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April 22, 2021

Darktrace Identifies APT35 in Pre-Infected State

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Apr 2021
Learn how Darktrace identified APT35 (Charming Kitten) in a pre-infected environment. Gain insights into the detection and mitigation of this threat.

What is APT35?

APT35, sometimes referred to as Charming Kitten, Imperial Kitten, or Tortoiseshell, is a notorious cyber-espionage group which has been active for nearly 10 years. Famous for stealing scripts from HBO’s Game of Thrones in 2017 and suspected of interfering in the U.S. presidential election last year, it has launched extensive campaigns against organizations and officials across North America and the Middle East. Public attribution has associated APT35 with an Iran-based nation state threat actor.

Darktrace regularly detects attacks by many known threat actors including Evil Corp and APT41, alongside large amounts of malicious but uncategorized activity from sophisticated attack groups. As Cyber AI doesn’t rely on pre-defined rules, signatures, or threat intelligence to detect cyber-attacks, it often detects new and previously unknown threats.

This blog post examines a real-world instance of APT35 activity in an organization in the EMEA region. Darktrace observed this activity last June, but due to ongoing investigations, details are only now being released with the wider community. It represents an interesting case for the value of self-learning AI in two key ways:

  • Identifying ‘low and slow’ attacks: How do you spot an attacker that is lying low and conducts very little detectable activity?
  • Detecting pre-existing infections without signatures: What if a threat actor is already inside the system when Cyber AI is activated?

Advanced Persistent Threats (APTs) lying low

APT35 had already infected a single corporate device, likely via a spear phishing email, when Cyber AI was deployed in the company’s digital estate for the first time.

The infected device exhibited no other signs of malicious activity beyond continued command and control (C2) beaconing, awaiting instructions from the attackers for several days. This is what we call ‘lying low’ – where the hacker stays present within a system, but remains under the radar, avoiding detection either intentionally, or because they’re focusing on another victim while being content with backdoor access into the organization.

Either way, this is a nightmare scenario for a security team and any security vendor: an APT which has established a foothold and is lying in wait to continue their attack – undetected.

Finding the infected device

When Darktrace’s AI was first activated, it spent five business days learning the unique ‘patterns of life’ for the organization. After this initial, short learning period, Darktrace immediately flagged the infected device and the C2 activity.

Although the breach device had been beaconing since before Darktrace was implemented, Cyber AI automatically clusters devices into ‘peer groups’ based on similar behavioral patterns, enabling Darktrace to identify the continued C2 traffic coming from the device as highly unusual in comparison to the wider, automatically identified peer group. None of its behaviorally close neighbors were doing anything remotely similar, and Darktrace was therefore able to determine that the activity was malicious, and that it represented C2 beaconing.

Darktrace detected the APT35 C2 activity without the use of any signatures or threat intelligence on multiple levels. Responding to the alerts, the internal security team quickly isolated the device and verified with the Darktrace system that no further reconnaissance, lateral movement, or data exfiltration had taken place.

APT35 ‘Charming Kitten’ analysis

Once the C2 was detected, Cyber AI Analyst immediately began analyzing the infected device. The Cyber AI Analyst only highlights the most severe incidents in any given environment and automates many of the typical level one and level two SOC tasks. This includes reviewing all alerts, investigating the scope and nature of each event, and reducing time to triage by 92%.

Figure 1: Similar Cyber AI Analyst report observing C2 communications

Numerous factors made the C2 activity stand out strongly to Darktrace. Combining all those small anomalies, Darktrace was able to autonomously prioritize this behavior and classify it as the most significant security incident in the week.

Figure 2: Example list of C2 detections for an APT35 attack

Some of the command and control destinations were known to threat intelligence and open-source intelligence (OSINT) – for instance, the domain cortanaservice[.]com is a known C2 domain for APT35.

However, the presence of a known malicious domain does not guarantee detection. In fact, the organization had a very mature security stack, yet they failed to discover the existing APT35 infection until Darktrace was activated in their environment.

