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Breakdown of a multi-account compromise within Office 365

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25
May 2022
25
May 2022
This blog details how rapidly accounts can become compromised from an internal phishing campaign. It also highlights the actions that Darktrace/Apps can take to stop this type of attack in the future.

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.
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Laura Leyland
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Quasar Remote Access Tool: When a Legitimate Admin Tool Falls into the Wrong Hands

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23
Feb 2024

The threat of interoperability

As the “as-a-Service” market continues to grow, indicators of compromise (IoCs) and malicious infrastructure are often interchanged and shared between multiple malware strains and attackers. This presents organizations and their security teams with a new threat: interoperability.

Interoperable threats not only enable malicious actors to achieve their objectives more easily by leveraging existing infrastructure and tools to launch new attacks, but the lack of clear attribution often complicates identification for security teams and incident responders, making it challenging to mitigate and contain the threat.

One such threat observed across the Darktrace customer base in late 2023 was Quasar, a legitimate remote administration tool that has becoming increasingly popular for opportunistic attackers in recent years. Working in tandem, the anomaly-based detection of Darktrace DETECT™ and the autonomous response capabilities of Darktrace RESPOND™ ensured that affected customers were promptly made aware of any suspicious activity on the attacks were contained at the earliest possible stage.

What is Quasar?

Quasar is an open-source remote administration tool designed for legitimate use; however, it has evolved to become a popular tool used by threat actors due to its wide array of capabilities.  

How does Quasar work?

For instance, Quasar can perform keylogging, take screenshots, establish a reverse proxy, and download and upload files on a target device [1].  A report released towards the end of 2023 put Quasar back on threat researchers’ radars as it disclosed the new observation of dynamic-link library (DLL) sideloading being used by malicious versions of this tool to evade detection [1].  DLL sideloading involves configuring legitimate Windows software to run a malicious file rather than the legitimate file it usually calls on as the software loads.  The evolving techniques employed by threat actors using Quasar highlights defenders’ need for anomaly-based detections that do not rely on pre-existing knowledge of attacker techniques, and can identify and alert for unusual behavior, even if it is performed by a legitimate application.

Although Quasar has been used by advanced persistent threat (APT) groups for global espionage operations [2], Darktrace observed the common usage of default configurations for Quasar, which appeared to use shared malicious infrastructure, and occurred alongside other non-compliant activity such as BitTorrent use and cryptocurrency mining.  

Quasar Attack Overview and Darktrace Coverage

Between September and October 2023, Darktrace detected multiple cases of malicious Quasar activity across several customers, suggesting probable campaign activity.  

Quasar infections can be difficult to detect using traditional network or host-based tools due to the use of stealthy techniques such as DLL side-loading and encrypted SSL connections for command-and control (C2) communication, that traditional security tools may not be able to identify.  The wide array of capabilities Quasar possesses also suggests that attacks using this tool may not necessarily be modelled against a linear kill chain. Despite this, the anomaly-based detection of Darktrace DETECT allowed it to identify IoCs related to Quasar at multiple stages of the kill chain.

Quasar Initial Infection

During the initial infection stage of a Quasar compromise observed on the network of one customer, Darktrace detected a device downloading several suspicious DLL and executable (.exe) files from multiple rare external sources using the Xmlst user agent, including the executable ‘Eppzjtedzmk[.]exe’.  Analyzing this file using open-source intelligence (OSINT) suggests this is a Quasar payload, potentially indicating this represented the initial infection through DLL sideloading [3].

Interestingly, the Xmlst user agent used to download the Quasar payload has also been associated with Raccoon Stealer, an information-stealing malware that also acts as a dropper for other malware strains [4][5]. The co-occurrence of different malware components is increasingly common across the threat landscape as MaaS operating models increases in popularity, allowing attackers to employ cross-functional components from different strains.

Figure 1: Cyber AI Analyst Incident summarizing the multiple different downloads in one related incident, with technical details for the Quasar payload included. The incident event for Suspicious File Download is also linked to Possible HTTP Command and Control, suggesting escalation of activity following the initial infection.  

