Stopping Corp-Internal Phishing Attacks with Darktrace
16
Jun 2021
Discover how Darktrace Email stopped a series of multi-language phishing attacks, including an Emotet campaign in Japanese. Learn how Darktrace can help!
Language is deceptive. In the realm of email security, language can deceive a recipient into clicking a link or completing a transaction, and it can trick a security tool into thinking an email is legitimate.
It is for this reason that Darktrace/Email is not reliant on language, but rather uses mathematics to develop an understanding of ‘normal’ for every email user in an organization. This enables it to neutralize anomalous emails indicative of a threat around the world, no matter in what format or language they come.
Natural language processing
When it comes to catching a compromised account or impersonation email, how can you teach a computer to understand intent or a change of tone, compared to the normal way a person corresponds?
One of the most common approaches in email security is natural language processing. NLP looks at how to program computers to analyze natural language, commonly by exposing them to a large volume of data.
The result is a computer capable of ‘understanding’ the contents of documents, including the nuances of the language within them. The technology can then extract information in the documents as well as categorize and organize the documents themselves.
Modern-day limitations
However, using NLP is limited in scope for email security as it will often misunderstand specific jargon or colloquialisms, as well as terms that had not been invented when the computer was programmed, unless it is trained on these too. Each additional language requires the computer to learn from zero every time. NLP only works on the regional languages it has been trained on, and it is not commercially viable to teach the technology to work in all small markets.
If a company hires an email security vendor based in America, therefore, it is probable that the security vendor has invested most of their time in detecting English-based phishing threats. That is fine if the company only communicates in English, but this is often not the case. In a 21st century globalized world, the need for security technology to be language-agnostic is more critical than ever.
Not all AI is the same: Unsupervised machine learning
Darktrace/Email relies on unsupervised machine learning, which can learn on the job and does not need to be fed large data sets. It can glean insights from NLP for good measure, but it does not depend on NLP for detection or understanding.
When working with AI it is crucial to understand how the AI learns: does it learn on the job or was it trained with a labeled data set? This is particularly important when looking to understand the intent behind an email, specifically to uncover solicitation attempts either through spoofing, phishing, impersonation of a supplier or any other form of email attack.
Rather than teaching a computer to understand language in an email, Darktrace Cyber AI dynamically assesses activity across inbound and outbound emails including senders, recipients, links, IP addresses, and attachment types. The movement of all these objects are then used by the AI to create the ‘patterns of life’ for every user across all communications, including communications with external users who frequently correspond with a given business.
By taking a mathematical approach, Darktrace/Email is able to understand ‘normal’ for any user regardless of the dialect they are corresponding in, uniquely interpreting all languages from Norwegian to Latin and Persian, and subsequently identifying subtle anomalies indicative of a phishing attack or an account takeover.
Catching Emotet in Japanese
Last year, Darktrace uncovered a sophisticated Spamware campaign which leveraged Emotet, the infamous banking malware. The campaign targeted various industries with highly sophisticated phishing emails.
At a food production company in Japan, Darktrace detected six phishing emails sent over a two-day period in July.
Figure 1: An email from the Emotet campaign.
In the email above, both the subject line and the filename translate to “Regarding the invoice,” followed by a number and the date. The attacker was clearly trying to imitate a legitimate business email here, spoofing a well-known Japanese company (三菱食品(株)) and a common Japanese name (‘藤沢 昭彦’).
Darktrace/Email revealed key metrics behind the email including that the real sender was using a domain name from GMO, a Japanese company which offers cheap web email services, and that the sender’s location was actually Portugal, not Japan.
Figure 2: Darktrace/Email detects the attempt at inducement.
Darktrace/Email’s models recognized the topic anomalies and inducement attempts in the emails, regardless of the language they had been written in – giving a high anomaly score of 85. Furthermore, Darktrace’s AI determined that the extension and the MIME type in the attachments were anomalous, when compared to the documents which the user normally exchanges via email.
Portuguese threat find
In another instance, a series of malicious emails were sent to an organization in Europe. These emails used several tactics to bypass the company’s security tools, including personalized subject lines and hidden malicious URLs.
Figure 3: An interactive snapshot of Darktrace/Email’s user interface. The subject line reads ‘Notice of transfer.’
As displayed above, the email contained a link that appeared to lead to a CaixaBank domain. However, Darktrace/Email recognized this as a deliberate attempt to mislead the recipient and revealed that the link in fact led to a WordPress domain, which Cyber AI identified as 100% rare for the business.