Assessing the impact of the intrusion

Once an intrusion has been identified, it is important to understand the extent of it – such as whether lateral movement is occurring and what connectivity the infected device has in general. Asset management is never perfect, so it can be very hard for organizations to determine what damage a compromised device is capable of inflicting.

Darktrace presents this information in real time, and from a bird’s-eye perspective, making the assessment very simple. It immediately highlights which subnet the device is located in and any further context.

Figure 3: Darktrace’s Threat Visualizer displaying the connectivity of a device

Based on this information, the organization confirmed that it was a corporate device that had been infected by APT35. As Darktrace shows any credentials associated with the device, a quick assessment could be made of potentially compromised accounts.

Figure 4: Similar and associated credentials of a device

Luckily, only a single local user account was associated with the device.

The exact level of privileges and connectivity which the infected device had, as well as the extent to which the intrusion might have spread from the initially infected device, was still uncertain. By looking at the device’s event log, this became rapidly clear within minutes.

Filtering first for internal connections only (excluding any connections going to the Internet) gave a good idea of the level of connectivity of the device. A cursory glance showed that the device did indeed have some level of internal connectivity. It made DNS requests to the internal domain controller and was making successful NetBIOS connections over ports 135 and 139 internally.

By filtering further in the event log, it quickly became clear that in this time the device had not used any administrative channels, such as RDP, SSH, Telnet, or SMB. This is a strong indicator that no lateral movement over common channels had taken place.

It is more difficult to assess whether the device was performing any other suspicious activity, like stealthy reconnaissance or staging data from other internal devices. Darktrace provided another capability to assess this quickly – filtering the device’s network connections to show only unusual or new connections.

Figure 5: Event device log filtered to show unusual connections only

Darktrace assesses each individual connection for every entity observed in context, using its unsupervised machine learning to evaluate how unusual a given connection is. This could be a single new failed internal connection attempt, indicating stealthy reconnaissance, or a connection over SMB at an unusual time to a new internal destination, implying lateral movement or data staging.

By filtering for only unusual or new connections, Darktrace’s AI produces further leads that can be pursued extremely quickly, thanks to the context and added visibility.

No further suspicious internal connections were observed, strengthening the hypothesis that APT35 was lying low at that time.

Unprecedented but not unpreventable

Darktrace’s 24/7 monitoring service, Proactive Threat Notifications, would have alerted on and escalated the incident. Darktrace RESPOND would have responded autonomously and enforced normal activity for the device, preventing the C2 traffic without interrupting regular business workflows.

It is impossible to predefine where the next attack will come from. APT35 is just one of the many sophisticated threat actors on the scene, and with such a diverse and volatile threat landscape, unsupervised machine learning is crucial in spotting and defending against anomalies, no matter what form they take.

This case study helps illustrate how Darktrace detects pre-existing infections and ‘low and slow’ attacks, and further shows how Darktrace can be used to quickly understand the scope and extent of an intrusion.

Learn how Cyber AI Analyst detected APT41 two weeks before public attribution

Shortened list of C2 detections over four days on the infected device:

  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compromise / Beaconing Meta Model
  • Compromise / Beaconing Activity To External Rare
  • Compromise / SSL Beaconing To Rare Destination
  • Compromise / Slow Beaconing To External Rare
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Unusual Connections to Rare Lets Encrypt
  • Compromise / Beacon for 4 Days
  • Compromise / Agent Beacon

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
Max Heinemeyer
Chief Product Officer

Max is a cyber security expert with over a decade of experience in the field, specializing in a wide range of areas such as Penetration Testing, Red-Teaming, SIEM and SOC consulting and hunting Advanced Persistent Threat (APT) groups. At Darktrace, Max is closely involved with Darktrace’s strategic customers & prospects. He works with the R&D team at Darktrace, shaping research into new AI innovations and their various defensive and offensive applications. Max’s insights are regularly featured in international media outlets such as the BBC, Forbes and WIRED. Max holds an MSc from the University of Duisburg-Essen and a BSc from the Cooperative State University Stuttgart in International Business Information Systems.

