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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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April 24, 2026

Email-Borne Cyber Risk: A Core Challenge for the CISO in the Age of Volume and Sophistication

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The challenge for CISOs

Despite continuous advances in security technologies, humans continue to be exploited by attackers. Credential abuse and social actions like phishing are major factors, accounting for around 60% of all breaches. These attacks rely less on technical vulnerabilities and more on exploiting human behavior and organizational processes. 

From my perspective as a former CISO, protecting humans concentrates three of today’s most pressing challenges: the sheer volume of email-based threats, their increasing sophistication, and the limitations of traditional employee awareness programs in moving the needle on risk. 

My personal experience of security awareness training as a CISO

With over 20 years’ experience as an ICT and Cybersecurity leader across various international organizations, I’ve seen security awareness training (SAT) in many guises. And while the cyber landscape is evolving in every direction, the effectiveness of SAT is reaching a plateau.  

Most programs I’ve seen follow a familiar pattern. Training is delivered through a combination of eLearning modules and internal sessions designed to reinforce IT policies. Employees are typically required to complete a slide deck or video, followed by a multiple-choice quiz. Occasional phishing simulations are distributed throughout the year.

The content is often static and unpersonalized, based on known threats that may already be outdated. Every employee regardless of role or risk exposure receives the same training and the same simulated phishing templates, from front-desk staff to the CEO.

The problem with traditional SAT programs

The issue with the approach to SAT outlined above is that the distribution of power is imbalanced. Humans will always be fallible, particularly when faced with increasingly sophisticated attacks. Providing generic, low-context training risks creating false confidence rather than genuine resilience. Let’s look at some of the problems in detail.

Timing and delivery

Employees today operate under constant cognitive load, making lots of rapid decisions every day to reduce their email volumes. Yet if employees are completing training annually, or on an ad hoc basis, it becomes a standalone occurrence rather than a continuous habit.  

As a result, retention is low. Employees often forget the lessons within weeks, a phenomenon known as the ‘Ebbinghaus Forgetting Curve.’

The graph illustrates that when you first learn something, the information disappears at an exponential rate without retention. In fact, according to the curve, you forget 50% of all new information within a day, and 90% of all new information within a week.  

Simultaneously, most training is conducted within a separate interface. Because it takes place away from the actual moment of decision-making, the "teachable moment" is lost. There is a cognitive disconnect between the action (clicking a link in Outlook) and the education (watching a video in a browser). 

People

In the context of professional risk management, the risks faced by different users are different. Static learning such as everyone receiving the same ‘Password Reset’ email doesn’t help users prepare for the specific threats they are likely to face. It also contributes to user fatigue, driven by repetitive training. And if users receive tests at the same time, news spreads among colleagues, hurting the efficacy of the test.  

Staff turnover introduces further risk. In many organizations, new employees gain access to systems before receiving meaningful training, reducing onboarding to little more than policy acknowledgment.

Measuring success

In my experience, solutions are standalone, without any correlation to other tools in the security stack. In some cases, the programs are delivered by HR rather than the security team, creating a complete silo.  

As a result, SAT is often perceived as a compliance exercise rather than a capability building function. The result is that poor-quality training does little to reduce the likelihood of compromise, regardless of completion rates or quiz performance.

What a modern SAT solution should look like

For today’s CISO, email represents the convergence point of high-volume, high-impact, and human-centric threats. Despite significant security investments, it remains one of the most difficult channels to secure effectively. Given these constraints, CISOs must evolve their approach to SAT.

Success lies in a balanced strategy one that combines advanced technology, attack surface reduction, and pragmatic user enablement, without over-relying on human vigilance as the final line of defense.

This means moving beyond traditional SAT toward continuous, contextual awareness, realistic simulations, and tight integration with security outcomes.

Three requirements for a modern SAT solution

  • Invisible protection: The optimum security solution is one that assists users without impeding their experience. The objective is to enhance human capabilities, rather than simply delivering a lecture. 
  • Real-time feedback: Rather than a monthly quiz, the ideal system would provide a prompt or warning when a user is about to engage with something suspicious. 
  • Positive culture: Shifting the focus away from a "gotcha" culture, which is a contributing factor to a resentment, and instead empowers employees to serve as "sensors" for the company. 

