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June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

We cover two real cases on how Darktrace stopped Microsoft 365 account takeovers by correlating insights across SaaS applications & email activity.
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
Dan Fein
VP, Product
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07
Jun 2020

‘Social engineering’. ‘Credential theft’. ‘Account takeover’. If you were a fly on the wall of a Security Operations Center in 2020, you would have heard these phrases far more often than ‘banking trojan’, ‘SQL injection’ or ‘exploit kit’. The reason for this is simple – the reality for most security teams now is that their perimeter has shifted into the cloud. Identities are being attacked more than devices.

‘Microsoft 365 account compromise’ is the current favorite, with 29% of organizations reporting a related incident in one month alone. Security teams struggle with these attacks because the evidence needed to detect them is scattered across the enterprise: they begin via email, are executed over the network, and progress in the cloud. This broad and spread out digital footprint means that following the breadcrumbs is not easy.

Darktrace’s Cyber AI Platform is designed to understand a user’s behavior as they move between devices and cloud services, tracking their activity to identify a compromise. To help understand how these attacks avoid detection, it is useful to look at a couple of examples of Microsoft Office 365 compromise detected recently in one of our customers.

Microsoft 365 compromised to launch external email threat

A Microsoft 365 account was recently compromised at a public accounting firm based in the United States. Darktrace initially picked up on several anomalies, including a sudden surge in outbound email traffic as well as the unusual login location – while the company and nearly all of its users were located in Wisconsin, an IP address located in Kansas was used to log in to the Microsoft 365 account. Along with the unusual login, a login to Microsoft Teams from the same Kansas IP address was detected.

Figure 1: Just after the new email rule was created, a Microsoft Teams 100% rare IP login occurred.

‘Impossible travel’ rules alone would have missed these anomalies, but an understanding of activity and behavior across different SaaS applications allowed Darktrace’s AI to recognize these events as one systematic case of credential theft. When the threat-actor subsequently created a new email rule, Darktrace was able to connect this event with the other anomalous behavior and understand its potentially malicious nature.

Figure 2: Darktrace’s SaaS Module noted a 100% rare IP logging into the user’s Microsoft 365 account and the creation of a new mailbox rules. All factors indicated 100% unusual SaaS activity.

Five minutes later, Antigena Email alerted on a large number of outbound emails containing a generic subject line and an attached PDF. The technology also detected that there was a clear spike in outbound emails from this user and flagged each of these emails with the “Out of Character” tag, which in this case denoted a change from normal behavior with the surge in recipients, and likely internal compromise.

Figure 3: Antigena Email detected a surge in recipients that indicated a serious breach of normal behavior for this user.

The unusual login behavior detected by Darktrace’s SaaS Module could be connected to the anomalous outbound email behavior flagged by Antigena Email, allowing the security team to see the extent of the attack and neutralize it as it emerged. It was clear that the account was being used to engage in malicious activity, as each of the 220 outbound emails used a generic subject line and contained a suspicious attachment. The security team therefore immediately disabled the compromised account.

Figure 4: A recreation of the email sent by the attacker, containing the malicious attachment.

‘Change of bank details’ sent from accounts department

When an Accounts Department’s Microsoft 365 account was compromised and used to send targeted phishing emails, Darktrace was able to track the attacker’s movement within the inbox, tying together information from Darktrace’s SaaS Module with Antigena Email’s alerts to understand the full picture of the threat and stop the attack.

The SaaS account appears to have been compromised via an inbound spear phishing attack, or some other form of attack that occurred before Darktrace began monitoring the organization. While Darktrace Cyber AI had no oversight of the initial compromise, it was still able to distinguish later attacker behavior as malicious, based on its actively evolving understanding of the organization and its workforce.

When the account user logged in from a 100% rare French IP address, Darktrace’s SaaS Module picked up on the anomaly immediately, and further detected a series of activities carried out after the unusual login. At the same time, Antigena Email noted an email being sent.

Figure 5: The login from a French IP was noted as 100% rare for this user and SaaS account.

