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June 9, 2021

Multi-Account Hijack Detection with AI

Discover the analysis of a sophisticated SaaS-based attack using Microsoft 365 accounts. Learn how attackers launch & maintain their offensive strategies.
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
Max Heinemeyer
Global Field CISO
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09
Jun 2021

The widespread and rapid adoption of Software-as-a-Service (SaaS) has opened up a breadth of security risks for IT teams. Unlike commercial off-the-shelf (COTS) software, SaaS security tends to be managed by third-party vendors rather than the end customer. Security teams therefore struggle with reduced visibility and control over these environments, and cyber-criminals have been quick to take advantage, launching a wave of cloud-based attacks, from Vendor Email Compromise to internal account hijacks.

Attackers often gain access to multiple accounts on the same domain, enabling them to attack from multiple angles, for example sending of hundreds of emails from one account, while maintaining persistence with another. This gives the hacker an opportunity to try multiple attack vectors, using tools native to the SaaS environment as well as external payloads.

While preventative controls such as Multi-Factor Authentication (MFA) provide an extra layer of protection, there are many techniques available to circumvent zero-trust approaches. Remote and flexible working is set to continue to varying degrees across many different regions and industries, so companies must now commit to securing their cloud architecture and developing proactive cyber security measures.

In this blog, we will analyze a persistent cyber-attack which targeted a real estate company in Europe and leveraged several compromised Microsoft 365 accounts. These SaaS takeovers are quickly becoming the new norm, but they are still misunderstood and poorly documented in the wider industry. Cyber AI detected every stage of this intrusion in real time, without the use of signatures or static rules.

A and B: Hijacking Microsoft 365 accounts

The organization had around 5,000 devices in its environment, with 1,000 active SaaS accounts. The timeline below shows how the threat actor leveraged the SaaS accounts of five different users to carry out the operation, as well as exploiting several other accounts on the final day.

Figure 1: Diagram of the infection chain, which occurred over three days. On the fourth day, the attacker tried again but was unsuccessful.

The actor initially compromised at least two SaaS credentials – which we’ll refer to here simply as ‘account A’ and ‘account B’ – and logged in from several unusual geographical locations, presumably using a VPN. Darktrace detected this as unusual login events for the SaaS accounts.

In account A, the attacker was observed previewing files likely to contain customer information, but did not perform any other follow-up activity. In account B, they set a new inbox rule three hours after the initial compromise, resulting in a high-severity alert.

At around this time, the threat actor sent a number of phishing emails from account B: emails that appeared to be sharing a harmless and legitimate-looking folder on OneDrive. The link probably led to a fake Microsoft login page, similar to the below, which could have recorded the victims’ credentials and sent them directly back to the attacker.

Figure 2: A seemingly legitimate Microsoft login page.

The phishing attempt was detected by Antigena Email, Darktrace’s email security technology. Antigena was in passive mode at the time, and so was not configured to take action on these threatening emails. But taking into account the highly anomalous sender surge coupled with the unusual login locations, it would have autonomously intercepted all the emails, reducing the impact of the attack.

The attacker was subsequently locked out of account B. After this, they tried (and failed) to use a legacy user agent to bypass any MFA which may have been enforced on the account. Darktrace detected this as a suspicious login and blocked the attempt.

Accounts C, D and E: The threat develops

The next day, the actor logged into a new account (account C) from the same autonomous system number (ASN), indicating that the account had been infected by the OneDrive phishing emails. In other words, the attacker had leveraged account B to compromise new users in the organization and ensure multiple points of intrusion.

Darktrace detected each stage of this, piecing together the different events into one meaningful security narrative.

Figure 3: Anomalous activity from accounts C, D, and E.

Account C was then used to preview a file likely containing contact information.

After being locked out of account C when trying to log in the next day, the hacker worked their way through two more accounts (account D and account E), which they had hijacked in the previous phishing attempts. They were locked out each time after generating alerts due to the unusual logins and new inbox rules created around the same time.

A to Z: End of the line

Running out of options, the attacker decided to go back to account A and set a new inbox rule, using it to send new phishing emails with a link to a non-Microsoft cloud storage domain (Tresorit). Again, Darktrace recognized this as highly unusual behavior, and the hacker was promptly locked out of the account.