Discover how personalized security coaching can strengthen your human layer and make your email defenses more resilient. Explore Darktrace / Adaptive Human Defense.

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About the author
Karim Benslimane
VP, Field CISO

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April 21, 2026

How a Compromised eScan Update Enabled Multi‑Stage Malware and Blockchain C2

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The rise of supply chain attacks

In recent years, the abuse of trusted software has become increasingly common, with supply chain compromises emerging as one of the fastest growing vectors for cyber intrusions. As highlighted in Darktrace’s Annual Threat Report 2026, attackers and state-actors continue to find significant value in gaining access to networks through compromised trusted links, third-party tools, or legitimate software. In January 2026, a supply chain compromise affecting MicroWorld Technologies’ eScan antivirus product was reported, with malicious updates distributed to customers through the legitimate update infrastructure. This, in turn, resulted in a multi‑stage loader malware being deployed on compromised devices [1][2].

An overview of eScan exploitation

According to eScan’s official threat advisory, unauthorized access to a regional update server resulted in an “incorrect file placed in the update distribution path” [3]. Customers associated with the affected update servers who downloaded the update during a two-hour window on January 20 were impacted, with affected Windows devices subsequently have experiencing various errors related to update functions and notifications [3].

While eScan did not specify which regional update servers were affected by the malicious update, all impacted Darktrace customer environments were located in the Europe, Middle East, and Africa (EMEA) region.

External research reported that a malicious 32-bit executable file , “Reload.exe”, was first installed on affected devices, which then dropped the 64-bit downloader, “CONSCTLX.exe”. This downloader establishes persistence by creating scheduled tasks such as “CorelDefrag”, which are responsible for executing PowerShell scripts. Subsequently, it evades detection by tampering with the Windows HOSTS file and eScan registry to prevent future remote updates intended for remediation. Additional payloads are then downloaded from its command-and-control (C2) server [1].

Darktrace’s coverage of eScan exploitation

Initial Access and Blockchain as multi-distributed C2 Infrastructure

On January 20, the same day as the aforementioned two‑hour exploit window, Darktrace observed multiple devices across affected networks downloading .dlz package files from eScan update servers, followed by connections to an anomalous endpoint, vhs.delrosal[.]net, which belongs to the attackers’ C2 infrastructure.

The endpoint contained a self‑signed SSL certificate with the string “O=Internet Widgits Pty Ltd, ST=SomeState, C=AU”, a default placeholder commonly used in SSL/TLS certificates for testing and development environments, as well as in malicious C2 infrastructure [4].

Utilizing a multi‑distributed C2 infrastructure, the attackers also leveraged domains linked with the Solana open‑source blockchain for C2 purposes, namely “.sol”. These domains were human‑readable names that act as aliases for cryptocurrency wallet addresses. As browsers do not natively resolve .sol domains, the Solana Naming System (formerly known as Bonfida, an independent contributor within the Solana ecosystem) provides a proxy service, through endpoints such as sol-domain[.]org, to enable browser access.

Darktrace observed devices connecting to blackice.sol-domain[.]org, indicating that attackers were likely using this proxy to reach a .sol domain for C2 activity. Given this behavior, it is likely that the attackers leveraged .sol domains as a dead drop resolver, a C2 technique in which threat actors host information on a public and legitimate service, such as a blockchain. Additional proxy resolver endpoints, such as sns-resolver.bonfida.workers[.]dev, were also observed.

Solana transactions are transparent, allowing all activity to be viewed publicly. When Darktrace analysts examined the transactions associated with blackice[.]sol, they observed that the earliest records dated November 7, 2025, which coincides with the creation date of the known C2 endpoint vhs[.]delrosal[.]net as shown in WHOIS Lookup information [4][5].

