Blog
/
/
October 10, 2021

AI Uncovered Outlaw's Crypto Mining Operation

Discover how Darktrace AI technology exposed a hidden cryptocurrency mining scheme. Learn about the power of Darktrace AI in cybersecurity.
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
Oakley Cox
Director of Product
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
10
Oct 2021

Infamy is a paradoxical calling for cyber-criminals. While for some, bragging rights are a motivation for cyber-crime in and of themselves, notoriety is usually not a sensible goal for those hoping to avoid detection. This is what threat actors behind the prolific Emotet botnet learned earlier in 2021, for instance, when a coordinated effort was launched by eight national law enforcement agencies to take down their operation. There are, however, certain names which appear again and again in cyber security media and consistently avoid detection – names like Outlaw.

How Outlaw plans an ambush

Despite being active since 2018, very little is known about the hacking group Outlaw, which has staged numerous botnet and crypto-jacking attacks in China and internationally. The group is recognized by a variety of calling cards, be they repeated filenames or a tendency to illicitly mine Monero cryptocurrency, but its success ultimately lies in its tendency to adapt and evolve during months of dormancy between attacks.

Outlaw’s attacks are marked by constant changes and updates, which they work on in relative silence, before targeting security systems which are too-often defeated by the unfamiliarity of the threat.

In 2020, Outlaw gained attention when they updated their botnet toolset to find and eradicate other criminals’ crypto-jacking software, maximizing their own payout from infected devices. While it might come as no surprise that there’s no honor among cyber-thieves, this update also implemented more troubling changes which allowed Outlaw’s malware to evade traditional security defenses.

By switching disguises between each big robbery, and laying low with the loot, Outlaw ensures that traditional security systems which rely on historical attack data will never be ready for them, no matter how much notoriety is attached to their name. When organizations move beyond these systems’ rules-based approaches, however, adopting Self-Learning AI to protect their digital estates, they can begin to turn the tables on groups like Outlaw.

This blog explores how two pre-infected zombie devices in two very different parts of the world were activated by Outlaw’s botnet in the summer of 2021, and how Darktrace was able to detect the activity despite the devices being pre-infected.

Bounty hunting: First signs of attack

Figure 1: Timeline of the attack.

When a new device was added to the network of a Central American telecomms company in July, Darktrace detected a series of regular connections to two suspicious endpoints which it identified as beaconing behavior. The same behavior was noticed independently, but almost simultaneously, at a financial company in the APAC region, which was implementing Darktrace for the first time. Darktrace’s Self-Learning AI was able to identify the pre-infected devices by clustering similarly-behaving devices into peer groups within the local digital estates and therefore recognize that both were acting unusually based on a range of behaviors.

The first sign that the zombie devices had been activated by Outlaw was the initiation of cryptocurrency mining. Both devices, despite their geographical distance, were discovered to be connected to a single crypto-account, exemplifying the indiscriminate and exponential nature by which a botnet grows.

Outlaw has in the past restricted its activities to devices within China in what was assumed to be a show of caution, but recent activities like this one speak to a growing confidence.

The botnet recruitment process

The subsequent initiation of Internet Relay Chat (IRC) connections across port 443, a port more often associated with HTTPS activity, was perfectly characteristic of the Outlaw botnet’s earlier activity in 2020. IRC is a tool regularly used for communication between botmasters and zombie devices, but by using port 443 the attacker was attempting to blend into normal Internet traffic.

Soon after this exchange, the devices downloaded a shell script. Darktrace’s Cyber AI Analyst was able to intercept and recreate this shell script as it passed through the network, revealing its full function. Intriguingly, the script identified and excluded devices utilizing ARM architecture from the botnet. Due to its notably low battery consumption, ARM architecture is used primarily by portable mobile devices.

This selectivity is evidence that malicious crypto-mining remains Outlaw’s primary objective. By circumventing smaller devices which offer limited crypto-mining capabilities, this shell script focuses the botnet on the most high-powered, and therefore profitable, devices, such as desktop computers and servers. In this way, it reduces the Indicators of Compromise (IOCs) left behind by the wider botnet without greatly affecting the scale of its crypto-mining operation.

The two devices in question did not employ ARM architecture, and minutes later received a secondary payload containing a file named dota3[.]tar[.]gz, a sequel of sorts to the previous incarnation of the Outlaw botnet, ‘dota2’, which itself referenced a popular video game of the same name. With the arrival of this file, the devices appear to have been updated with the latest version of Outlaw’s world-spanning botnet.

This download was made possible in part by the attacker’s use of ‘Living off the Land’ tactics. By using only common Linux programs already present on the devices (‘curl’ and ‘Wget’ respectively), Outlaw had avoided having its activity flagged by traditional security systems. Wget, for instance, is ostensibly a reputable program used for retrieving content from web servers, and was never previously recorded as part of Outlaw’s TTPs (Tactics, Techniques, and Procedures).

By evolving and adapting its approach, Outlaw is continually able to outsmart and outrun rules-based security. Darktrace’s Self-Learning AI, however, kept pace, immediately identifying this Wget connection as suspicious and advising further investigation.

Figure 2: Cyber AI Analyst identifies Wget use on the morning of July 15 as suspicious and begins investigating potentially related HTTP connections made on the morning of July 14. In this way, it builds a complete picture of the attack.

The botnet unchained

In the following 36 hours, Darktrace detected over 6 million TCP and SSH connections directed to rare external IP addresses using ports often associated with SSH, such as 22, 2222, and 2022.

Exactly what the botnet was undertaking with these connections can only be speculated on. The devices may have been made part of a DDoS (Distributed Denial of Service) attack, bruteforce attempts on targeted SSH accounts, or simply have taken up the task of seeking and infecting new targets, further expanding the botnet. Darktrace recognized that neither device had made SSH connections prior to this event and, had Antigena been in active mode, would have enacted measures to stop them.

Figure 3: The behavior on the device before and after the bot was activated on July 14, 2021. The large spike in model breaches shows clear deviation from the established ‘pattern of life’.

Thankfully, the owners of both devices responded to Darktrace’s detection alerts soon enough to prevent any serious damage to their own digital estates. Had these devices remained under the influence of the botnet, the ramifications may have been far graver.

The use of SSH protocol would have allowed Outlaw to pivot into any number of activities, potentially compromising each device’s network further and causing data or monetary loss to their respective organizations.

Call the sheriff: Self-Learning AI

Rules-based security solutions operate much like the ‘wanted’ posters of the old west, looking out for the criminals who came through town last week without preparing for those riding over the hill today. When black hats and outlaws are adopting new looks and employing new techniques with every attack, a new way of responding to threats is needed.

Darktrace doesn’t need to know the name ‘Outlaw’, or the group’s history of evolving attacks, in order to stop them. With its fundamental self-learning approach, Darktrace learns its surroundings from the ground up, and identifies subtle deviations indicative of a cyber-threat. And with Autonomous Response, it will even take targeted action to neutralize the threat at machine speed, without the need for human intervention.

Thanks to Darktrace analyst Jun Qi Wong for his insights on the above threat find.

Learn more about how Cyber AI Analyst sheds light on complex attacks

Technical details

Darktrace model detections

  • Compliance / Crypto Currency Mining Activity
  • Compromise / High Priority Crypto Currency Mining [Enhanced Monitoring]
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Device / Increased External Connectivity
  • Unusual Activity / Unusual External Activity
  • Compromise / SSH Beacon
  • Compromise / High Frequency SSH Beacon
  • Anomalous Connection / Multiple Connections to New External TCP Port

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
Oakley Cox
Director of Product

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
Your data. Our AI.
Elevate your network security with Darktrace AI