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November 28, 2024

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Cloud

Cloud security: addressing common CISO challenges with advanced solutions

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Cloud adoption is a cornerstone of modern business with its unmatched potential for scalability, cost efficiency, flexibility, and net-zero targets around sustainability. However, as organizations migrate more workloads, applications, and sensitive data to the cloud it introduces more complex challenges for CISO’s. Let’s dive into the most pressing issues keeping them up at night—and how Darktrace / CLOUD provides a solution for each.

1. Misconfigurations: The Silent Saboteur

Misconfigurations remain the leading cause of cloud-based data breaches. In 2023 alone over 80%  of data breaches involved data stored in the cloud.1  Think open storage buckets or overly permissive permissions; seemingly minor errors that are easily missed and can snowball into major disasters. The fallout of breaches can be costly—both financially and reputationally.

How Darktrace / CLOUD Helps:

Darktrace / CLOUD continuously monitors your cloud asset configurations, learning your environment and using these insights to flag potential misconfigurations. New scans are triggered when changes take place, then grouped and prioritised intelligently, giving you an evolving and prioritised view of vulnerabilities, best practice and mitigation strategies.

2. Hybrid Environments: The Migration Maze

Many organizations are migrating to the cloud, but hybrid setups (where workloads span both on-premises and cloud environments) create unique challenges and visibility gaps which significantly increase complexity. More traditional and most cloud native security tooling struggles to provide adequate monitoring for these setups.

How Darktrace / CLOUD Helps:

Provides the ability to monitor runtime activity for both on-premises and cloud workloads within the same user interface. By leveraging the right AI solution across this diverse data set, we understand the behaviour of your on-premises workloads and how they interact with cloud systems, spotting unusual connectivity or data flow activity during and after the migration process.

This unified visibility enables proactive detection of anomalies, ensures seamless monitoring across hybrid environments, and provides actionable insights to mitigate risks during and after the migration process.

3. Securing Productivity Suites: The Last Mile

Cloud productivity suites like Microsoft 365 (M365) are essential for modern businesses and are often the first step for an organization on a journey to Infrastructure as a Service (IaaS) or Platform as a Service (PaaS) use cases. They also represent a prime target for attackers. Consider a scenario where an attacker gains access to an M365 account, and proceeds to; access sensitive emails, downloading files from SharePoint, and impersonating the user to send phishing emails to internal employees and external partners. Without a system to detect these behaviours, the attack may go unnoticed until significant damage is done.

How Darktrace helps:

Darktrace’s Active AI platform integrates with M365 and establishes an understanding of normal business activity, enabling the detection of abnormalities across its suite including Email, SharePoint and Teams. By identifying subtle deviations in behaviour, such as:

   •    Unusual file accesses

   •    Anomalous login attempts from unexpected locations or devices.

   •    Suspicious email forwarding rules created by compromised accounts.

Darktrace’s Autonomous Response can act precisely to block malicious actions, by disabling compromised accounts and containing threats before they escalate. Precise actions also ensure that critical business operations are maintained even when a response is triggered.  

4. Agent Fatigue: The Visibility Struggle

To secure cloud environments, visibility is critical. If you don’t know what’s there, how can you secure it? Many solutions require agents to be deployed on every server, workload, and endpoint. But managing and deploying agents across sprawling hybrid environments can be both complex and time-consuming when following change controls, and especially as cloud resources scale dynamically.

How Darktrace / CLOUD Helps:

Darktrace reduces or eliminates the need for widespread agent deployment. Its agentless by default, integrating directly with cloud environments and providing instant visibility without the operational headache. Darktrace ensures coverage with minimal friction. By intelligently graphing the relationships between assets and logically grouping your deployed Cloud resources, you are equipped with real-time visibility to quickly understand and protect your environment.

So why Darktrace / CLOUD?

Darktrace’s Self-Learning AI redefines cloud security by adapting to your unique environment, detecting threats as they emerge, and responding in real-time. From spotting misconfigurations to protecting productivity suites and securing hybrid environments. Darktrace / CLOUD simplifies cloud security challenges without adding operational burdens.