Quasar Establishing C2 Communication

During this phase, devices on multiple customer networks were identified making unusual external connections to the IP 193.142.146[.]212, which was not commonly seen in their networks. Darktrace analyzed the meta-properties of these SSL connections without needing to decrypt the content, to alert the usage of an unusual port not typically associated with the SSL protocol, 4782, and the usage of self-signed certificates.  Self-signed certificates do not provide any trust value and are commonly used in malware communications and ill-reputed web servers.  

Further analysis into these alerts using OSINT indicated that 193.142.146[.]212 is a Quasar C2 server and 4782 is the default port used by Quasar [6][7].  Expanding on the self-signed certificate within the Darktrace UI (see Figure 3) reveals a certificate subject and issuer of “CN=Quasar Server CA”, which is also the default self-signed certificate compiled by Quasar [6].

Figure 2: Cyber AI Analyst Incident summarizing the repeated external connections to a rare external IP that was later associated with Quasar.
Figure 3: Device Event Log of the affected device, showing Darktrace’s analysis of the SSL Certificate associated with SSL connections to 193.142.146[.]212.

A number of insights can be drawn from analysis of the Quasar C2 endpoints detected by Darktrace across multiple affected networks, suggesting a level of interoperability in the tooling used by different threat actors. In one instance, Darktrace detected a device beaconing to the endpoint ‘bittorrents[.]duckdns[.]org’ using the aforementioned “CN=Quasar Server CA” certificate. DuckDNS is a dynamic DNS service that could be abused by attackers to redirect users from their intended endpoint to malicious infrastructure, and may be shared or reused in multiple different attacks.

Figure 4: A device’s Model Event Log, showing the Quasar Server CA SSL certificate used in connections to 41.233.139[.]145 on port 5, which resolves via passive replication to ‘bittorrents[.]duckdns[.]org’.  

The sharing of malicious infrastructure among threat actors is also evident as several OSINT sources have also associated the Quasar IP 193.142.146[.]212, detected in this campaign, with different threat types.

While 193.142.146[.]212:4782 is known to be associated with Quasar, 193.142.146[.]212:8808 and 193.142.146[.]212:6606 have been associated with AsyncRAT [11], and the same IP on port 8848 has been associated with RedLineStealer [12].  Aside from the relative ease of using already developed tooling, threat actors may prefer to use open-source malware in order to avoid attribution, making the true identity of the threat actor unclear to incident responders [1][13].  

Quasar Executing Objectives

On multiple customer deployments affected by Quasar, Darktrace detected devices using BitTorrent and performing cryptocurrency mining. While these non-compliant, and potentially malicious, activities are not necessarily specific IoCs for Quasar, they do suggest that affected devices may have had greater attack surfaces than others.

For instance, one affected device was observed initiating connections to 162.19.139[.]184, a known Minergate cryptomining endpoint, and ‘zayprostofyrim[.]zapto[.]org’, a dynamic DNS endpoint linked to the Quasar Botnet by multiple OSINT vendors [9].

Figure 5: A Darktrace DETECT Event Log showing simultaneous connections to a Quasar endpoint and a cryptomining endpoint 162.19.139[.]184.

Not only does cryptocurrency mining use a significant amount of processing power, potentially disrupting an organization’s business operations and racking up high energy bills, but the software used for this mining is often written to a poor standard, thus increasing the attack surfaces of devices using them. In this instance, Quasar may have been introduced as a secondary payload from a user or attacker-initiated download of cryptocurrency mining malware.

Similarly, it is not uncommon for malicious actors to attach malware to torrented files and there were a number of examples of Darktrace detect identifying non-compliant activity, like BitTorrent connections, overlapping with connections to external locations associated with Quasar. It is therefore important for organizations to establish and enforce technical and policy controls for acceptable use on corporate devices, particularly when remote working introduces new risks.  

Figure 6: A device’s Event Log filtered by Model Breaches, showing a device connecting to BitTorrent shortly before making new or repeated connections to unusual endpoints, which were subsequently associated to Quasar.

In some cases observed by Darktrace, devices affected by Quasar were also being used to perform data exfiltration. Analysis of a period of unusual external connections to the aforementioned Quasar C2 botnet server, ‘zayprostofyrim[.]zapto[.]org’, revealed a small data upload, which may have represented the exfiltration of some data to attacker infrastructure.

