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May 25, 2022

Multi-Account Compromise in Office 365

Learn how internal phishing can compromise accounts swiftly & how Darktrace/Apps can prevent future attacks effectively.
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
Laura Leyland
Cyber Analyst
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25
May 2022

In February 2022, Darktrace detected the compromise of three SaaS accounts within a customer’s Office 365 environment. This incident provides an effective use case for highlighting how Darktrace/Apps and Darktrace/Email can work together to alert to unusual logins, app permission changes, new email rules and outbound spam. It also emphasizes an instance where Darktrace RESPOND/Apps could have been set to autonomous mode and stopped additional compromise.

Account Compromise Timeline

February 9 2022

Account A was logged into from a rare IP from Nigeria with the BAV2ROPC user agent which is commonly associated with SaaS account attacks. BAV2ROPC stands for ‘Basic Authentication Version 2 Resource Owner Password Credential’ and is commonly used by old email apps such as iOS Mail. It is often seen in SaaS/email account compromises where accounts have ‘legacy authentication’ enabled. This is because, even if multi-factor authentication (MFA) is activated, legacy protocols like IMAP/POP3 are not configured for MFA and so do not result in an MFA notification being sent.[1][2]

Account A then created a new email rule which was named as a single full stop. Attackers commonly create new email rules to give themselves persistent access by using the ability to forward certain emails to external email accounts they own. This means that even if the account’s password is changed or MFA is turned on, the attacker keeps getting the forwarded emails as long as the rule remains in place. In this case, the attacker configured the new email rule using the following fields and features:

  • AlwaysDeleteOutlookRulesBlob – hides any warning messages when using Outlook on the web or Powershell to edit inbox rules. It is likely that the attacker had a set list of commands to run and didn’t want to be slowed down in the exploitation of the account by having to click confirmation messages.
  • Force – hides warning or confirmation messages.
  • MoveToFolder – moves emails to a folder. This is often used to move bounced emails away from the inbox in order to hide the fact the account is being used to send emails by the attacker.
  • Name – specifies the name of the rule, in this case a single full stop.
  • SubjectOrBodyContainsWords – emails with key words are actioned.
  • StopProcessingRules – determines whether subsequent rules are processed if the conditions of this rule are met. It is likely in this case the attacker set this to false so that any subsequent rules would still be processed to avoid raising suspicion.

Account A was then observed giving permission to the email management app Spike. This was likely to allow the rapid automated exploitation of the compromised account. Attackers want to speed up this process to reduce the time between account compromise and malicious use of the account, thus reducing the time security teams have to respond.

Figure 1: Screenshot from SaaS console showing the timeline of giving consent to the email management application Spike and the creation of the new inbox rule

The account was then observed sending 794 emails over a 15 minute period to both internal and external recipients. These emails shared similar qualities including the same subject line and related phishing links. This mass spam was likely due to the attacker wanting to compromise as many accounts and credentials as possible within the shortest timeframe. The domain of the link sent in the emails was spikenow[.]com and was hidden by the text ‘View Shared Link’. This suggests that the attacker used Spike to send the emails and host the phishing link.

Figure 2: Screenshot of AGE UI showing the spike in outbound messages from the compromised account – the messages all appear to be the same format
Figure 3: Screenshot from Darktrace/Email of the link and text that masked the link: ‘View Shared File’

Within 15 minutes of this large volume of outbound email from Account A, Account B was accessed from the same rare IP located in Nigeria. Account B also created a new email rule which was named a single full stop. In addition to the previous rules, the following rules were observed:

  • From – specifies that emails from certain addresses will be processed by the rule.
  • MarkAsRead – specifies that emails are to be marked as read.

Due to the short timeframe between the phishing emails and the anomalous behavior from Account B, it is possible that Account B was an initial phishing victim.

Figure 4: Screenshot of the SaaS console showing Account B login failures, then successful login and inbox rule creation from the rare Nigerian IP

February 10 2022

The next day, a third account (Account C) was also accessed from the same rare IP. This occurred on two occasions, once with the user agent Mozilla/5.0 and once with BAV2ROPC. After the login at 13:08 with BAV2ROPC, the account gave the same permission as Account A to the email management app Spike. It then created what appears to be the same email rule, named a single full stop. As with Account B, it is possible that this account was compromised by one of the phishing emails sent by Account A.

