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How Darktrace’s AI caught two Microsoft 365 account takeovers

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07
Jun 2020
07
Jun 2020
This blog outlines two cases of Microsoft 365 account takeover, detailing how Darktrace’s ability to correlate insights across SaaS applications and email activity enabled it to neutralize the threats.

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
ABOUT ThE 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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Detecting Attacks Across Email, SaaS, and Network Environments with Darktrace’s AI Platform Approach

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30
Apr 2024

The State of AI in Cybersecurity

In a recent survey outlined in Darktrace’s State of AI Cyber Security whitepaper, 95% of cyber security professionals agree that AI-powered security solutions will improve their organization’s detection of cyber-threats [1]. Crucially, a combination of multiple AI methods is the most effective to improve cybersecurity; improving threat detection, accelerating threat investigation and response, and providing visibility across an organization’s digital environment.

In March 2024, Darktrace’s AI-led security platform was able to detect suspicious activity affecting a customer’s email, Software-as-a-Service (SaaS), and network environments, whilst its applied supervised learning capability, Cyber AI Analyst, autonomously correlated and connected all of these events together in one single incident, explained concisely using natural language processing.

Attack Overview

Following an initial email attack vector, an attacker logged into a compromised SaaS user account from the Netherlands, changed inbox rules, and leveraged the account to send thousands of phishing emails to internal and external users. Internal users fell victim to the emails by clicking on contained suspicious links that redirected them to newly registered suspicious domains hosted on same IP address as the hijacked SaaS account login. This activity triggered multiple alerts in Darktrace DETECT™ on both the network and SaaS side, all of which were correlated into one Cyber AI Analyst incident.

In this instance, Darktrace RESPOND™ was not active on any of the customer’s environments, meaning the compromise was able to escalate until their security team acted on the alerts raised by DETECT. Had RESPOND been enabled at the time of the attack, it would have been able to apply swift actions to contain the attack by blocking connections to suspicious endpoints on the network side and disabling users deviating from their normal behavior on the customer’s SaaS environment.

Nevertheless, thanks to DETECT and Cyber AI Analyst, Darktrace was able to provide comprehensive visibility across the customer’s three digital estate environments, decreasing both investigation and response time which enabled them to quickly enact remediation during the attack. This highlights the crucial role that Darktrace’s combined AI approach can play in anomaly detection cyber defense

Attack Details & Darktrace Coverage

Attack timeline

1. Email: the initial attack vector  

The initial attack vector was likely email, as on March 18, 2024, Darktrace observed a user device making several connections to the email provider “zixmail[.]net”, shortly before it connected to the first suspicious domain. Darktrace/Email identified multiple unusual inbound emails from an unknown sender that contained a suspicious link. Darktrace recognized these emails as potentially malicious and locked the link, ensuring that recipients could not directly click it.

Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.
Figure 1: Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.

2. Escalation to Network

Later that day, despite Darktrace/Email having locked the link in the suspicious email, the user proceeded to click on it and was directed to a suspicious external location, namely “rz8js7sjbef[.]latovafineart[.]life”, which triggered the Darktrace/Network DETECT model “Suspicious Domain”. Darktrace/Email was able to identify that this domain had only been registered 4 days before this activity and was hosted on an IP address based in the Netherlands, 193.222.96[.]9.

3. SaaS Account Hijack

Just one minute later, Darktrace/Apps observed the user’s Microsoft 365 account logging into the network from the same IP address. Darktrace understood that this represented unusual SaaS activity for this user, who had only previously logged into the customer’s SaaS environment from the US, triggering the “Unusual External Source for SaaS Credential Use” model.

4. SaaS Account Updates

A day later, Darktrace identified an unusual administrative change on the user’s Microsoft 365 account. After logging into the account, the threat actor was observed setting up a new multi-factor authentication (MFA) method on Microsoft Authenticator, namely requiring a 6-digit code to authenticate. Darktrace understood that this authentication method was different to the methods previously used on this account; this, coupled with the unusual login location, triggered the “Unusual Login and Account Update” DETECT model.

5. Obfuscation Email Rule

On March 20, Darktrace detected the threat actor creating a new email rule, named “…”, on the affected account. Attackers are typically known to use ambiguous or obscure names when creating new email rules in order to evade the detection of security teams and endpoints users.