Darktrace’s Autonomous Response to Quasar Attacks

On customer networks that had Darktrace RESPOND™ enabled in autonomous response mode, the threat of Quasar was mitigated and contained as soon as it was identified by DETECT. If RESPOND is not configured to respond autonomously, these actions would instead be advisory, pending manual application by the customer’s security team.

For example, following the detection of devices downloading malicious DLL and executable files, Darktrace RESPOND advised the customer to block specific connections to the relevant IP addresses and ports. However, as the device was seen attempting to download further files from other locations, RESPOND also suggested enforced a ‘pattern of life’ on the device, meaning it was only permitted to make connections that were part its normal behavior. By imposing a pattern of life, Darktrace RESPOND ensures that a device cannot perform suspicious behavior, while not disrupting any legitimate business activity.

Had RESPOND been configured to act autonomously, these mitigative actions would have been applied without any input from the customer’s security team and the Quasar compromise would have been contained in the first instance.

Figure 7: The advisory actions Darktrace RESPOND initiated to block specific connections to a malicious IP and to enforce the device’s normal patterns of life in response to the different anomalies detected on the device.

In another case, one customer affected by Quasar did have enabled RESPOND to take autonomous action, whilst also integrating it with a firewall. Here, following the detection of a device connecting to a known Quasar IP address, RESPOND initially blocked it from making connections to the IP via the customer’s firewall. However, as the device continued to perform suspicious activity after this, RESPOND escalated its response by blocking all outgoing connections from the device, effectively preventing any C2 activity or downloads.

Figure 8: RESPOND actions triggered to action via integrated firewall and TCP Resets.

Conclusion

When faced with a threat like Quasar that utilizes the infrastructure and tools of both legitimate services and other malicious malware variants, it is essential for security teams to move beyond relying on existing knowledge of attack techniques when safeguarding their network. It is no longer enough for organizations to rely on past attacks to defend against the attacks of tomorrow.

Crucially, Darktrace’s unique approach to threat detection focusses on the anomaly, rather than relying on a static list of IoCs or "known bads” based on outdated threat intelligence. In the case of Quasar, alternative or future strains of the malware that utilize different IoCs and TTPs would still be identified by Darktrace as anomalous and immediately alerted.

By learning the ‘normal’ for devices on a customer’s network, Darktrace DETECT can recognize the subtle deviations in a device’s behavior that could indicate an ongoing compromise. Darktrace RESPOND is subsequently able to follow this up with swift and targeted actions to contain the attack and prevent it from escalating further.

Credit to Nicole Wong, Cyber Analyst, Vivek Rajan Cyber Analyst

Appendices

Darktrace DETECT Model Breaches

  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Anomalous Connection / Anomalous SSL without SNI to New External
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Anomalous Connection / Rare External SSL Self-Signed
  • Compromise / New or Repeated to Unusual SSL Port
  • Compromise / Beaconing Activity To External Rare
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Large Number of Suspicious Failed Connections
  • Unusual Activity / Unusual External Activity

List of IoCs

IP:Port

193.142.146[.]212:4782 -Quasar C2 IP and default port

77.34.128[.]25: 8080 - Quasar C2 IP

Domain

zayprostofyrim[.]zapto[.]org - Quasar C2 Botnet Endpoint

bittorrents[.]duckdns[.]org - Possible Quasar C2 endpoint

Certificate

CN=Quasar Server CA - Default certificate used by Quasar

Executable

Eppzjtedzmk[.]exe - Quasar executable

IP Address

95.214.24[.]244 - Quasar C2 IP

162.19.139[.]184 - Cryptocurrency Miner IP

41.233.139[.]145[VR1] [NW2] - Possible Quasar C2 IP

MITRE ATT&CK Mapping

Command and Control

T1090.002: External Proxy

T1071.001: Web Protocols

T1571: Non-Standard Port

T1001: Data Obfuscation

T1573: Encrypted Channel

T1071: Application Layer Protocol

Resource Development

T1584: Compromise Infrastructure

References

[1] https://thehackernews.com/2023/10/quasar-rat-leverages-dll-side-loading.html

[2] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/cicada-apt10-japan-espionage

