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May 25, 2022

Uncovering the Sysrv-Hello Crypto-Jacking Bonet

Discover the cyber kill chain of a Sysrv-hello botnet infection in France and gain insights into the latest TTPs of the botnet in March and April 2022.
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
Shuh Chin Goh
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25
May 2022

In recent years, the prevalence of crypto-jacking botnets has risen in tandem with the popularity and value of cryptocurrencies. Increasingly crypto-mining malware programs are distributed by botnets as they allow threat actors to harness the cumulative processing power of a large number of machines (discussed in our other Darktrace blogs.1 2 One of these botnets is Sysrv-hello, which in addition to crypto-mining, propagates aggressively across the Internet in a worm-like manner by trolling for Remote Code Execution (RCE) vulnerabilities and SSH worming from the compromised victim devices. This all has the purpose of expanding the botnet.

First identified in December 2020, Sysrv-hello’s operators constantly update and change the bots’ behavior to evolve and stay ahead of security researchers and law enforcement. As such, infected systems can easily go unnoticed by both users and organizations. This blog examines the cyber kill chain sequence of a Sysrv-hello botnet infection detected at the network level by Darktrace DETECT/Network, as well as the botnet’s tactics, techniques, and procedures (TTPs) in March and April 2022.

Figure 1: Timeline of the attack

Delivery and exploitation

The organization, which was trialing Darktrace, had deployed the technology on March 2, 2022. On the very same day, the initial host infection was seen through the download of a first-stage PowerShell loader script from a rare external endpoint by a device in the internal network. Although initial exploitation of the device happened prior to the installation and was not observed, this botnet is known to target RCE vulnerabilities in various applications such as MySQL, Tomcat, PHPUnit, Apache Solar, Confluence, Laravel, JBoss, Jira, Sonatype, Oracle WebLogic and Apache Struts to gain initial access to internal systems.3 Recent iterations have also been reported to have been deployed via drive-by-downloads from an empty HTML iframe pointing to a malicious executable that downloads to the device from a user visiting a compromised website.4

Initial intrusion

The Sysrv-hello botnet is distributed for both Linux and Windows environments, with the corresponding compatible script pulled based on the architecture of the system. In this incident, the Windows version was observed.

On March 2, 2022 at 15:15:28 UTC, the device made a successful HTTP GET request to a malicious IP address5 that had a rarity score of 100% in the network. It subsequently downloaded a malicious PowerShell script named ‘ldr.ps1'6 onto the system. The associated IP address ‘194.145.227[.]21’ belongs to ‘ASN AS48693 Rices Privately owned enterprise’ and had been identified as a Sysrv-hello botnet command and control (C2) server in April the previous year. 3

Looking at the URI ‘/ldr.ps1?b0f895_admin:admin_81.255.222.82:8443_https’, it appears some form of query was being executed onto the object. The question mark ‘?’ in this URI is used to delimit the boundary between the URI of the queryable object and the set of strings used to express a query onto that object. Conventionally, we see the set of strings contains a list of key/value pairs with equal signs ‘=’, which are separated by the ampersand symbol ‘&’ between each of those parameters (e.g. www.youtube[.]com/watch?v=RdcCjDS0s6s&ab_channel=SANSCyberDefense), though the exact structure of the query string is not standardized and different servers may parse it differently. Instead, this case saw a set of strings with the hexadecimal color code #b0f895 (a light shade of green), admin username and password login credentials, and the IP address ‘81.255.222[.]82’ being applied during the object query (via HTTPS protocol on port 8443). In recent months this French IP has also had reports of abuse from the OSINT community.7

On March 2, 2022 at 15:15:33 UTC, the PowerShell loader script further downloaded second-stage executables named ‘sys.exe’ and ‘xmrig.2 sver.8 9 These have been identified as the worm and cryptocurrency miner payloads respectively.

