milliseconds, organizations must rely on AI-driven tools that can quickly identify and automatically respond to suspicious events without latency. As such, the value of Darktrace DETECT and Darktrace RESPOND cannot be overstated. Given the efficacy and efficiency of Darktrace’s detection and autonomous response capabilities, a more severe network compromise in the form of the DarkGate commodity loader was ultimately averted.

Credit to Natalia Sánchez Rocafort, Cyber Security Analyst, Zoe Tilsiter.

Appendices

Darktrace DETECT Model Detections

[Model Breach: Device / Initial Breach Chain Compromise 100% –– Breach URI: /#modelbreach/114039 ] (Enhanced Monitoring)· [Model Breach: Device / Initial Breach Chain Compromise 100% –– Breach URI: /#modelbreach/114124 ] (Enhanced Monitoring)
[Model Breach: Device / New User Agent and New IP 62% –– Breach URI: /#modelbreach/114030 ]
[Model Breach: Anomalous Connection / Application Protocol on Uncommon Port 46% –– Breach URI: /#modelbreach/114031 ]
[Model Breach: Anomalous Connection / New User Agent to IP Without Hostname 62% –– Breach URI: /#modelbreach/114032 ]
[Model Breach: Device / New User Agent 32% –– Breach URI: /#modelbreach/114035 ]
[Model Breach: Device / Three Or More New User Agents 31% –– Breach URI: /#modelbreach/114036 ]
[Model Breach: Anomalous Server Activity / Anomalous External Activity from Critical Network Device 62% –– Breach URI: /#modelbreach/612173 ]
[Model Breach: Anomalous File / EXE from Rare External Location 61% –– Breach URI: /#modelbreach/114037 ]
[Model Breach: Anomalous Connection / Multiple Connections to New External TCP Port 61% –– Breach URI: /#modelbreach/114042 ]
[Model Breach: Security Integration / Integration Ransomware Detected 100% –– Breach URI: /#modelbreach/114049 ]
[Model Breach: Compromise / Beaconing Activity To External Rare 62% –– Breach URI: /#modelbreach/114059 ]
[Model Breach: Compromise / HTTP Beaconing to New Endpoint 30% –– Breach URI: /#modelbreach/114067 ]
[Model Breach: Security Integration / C2 Activity and Integration Detection 100% –– Breach URI: /#modelbreach/114069 ]
[Model Breach: Anomalous File / EXE from Rare External Location 55% –– Breach URI: /#modelbreach/114077 ]
[Model Breach: Compromise / High Volume of Connections with Beacon Score 66% –– Breach URI: /#modelbreach/114260 ]
[Model Breach: Security Integration / Low Severity Integration Detection 59% –– Breach URI: /#modelbreach/114293 ]
[Model Breach: Security Integration / Low Severity Integration Detection 33% –– Breach URI: /#modelbreach/114462 ]
[Model Breach: Security Integration / Integration Ransomware Detected 100% –– Breach URI: /#modelbreach/114109 ]· [Model Breach: Device / Three Or More New User Agents 31% –– Breach URI: /#modelbreach/114118 ]· [Model Breach: Anomalous Connection / Application Protocol on Uncommon Port 46% –– Breach URI: /#modelbreach/114113 ] · [Model Breach: Anomalous Connection / New User Agent to IP Without Hostname 62% –– Breach URI: /#modelbreach/114114 ]· [Model Breach: Device / New User Agent 32% –– Breach URI: /#modelbreach/114117 ]· [Model Breach: Anomalous File / EXE from Rare External Location 61% –– Breach URI: /#modelbreach/114122 ]· [Model Breach: Security Integration / Low Severity Integration Detection 54% –– Breach URI: /#modelbreach/114310 ]
[Model Breach: Security Integration / Integration Ransomware Detected 65% –– Breach URI: /#modelbreach/114662 ]Darktrace/Respond Model Breaches
[Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 61% –– Breach URI: /#modelbreach/114033 ]
[Model Breach: Antigena / Network::External Threat::Antigena File then New Outbound Block 100% –– Breach URI: /#modelbreach/114038 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block 100% –– Breach URI: /#modelbreach/114040 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block 87% –– Breach URI: /#modelbreach/114041 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach 87% –– Breach URI: /#modelbreach/114043 ]
[Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 100% –– Breach URI: /#modelbreach/114052 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Security Integration and Network Activity Block 87% –– Breach URI: /#modelbreach/114070 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 87% –– Breach URI: /#modelbreach/114071 ]
[Model Breach: Antigena / Network::External Threat::Antigena Suspicious Activity Block 87% –– Breach URI: /#modelbreach/114072 ]
[Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 53% –– Breach URI: /#modelbreach/114079 ]
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 64% –– Breach URI: /#modelbreach/114539 ]
[Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 66% –– Breach URI: /#modelbreach/114667 ]
[Model Breach: Antigena / Network::External Threat::Antigena Suspicious Activity Block 79% –– Breach URI: /#modelbreach/114684 ]·
[Model Breach: Antigena / Network::External Threat::Antigena Ransomware Block 100% –– Breach URI: /#modelbreach/114110 ]·
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block 87% –– Breach URI: /#modelbreach/114111 ]·
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach 87% –– Breach URI: /#modelbreach/114115 ]·
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block 87% –– Breach URI: /#modelbreach/114116 ]·
[Model Breach: Antigena / Network::External Threat::Antigena Suspicious File Block 61% –– Breach URI: /#modelbreach/114121 ]·
[Model Breach: Antigena / Network::External Threat::Antigena File then New Outbound Block 100% –– Breach URI: /#modelbreach/114123 ]·
[Model Breach: Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block 100% –– Breach URI: /#modelbreach/114125 ]

