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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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September 23, 2025

It’s Time to Rethink Cloud Investigations

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Cloud Breaches Are Surging

Cloud adoption has revolutionized how businesses operate, offering speed, scalability, and flexibility. But for security teams, this transformation has introduced a new set of challenges, especially when it comes to incident response (IR) and forensic investigations.

Cloud-related breaches are skyrocketing – 82% of breaches now involve cloud-stored data (IBM Cost of a Data Breach, 2023). Yet incidents often go unnoticed for days: according to a 2025 report by Cybersecurity Insiders, of the 65% of organizations experienced a cloud-related incident in the past year, only 9% detected it within the first hour, and 62% took more than 24 hours to remediate it (Cybersecurity Insiders, Cloud Security Report 2025).

Despite the shift to cloud, many investigation practices remain rooted in legacy on-prem approaches. According to a recent report, 65% of organizations spend approximately 3-5 days longer when investigating an incident in the cloud vs. on premises.

Cloud investigations must evolve, or risk falling behind attackers who are already exploiting the cloud’s speed and complexity.

4 Reasons Cloud Investigations Are Broken

The cloud’s dynamic nature – with its ephemeral workloads and distributed architecture – has outpaced traditional incident response methods. What worked in static, on-prem environments simply doesn’t translate.

Here’s why:

  1. Ephemeral workloads
    Containers and serverless functions can spin up and vanish in minutes. Attackers know this as well – they’re exploiting short-lived assets for “hit-and-run” attacks, leaving almost no forensic footprint. If you’re relying on scheduled scans or manual evidence collection, you’re already too late.
  2. Fragmented tooling
    Each cloud provider has its own logs, APIs, and investigation workflows. In addition, not all logs are enabled by default, cloud providers typically limit the scope of their logs (both in terms of what data they collect and how long they retain it), and some logs are only available through undocumented APIs. This creates siloed views of attacker activity, making it difficult to piece together a coherent timeline. Now layer in SaaS apps, Kubernetes clusters, and shadow IT — suddenly you’re stitching together 20+ tools just to find out what happened. Analysts call it the ‘swivel-chair Olympics,’ and it’s burning hours they don’t have.
  3. SOC overload
    Analysts spend the bulk of their time manually gathering evidence and correlating logs rather than responding to threats. This slows down investigations and increases burnout. SOC teams are drowning in noise; they receive thousands of alerts a day, the majority of which never get touched. False positives eat hundreds of hours a month, and consequently burnout is rife.  
  4. Cost of delay
    The longer an investigation takes, the higher its cost. Breaches contained in under 200 days save an average of over $1M compared to those that linger (IBM Cost of a Data Breach 2025).

These challenges create a dangerous gap for threat actors to exploit. By the time evidence is collected, attackers may have already accessed or exfiltrated data, or entrenched themselves deeper into your environment.

What’s Needed: A New Approach to Cloud Investigations

It’s time to ditch the manual, reactive grind and embrace investigations that are automated, proactive, and built for the world you actually defend. Here’s what the next generation of cloud forensics must deliver:

  • Automated evidence acquisition
    Capture forensic-level data the moment a threat is detected and before assets disappear.
  • Unified multi-cloud visibility
    Stitch together logs, timelines, and context across AWS, Azure, GCP, and hybrid environments into a single unified view of the investigation.
  • Accelerated investigation workflows
    Reduce time-to-insight from hours or days to minutes with automated analysis of forensic data, enabling faster containment and recovery.
  • Empowered SOC teams
    Fully contextualised data and collaboration workflows between teams in the SOC ensure seamless handover, freeing up analysts from manual collection tasks so they can focus on what matters: analysis and response.

Attackers are already leveraging the cloud’s agility. Defenders must do the same — adopting solutions that match the speed and scale of modern infrastructure.

Cloud Changed Everything. It’s Time to Change Investigations.  

The cloud fundamentally reshaped how businesses operate. It’s time for security teams to rethink how they investigate threats.

Forensics can no longer be slow, manual, and reactive. It must be instant, automated, and cloud-first — designed to meet the demands of ephemeral infrastructure and multi-cloud complexity.

The future of incident response isn’t just faster. It’s smarter, more scalable, and built for the environments we defend today, not those of ten years ago.  

On October 9th, Darktrace is revealing the next big thing in cloud security. Don’t miss it – sign up for the webinar.

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About the author
Kellie Regan
Director, Product Marketing - Cloud Security

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September 22, 2025

Understanding the Canadian Critical Cyber Systems Protection Act

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Introduction: The Canadian Critical Cyber Systems Protection Act

On 18 June 2025, the Canadian federal Government introduced Bill C-8 which, if adopted following completion of the legislative process, will enact the Critical Cyber Systems Protection Act (CCSPA) and give Canada its first federal, cross-sector and legally binding cybersecurity regime for designated critical infrastructure providers. As of August 2025, the Bill has completed first reading and stands at second reading in the Canadian House of Commons.