During this burst of activity, Darktrace also observed a Microsoft Teams session from one of the suspicious ASNs. This was likely a social engineering attempt and another possible attack vector. Microsoft Teams could have been leveraged to share a malicious link over instant message, extract sensitive information, or send spam internally and externally on the chat function.

The threat actor could have then used this to pivot across various applications and accounts, assuming that the company had a siloed security approach – with different tools for cloud, SaaS, email, and endpoint – and so could not pick up on the malicious cross-platform movement.

On the following day, the attacker attempted logins on multiple accounts again, but with no success. Cyber AI had pinpointed all the anomalous activity – no matter where it originated – and alerted the security team immediately.

SaaS attack under the microscope

Multi-account compromises can be incredibly persistent and are difficult for traditional security tools to identify. The hacker used several tactics to circumvent the customer’s existing email security products:

  1. The initial use of two compromised credentials – account A and account B – allowed the hacker to stay under the radar and not raise too much suspicion on a single account. Account A was kept quiet until other avenues had been exhausted.
  2. Activity was generated from multiple ASNs in at least three different geographical locations, probably utilizing a VPN: one in Africa where much of the activity originated, and two in North America, including some widely used ASNs which were highly unusual for the customer.
  3. The attacker entirely used Microsoft services until the final emails, choosing to ‘live off the land’ rather than sending links that may have been caught by gateways.
  4. The attacker logged into Microsoft Teams in their final movements – a fairly benign-looking event which could have been used to compromise more accounts and move laterally, and would have gone undetected.

Darktrace identified every stage of the attack – including spotting the anomalous ASNs – and launched an automatic, in-depth investigation with Cyber AI Analyst. The organization was thus able to take action before the damage was done.

Figure 4: Darktrace’s SaaS console gives a clear overview of activity across all different applications.

ABCs of SaaS security

The approach of using various accounts to mount the offensive, while keeping one to maintain persistence, prolonged this intrusion. Such tactics will likely be seen again in the near future.

Tracking the number of factors involved in an attack with multiple credentials, multiple attack vectors, and multiple attacker-IPs, is a serious challenge. In these situations, it is essential to have a security solution which can detect activity across different applications, forming a unified and holistic understanding over the entire digital enterprise.

While not active in this case, Antigena SaaS would have taken autonomous action and prevented the threat from escalating by enforcing normal behavior, stopping the hacker from logging in from malicious infrastructure or performing any out-of-character SaaS actions, such as creating new inbox rules.

Following the intrusion, the company decided to adopt Antigena SaaS, which now mitigates their cloud security risks and guards against sensitive data loss and reputational damage.

Thanks to Darktrace analyst Daniel Gentle for his insights on the above threat find.

Darktrace model detections:

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compliance / New Email Rule
  • SaaS / Unusual Activity / Unusual External Source for SaaS Credential Use
  • SaaS / Access / Suspicious Login Attempt
  • Antigena Email: Unusual Login Location + Sender Surge
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
Max Heinemeyer
Global Field CISO

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June 2, 2026

Stopping Stealth Attacks with Precision: How Núclea Prevented a Breach Without Disruption

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Núclea is a Brazilian data and technology company that supports the country’s financial system by delivering digital services exclusively to banks and financial institutions. Operating in an environment where trust, availability, and data integrity are critical, the company faces a threat landscape that has evolved rapidly—particularly with the rise of AI-driven cyberattacks.

Brazil has experienced a wave of successful cyber incidents targeting financial institutions, many of them enabled by insiders or compromised credentials. The result was a noticeable shift in attacker strategy: instead of focusing on end customers, threat actors began targeting the institutions and platforms that underpin the financial ecosystem itself.

“Attacks became far more directed and contextual,” explains Guilherme, who leads incident response within Núclea’s security platform engineering team. “They weren’t noisy or obviously malicious—they were precise, patient, and designed to blend into normal operations.”

That precision was on full display in January 2026, when Núclea faced one of the most convincing phishing attacks the team had seen.