Darktrace then identified more activity occurring from a second rare login location, a Swiss IP address. Very little email activity occurred when the account was logged in from this IP. Instead, Cyber AI saw the threat-actor using their illegitimate SaaS access to view information on the legitimate account user and files related to banking, invoices, and payments.

Antigena Email then identified a series of email communications that, when seen in the context of the SaaS account compromise, pointed to a clear threat. There were no obvious malicious attachments or links in the emails. However, the subject of the final reply was ‘Change of Bank Details’, and the email prompted a high Solicitation Inducement Score within Antigena Email, strongly implying that the malicious actor had sent emails instructing the destination to change payment details in order to route money to the attacker, instead of the company.

It seems the attackers went through the banking and invoicing files in order to find a customer with a big bill to pay, then used the compromised email account to launch an outbound phishing attack, changing the billing details. With Darktrace AI correlating information within the SaaS platform and insights from Antigena Email, this targeted phishing attack could be contained before further compromise or damage could occur.

The below screenshot also indicates a series of inbox processing rules made on the compromised account, showing actions that are typical of an account takeover.

Figure 6: Darktrace’s records of new inbox rules being set up on the compromised SaaS account.

The benefits of a unified approach

These stories are all too familiar. Most security tools would not be able to take action on any one of these steps individually. But the combination reveals the tell-tale sign of a Microsoft 365 account hijack. Organizations are struggling to manage their user identities across their cloud infrastructure, and rule and policy-based detection is no longer feasible.

However, by learning identities and behavior across the enterprise, Darktrace is able to detect, and seamlessly respond, to combat these threats. Hundreds of organizations are now using Antigena Email to protect their email and cloud environments continuously, trusting it to dynamically enforce MFA, lock accounts, block network traffic, and withhold emails when necessary.

As cloud-native applications become more popular, organizations face the growing problem of separate end-to-end security solutions for each type of workload. With Antigena Email working in conjunction with Darktrace’s Enterprise Immune System, defenders can be assured that a single, unified platform is tracking every suspicious behavior, wherever it arises in the organization.

Learn more about Antigena Email

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
Dan Fein
VP, Product

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September 30, 2026

AI-Assisted Attacks Still Leave a Behavioral Trace  

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Key Insights

  • Darktrace identified behavioral indicators associated with two campaigns linked to AI-assisted threat activity, highlighting the growing role of AI in modern cyber-attacks.
  • Observed activity involved suspicious WebDAV file transfers, disguised executable downloads, beaconing to rare infrastructure, unusual process execution, and communications with C2 infrastructure linked to active intrusion campaigns.

Introduction

Just as organizations are incorporating AI into their operations to take advantage of its benefits, threat actors are doing the same, creating new challenges for defenders.

Much of the discussion around AI risk has focused on the expanding attack surface created by AI systems within organizations. These systems are often granted privileged access and heightened permissions to carry out their duties, introducing new security risks and unintended consequences.

At the same time, threat actors are learning to leverage AI to enable malicious activities such as vulnerability discovery, exploit creation, and progressing through the Cyber Kill Chain more quickly. By accelerating development, adaptation, and scaling, AI enables attackers to operate more efficiently while making some capabilities more accessible to less skilled operators.

Whether AI is the target or the enabler, the resulting activity still manifests through networks, identities, endpoints and cloud services. Those interactions create observable signals that defenders can investigate, regardless of how the attack was developed.

AI as part of the attacker’s workflow

Darktrace has previously documented how threat actors are increasingly incorporating AI into offensive operations [1]. Two recent investigations from open-source intelligence (OSINT) illustrate this. In both cases, researchers identified the role of AI within malicious operations. Separately, Darktrace detected activity in customer environments that aligned with the infrastructure and techniques reported in those campaigns. These perspectives provide a view of both attacker workflow and operational consequences.

Although AI played different roles in each campaign, it did not remove the need for the attackers to interact with their targets. Payloads still had to be delivered, processes executed, and command-and-control (C2) connections established, creating behavioral anomalies that Darktrace was able to identify.