Political context

The measure revives most of the stalled 2022 Bill C-26 “An Act Respecting Cyber Security” which “died on Paper” when Parliament was prorogued in January 2025, in the wake of former Prime Minister Justin Trudeau’s resignation.

The new government, led by Mark Carney since March 2025, has re-tabled the package with the same two-part structure: (1) amendments to the Telecommunications Act that enable security directions to telecoms; and (2) a new CCSPA setting out mandatory cybersecurity duties for designated operators. This blog focuses on the latter.

If enacted, Canada will join fellow Five Eyes partners such as the United Kingdom and Australia, which already impose statutory cyber-security duties on operators of critical national infrastructure.

The case for new cybersecurity legislation in Canada

The Canadian cyber threat landscape has expanded. The country's national cyber authority, the Canadian Centre for Cybersecurity (Cyber Centre), recently assessed that the number of cyber incidents has “sharply increased” in the last two years, as has the severity of those incidents, with essential services providers among the targets. Likewise, in its 2025-2026 National Cyber Threat Assessment, the Cyber Centre warned that AI technologies are “amplifying cyberspace threats” by lowering barriers to entry, improving the speed and sophistication of social-engineering attacks and enabling more precise operations.

This context mirrors what we are seeing globally: adversaries, including state actors, are taking advantage of the availability and sophistication of AI tools, which they have leverage to amplify the effectiveness of their operations. In this increasingly complex landscape, regulation must keep pace and evolve in step with the risk.

What the Canadian Critical Cyber Systems Protection Act aims to achieve

  • If enacted, the CCSPA will apply to operators in federally regulated critical infrastructure sectors which are vital to national security and public safety, as further defined in “Scope” below (the “Regulated Entities”), to adopt and comply with a minimum standard of cybersecurity duties (further described below)  which align with those its Five Eyes counterparts are already adhering to.

Who does the CCSPA apply to

The CCSPA would apply to designated operators that deliver services or systems within federal jurisdiction in the following priority areas:

  • telecommunications services
  • interprovincial or international pipeline and power line systems, nuclear energy systems, transportation systems
  • banking and clearing  
  • settlement systems

The CCSPA would also grant the Governor in Council (Federal Cabinet) with powers to add or remove entities in scope via regulation.

Scope of the CCSPA

The CCSPA introduces two key instruments:

First, it strengthens cyber threat information sharing between responsible ministers, sector regulators, and the Communications Security Establishment (through the Cyber Centre).

Second, it empowers the Governor in Council (GIC) to issue Cyber Security Directions (CSDs) - binding orders requiring a designated operator to implement specified measures to protect a critical cyber system within defined timeframes.

CSDs may be tailored to an individual operator or applied to a class of operators and can address technology, process, or supplier risks. To safeguard security and commercial confidentiality, the CCSPA restricts disclosure of the existence or content of a CSD except as necessary to carry it out.

Locating decision-making with the GIC ensures that CSDs are made with a cross-government view that weighs national security, economic priorities and international agreement.

New obligations for designated providers

The CCSPA would impose key cybersecurity compliance and obligations on designated providers. As it stands, this includes:

  1. Establishing and maintaining cybersecurity programs: these will need to be comprehensive, proportionate and developed proactively. Once implemented, they will need to be continuously reviewed
  2. Mitigating supply chain risks: Regulated Entities will be required to assess their third-party products and services by conducting a supply chain analysis, and take active steps to mitigate any identified risks
  3. Reporting incidents:  Regulated Entities will need to be more transparent with their reporting, by making the Communications Security Establishment (CSE) aware of any incident which has, or could potentially have, an impact on a critical system. The reports must be made within specific timelines, but in any event within no more than 72 hours;
  4. Compliance with cybersecurity directions:  the government will, under the CCSPA, have the authority to issue cybersecurity directives in an effort to remain responsive to emerging threats, which Regulated Entities will be required to follow once issued
  5. Record keeping: this shouldn’t be a surprise to many of those Regulated Entities which fall in scope, which are already likely to be subject to record keeping requirements. Regulated Entities should expect to be maintaining records and conducting audits of their systems and processes against the requirements of the CCSPA

It should be noted, however, that this may be subject to change, so Regulated Entities should keep an eye on the progress of the Bill as it makes its way through parliament.

Enforcement of the Act would be carried out by sector-specific regulators identified in the Act such as the Office of the Superintendent of Financial Institutions, Minister of Transport, Canada Energy Regulator, Canadian Nuclear Safety Commission and the Ministry of Industry.

What are the penalties for CCSPA non-compliance?

When assessing the penalties associated with non-compliance with the requirements of the CCSPA, it is clear that such non-compliance will be taken seriously, and the severity of the penalties follows the trend of those applied by the European Union to key pieces of EU legislation. The “administrative monetary penalties” (AMPs) set by regulation could see fines being applied of up to C$1 million for individuals and up to C$15 million for organizations.

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