A real attack, built on trust and context

The attack began with a seemingly routine email.

It was sent from a real Brazilian government institution, using legitimate infrastructure and valid credentials that were later confirmed to have been compromised. Núclea had an established, ongoing relationship with this organization, and the email’s language, tone, and subject matter aligned perfectly with the type of communication the recipient team handled every day.

Attached to the email was a PDF document containing content that looked entirely legitimate.

The problem? A single URL embedded inside that PDF.

“The message itself was correct. The sender was real. The context was familiar. Even the document content made sense,” Guilherme explains. “There was just one small element that didn’t belong.”

That small detail was enough to initiate a full attack chain.

What the attackers were trying to do

If clicked, the URL would have downloaded a malicious payload designed to:

  • Collect information about the user and device
  • Identify where the system was located within the financial ecosystem
  • Install remote access tools to maintain control
  • Deploy an infostealer to extract sensitive data
  • Execute anti-forensic scripts to erase traces of the intrusion

In other words, it was a carefully engineered operation designed for persistence and stealth, not immediate disruption.

The attack also employed urgency—a classic social engineering technique. When the link didn’t open as expected, employees requested assistance from the security team, insisting the document was important and needed to be accessed quickly.

This is precisely the kind of scenario where traditional security tools struggle: almost everything about the interaction is legitimate.

Where Darktrace made the difference

Instead of blocking the entire message or relying on known indicators of compromise, Darktrace focused on behavioral context.

Darktrace recognized:

  • That the sending organization was normally trusted
  • That the communication pattern matched historical behavior
  • That the PDF content itself was not suspicious

But it also identified that the URL embedded within the document deviated from established behavioral patterns.

Rather than disrupting business operations, Darktrace took precise action: it rewrote the URL, preventing the malicious download while leaving the rest of the email untouched.

“When we analyzed it afterward, it became clear how dangerous the attack would have been,” says Guilherme. “But it never progressed—because Darktrace acted at exactly the right point.”

Subsequent forensic analysis confirmed the payload’s malicious intent. The attack never succeeded.

Precision over disruption

For Núclea, this incident reinforced a critical lesson: modern attacks don’t always look malicious—they hide within normal activity.

“What stands out to me is the precision,” Guilherme says. “Darktrace doesn’t rely on big, obvious signals. It’s effective in situations that fall outside the standard patterns we all know.”

Building resilience in a high trust ecosystem

For Núclea, cybersecurity is not just a defensive measure—it’s a business enabler.

Availability failures or successful breaches in the financial ecosystem can have immediate, large-scale consequences, from financial loss to reputational damage. Preventing those outcomes protects not just Núclea, but its partners and customers as well.

“Cyber resilience means keeping the business running—even under attack,” Guilherme explains. “And that requires people, processes, and technology working together.”

As AI continues to accelerate both attacks and defenses, the role of security is evolving. Precision, behavioral understanding, and intelligent automation are no longer optional—they’re essential.

“The easy days were yesterday,” Guilherme says. “The challenges ahead are bigger. We need to be prepared—internally and with partners that help us build resilience.”

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About the author
Mariana Pereira
VP, Field CISO

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June 1, 2026

Defend What You Trust: Stories from the Front Lines of Modern Cyber Defense

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Modern attacks don’t always announce themselves, follow obvious patterns, or rely on known malware. Often, they move quietly inside trusted systems, authenticated sessions, and everyday behavior.

They don’t break in. They blend in.

That’s why an AI-powered defense is essential. It turns invisible signals into actionable insights at a scale neither analysts nor traditional tools can achieve alone.

Confidence is creating risk

One of the most dangerous assumptions in cybersecurity today is that strong controls equal strong protection.

Multi-factor authentication (MFA), for example, is widely viewed as a foundational safeguard. But as the CISO for a professional sports organization explains, that confidence can be misplaced. “A lot of organizations assume that once you have MFA, those accounts are safe. That’s not true.”

In one instance, his team identified a sophisticated attack where a threat actor bypassed MFA entirely, not by breaking it, but by going around it. A user’s authenticated session was hijacked and re-used, allowing the attacker to impersonate them without triggering traditional controls.