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Case 1: A Mexican government impersonation campaign with LLM-assisted malware development

Rapid7 reported on a malware delivery operation that used generative AI to assist development, testing, documentation and refinement of attacker infrastructure. Between May and June 2026, Darktrace similarly observed two chains of suspicious activity across customer environments in the Americas that exhibited clear similarities in behavior.

In both cases Darktrace observed:

  • WebDAV communication with onedrive[.]cv·138.124.123[.]87, retrieving a file from the path /Downloads/CURP/
  • Transfer of a masqueraded .scr executable
  • Subsequent communication with google.services[.]ug·77.110.127[.]205 over unusual high ports
  • Additional Darktrace detections correlating the unusual behavior seen spanning payload delivery and C2 communication
  • Darktrace’s Autonomous Response capability alerted across multiple stages of the attack

The infrastructure and behavior observed by Darktrace closely aligned with a campaign reported by Rapid7, in which a WebDAV malware delivery environment was exposed. Rapid7 assessed that threat actors had used generative AI to support the development, testing, documentation and refinement of the operation. The observed activity also aligned with reporting on a campaign in which impersonation of Mexico’s government Unique Population Registry Code (CURP) identity-record service led to delivery of PureRAT, a .NET-based information stealer and remote access trojan (RAT) [2]. The infrastructure overlap and consistent behavioural sequence provides strong alignment and offers a view of how an AI-assisted development pipeline ultimately manifested inside target environments.

Case 2: A suspected China-linked intrusion campaign with AI-assisted automation

In July 2026, Hunt.io published research into a suspected China-based intrusion operation targeting government and financial services organizations [3]. Material recovered from exposed attacker infrastructure by Hunt.io indicated that Claude Code and DeepSeek-v4-pro were being used as active components of the attacker’s workflow. According to the research, the models supported activities including attack reasoning, script generation, execution, exploit adaptation, and phishing-page development.

The investigation identified 192.229.115[.]229 and 192.229.115[.]230 as infrastructure associated with suspected TencShell operations and a possible second C2 framework known as Gshell [3].

Darktrace identified likely related activity within a financial services customer environment involving a newly observed laptop running the Windows 11 Pro operating system. Over a six-day period in July, the device made repeated outbound connections to 192.229.115[.]229 over port 8083.

Darktrace recognized the destination was highly rare for the environment, and the connectivity exhibited beaconing characteristics. During the same timeframe, Darktrace also identified suspicious process behavior associated with process chains involving svchost.exe and cmd.exe. The device repeatedly communicated with infrastructure identified in the Hunt.io research while exhibiting beaconing characteristics and suspicious process activity, strengthening the assessment that the activity likely was associated with the same operation.

Unlike many previous examples of AI-assisted cybercrime, the Hunt.io investigation provided rare visibility into how large language models were being incorporated directly into operational workflows rather than being used solely for content generation. Darktrace, meanwhile, observed how activity associated with that operation ultimately manifested inside a target environment, providing a complementary view of its operational impact.

Operational consequences of AI-assisted attacks

These investigations provide two complementary perspectives on AI-assisted cyber operations. OSINT research revealed how AI was incorporated into attacker workflows, while Darktrace observed the resulting activity within customer environments.

Although AI played different roles in each campaign, it did not remove the need for attackers to interact with their targets, deliver payloads, execute processes, and communicate with C2, all of which generated observable signals.

In these cases, Darktrace identified suspicious file delivery, unusual process behavior, beaconing activity, and communication with rare external infrastructure that aligned with campaigns later linked to AI-assisted operations. While AI may influence how attacks are developed, adapted, and scaled, it does not make them operationally invisible.

For defenders, the broader lesson extends beyond these specific campaigns. As AI becomes increasingly embedded within both enterprise operations and attacker workflows, understanding what a model was asked to do is often less important than understanding the actions it ultimately took and the consequences those actions produced. Whether the actor is human, AI-assisted, or increasingly autonomous, activity still manifests through identities, endpoints, applications, cloud services and network infrastructure.

