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June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

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

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.
Author
Dan Fein
VP, Product

Based in New York, Dan joined Darktrace’s technical team in 2015, helping customers quickly achieve a complete and granular understanding of Darktrace’s product suite. Dan has a particular focus on Darktrace/Email, ensuring that it is effectively deployed in complex digital environments, and works closely with the development, marketing, sales, and technical teams. Dan holds a Bachelor’s degree in Computer Science from New York University.

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Company Shuts Down Cyber-attacks with “Flawless” Detection and Response from Darktrace

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Growing pains: Balancing efficiency with risk  

This organization has recently scaled its operations, and numerous acquisitions have significantly boosted the organization’s capabilities and growth. However, this also creates work and high expectations for the organization’s IT and security teams. Within 12 months of an acquisition, the teams must fully integrate each new business onto the company’s platform. “A huge piece of that integration plan is rolling out our security controls,” said the CISO. “While our goal is to connect those facilities up as quickly as possible to drive efficiency, we also need to implement the proper security controls to protect the enterprise.”

Gap beyond the perimeter  

The organization had established strong security measures to safeguard its perimeter; however, the CISO identified a critical gap in real-time network monitoring. If the perimeter were breached, threats were only discovered after an endpoint was compromised and the issue was manually reported.

As digital transformation progresses, the need to adopt advanced technologies is becoming essential, particularly as organizations begin to open up operational environments to greater connectivity. Many processes still rely on traditional methods, and integrating innovative solutions could drive significant improvements in efficiency and productivity. “We’re committed to adopting cutting-edge technologies,” the CISO explained. “But we understood that without more robust network security controls, opening up our operational environments would expose us to heightened risks, including advanced threats like ransomware.”

Building a layered, proactive security strategy with Darktrace  

To close the gap beyond the perimeter, the company embarked on a free trial with Darktrace. The CISO recalls: “The trials were fantastic. It was obvious that Darktrace was exactly what we needed. The Darktrace team was also very knowledgeable and helpful throughout the process, which was impressive.”  

Today, the organization is using a combination of Darktrace solutions for its layered security approach, including:

Detecting unusual behavior with AI  

Darktrace’s use of machine learning and Self-Learning AI is one of the reasons the company chose Darktrace. Instead of teaching an AI system what an ‘attack’ looks like, training it on large data lakes of thousands of organizations’ data, Darktrace AI learns from the company’s own unique data and user activity to learn and create baseline models of what ‘normal’ looks like for their business.

Darktrace can then detect subtle deviations and unusual activity that signals a possible threat. “That fascinated us because what it really means is this technology doesn’t need to know about every single threat because the threat itself isn’t important, it’s the behavior of the activity that’s important. That capability is unique when it when it comes to threat detection,” said the CISO.

Identifying and mitigating high-impact attack paths

The security team appreciated that with Darktrace they could take a more proactive approach to security by exposing high-risk attack paths through modeling and AI risk assessments. Darktrace / Proactive Exposure Management gives them visibility into vulnerable entry points and assets, identifies active risks, and prioritizes the most important security issues to be addressed.

“Specific users and assets within our business have a higher risk of being targeted by a cyber-attack, for example our executives,” said the CISO. “With Darktrace, we get an adversarial view of our risk. We can see the attack path around those potential targets and proactively take measures to mitigate that vulnerability and prevent an attack.”

Driving up productivity while putting the brakes on cyber-attacks  

The security team collaborated with Darktrace to fine tune the models that really fit their business. With Darktrace now automating most of their threat detection and response efforts, productivity has soared, the security team is now focused on delivering greater value to the business and, most importantly, Darktrace proved it could quickly detect and shut down a major cyber-attack–and do so without impacting business operations.

Fueling team productivity with automation and AI

Prior to using Darktrace, the security team had little visibility into potential risks beyond the perimeter. Today, the team has full control and visibility over the network. “My team is now spending 80-90% of their time doing proactive work because Darktrace is managing the vast majority of our detect and response needs. The team really has faith in the Darktrace system,” said the CISO.  