From Chaos to Clarity

Cloud security doesn’t have to be a game of endless whack-a-mole. With Darktrace / CLOUD, CISOs can achieve the visibility, control, and proactive protection they need to navigate today’s complex cloud ecosystems confidently.

[1] https://hbr.org/2024/02/why-data-breaches-spiked-in-2023

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About the author
Adam Stevens
Director of Product, Cloud Security

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November 27, 2024

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Inside the SOC

Behind the veil: Darktrace's detection of VPN exploitation in SaaS environments

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Introduction

In today’s digital landscape, Software-as-a-Service (SaaS) platforms have become indispensable for businesses, offering unparalleled flexibly, scalability, and accessibly across locations. However, this convenience comes with a significant caveat - an expanded attack surface that cyber criminals are increasingly exploiting. In 2023, 96.7% of organizations reported security incidents involving at least one SaaS application [1].

Virtual private networks (VPNs) play a crucial role in SaaS security, acting as gateways for secure remote access and safeguarding sensitive data and systems when properly configured. However, vulnerabilities in VPNs can create openings for attacks to exploit, allowing them to infiltrate SaaS environments, compromise data, and disrupt business operations. Notably, in early 2024, the Darktrace Threat Research team investigated the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPNs, which would allow threat actors to gain access to sensitive systems and execute remote code.

More recently, in August, Darktrace identified a SaaS compromise where a threat actor logged into a customer’s VPN from an unusual IP address, following an initial email compromise. The attacker then used a separate VPN to create a new email rule designed to obfuscate the phishing campaign they would later launch.

Attack Overview

The initial attack vector in this case appeared to be through the customer’s email environment. A trusted external contact received a malicious email from another mutual contact who had been compromised and forwarded it to several of the organization’s employees, believing it to be legitimate. Attackers often send malicious emails from compromised accounts to their past contacts, leveraging the trust associated with familiar email addresses. In this case, that trust caused an external victim to unknowingly propagate the attack further. Unfortunately, an internal user then interacted with a malicious payload included in the reply section of the forwarded email.

Later the same day, Darktrace / IDENTITY detected unusual login attempts from the IP 5.62.57[.]7, which had never been accessed by other SaaS users before. There were two failed attempts prior to the successful logins, with the error messages “Authentication failed due to flow token expired” and “This occurred due to 'Keep me signed in' interrupt when the user was signing in.” These failed attempts indicate that the threat actor may have been attempting to gain unauthorized access using stolen credentials or exploiting session management vulnerabilities. Furthermore, there was no attempt to use multi-factor authentication (MFA) during the successful login, suggesting that the threat actor had compromised the account’s credentials.

Following this, Darktrace detected the now compromised account creating a new email rule named “.” – a telltale sign of a malicious actor attempting to hide behind an ambiguous or generic rule name.

The email rule itself was designed to archive incoming emails and mark them as read, effectively hiding them from the user’s immediate view. By moving emails to the “Archive” folder, which is not frequently checked by end users, the attacker can conceal malicious communications and avoid detection. The settings also prevent any automatic deletion of the rules or forced overrides, indicating a cautious approach to maintaining control over the mailbox without raising suspicion. This technique allows the attacker to manipulate email visibility while maintaining a façade of normality in the compromised account.

Email Rule:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: .
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace further identified that this email rule had been created from another IP address, 95.142.124[.]42, this time located in Canada. Open-source intelligence (OSINT) sources indicated this endpoint may have been malicious [2].

Given that this new email rule was created just three minutes after the initial login from a different IP in a different country, Darktrace recognized a geographic inconsistency. By analyzing the timing and rarity of the involved IP addresses, Darktrace identified the likelihood of malicious activity rather than legitimate user behavior, prompting further investigation.

Figure 1: The compromised SaaS account making anomalous login attempts from an unusual IP address in the US, followed by the creation of a new email rule from another VPN IP in Canada.