Establish foothold

On March 2, 2022 at 17:46:55 UTC, after the downloads of the worm and cryptocurrency miner payloads, the device initiated multiple SSL connections in a regular, automated manner to Pastebin – a text storage website. This technique was used as a vector to download/upload data and drop further malicious scripts onto the host. OSINT sources suggest the JA3 client SSL fingerprint (05af1f5ca1b87cc9cc9b25185115607d) is associated with PowerShell usage, corroborating with the observation that further tooling was initiated by the PowerShell script ‘ldr.ps1’.

Continual Pastebin C2 connections were still being made by the device almost two months since the initiation of such connections. These Pastebin C2 connections point to new tactics and techniques employed by Sysrv-hello — reports earlier than May do not appear to mention any usage of the file storage site. These new TTPs serve two purposes: defense evasion using a web service/protocol and persistence. Persistence was likely achieved through scheduling daemons downloaded from this web service and shellcode executions at set intervals to kill off other malware processes, as similarly seen in other botnets.10 Recent reports have seen other malware programs also switch to Pastebin C2 tunnels to deliver subsequent payloads, scrapping the need for traditional C2 servers and evading detection.11

Figure 2: A section of the constant SSL connections that the device was still making to ‘pastebin[.]com’ even in the month of April, which resembles beaconing scheduled activity

Throughout the months of March and April, suspicious SSL connections were made from a second potentially compromised device in the internal network to the infected breach device. The suspicious French IP address ‘81.255.222[.]82’ previously seen in the URI object query was revealed as the value of the Server Name Indicator (SNI) in these SSL connections where, typically, a hostname or domain name is indicated.

After an initial compromise, attackers usually aim to gain long-term remote shell access to continue the attack. As the breach device does not have a public IP address and is most certainly behind a firewall, for it to be directly accessible from the Internet a reverse shell would need to be established. Outgoing connections often succeed because firewalls generally filter only incoming traffic. Darktrace observed the device making continuous outgoing connections to an external host listening on an unusual port, 8443, indicating the presence of a reverse shell for pivoting and remote administration.

Figure 3: SSL connections to server name ‘81.255.222[.]8’ at end of March and start of April

Accomplish mission

On March 4, 2022 at 15:07:04 UTC, the device made a total of 16,029 failed connections to a large volume of external endpoints on the same port (8080). This behavior is consistent with address scanning. From the country codes, it appears that public IP addresses for various countries around the world were contacted (at least 99 unique addresses), with the US being the most targeted.

From 19:44:36 UTC onwards, the device performed cryptocurrency mining using the Minergate mining pool protocol to generate profits for the attacker. A login credential called ‘x’ was observed in the Minergate connections to ‘194.145.227[.]21’ via port 5443. JSON-RPC methods of ‘login’ and ‘submit’ were seen from the connection originator (the infected breach device) and ‘job’ was seen from the connection responder (the C2 server). A high volume of connections using the JSON-RPC application protocol to ‘pool-fr.supportxmr[.]com’ were also made on port 80.

When the botnet was first discovered in December 2020, mining pools MineXMR and F2Pool were used. In February 2021, MineXMR was removed and in March 2021, Nanopool mining pool was added,12 before switching to the present SupportXMR and Minergate mining pools. Threat actors utilize such proxy pools to help hide the actual crypto wallet address where the contributions are made by the crypto-mining activity. From April onwards, the device appears to download the ‘xmrig.exe’ executable from a rare IP address ‘61.103.177[.]229’ in Korea every few days – likely in an attempt to establish persistency and ensure the cryptocurrency mining payload continues to exist on the compromised system for continued mining.

On March 9, 2022 from 18:16:20 UTC onwards, trolling for various RCE vulnerabilities (including but not limited to these four) was observed over HTTP connections to public IP addresses:

  1. Through March, the device made around 5,417 HTTP POSTs with the URI ‘/vendor/phpunit/phpunit/src/Util/PHP/eval-stdin.php’ to at least 99 unique public IPs. This appears to be related to CVE-2017-9841, which in PHPUnit allows remote attackers to execute arbitrary PHP code via HTTP POST data beginning with a ‘13 PHPUnit is a common testing framework for PHP, used for performing unit tests during application development. It is used by a variety of popular Content Management Systems (CMS) such as WordPress, Drupal and Prestashop. This CVE has been called “one of the most exploitable CVEs of 2019,” with around seven million attack attempts being observed that year.14 This framework is not designed to be exposed on the critical paths serving web pages and should not be reachable by external HTTP requests. Looking at the status messages of the HTTP POSTs in this incident, some ‘Found’ and ‘OK’ messages were seen, suggesting the vulnerable path could be accessible on some of those endpoints.