With less time spent on low-level manual tasks, the security team can now focus on higher priority initiatives. For example, they have expanded their internal vulnerability assessments across the entire group. The team couldn’t focus on this additional audit and vulnerability management work if Darktrace wasn’t taking care of most of their security monitoring. “Darktrace has allowed us to move on to these additional kinds of governance projects that we otherwise would have to hire an army of staff to get through”.

Stopping email threats in their tracks

Using Darktrace / EMAIL, the company has identified and blocked a significant percentage of emails that were making it past their native email filters. “Darktrace is especially good at detecting impersonation emails, and we really appreciate its ability to automatically remove suspicious emails directly from a user’s inbox. It adds an extra level of confidence,” said the CISO.

Self-Learning AI understands anomalies within unique communication patterns to stop known and unknown threats. For example, when an employee sent an email to a brand new domain, Darktrace identified the behavior as unusual and inconsistent with baseline models and blocked the email.

Darktrace passes the biggest test of all

In 2024, the company experienced the value of the security system firsthand when attackers exploited a vulnerability in a third-party remote support solution that they was using. This solution provided remote access and tech support capabilities. If successful, the attackers could have infiltrated high-value end points and created their own administrative user, giving them full control over the server.

“We first became aware of the attack when Darktrace notified us of unusual behavior coming from the remote support server,” said the CISO. The attackers were attempting to put backdoors onto the service with the intent of selling access to the highest bidder who would then install ransomware on their servers. It all happened very quickly, as the attackers tried to connect to the internal network and other servers, while also firing off a host of other actions, like PowerShell commands, to escalate their privileges.  

“Darktrace worked flawlessly. There was no chance that ransomware was ever going to come in,” the CISO said. “Even though there was no signature to really look at, Darktrace realized this was not normal behavior for this server, shutting down connections and doing everything it could do to stop the attack.” Within eight hours, the security team identified and stopped the attack, severed its connection to the third-party solution, and completed additional analysis and clean-up. “In addition to our own investigation, third parties like our external SOC and legal department also confirmed that Darktrace performed as expected. We were able to report back to the executive team that there was zero risk that any data or systems were compromised.”

Post-attack, there was no need to make any changes to Darktrace. The team consistently reviews its models and baselines, often collaborating with Darktrace to make adjustments when needed to continuously improve performance. “Because of this relationship and constant engagement with Darktrace’s technical teams, we didn't have to go back and ask: ‘why wasn’t this updated’ or ‘why didn’t this model work.’ The models worked.”

His advice to other organizations facing similar challenges? First, focus on updating, patching, and vulnerability management, and act quickly when vulnerabilities are identified. His second piece of advice: “have an automated detection system like Darktrace in place so you can respond at the speed that these attacks evolve. Humans can no longer keep up with a scripted attack as it moves around and tries to compromise items on your network. You need the right technology to fight these types of attacks.”

Dynamic capabilities for a dynamic future

Real-time playbooks

With a proactive, enterprise-wide security strategy in place, the CISO now has the time to think about future projects and innovations. He’s particularly interested in the idea of generating playbooks on the fly in response to real-time events. He believes cyber-attacks are far too varied for a static playbook to be useful; when an attack strikes, teams need to quickly understand exactly what’s in front of them and how to shut it down. “This fits into our future cybersecurity strategy, and Darktrace is the only company I’ve seen talking about building playbooks dynamically. This kind of technology would really help bring our cybersecurity strategy full circle.”

“Darktrace ’s technology, experience and expertise is helping us staying ahead of cyber-attacks, minimizing our risk and driving greater productivity for our team,” said the CISO. In collaboration with Darktrace, the team have created a security foundation that is both powerful and agile. “While Darktrace is detecting and responding to attacks targeting our business today, we know that it’s always learning, adapting and scaling to ensure we’re protected tomorrow. That gives me peace of mind and the freedom to focus on our future.”