A closer inspection revealed that these emails were sent from Vietnam. The sender had never been in any previous correspondence with the business, and the isolated link within the email was also marked as a 100% rare domain. Darktrace/Email held these malicious emails back, protecting the organization from harm.
Universal defense
These two examples demonstrate the benefits of an unsupervised machine learning approach. An AI security solution which analyzes hundreds of different metrics and does not rely on pre-existing data is a groundbreaking advantage when faced with global phishing threats that now utilize a wide range of languages.
Email-based attacks are becoming more targeted and more convincing by the day. Targeted social engineering and spear phishing with advanced translation tools bombard companies daily, in all languages.
Whether it’s a phishing attack against a local office in Korea or a solicitation attempt in Arabic – even a malicious email written in Klingon from a Star Trek convention – or any of the thousands of email exchanges which occur in countless vernaculars and tones, Darktrace/Email can keep your company safe across the world, and beyond.
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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.
Bytesize Security: Insider Threats in Google Workspace
What is an insider threat?
An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.
Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.
For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.
Attack overview: Insider threat
In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.
While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.
In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.
Conclusion
Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.
Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.
Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)
Appendices
Darktrace Model Detections
SaaS / Resource::Unusual Download Of Externally Shared Google Workspace File
RansomHub Ransomware: Darktrace’s Investigation of the Newest Tool in ShadowSyndicate's Arsenal
What is ShadowSyndicate?
ShadowSyndicate, also known as Infra Storm, is a threat actor reportedly active since July 2022, working with various ransomware groups and affiliates of ransomware programs, such as Quantum, Nokoyawa, and ALPHV. This threat actor employs tools like Cobalt Strike, Sliver, IcedID, and Matanbuchus malware in its attacks. ShadowSyndicate utilizes the same SSH fingerprint (1ca4cbac895fc3bd12417b77fc6ed31d) on many of their servers—85 as of September 2023. At least 52 of these servers have been linked to the Cobalt Strike command and control (C2) framework [1].
What is RansomHub?
First observed following the FBI's takedown of ALPHV/BlackCat in December 2023, RansomHub quickly gained notoriety as a Ransomware-as-a-Service (RaaS) operator. RansomHub capitalized on the law enforcement’s disruption of the LockBit group’s operations in February 2024 to market themselves to potential affiliates who had previously relied on LockBit’s encryptors. RansomHub's success can be largely attributed to their aggressive recruitment on underground forums, leading to the absorption of ex-ALPHV and ex-LockBit affiliates. They were one of the most active ransomware operators in 2024, with approximately 500 victims reported since February, according to their Dedicated Leak Site (DLS) [2].
ShadowSyndicate and RansomHub
External researchers have reported that ShadowSyndicate had as many as seven different ransomware families in their arsenal between July 2022, and September 2023. Now, ShadowSyndicate appears to have added RansomHub’s their formidable stockpile, becoming an affiliate of the RaaS provider [1].
Darktrace’s analysis of ShadowSyndicate across its customer base indicates that the group has been leveraging RansomHub ransomware in multiple attacks in September and October 2024. ShadowSyndicate likely shifted to using RansomHub due to the lucrative rates offered by this RaaS provider, with affiliates receiving up to 90% of the ransom—significantly higher than the general market rate of 70-80% [3].
In many instances where encryption was observed, ransom notes with the naming pattern “README_[a-zA-Z0-9]{6}.txt” were written to affected devices. The content of these ransom notes threatened to release stolen confidential data via RansomHub’s DLS unless a ransom was paid. During these attacks, data exfiltration activity to external endpoints using the SSH protocol was observed. The external endpoints to which the data was transferred were found to coincide with servers previously associated with ShadowSyndicate activity.
Darktrace’s coverage of ShadowSyndicate and RansomHub
Darktrace’s Threat Research team identified high-confidence indicators of compromise (IoCs) linked to the ShadowSyndicate group deploying RansomHub. The investigation revealed four separate incidents impacting Darktrace customers across various sectors, including education, manufacturing, and social services. In the investigated cases, multiple stages of the kill chain were observed, starting with initial internal reconnaissance and leading to eventual file encryption and data exfiltration.
Attack Overview
Internal Reconnaissance
The first observed stage of ShadowSyndicate attacks involved devices making multiple internal connection attempts to other internal devices over key ports, suggesting network scanning and enumeration activity. In this initial phase of the attack, the threat actor gathers critical details and information by scanning the network for open ports that might be potentially exploitable. In cases observed by Darktrace affected devices were typically seen attempting to connect to other internal locations over TCP ports including 22, 445 and 3389.