Credit to Angel Arribas Lopez (Associate Principal Cyber Analyst), Emma Foulger (Global Threat Research Operations Lead), Nathaniel Jones, SVP Global Threat Intelligence
Edited by Ryan Traill (Content Manager)

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Appendices

Darktrace Model Detections

Case 1

Anomalous File / Masqueraded File Transfer from New External Endpoint

Anomalous File / Script from Rare External Location

Anomalous File / EXE from Rare External Location

Anomalous File / Script and EXE from Rare External

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Anomalous Connection / Rare External SSL Self-Signed

Compromise / New or Repeated to Unusual SSL Port

Compromise / Large Number of Suspicious Failed Connections

Device / Initial Attack Chain Activity

Antigena / Network / External Threat::Antigena Suspicious File Block

Antigena / Network / Significant Anomaly::Antigena Enhanced Monitoring from Client Block

Antigena / Network / Significant Anomaly::Antigena Controlled and Model Alert

Antigena / Network / External Threat::Antigena File then New Outbound Block

Antigena / Network / Significant Anomaly::Antigena Significant Anomaly from Client Block

Antigena / Network / Significant Anomaly::Antigena Alerts Over Time Block

Case 2

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Compromise / High Volume of Connections with Beacon Score

Compromise / Large Number of Suspicious Failed Connections

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Indicators of Compromise (IoCs)

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Case 1

                                                                                                                                                                                                                                                 
IoCTypeDescription + Confidence
onedrive[.]cvHostnameLikely C2 server
138.124.123[.]87IP AddressPossible C2 server
hXXp://onedrive[.]cv/Downloads/CURP/ReportFinal.%E2%80%AE%E1%BA%9D%D4%81%EF%BD%90.scrURIPossible payload
google.services[.]ugHostnameLikely C2 server
77.110.127[.]205IP AddressLikely C2 server
google.services[.]ug:57666Hostname + PortLikely C2 communication
google.services[.]ug:57888Hostname + PortLikely C2 communication
google.services[.]ug:56001Hostname + PortLikely C2 communication

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Case 2

IoC Type Description + Confidence
192.229.115[.]229 IP Address Likely C2 communication
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About the author
Angel Arribas Lopez
Associate Principal Cyber Analyst

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September 30, 2026

A Chain Reaction: Blockchain-Hosted Infostealer Campaign Targets Windows and macOS

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Key Insights

  • Darktrace detected a blockchain-hosted infostealer campaign targeting Windows and macOS devices across multiple customer environments.
  • The campaign combined ClickFix social engineering with trusted services and decentralized blockchain infrastructure to support malware delivery and C2 activity.
  • Compromised devices were observed connecting to rare and unusual external endpoints, including DGA C2 domains, blockchain-related endpoints, and cryptocurrency mining infrastructure.
  • The activity was associated with information-stealing malware strains including Atomic macOS Stealer (AMOS), Lumma, Rhadamanthys, Vidar, and Phexia.
  • Darktrace identified anomalous device behavior, beaconing patterns, rare external connections, cryptomining activity, and suspicious TLS/SSL communications without relying solely on prior knowledge or static indicators of compromise.
  • The campaign highlights how attackers are increasingly using legitimate and decentralized infrastructure to make detection, disruption, and attribution more challenging for defenders.

The Infostealer Ecosystem

The information stealer malware ecosystem continues to grow in value for threat actors across the digital threat landscape. Infostealers are increasingly delivered through Malware-as-a-Service (MaaS) operating models, distributed through affiliate networks, and designed to withstand infrastructure takedowns. This resilience was demonstrated by the recent takedown of Lumma Stealer malicious domains by Microsoft’s Digital Crimes Unit (DCU) [1].

Infostealers are used to gather and exfiltrate sensitive information, including non-human identity (NHI) data, from compromised systems across cloud, Software-as-a-Service (SaaS), Virtual Private Network (VPN), and development environments. They can also support ransomware operations by expanding the credentials and access paths available to threat actors, contributing to the high volume of identity-based attacks observed across the broader threat landscape [2][3].

Darktrace’s Observations of ClickFix and Infostealers

Throughout 2026, Darktrace has observed multiple campaigns using ClickFix social engineering to trick users into carrying out malicious actions and downloading initial payloads, including information stealers. More recently, Darktrace’s Threat Research team identified a specific ClickFix campaign involving a blockchain-hosted infostealer targeting Windows and macOS devices.