“Darktrace picked up that a session had been re-injected by the hacker, and we were able to block it right away,” he explains.

Attackers anticipate what we miss

Even well-trained users can become entry points.

“An email bypassed our existing security tools,” shares the VP of IT at a U.S.-based risk management services provider.  “The user missed one signal and entered their credentials into a malicious site. That’s what the bad guys count on.”

The organization responded quickly, but not before damage was done. Crucially, this occurred while Darktrace was in “watch mode,” before autonomous response was fully enabled. “Darktrace would have seen that and shut it down immediately,” he notes.

Mistakes and oversights like misconfigurations, forgotten machines, and missed patches can create serious vulnerabilities.

The CIO of a utility services organization shares an instance when Darktrace detected a breach to a client’s network via their ZTNA VPN due to misconfigured MFA. “Darktrace alerted us and autonomously blocked the scanning, preventing what could have been a ransomware-type incident.”  

The most dangerous threats are already inside

The Head of Security at a global business services provider knows firsthand how blind spots can persist inside environments. His team uncovered evidence of dormant ransomware artifacts sitting unnoticed within a company’s environment ¬¬– long before modern detection was in place.

“During a routine file transfer, Darktrace flagged the suspicious activity, identified the ransomware, and immediately quarantined the server,” he recalls.  While the attack was never executed, the implication was significant: the risk existed long before it was finally detected.

Cyber threats are also successful because they take advantage of normal human behavior, exploiting moments of cognitive overload, urgency, and trust.

The Executive Director of IT and Business Applications at a pharmaceutical lab describes the time Darktrace flagged an employee logging into Microsoft 365 from Singapore, despite him being physically located in the U.S. Darktrace immediately cut off his access and within minutes revealed that the employee’s son was using a VPN to play a video game.

While the threat was benign, it demonstrated the strength of AI to use contextual information to detect threats other tools miss. The information also saved security analysts hours of investigation and minimized downtime for the employee. “That level of precision and speed isn’t just convenient, it’s game changing.”

“Unusual” behavior is the new red flag

Detecting modern threats requires an understanding of what “normal” looks like and recognizing when something subtly deviates.

One security leader  at an AI technology enterprise described a scenario in which an employee connected to a proxy service in China. The service itself was legitimate, and although traditional tools didn’t flag it, the behavior was unusual for that user specifically.

“That’s what Darktrace picked up on. The activity turned out to be benign, but without visibility into behavioral deviations, it could just as easily have been something more serious.”

AI shifts defense from reaction to anticipation

These stories point to a fundamental shift by cyber attackers, both tactically and strategically. Because traditional security tools were built to detect what’s already known, modern attacks are often:

  • Credential-based, not malware-based
  • Behavioral, not signature-based
  • Subtle, not overt

They may operate within the boundaries of what appears normal, exploiting what organizations trust, not what they block:

  • Trusted sessions
  • Legitimate services
  • Human error

This is where AI is changing the equation. Rather than relying on predefined rules or known threat signatures, AI can:

  • Establish a baseline of normal behavior
  • Detect subtle anomalies in real time
  • Act autonomously to contain potential threats

Resilience, not perfection, is the new security standard

As these frontline experiences show, the organizations that lead are those that move beyond reactive defense and embrace AI as a core part of their strategy.

It eliminates the blind spots and uncertainty, says the CISO of a professional sports organization. “If you lack visibility, you’re not managing risk, you’re assuming it. AI gives you the actionable insights needed to turn uncertainty into control.”

And it provides the speed and agility that are vital when seconds matter, says the Executive Director of IT and Business Applications. “When Darktrace alerted us at 3:00 am to a ransomware attack, it had already quarantined the affected systems, blocked the attacker’s access, and provided us with the critical details and time needed to investigate. That action likely saved us hundreds of thousands, if not millions, of dollars.”

The modern SOC has become a cornerstone of enterprise resilience, responsible for protecting data and operational continuity while enabling digital growth and innovation. For today’s security professional, that means success is no longer measured by what they keep out, but by what they protect: revenue, reputation, and trust.

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