The parameters for the email rule were:

“AlwaysDeleteOutlookRulesBlob: False, Force: False, MoveToFolder: RSS Feeds, Name: ..., MarkAsRead: True, StopProcessingRules: True.”

This rule was seemingly created with the intention of obfuscating the sending of malicious emails, as the rule would move sent emails to the "RSS Feeds” folder, a commonly used tactic by attackers as the folder is often left unchecked by endpoint users. Interestingly, Darktrace identified that, despite the initial unusual login coming from the Netherlands, the email rule was created from a different destination IP, indicating that the attacker was using a Virtual Private Network (VPN) after gaining a foothold in the network.

Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.
Figure 2: Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.

6. Outbound Phishing Emails Sent

Later that day, the attacker was observed using the compromised customer account to send out numerous phishing emails to both internal and external recipients. Darktrace/Email detected a significant spike in inbound emails on the compromised account, with the account receiving bounce back emails or replies in response to the phishing emails. Darktrace further identified that the phishing emails contained a malicious DocSend link hidden behind the text “Click Here”, falsely claiming to be a link to the presentation platform Prezi.

Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.
Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.

7. Suspicious Domains and Redirects

After the phishing emails were sent, multiple other internal users accessed the DocSend link, which directed them to another suspicious domain, “thecalebgroup[.]top”, which had been registered on the same day and was hosted on the aforementioned Netherlands-based IP, 193.222.96[.]91. At the time of the attack, this domain had not been reported by any open-source intelligence (OSINT), but it has since been flagged as malicious by multiple vendors [2].

External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.
Figure 4: External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.  

8. Cyber AI Analyst’s Investigation

As this attack was unfolding, Darktrace’s Cyber AI Analyst was able to autonomously investigate the events, correlating them into one wider incident and continually adding a total of 14 new events to the incident as more users fell victim to the phishing links.

Cyber AI Analyst successfully weaved together the initial suspicious domain accessed in the initial email attack vector (Figure 5), the hijack of the SaaS account from the Netherlands IP (Figure 6), and the connection to the suspicious redirect link (Figure 7). Cyber AI Analyst was also able to uncover other related activity that took place at the time, including a potential attempt to exfiltrate data out of the customer’s network.

By autonomously analyzing the thousands of connections taking place on a network at any given time, Darktrace’s Cyber AI Analyst is able to detect seemingly separate anomalous events and link them together in one incident. This not only provides organizations with full visibility over potential compromises on their networks, but also saves their security teams precious time ensuring they can quickly scope out the ongoing incident and begin remediation.

Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.
Figure 7: Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.

Conclusion

In this scenario, Darktrace demonstrated its ability to detect and correlate suspicious activities across three critical areas of a customer’s digital environment: email, SaaS, and network.

It is essential that cyber defenders not only adopt AI but use a combination of AI technology capable of learning and understanding the context of an organization’s entire digital infrastructure. Darktrace’s anomaly-based approach to threat detection allows it to identify subtle deviations from the expected behavior in network devices and SaaS users, indicating potential compromise. Meanwhile, Cyber AI Analyst dynamically correlates related events during an ongoing attack, providing organizations and their security teams with the information needed to respond and remediate effectively.

Credit to Zoe Tilsiter, Analyst Consulting Lead (EMEA), Brianna Leddy, Director of Analysis

Appendices

References

[1] https://darktrace.com/state-of-ai-cyber-security

[2] https://www.virustotal.com/gui/domain/thecalebgroup.top

Darktrace DETECT Model Coverage

SaaS Models

- SaaS / Access / Unusual External Source for SaaS Credential Use

- SaaS / Compromise / Unusual Login and Account Update

- SaaS / Compliance / Anomalous New Email Rule

- SaaS / Compromise / Unusual Login and New Email Rule

Network Models

- Device / Suspicious Domain

- Multiple Device Correlations / Multiple Devices Breaching Same Model

Cyber AI Analyst Incidents

- Possible Hijack of Office365 Account

- Possible SSL Command and Control

Indicators of Compromise (IoCs)

IoC – Type – Description

193.222.96[.]91 – IP – Unusual Login Source

thecalebgroup[.]top – Domain – Possible C2 Endpoint

rz8js7sjbef[.]latovafineart[.]life – Domain – Possible C2 Endpoint

https://docsend[.]com/view/vcdmsmjcskw69jh9 - Domain - Phishing Link

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Zoe Tilsiter
Cyber Analyst

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Attack trends: Cloud-Based Cyber-Attacks and the Rise of Alternative Initial Access Methods

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29
Apr 2024

What is the primary entry point for malware attacks?