Download the Darktrace / NETWORK Solution Brief

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Protect in real time: Defend against known and emerging threats without relying on historical data or external intelligence.

Full visibility: Gain comprehensive insights across all network environments, including on-premises, cloud, and remote devices.

AI-powered efficiency: Streamline incident response with AI automation, saving time and resources while ensuring minimal disruption to operations.

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Darktrace is Positioned as a Leader in the IDC MarketScape: Worldwide Network Detection and Response 2024 Vendor Assessment

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Darktrace is pleased to announce that we have been positioned as a Leader in the IDC MarketScape: Worldwide Network Detection and Response 2024 Vendor Assessment. We believe this further highlights Darktrace’s position as a pioneer in the NDR market and follows similar recognition from KuppingerCole, who recently named Darktrace as an Overall Leader, Product Leader, Market Leader and Innovation Leader in the KuppingerCole Leadership Compass: Network Detection and Response (2024).

Network Detection and Response (NDR) solutions are uniquely positioned to provide visibility over the core hub of a business and employee activity, analyzing North-South and East-West traffic to identify threats across the modern network. NDR provides a rich and true source of anomalies and goes beyond process level data that is relied on by Endpoint Detection and Response (EDR) agents that do not provide network level visibility and can be misconfigured at any time.1

Metadata from network traffic can be used to detect a variety of different threats based on events such as anomalous port usage, unusual upload/download activity, impossible travel and many other activities. This has been accelerated by the increased usage of user behavioral analytics (UBA) in network security, which establishes statistical baselines about network entities and highlights deviations from expected activity.1

Darktrace is recognized as a Leader in the IDC MarketScape due to our leadership in the market and our pioneering leadership in AI over the past decade, alongside a variety of other unique differentiators and innovations in the NDR industry.

Darktrace / NETWORK™ delivers full visibility, real time threat detection and Autonomous Response capabilities across an organization’s on-premises, cloud, hybrid and virtual environments, including remote worker endpoints.

Unique Approach to AI

Most NDR vendors and network security tools such as IDS/IPS rely on detecting known attacks with historical data and supervised machine learning, leaving organizations blind and vulnerable to novel threats such as zero-days, variants of known attacks, supply chain attacks and insider threats.

These vendors also tend to apply AI models that are trained globally, and are not unique to each organization’s environment, which creates a high number of false positives and alerts that ultimately lack business context.

The IDC MarketScape recognizes that Darktrace takes a differentiated approach in the market with regards to delivering network detection and response capabilities, noting; “Darktrace is unique in that it does not rely on rules and signatures but rather learns what constitutes as normal for an organization and generates alerts when there is a deviation.”1

Darktrace / NETWORK achieves this through the use of Self-Learning AI and unsupervised machine learning to understand what is normal network behavior, continuously analyzing, mapping and modeling every connection to create a full picture of devices, identities, connections and potential attack paths. Darktrace Self-Learning AI autonomously optimizes itself to cut through the noise and quickly surface genuine, prioritized network security incidents – significantly reducing false positives and removing the hassle of needing to continually tuning alerts manually.

Darktrace’s unique approach to AI also extends to the investigation and triage of network alerts with Cyber AI Analyst. Unlike a chat or prompt based LLM, Cyber AI Analyst investigates all relevant alerts in an environment, including third party alerts, autonomously forming hypotheses and reaching conclusions just like a human analyst would, accelerating SOC Level 2 analyses of incidents by 10x. Cyber AI Analyst also typically providing SOC teams with up to 50,000 additional hours annually of Level 2 analysis producing high level alerts and written reporting, transforming security operations.2

Darktrace also uses its deep understanding of what is normal for a network to identify suspicious behavior, leveraging Autonomous Response capabilities to shut down both known and novel threats in real time, taking targeted actions without disrupting business operations. Darktrace / NETWORK is the only NDR solution that can autonomously enforce a pattern of life based on what is normal for a standalone device or group of peers, rapidly containing and disarming threats based on the overall context of the environment and a granular understanding of what is normal for a device or user – instead of relying on historical attack data.