C2 Communication and Data Exfiltration
In most of the RansomHub cases investigated by Darktrace, unusual connections to endpoints associated with Splashtop, a remote desktop access software, were observed briefly before outbound SSH connections were identified.
Following this, Darktrace detected outbound SSH connections to the external IP address 46.161.27[.]151 using WinSCP, an open-source SSH client for Windows used for secure file transfer. The Cybersecurity and Infrastructure Security Agency (CISA) identified this IP address as malicious and associated it with ShadowSyndicate’s C2 infrastructure [4]. During connections to this IP, multiple gigabytes of data were exfiltrated from customer networks via SSH.
Data exfiltration attempts were consistent across investigated cases; however, the method of egress varied from one attack to another, as one would expect with a RaaS strain being employed by different affiliates. In addition to transfers to ShadowSyndicate’s infrastructure, threat actors were also observed transferring data to the cloud storage and file transfer service, MEGA, via HTTP connections using the ‘rclone’ user agent – a command-line program used to manage files on cloud storage. In another case, data exfiltration activity occurred over port 443, utilizing SSL connections.
Lateral Movement
In investigated incidents, lateral movement activity began shortly after C2 communications were established. In one case, Darktrace identified the unusual use of a new administrative credential which was quickly followed up with multiple suspicious executable file writes to other internal devices on the network.
The filenames for this executable followed the regex naming convention “[a-zA-Z]{6}.exe”, with two observed examples being “bWqQUx.exe” and “sdtMfs.exe”.
Figure 1: Cyber AI Analyst Investigation Process for the SMB Writes of Suspicious Files to Multiple Devices' incident.
Additionally, script files such as “Defeat-Defender2.bat”, “Share.bat”, and “def.bat” were also seen written over SMB, suggesting that threat actors were trying to evade network defenses and detection by antivirus software like Microsoft Defender.
File Encryption
Among the three cases where file encryption activity was observed, file names were changed by adding an extension following the regex format “.[a-zA-Z0-9]{6}”. Ransom notes with a similar naming convention, “README_[a-zA-Z0-9]{6}.txt”, were written to each share. While the content of the ransom notes differed slightly in each case, most contained similar text. Clear indicators in the body of the ransom notes pointed to the use of RansomHub ransomware in these attacks. As is increasingly the case, threat actors employed double extortion tactics, threatening to leak confidential data if the ransom was not paid. Like most ransomware, RansomHub included TOR site links for communication between its "customer service team" and the target.
Figure 2: The graph shows the behavior of a device with encryption activity, using the “SMB Sustained Mimetype Conversion” and “Unusual Activity Events” metrics over three weeks.
Since Darktrace’s Autonomous Response capability was not enabled during the compromise, the ransomware attack succeeded in its objective. However, Darktrace’s Cyber AI Analyst provided comprehensive coverage of the kill chain, enabling the customer to quickly identify affected devices and initiate remediation.
Figure 3: Cyber AI Analyst panel showing the critical incidents of the affected device from one of the cases investigated.
In lieu of Autonomous Response being active on the networks, Darktrace was able to suggest a variety of manual response actions intended to contain the compromise and prevent further malicious activity. Had Autonomous Response been enabled at the time of the attack, these actions would have been quickly applied without any human interaction, potentially halting the ransomware attack earlier in the kill chain.
Figure 4: A list of suggested Autonomous Response actions on the affected devices."
Conclusion
The Darktrace Threat Research team has noted a surge in attacks by the ShadowSyndicate group using RansomHub’s RaaS of late. RaaS has become increasingly popular across the threat landscape due to its ease of access to malware and script execution. As more individual threat actors adopt RaaS, security teams are struggling to defend against the increasing number of opportunistic attacks.
For customers subscribed to Darktrace’s Security Operations Center (SOC) services, the Analyst team promptly investigated detections of the aforementioned unusual and anomalous activities in the initial infection phases. Multiple alerts were raised via Darktrace’s Managed Threat Detection to warn customers of active ransomware incidents. By emphasizing anomaly-based detection and response, Darktrace can effectively identify devices affected by ransomware and take action against emerging activity, minimizing disruption and impact on customer networks.
Credit to Kwa Qing Hong (Senior Cyber Analyst and Deputy Analyst Team Lead, Singapore) and Signe Zahark (Principal Cyber Analyst, Japan)