Darktrace identified affected customer environments across Europe, the United States, Asia, and the Middle East where blockchain-hosted infostealer malware appears to have been delivered to compromised systems following likely ClickFix-driven initial access. Darktrace investigated the activity and found that decentralized blockchain infrastructure, alongside widely trusted legitimate services, was used to support malware delivery and information theft across Windows and macOS systems.

Following initial access, compromised systems established C2 communication, with C2 configuration and payloads hosted on public blockchain infrastructure. The ultimate objective appears to be credential and cryptocurrency theft through the deployment of information stealers such as Atomic macOS Stealer (AMOS), Lumma, Rhadamanthys, and Vidar [5][6][7].

Darktrace’s Investigation

Affected devices across the Darktrace customer base were observed making outbound connections to rare external endpoints in patterns consistent with beaconing and C2 activity. Darktrace primarily detected devices making repeated connections to algorithmically generated domains (DGA) such as hf98x4d[.]site [8]. In many cases, these domains were linked through open-source intelligence (OSINT) to information-stealing malware families including AMOS and Phexia [5][6][7][8][9].

In multiple cases, devices were also observed connecting to blockchain-related endpoints, such as polygon[.]drpc[.]org, as well as legitimate public services, including GitHub. The use of decentralized blockchain infrastructure and trusted services such as GitHub to facilitate malware distribution and C2 activity can make disruption and attribution significantly more difficult for defenders.

Darktrace also detected a significant proportion of impacted devices making outbound connections to cryptocurrency mining infrastructure associated with the legitimate open-source XMRig mining software and the HashVault mining pool, including pool.hashvault[.]pro and donate[.]ssl[.]xmrig[.]com, which were abused by the attackers, indicating, including pool.hashvault[.]pro and donate[.]ssl[.]xmrig[.]com, indicating active cryptomining on compromised systems.

In one case, mining activity was observed before and during connections to the DGA endpoint hf98x4d[.]site. Due to its highly anomalous nature, Darktrace's Real-Time AI Analyst autonomously investigated the activity as it occurred, correlating the two events into a single cryptocurrency mining incident and providing comprehensive visibility into the broader attack.

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Figure 1: Real-Time AI Analyst investigation of suspicious SSL and C2 communications with hf98x4d[.]site over port 443.

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Figure 2: Real-Time AI Analyst investigation into cryptocurrency mining activity involving pool[.]hashvault[.]pro over SSL on port 443.

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Around the same time, Darktrace identified the same device initiating connections to the GitHub endpoint release-assets[.]githubusercontent[.]com while continuing to make repeated connections to hf98x4d[.]site.

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Figure 3: Darktrace's detection of an affected device connecting to a GitHub endpoint between repeated connections to the anomalous external endpoint hf98x4d[.]site.

On the network of another customer, Darktrace observed an affected device making highly unusual outbound connections consistent with beaconing activity. The device initiated multiple connections over port 443 to the external hostname polygon[.]drpc[.]org. According to OSINT, this hostname is a Remote Procedure Call (RPC) endpoint provided by dRPC, a legitimate service enabling decentralized applications (dApps), cryptocurrency wallets, and developer tools to interact with the Polygon blockchain [10].

The same device was later observed making repeated TLS/SSL connections to the previously mentioned DGA C2 domain. In addition, it made outbound connections to the external IP 195.242.214[.]34 over destination port 51820, an endpoint associated with the ProtonVPN service. Collectively, these connections to blockchain-related infrastructure, the DGA C2 domain, and ProtonVPN-associated infrastructure suggested the device had been affected by the campaign.

Conclusion

This campaign demonstrates how attackers can combine ClickFix social engineering with trusted services and decentralized blockchain infrastructure to create a resilient, cross-platform malware delivery chain. By using services such as GitHub alongside blockchain RPC endpoints and rapidly replaceable DGA domains, the activity can blend into legitimate traffic while making infrastructure disruption and attribution more difficult.