Continued NDR Market Leadership

Darktrace has been recognized as a Leader in the NDR market, and the IDC MarketScape listed a variety of strengths:

  • Darktrace achieves roughly one-fifth of all global NDR revenue. This is important because other IT and cybersecurity solutions providers necessarily want to have integration with Darktrace.
  • The AI algorithms that Darktrace uses for NDR have had 10 years of deployments, tuning, and learning to draw from.
  • Darktrace is available as a SaaS, as an enterprise license, and as physical, hybrid, or virtual appliances. Darktrace also offers an endpoint agent and visibility into VPN and ZTNA.
  • Darktrace integrates with 30+ different interfaces including SIEM, SOAR, XDR platforms, IT ticketing solutions, and their own dashboards. The Darktrace Threat Visualizer highlights events and incidents from the entire deployment including cloud, apps, email, endpoint, zero trust, network, and OT.
  • Darktrace / NETWORK charts the progress that the SOC is making over time with key metrics such as MTTD/MTTR, alerts generated and processed, and other criteria.
  • Darktrace reported coverage of 14 MITRE ATT&CK categories, 158 techniques, and 184 subtechniques

Proactive Network Resilience

The IDC MarketScape notes, “Ultimately, NDR shines as a standalone detection and response technology but is especially powerful when combined with other platforms. NDR in combination with other control points such as endpoint, data, identity, and application provides the proper context when winnowing alerts and trying to uncover a single source of truth.” . Darktrace comprehensively addresses this as part of the ActiveAI Security Platform, by combining network alerts with data from / EMAIL, / IDENTITY, / ENDPOINT, / CLOUD and / OT, providing deeper contextual analysis for each network alert and automatically enriching investigations.

Darktrace also goes beyond NDR solutions with capabilities that are closely linked to our NDR offering, helping clients to achieve and maintain a state of proactive network resilience:

  • Darktrace / Proactive Exposure Management – look beyond just CVE risks to discover, prioritize and validate risks by business impact and how to address them early, reducing the number of real threats that security teams need to handle.
  • Darktrace / Incident Readiness & Recovery – lets teams respond in the best way to each incident and proactively test their familiarity and effectiveness of IR workflows with sophisticated incident simulations based on their own analysts and assets.

Together, these solutions allow Darktrace / NETWORK to go beyond the traditional approach to NDR and shift teams to a more hardened and proactive stance.

Protecting Clients with Continued Innovation

Darktrace invests heavily in Research and Development to continue providing customers with market-leading NDR capabilities and innovations, which was reflected in our position in the Leader category of the MarketScape report for both capabilities and strategy. We are led by the needs and challenges of our customers, which serve as the driving force behind our continued innovation and leadership in the NDR market. The IDC MarketScape report underlines this approach with the following feedback presented by Darktrace customers:

“A customer intimated that 99% of their detections were OOTB with little need to tune or define parameters.”
“A customer reported that it had early warnings for adversarial tactics such as suspicious SMB scanning, suspicious remote execution, remote desktop protocol (RDP) scanning, data exfiltration, C2C, LDAP query, and suspicious Kerberos activity.”
“The client could use Regex to determine if suspicious behavior was found elsewhere on the network.”

Thousands of customers around the world across all industries and sectors rely on Darktrace / NETWORK to protect against known and novel threats. From the latest vulnerabilities in network hardware to sophisticated new strains of ransomware and everything in-between, Darktrace helps clients detect and respond to all types of threats affecting their networks and avoid business disruption, even from the latest attacks.

Find out more about the unique capabilities of Darktrace / NETWORK and our application of AI in network security in the IDC MarketScape excerpt.

References

  1. IDC MarketScape: Worldwide Network Detection and Response 2024 Vendor Assessment (Doc #US51752324, November 2024)
  2. Darktrace Cyber AI Analyst Customer Fleet Data
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About the author
Mikey Anderson
Product Manager, Network Detection & Response
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