Figure 5: Timeline of key incidents with Darktrace/Apps actions

Whilst the motive of the threat actor was unclear, this may have been the result of:

  • Credential harvesting for future use against the organization or to sell to a third party.
  • Possible impersonation of compromised users on professional websites (LinkedIn, Indeed) to phish further company accounts:
  • Fake accounts of one user were discovered on LinkedIn.
  • Emails registering for Indeed for this same user were seen during compromise.

How did the attack bypass the rest of the security stack?

  • Compromised Office 365 credentials, combined with the use of the user agent BAV2ROPC meant MFA could not stop the suspicious login.
  • RESPOND was in Human Confirmation Mode and was therefore not confirmed to take autonomous action, showing only the detections. Disabling Account A would likely have prevented the phishing emails and the subsequent compromise of Accounts B and C.
  • The organization was not signed up to Darktrace Proactive Threat Notifications or Ask The Expert services which could have allowed further triage from Darktrace SOC analysts.

Cyber AI Analyst Investigates

Darktrace’s Cyber AI Analyst automates investigations at speed and scale, prioritizing relevant incidents and creating actionable insights, allowing security teams to rapidly understand and act against a threat.

In this case, AI Analyst automatically investigated all three account compromises, saving time for the customer’s security team and allowing them to quickly investigate the incident themselves in more detail. The technology also highlighted some of the viewed files by the compromised accounts which was not immediately obvious from the model breaches alone.

Figure 6: Screenshot of AI Analyst for Account A
Figure 7: Screenshot of AI Analyst for Account B
Figure 8: Screenshot of AI Analyst for Account C

Darktrace RESPOND (Antigena) actions

The organization in question did not have RESPOND/Apps configured in Active Mode, and so it did not take any action in this case. The table below shows the critical defensive actions RESPOND would have taken.[3]

Nonetheless, we can see what actions RESPOND would have taken, and when, had the technology been enabled.

The above tables illustrate that all three users would have been disabled during the incident had RESPOND been active. The highlighted row shows that Account A would have been disabled when the internal phishing emails were sent and possibly then prevented the cascade of compromised email accounts (B and C).

Conclusion

SaaS accounts greatly increase a company’s attack surface. Not only is exploitation of compromised accounts quick, but a single compromised account can easily lead to further compromises via an internal phishing campaign. Together this reinforces the ongoing need for autonomous and proactive security to complement existing IT teams and reduce threats at the point of compromise. Whilst disabling ‘legacy authentication’ for all accounts and providing MFA would give some extra protection, Darktrace/Apps has the ability to block all further infection.

Credit to: Adam Stevens and Anthony Wong for their contributions.

Appendix

List of Darktrace Model Detections

User A – February 9 2022

  • 04:55:51 UTC | SaaS / Access / Suspicious Login User-Agent
  • 04:55:51 UTC | SaaS / Access / Unusual External Source for SaaS Credential Use
  • 04:55:52 UTC | Antigena / SaaS / Antigena Suspicious SaaS and Email Activity Block
  • 04:55:52 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block
  • 14:16:48 UTC | SaaS / Compliance / New Email Rule
  • 14:16:48 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 14:16:49 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 14:16:49 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block
  • 14:45:06 UTC | IaaS / Admin / Azure Application Administration Activities
  • 14:45:07 UTC | SaaS / Admin / OAuth Permission Grant
  • 14:45:07 UTC | Device / Multiple Model Breaches
  • 14:45:08 UTC | SaaS / Compliance / Multiple Unusual SaaS Activities
  • 15:03:25 UTC | SaaS / Email Nexus / Possible Outbound Email Spam
  • 15:03:25 UTC | SaaS / Compromise / Unusual Login and Outbound Email Spam

User B – February 9 2022

  • 15:18:21 UTC | SaaS / Compliance / New Email Rule
  • 15:18:21 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 15:18:22 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 15:18:22 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block

User C – February 10 2022

  • 14:25:20 UTC | SaaS / Admin / OAuth Permission Grant
  • 14:38:09 UTC | SaaS / Compliance / New Email Rule
  • 14:38:09 UTC | SaaS / Compromise / Unusual Login and New Email Rule
  • 14:38:10 UTC | Antigena / SaaS / Antigena Significant Compliance Activity Block
  • 14:38:10 UTC | Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Refrences

1. https://www.ncsc.gov.uk/guidance/phishing#section_3

2. https://www.bleepingcomputer.com/news/security/microsoft-scammers-bypass-office-365-mfa-in-bec-attacks/

3. https://customerportal.darktrace.com/product-guides/main/antigena-saas-inhibitors

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
Laura Leyland
Cyber Analyst

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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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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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