WHOIS Look records of the C2 endpoint vhs[.]delrosal[.]net.
Figure 1: WHOIS Look records of the C2 endpoint vhs[.]delrosal[.]net.
 Earliest observed transaction record for blackice[.]sol on public ledgers.
Figure 2: Earliest observed transaction record for blackice[.]sol on public ledgers.

Subsequent instructions found within the transactions contained strings such as “CNAME= vhs[.]delrosal[.]net”, indicating attempts to direct the device toward the malicious endpoint. A more recent transaction recorded on January 28 included strings such as “hxxps://96.9.125[.]243/i;code=302”, suggesting an effort to change C2 endpoints. Darktrace observed multiple alerts triggered for these endpoints across affected devices.

Similar blockchain‑related endpoints, such as “tumama.hns[.]to”, were also observed in C2 activities. The hns[.]to service allows web browsers to access websites registered on Handshake, a decentralized blockchain‑based framework designed to replace centralized authorities and domain registries for top‑level domains. This shift toward decentralized, blockchain‑based infrastructure likely reflects increased efforts by attackers to evade detection.

In outgoing connections to these malicious endpoints across affected networks, Darktrace / NETWORK recognized that the activity was 100% rare and anomalous for both the devices and the wider networks, likely indicative of malicious beaconing, regardless of the underlying trusted infrastructure. In addition to generating multiple model alerts to capture this malicious activity across affected networks, Darktrace’s Cyber AI Analyst was able to compile these separate events into broader incidents that summarized the entire attack chain, allowing customers’ security teams to investigate and remediate more efficiently. Moreover, in customer environments where Darktrace’s Autonomous Response capability was enabled, Darktrace took swift action to contain the attack by blocking beaconing connections to the malicious endpoints, even when those endpoints were associated with seemingly trustworthy services.

Conclusion

Attacks targeting trusted relationships continue to be a popular strategy among threat actors. Activities linked to trusted or widely deployed software are often unintentionally whitelisted by existing security solutions and gateways. Darktrace observed multiple devices becoming impacted within a very short period, likely because tools such as antivirus software are typically mass‑deployed across numerous endpoints. As a result, a single compromised delivery mechanism can greatly expand the attack surface.

Attackers are also becoming increasingly creative in developing resilient C2 infrastructure and exploiting legitimate services to evade detection. Defenders are therefore encouraged to closely monitor anomalous connections and file downloads. Darktrace’s ability to detect unusual activity amidst ever‑changing tactics and indicators of compromise (IoCs) helps organizations maintain a proactive and resilient defense posture against emerging threats.

Credit to Joanna Ng (Associate Principal Cybersecurity Analyst) and Min Kim (Associate Principal Cybersecurity Analyst) and Tara Gould (Malware Researcher Lead)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

  • Anomalous File::Zip or Gzip from Rare External Location
  • Anomalous Connection / Suspicious Self-Signed SSL
  • Anomalous Connection / Rare External SSL Self-Signed
  • Anomalous Connection / Suspicious Expired SSL
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device

List of Indicators of Compromise (IoCs)

  • vhs[.]delrosal[.]net – C2 server
  • tumama[.]hns[.]to – C2 server
  • blackice.sol-domain[.]org – C2 server
  • 96.9.125[.]243 – C2 Server

MITRE ATT&CK Mapping

  • T1071.001 - Command and Control: Web Protocols
  • T1588.001 - Resource Development
  • T1102.001 - Web Service: Dead Drop Resolver
  • T1195 – Supple Chain Compromise

References

[1] https://www.morphisec.com/blog/critical-escan-threat-bulletin/

[2] https://www.bleepingcomputer.com/news/security/escan-confirms-update-server-breached-to-push-malicious-update/

[3] hxxps://download1.mwti.net/documents/Advisory/eScan_Security_Advisory_2026[.]pdf

[4] https://www.virustotal.com/gui/domain/delrosal.net

[5] hxxps://explorer.solana[.]com/address/2wFAbYHNw4ewBHBJzmDgDhCXYoFjJnpbdmeWjZvevaVv

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About the author
Joanna Ng
Associate Principal Analyst
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