[3]https://www.virustotal.com/gui/file/bd275a1f97d1691e394d81dd402c11aaa88cc8e723df7a6aaf57791fa6a6cdfa/community

[4] https://twitter.com/g0njxa/status/1691826188581298389

[5] https://www.linkedin.com/posts/grjk83_raccoon-stealer-announce-return-after-hiatus-activity-7097906612580802560-1aj9

[6] https://community.netwitness.com/t5/netwitness-community-blog/using-rsa-netwitness-to-detect-quasarrat/ba-p/518952

[7] https://www.cisa.gov/news-events/analysis-reports/ar18-352a

[8]https://any.run/report/6cf1314c130a41c977aafce4585a144762d3fb65f8fe493e836796b989b002cb/7ac94b56-7551-4434-8e4f-c928c57327ff

[9] https://threatfox.abuse.ch/ioc/891454/

[10] https://www.virustotal.com/gui/ip-address/41.233.139.145/relations

[11] https://raw.githubusercontent.com/stamparm/maltrail/master/trails/static/malware/asyncrat.txt

[12] https://sslbl.abuse.ch/ssl-certificates/signature/RedLineStealer/

[13] https://www.botconf.eu/botconf-presentation-or-article/hunting-the-quasar-family-how-to-hunt-a-malware-family/

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Nicole Wong
Cyber Security Analyst

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Attack Trends: VIP Impersonation Across the Business Hierarchy

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22
Feb 2024

What is VIP impersonation?

VIP impersonation involves a threat actor impersonating a trusted, prominent figure at an organization in an attempt to solicit sensitive information from an employee.

VIP impersonation is a high-priority issue for security teams, but it can be difficult to assess the exact risks, and whether those are more critical than other types of compromise. Looking across a range of Darktrace/Email™ customer deployments, this blog explores the patterns of individuals targeted for impersonation and evaluates if these target priorities correspond with security teams' focus on protecting attack pathways to critical assets.

How do security teams stop VIP Impersonation?

Protecting VIP entities within an organization has long been a traditional focus for security teams. The assumption is that VIPs, due to their prominence, possess the greatest access to critical assets, making them prime targets for cyber threats.  

Email remains the predominant vector for attacks, with over 90% of breaches originating from malicious emails. However, the dynamics of email-based attacks are shifting, as the widespread use of generative AI is lowering the barrier to entry by allowing adversaries to create hyper-realistic emails with minimal errors.

Given these developments, it's worth asking the question – which entities (VIP/non-VIP) are most targeted by threat actors via email? And, more importantly – which entities (VIP/non-VIP) are more valuable if they are successfully compromised?

There are two types of VIPs:  

1. When referring to emails and phishing, VIPs are the users in an organization who are well known publicly.  

2. When referring to attack paths, VIPs are users in an organization that are known publicly and have access to highly privileged assets.  

Not every prominent user has access to critical assets, and not every user that has access to critical assets is prominent.  

Darktrace analysis of VIP impersonation

We analyzed patterns of attack pathways and phishing attempts across 20 customer deployments from a large, randomized pool encompassing a diverse range of organizations.  

Understanding Attack Pathways

Our observations revealed that 57% of low-difficulty attack paths originated from VIP entities, while 43% of observed low-difficulty attack paths towards critical assets or entities began through non-VIP users. This means that targeting VIPs is not the only way attackers can reach critical assets, and that non-VIP users must be considered as well.  

While the sample size prevents us from establishing statistical significance across all customers, the randomized selection lends credence to the generalizability of these findings to other environments.

Phishing Attempts  

On average, 1.35% of total emails sent to these customers exhibited significantly malicious properties associated with phishing or some form of impersonation. Strikingly, nearly half of these malicious emails (49.6%) were directed towards VIPs, while the rest were sent to non-VIPs. This near-equal split is worth noting, as attack paths show that non-VIPs also serve as potential entry points for targeting critical assets.  