Figure 4: PCAP of CVE-2017-9841 vulnerability trolling

Figure 5: The CVE-2017-9841 vulnerable path appears to be reachable on some endpoints

  1. Through March, the device also made around 5,500 HTTP POSTs with the URI ‘/_ignition/execute-solution’ to at least 99 unique public IPs. This appears related to CVE-2021-3129, which allows unauthenticated remote attackers to execute arbitrary code using debug mode with Laravel, a PHP web application framework in versions prior to 8.4.2.15 The POST request below makes the variable ‘username’ optional, and the ‘viewFile’ parameter is empty, as a test to see if the endpoint is vulnerable.16

Figure 6: PCAP of CVE-2021-3129 vulnerability trolling

  1. The device made approximately a further 252 HTTP GETs with URIs containing ‘invokefunction&function’ to another minimum of 99 unique public IPs. This appears related to a RCE vulnerability in ThinkPHP, an open-source web framework.17

Figure 7: Some of the URIs associated with ThinkPHP RCE vulnerability

  1. A HTTP header related to a RCE vulnerability for the Jakarta Multipart parser used by Apache struts2 in CVE-2017-563818 was also seen during the connection attempts. In this case the payload used a custom Content-Type header.

Figure 8: PCAP of CVE-2017-5638 vulnerability trolling

Two widely used methods of SSH authentication are public key authentication and password authentication. After gaining a foothold in the network, previous reports3 19 have mentioned that Sysrv-hello harvests private SSH keys from the compromised device, along with identifying known devices. Being a known device means the system can communicate with the other system without any further authentication checks after the initial key exchange. This technique was likely performed in conjunction with password brute-force attacks against the known devices. Starting from March 9, 2022 at 20:31:25 UTC, Darktrace observed the device making a large number of SSH connections and login failures to public IP ranges. For example, between 00:05:41 UTC on March 26 and 05:00:02 UTC on April 14, around 83,389 SSH connection attempts were made to 31 unique public IPs.

Figure 9: Darktrace’s Threat Visualizer shows large spikes in SSH connections by the breach device

Figure 10: Beaconing SSH connections to a single external endpoint, indicating a potential brute-force attack

Darktrace coverage

Cyber AI Analyst was able to connect the events and present them in a digestible, chronological order for the organization. In the aftermath of any security incidents, this is a convenient way for security users to conduct assisted investigations and reduce the workload on human analysts. However, it is good to note that this activity was also easily observed in real time from the model section on the Threat Visualizer due to the large number of escalating model breaches.

Figure 11: Cyber AI Analyst consolidating the events in the month of March into a summary

Figure 12: Cyber AI Analyst shows the progression of the attack through the month of March

As this incident occurred during a trial, Darktrace RESPOND was enabled in passive mode – with a valid license to display the actions that it would have taken, but with no active control performed. In this instance, no Antigena models breached for the initial compromised device as it was not tagged to be eligible for Antigena actions. Nonetheless, Darktrace was able to provide visibility into these anomalous connections.

Had Antigena been deployed in active mode, and the breach device appropriately tagged with Antigena All or Antigena External Threat, Darktrace would have been able to respond and neutralize different stages of the attack through network inhibitors Block Matching Connections and Enforce Group Pattern of Life, and relevant Antigena models such as Antigena Suspicious File Block, Antigena Suspicious File Pattern of Life Block, Antigena Pastebin Block and Antigena Crypto Currency Mining Block. The first of these inhibitors, Block Matching Connections, will block the specific connection and all future connections that matches the same criteria (e.g. all future outbound HTTP connections from the breach device to destination port 80) for a set period of time. Enforce Group Pattern of Life allows a device to only make connections and data transfers that it or any of its peer group typically make.