List of IoCs

IoC - Type - Description + Confidence

5.188.87[.]58 - IP address - C2 endpoint

80.66.88[.]145 - IP address - C2 endpoint

/bfyxraav - URI - Possible C2 endpoint URI

/msibfyxraav - URI - Possible C2 endpoint URI

Mozilla/4.0 (compatible; Win32; WinHttp.WinHttpRequest.5) - User agent - Probable user agent leveraged

curl - User agent - Probable user agent leveraged

curl/8.0.1 - User agent - Probable user agent leveraged

Mozilla/4.0 (compatible; Synapse) - User agent - Probable user agent leveraged

Autoit3.exe - Filename - Exe file

CvUYLoTv.au3

eDVeqcCe.au3

FeLlcFRS.au3

FTEZlGhe.au3

HOrzcEWV.au3

rKlArXHH.au3

SjadeWUz.au3

ZgOLxJQy.au3

zSrxhagw.au3

ALOXitYE.au3

DKRcfZfV.au3

gQZVKzek.au3

JZrvmJXK.au3

kLECCtMw.au3

LEXCjXKl.au3

luqWdAzF.au3

mUBNrGpv.au3

OoCdHeJT.au3

PcEJXfIl.au3

ssElzrDV.au3

TcBwRRnp.au3

TFvAUIgu.au3

xkwtvq.au3

otxynh.au3

dcthbq.au3 - Filenames - Possible exe files delivered in response to curl/8.0.1 GET requests with Target URI '/msibfyxraav

f3a0a85fe2ea4a00b3710ef4833b07a5d766702b263fda88101e0cb804d8c699 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

afa3feea5964846cd436b978faa7d31938e666288ffaa75d6ba75bfe6c12bf61 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

63aeac3b007436fa8b7ea25298362330423b80a4cb9269fd2c3e6ab1b1289208 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

ab6704e836a51555ec32d1ff009a79692fa2d11205f9b4962121bda88ba55486 - SHA256 file hash - Possible SHA256 hashes of 'Autoit3.exe' files

References

1. https://www.truesec.com/hub/blog/darkgate-loader-delivered-via-teams

2. https://feedit.cz/wp-content/uploads/2023/03/YiR2022_onepager_ransomware_loaders.pdf

‍3. https://www.virustotal.com/gui/ip-address/5.188.87[.]58

‍4. https://www.forescout.com/resources/darkgate-loader-malspam-campaign/

‍5. https://otx.alienvault.com/indicator/ip/80.66.88[.]145

執筆者

Natalia Sánchez Rocafort

Cyber Security Analyst

Inside the SOC

Written by

Natalia Sánchez Rocafort

Cyber Security Analyst

Senior Product Marketing Manager, Email

Watch the NIS2 Webinar

Blog

Email

December 18, 2025

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

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]

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

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 / EMAIL^TM and Darktrace / IDENTITY^TM 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.

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”.

Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.

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.

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.

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

About the author

あなたのデータ × DarktraceのAI

唯一無二のDarktrace AIで、ネットワークセキュリティを次の次元へ

デモを予約

Check out this article by Darktrace: How Darktrace Halted A DarkGate in MS Teams

How Darktrace Halted A DarkGate in MS Teams

Securing Microsoft Teams and SharePoint

DarkGate Attack Overview

Conclusion

Appendices

Darktrace DETECT Model Detections

List of IoCs

References

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

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

ブログをお楽しみ頂けましたか？

More in this series

From VPS to Phishing: How Darktrace Uncovered SaaS Hijacks through Virtual Infrastructure Abuse

Defending the Cloud: Stopping Cyber Threats in Azure and AWS with Darktrace

Top Eight Threats to SaaS Security and How to Combat Them

Blog

Email

December 18, 2025

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

Why outbound email DLP needs reinventing

How data loss actually happens

What traditional DLP approaches offer (and where gaps remain)

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

1) Label-free (vs. data classification)

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

3) Proprietary DSLM (vs. generic LLM)

The Darktrace approach to DLP

A buyer’s checklist for DLP solutions

Blog

Email

December 17, 2025

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

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

What does an AiTM attack look like?

Inbound phishing email

Proxy-based credential theft and session hijacking

Follow-on attacks

Darktrace’s detection of an AiTM attack

Internal and external phishing

Darktrace’s Response

Conclusion

Appendices

Models