Darktrace/Email UI
Figure 1: A phishing email actioned by Darktrace, sent to multiple VIP and non-VIP entities

For example, a recent phishing campaign targeted multiple customers across deployments, with five out of 13 emails specifically aimed at VIP users. Darktrace/Email actioned the malicious emails by double locking the links, holding the messages, and stripping the attachments.

Given that non-VIP users receive nearly half of the phishing or impersonation emails, it underscores the critical importance for security teams to recognize their blind spots in protecting critical assets. Overlooking the potential threat originating from non-VIP entities could lead to severe consequences. For instance, if a non-VIP user falls victim to a phishing attack or gets compromised, their credentials could be exploited to move laterally within the organization, potentially reaching critical assets.

This highlights the necessity for a sophisticated security tool that can identify targeted users, without the need for extensive customization and regardless of VIP status. By deploying a solution capable of promptly responding to email threats – including solicitation, phishing attempts, and impersonation – regardless of the status of the targeted user, security teams can significantly enhance their defense postures.

Darktrace vs Traditional Email Detection Methods

Traditional rules and signatures-based detection mechanisms fall short in identifying the evolving threats we’ve observed, due to their reliance on knowledge of past attacks to categorize emails.

Secure Email Gateway (SEG) or Integrated Cloud Email Security (ICES) tools categorize emails based on previous or known attacks, operating on a known-good or known-bad model. Even if tools use AI to automate this process, the approach is still fundamentally looking to the past and therefore vulnerable to unknown and zero-day threats.  

Darktrace uses AI to understand each unique organization and how its email environment interoperates with each user and device on the network. Consequently, it is able to identify the subtle deviations from normal behavior that qualify as suspicious. This approach goes beyond simplistic categorizations, considering factors such as the sender’s history and recipient’s exposure score.  

This nuanced analysis enables Darktrace to differentiate between genuine communications and malicious impersonation attempts. It automatically understands who is a VIP, without the need for manual input, and will action more strongly on incoming malicious emails  based on a user’s status.

Email does determine who is a VIP, without a need of manual input, and will action more strongly on incoming malicious emails.

Darktrace/Email also feeds into Darktrace’s preventative security tools, giving the interconnected AI engines further context for assessing the high-value targets and pathways to vital internal systems and assets that start via the inbox.

Leveraging AI for Enhanced Protection Across the Enterprise  

The efficacy of AI-driven security solutions lies in their ability to make informed decisions and recommendations based on real-time business data. By leveraging this data, AI driven solutions can identify exploitable attack pathways and an organizations most critical assets. Darktrace uniquely uses several forms of AI to equip security teams with the insights needed to make informed decisions about which pathways to secure, reducing human bias around the importance of protecting VIPs.

With the emergence of tools like AutoGPT, identifying potential targets for phishing attacks has become increasingly simplified. However, the real challenge lies in gaining a comprehensive understanding of all possible and low-difficulty attack paths leading to critical assets and identities within the organization.

At the same time, organizations need email tools that can leverage the understanding of users to prevent email threats from succeeding in the first instance. For every email and user, Darktrace/Email takes into consideration changes in behavior from the sender, recipient, content, and language, and many other factors.

Integrating Darktrace/Email with Darktrace’s attack path modeling capabilities enables comprehensive threat contextualization and facilitates a deeper understanding of attack pathways. This holistic approach ensures that all potential vulnerabilities, irrespective of the user's status, are addressed, strengthening the overall security posture.  

Conclusion

Contrary to conventional wisdom, our analysis suggests that the distinction between VIPs and non-VIPs in terms of susceptibility to impersonation and low-difficulty attack paths is not as pronounced as presumed. Therefore, security teams must adopt a proactive stance in safeguarding all pathways, rather than solely focusing on VIPs.  

Attack path modeling enhances Darktrace/Email's capabilities by providing crucial metrics on potential impact, damage, exposure, and weakness, enabling more targeted and effective threat mitigation strategies. For example, stronger email actions can be enforced for users who are known to have a high potential impact in case of compromise. 

In an era where cyber threats continue to evolve in complexity, an adaptive and non-siloed approach to securing inboxes, high-priority individuals, and critical assets is indispensable.  

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About the author
Kendra Gonzalez Duran
Director of Technology Innovation

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