Conclusion

Resource hijacking results in unauthorized consumption of system resources and monetary loss for affected organizations. Compromised devices can potentially be rented out to other threat actors and botnet operators could switch from conducting crypto-mining to other more destructive illicit activities (e.g. DDoS or dropping of ransomware) whilst changing their TTPs in the future. Defenders are constantly playing catch-up to this continual evolution, and retrospective rules and signatures solutions or threat intelligence that relies on humans to spot future threats will not be able to keep up.

In this case, it appears the botnet operator has added an object query in the URL of the initial PowerShell loader script download, added Pastebin C2 for evasion and persistence, and utilized new cryptocurrency mining pools. Despite this, Darktrace’s Self-Learning AI was able to identify the threats the moment attackers changed their approach, detecting every step of the attack in the network without relying on known indicators of threat.

Appendix

Darktrace model detections

  • Anomalous File / Script from Rare Location
  • Anomalous File / EXE from Rare External Location
  • Compromise / Agent Beacon (Medium Period)
  • Compromise / Slow Beaconing Activity To External Rare
  • Compromise / Beaconing Activity To External Rare
  • Device / External Address Scan
  • Compromise / Crypto Currency Mining Activity
  • Compromise / High Priority Crypto Currency Mining
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / SSL Beaconing to Rare Destination
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
  • Device / Large Number of Model Breaches
  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Anomalous Connection / SSH Brute Force
  • Compromise / SSH Beacon
  • Compliance / SSH to Rare External AWS
  • Compromise / High Frequency SSH Beacon
  • Compliance / SSH to Rare External Destination
  • Device / Multiple C2 Model Breaches
  • Anomalous Connection / POST to PHP on New External Host

MITRE ATT&CK techniques observed:

IoCs

Thanks to Victoria Baldie and Yung Ju Chua for their contributions.

Footnotes

1. https://www.darktrace.com/en/blog/crypto-botnets-moving-laterally

2. https://www.darktrace.com/en/blog/how-ai-uncovered-outlaws-secret-crypto-mining-operation

3. https://www.lacework.com/blog/sysrv-hello-expands-infrastructure

4. https://www.riskiq.com/blog/external-threat-management/sysrv-hello-cryptojacking-botnet

5. https://www.virustotal.com/gui/ip-address/194.145.227.21

6. https://www.virustotal.com/gui/url/c586845daa2aec275453659f287dcb302921321e04cb476b0d98d731d57c4e83?nocache=1

7. https://www.abuseipdb.com/check/81.255.222.82

8. https://www.virustotal.com/gui/file/586e271b5095068484446ee222a4bb0f885987a0b77e59eb24511f6d4a774c30

9. https://www.virustotal.com/gui/file/f5bef6ace91110289a2977cfc9f4dbec1e32fecdbe77326e8efe7b353c58e639

10. https://www.ironnet.com/blog/continued-exploitation-of-cve-2021-26084

11. https://www.zdnet.com/article/njrat-trojan-operators-are-now-using-pastebin-as-alternative-to-central-command-server

12. https://blogs.juniper.net/en-us/threat-research/sysrv-botnet-expands-and-gains-persistence

13. https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2017-9841

14. https://www.imperva.com/blog/the-resurrection-of-phpunit-rce-vulnerability

15. https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-3129

16. https://isc.sans.edu/forums/diary/Laravel+v842+exploit+attempts+for+CVE20213129+debug+mode+Remote+code+execution/27758

17. https://securitynews.sonicwall.com/xmlpost/thinkphp-remote-code-execution-rce-bug-is-actively-being-exploited

18. https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2017-5638

19. https://sysdig.com/blog/crypto-sysrv-hello-wordpress

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
Shuh Chin Goh

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December 18, 2025

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

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

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

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

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

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

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

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

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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