Just one minute later, Darktrace observed the attacker sending a large number of phishing emails to both internal and external recipients.

Figure 2: The compromised SaaS user account sending a high volume of outbound emails to new recipients or containing suspicious content.

Darktrace / EMAIL detected a significant spike in inbound emails for the compromised account, likely indicating replies to phishing emails.

Figure 3: The figure demonstrates the spike in inbound emails detected for the compromised account, including phishing-related replies.

Furthermore, Darktrace identified that these phishing emails contained a malicious DocSend link. While docsend[.]com is generally recognized as a legitimate file-sharing service belonging to Dropbox, it can be vulnerable to exploitation for hosting malicious content. In this instance, the DocSend domain in question, ‘hxxps://docsend[.]com/view/h9t85su8njxtugmq’, was flagged as malicious by various OSINT vendors [3][4].

Figure 4: Phishing emails detected containing a malicious DocSend link.

In this case, Darktrace Autonomous Response was not in active mode in the customer’s environment, which allowed the compromise to escalate until their security team intervened based on Darktrace’s alerts. Had Autonomous Response been enabled during the incident, it could have quickly mitigated the threat by disabling users and inbox rules, as suggested by Darktrace as actions that could be manually applied, exhibiting unusual behavior within the customer’s SaaS environment.

Figure 5: Suggested Autonomous Response actions for this incident that required human confirmation.

Despite this, Darktrace’s Managed Threat Detection service promptly alerted the Security Operations Center (SOC) team about the compromise, allowing them to conduct a thorough investigation and inform the customer before any further damage could take place.

Conclusion

This incident highlights the role of Darktrace in enhancing cyber security through its advanced AI capabilities. By detecting the initial phishing email and tracking the threat actor's actions across the SaaS environment, Darktrace effectively identified the threat and brought it to the attention of the customer’s security team.

Darktrace’s proactive monitoring was crucial in recognizing the unusual behavior of the compromised account. Darktrace / IDENTITY detected unauthorized access attempts from rare IP addresses, revealing the attacker’s use of a VPN to hide their location.

Correlating these anomalies allowed Darktrace to prompt immediate investigation, showcasing its ability to identify malicious activities that traditional security tools might miss. By leveraging AI-driven insights, organizations can strengthen their defense posture and prevent further exploitation of compromised accounts.

Credit to Priya Thapa (Cyber Analyst), Ben Atkins (Senior Model Developer) and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Models

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compromise / High Priority New Email Rule
  • SaaS / Compromise / New Email Rule and Unusual Email Activity
  • SaaS / Compromise / Unusual Login and Outbound Email Spam
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
  • SaaS / Email Nexus / Possible Outbound Email Spam

Autonomous Response Models

  • Antigena / SaaS / Antigena Email Rule Block
  • Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Technique Name Tactic ID Sub-Technique of

  • Cloud Accounts. DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS T1078.004 T1078
  • Compromise Accounts RESOURCE DEVELOPMENT T1586
  • Email Accounts RESOURCE DEVELOPMENT T1586.002 T1586
  • Internal Spearphishing LATERAL MOVEMENT T1534 -
  • Outlook Rules PERSISTENCE T1137.005 T1137
  • Phishing INITIAL ACCESS T1566 -

Indicators of Compromise (IoCs)

IoC – Type – Description

5.62.57[.]7 – Unusual Login Source

95.142.124[.]42– IP – Unusual Source for Email Rule

hxxps://docsend[.]com/view/h9t85su8njxtugmq - Domain - Phishing Link

References

[1] https://wing.security/wp-content/uploads/2024/02/2024-State-of-SaaS-Report-Wing-Security.pdf

[2] https://www.virustotal.com/gui/ip-address/95.142.124.42

[3] https://urlscan.io/result/0caf3eee-9275-4cda-a28f-6d3c6c3c1039/

[4] https://www.virustotal.com/gui/url/8631f8004ee000b3f74461e5060e6972759c8d38ea8c359d85da9014101daddb

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About the author
Priya Thapa
Cyber Analyst
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