Phishing attacks targeting employee inboxes are the most common initial access method used by malicious threat actors to deliver malware.

Because email remains the lifeblood of how organizations operate attackers continue to develop new techniques for creating more convincing and sophisticated phishing messages at scale.

What are new entry points cyber attackers are using?

While traditional phishing attacks are very common for attackers, they are not the only method threat actors are using to initiate malware delivery and other malicious campaigns of cyber disruption.

For its End of Year Threat Report, Darktrace analyzed attacks targeting customer environments. While email remains the most common means of attempted initial compromise, the second half of 2023 saw a significant rise in alternative initial access methods.

Much of this is taking advantage of cloud-base applications and collaboration tools including Dropbox, Microsoft Teams, and SharePoint which have become fundamental to how organizations operate in the era of hybrid work.

DarkGate exploits Microsoft Teams

Darktrace analysts have seen threat actors attempting to infect target networks with malware by leveraging Microsoft Teams and SharePoint.  

In one example, Darktrace detected an attacker delivering DarkGate a trojan used to download other malware, by sending messages and attachments in Microsoft Teams and SharePoint.

The External Access functionality in Microsoft Teams allows users to contact people who aren’t in their organization. It’s designed as a tool to aid collaboration, but threat actors have realized they can abuse it for their own gain.  

Users are told to lookout for suspicious email phishing messages, but often this thinking isn’t applied to Microsoft Teams and other collaboration platforms.  

Messages from outside the organization are marked with a note that they are coming from an external source, but a well-designed phishing message with an urgent call to action can persuade the target to ignore this, driving them towards an external SharePoint URL, which tricks the user into downloading and installing malware.

Because this happens outside of the inbox, the activity can be missed by traditional email security solutions. Fortunately, in this case, it was detected by Darktrace DETECT and the activity was contained by Darktrace RESPOND before it could drop any additional malware.  

Dropbox has established itself as a leading cloud storage service by allowing users to share and access files, no matter where they are in the world or what device they’re using. But while this is legitimate and useful for organizations, it has also opened a new avenue for threat actors to exploit.

Dropbox as an attack vector

Darktrace recently detected attackers attempting to leverage Dropbox as an initial access method. Emails from ‘no-reply@dropbox[.]com’ – a legitimate email address – were sent to employees at a Darktrace customer.

The emails contained a link to push users towards to a PDF file hosted on Dropbox, which in turn contained a phishing link which if followed, took users to a convincing looking spoof of a Microsoft 365 login page designed to steal usernames and passwords.

A user fell victim to this campaign, unwittingly entering their Microsoft 365 credentials. Shortly after that, Darktrace/Apps started to see suspicious activity relating to the account, with multiple logins from unusual locations which had never been associated with the account previously.  

While many traditional security solutions successfully detect and disrupt email-based attacks, many struggle with cloud-based apps and services like Dropbox, Microsoft 365 and others.  

There are several reasons for this, including the way in which the use of multiple different cloud services fragments the attack surface, making it hard for network administrators to keep track of everything, alongside the way in which some security solutions don’t take behavior into account in a system which can be accessed from anywhere. That means even from the other side of the world, attackers who have the right cloud credentials could access the network, potentially without being disrupted.  

Why are attackers turning to alternative access methods?

Attackers are turning to alternative methods because delivering malicious links and payloads via cloud-based services potentially bypasses traditional cybersecurity protections. That, combined with how attackers can take legitimate login credentials to access system means attackers actions can’t be easily traced.  

This rise in alternative initial access methods is likely a result of the continued development and enhancement of traditional email security solutions. But in the cat and mouse game of cybersecurity, threat actors continue to evolve new techniques to get by defenses.  

Darktrace’s Self-Learning AI learns the unique digital environment and patterns of each business, meaning it can recognize subtle deviations in activity, even within cloud services, helping to mitigate and neutralize attacks and helping to keep your organization safe from cyber disruption.

Learn more about Darktrace

Join Darktrace LIVE half-day event to understand the reality versus the hype surrounding AI and how to achieve cyber resilience.

For more information on emerging threats read the Darktrace End of Year Threat Report 2023 here.

To learn more about Darktrace’s latest innovations watch the Darktrace Virtual Innovation Launch video here.  

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