For defenders, it’s a reminder that trusted infrastructure does not automatically mean trusted activity. Security teams should look for the behaviors surrounding these connections, including unusual outbound communication, repeated beaconing, unexpected access to blockchain services, suspicious TLS/SSL activity and cryptomining. In this campaign, Darktrace identified and correlated these deviations without depending solely on previously known indicators, providing visibility as affected devices moved between legitimate services, decentralized infrastructure and malicious C2 endpoints

Credit to Nahisha Nobregas (Associate Principal Cyber Analyst), Manoel Kadja (Senior Cyber Analyst)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

▪ Compromise / Beaconing Activity To External Rare

▪ Compromise / Beacon to Young Endpoint

▪ Compromise / Fast Beaconing to DGA

▪ Compromise / High Volume of Connections with Beacon Score

▪ Compromise / DGA Beacon

▪ Compromise / Slow Beaconing Activity To External Rare

▪ Compromise / Agent Beacon (Long Period)

▪ Compromise / Agent Beacon (Medium Period)

▪ Compromise / Sustained SSL or HTTP Increase

▪ Compromise / Large Number of Suspicious Failed Connections

▪ Compromise / SSL Beaconing to Rare Destination

▪ Compromise / Beacon for 4 Days

▪ Compromise / High Priority Crypto Currency Mining

▪ Compromise / Monero Mining

▪ Device / Long Agent Connection to New Endpoint

▪ Device / New Connections On Suspicious Port

▪ Anomalous Connection / High Volume of Connections to Rare Domain

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List of Indicators of Compromise (IoCs)

 
Indicator Description
hf98x4d[.]site C2 Endpoint (Hostname)
sj98xe4[.]xyz C2 Endpoint (Hostname)
citcix6[.]xyz C2 Endpoint (Hostname)
bduwih8[.]pro C2 Endpoint (Hostname)

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MITRE ATT&CK Mapping

 
Tactic (ID) Technique
Persistence (T1176) Browser Extensions (T1176.001)
Persistence (T1176) Software Extensions
Command and Control (T1071) Web Protocols (T1071.001)
Command and Control (T1568) Domain Generation Algorithms (T1568.002)
Command and Control (T1071) Application Layer Protocol
Command and Control (T1102) One-Way Communication (T1102.003)
Command and Control (T1571) Non-Standard Port
Command and Control (T1104) Multi-Stage Channels
Command and Control (T1573) Encrypted Channel
Command and Control (T1008) Fallback Channels
Initial Access ICS (T0862) Supply Chain Compromise
Command and Control ICS (T0885) Commonly Used Port
Collection (T1185) Browser Session Hijacking
Impact (T1496) Compute Hijacking (T1496.001)
Impact (T1496) Resource Hijacking
Command and Control (T1071) Publish/Subscribe Protocols (T1071.001)
Lateral Movement (T1210) Exploitation of Remote Services

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References:

1.        https://www.microsoft.com/en-us/security/blog/2025/05/21/lumma-stealer-breaking-down-the-delivery-techniques-and-capabilities-of-a-prolific-infostealer/

2.        https://spycloud.com/resource/report/spycloud-annual-identity-exposure-report-2026/

3.        https://www.darktrace.com/blog/why-trust-is-the-new-attack-surface-darktraces-mid-year-threat-update-2026

4.        https://www.darktrace.com/blog/unpacking-clickfix-darktraces-detection-of-a-prolific-social-engineering-tactic

5.        https://abekweng.medium.com/inside-a-blockchain-hosted-malware-campaign-targeting-windows-and-macos-f5bcdeffed66

6.        https://cloud.google.com/blog/topics/threat-intelligence/unc5142-etherhiding-distribute-malware

7.        https://haveibeensquatted.com/blog/from-typosquatting-to-macos-backdoor-clickfix-blockchain-c2

8.        https://www.virustotal.com/gui/domain/hf98x4d.site/community

9.        https://x.com/FABO97662188/status/2074125545026244795

10.  https://www.virustotal.com/gui/url/b0e5c51a411065864119c305fddf218b7c120731f655932cc1c3307ad5b43f94/gti-summary

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About the author
Nahisha Nobregas
SOC Analyst
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