Discover how AI cyber defenses safeguard SaaS applications from cyber threats, ensuring efficiency without compromising security.
It’s no secret that collaboration is the bedrock of business. In fact, a Stanford University study demonstrated that merely priming employees to act in a collaborative fashion — without changing their environment or workflow — makes them more engaged, more persistent, more successful, and less fatigued.
To digitally optimize this biologically ingrained capacity for teamwork, businesses the world over have adopted Software as a Service (SaaS) applications that facilitate the sharing of information between multiple users. Run via centralized, cloud-hosted data centers rather than on local hardware, such applications offer financial and technical benefits to companies of all sizes, from storage savings to reliable connectivity to support speed. Yet it is their collaborative nature that has positioned SaaS software at the heart of the modern enterprise.
Figure 1: The projected number of applications used. Source: Blissfully.
At the same time, the interactivity of cloud services renders them an attractive target for advanced cyber-criminals, who can often leverage a single user’s credentials to compromise dozens of other accounts. And while leading vendors conform to high security standards, the cyber defenses they employ nonetheless have a common weakness: human error on the customer end. By launching sophisticated attacks like those in the case studies below, today’s threat actors are increasingly gaining access to cloud services through the front door, necessitating a fundamentally different security approach that can detect when credentialed users behave — ever so slightly — out of character.
SaaS security issues: Sensitive file access
Among the key challenges is balancing the convenience of open access to information with the imperative of protecting privileged assets. Indeed, with hundreds or even thousands of employees sharing a welter of files and databases at all times, safeguarding SaaS applications against insider threat is extraordinarily difficult with traditional security tools, which use fixed rules and signatures to catch only known, external cyber-attacks. Rather, detecting when credentialed users enter parts of these applications where they don’t belong requires AI security systems that understand their typical online behavior well enough to spot subtle anomalies. And as employees’ responsibilities and privileges inevitably change, such systems must be able to adapt while ‘on the job’.
The necessity of this AI-driven approach to cyber defense recently came to light when Darktrace detected a serious threat on the network of a European bank. After stealing credentials or otherwise gaining access, cyber-criminals will frequently run scripts to identify files containing keywords like “password.” Such was the case with the attackers that Darktrace thwarted, who had managed to find an Office 365 SharePoint file that stored unencrypted passwords. As they had already breached the network, the attackers could have reasonably expected to be in the clear — having already successfully bypassed any conventional security controls.
However, while these attackers would likely have exploited the cleartext passwords to escalate their privileges and further infiltrate the organization, Darktrace AI flagged the activity as anomalous for the bank’s particular network because it breached the following model: “Unusual SaaS Sensitive File Access.” Ultimately, the AI’s nuanced and evolving understanding of what constitutes “unusual” behavior for each of the bank’s users and devices proved critical, given that the suspicious file access may well have been benign in other circumstances.
Social engineering attacks
Perhaps the most difficult cloud-based attacks to counter are those that rely on social engineering, since they involve deceiving employees into handing over their credentials and other lucrative information voluntarily. In these cases, AI anomaly detection is the optimal security strategy, as thwarting a social engineering threat before it’s too late means protecting employees from their own mistakes.
In 2018, Darktrace detected a device on the network of a UK property development company that had attempted to connect to a rare external domain — two seconds after landing on office365.com. The domain had a suspicious name and offered HTTP connections to a form containing sensitive data transmitted in plain text, which would be vulnerable to a man-in-the-middle (MITM) attack. Further investigation indicated that an employee at the property development company had been tricked by a shortened URL in a phishing email to visit the suspicious domain, showing the legitimate looking Office 365 login page below:
Figure 2: A screenshot of the suspicious domain. A minor spelling mistake — “someone” spelt as “sorneone” — appears in the login field of the otherwise legitimate-looking pop-up window.
Despite the user actively clicking on the URL to visit the page, Darktrace flagged the event as threatening due to the rarity of the destination domain in comparison to company’s normal network activity. Artificial intelligence has consistently demonstrated this ability to provide a safety net for human error — flagging anomalous connections and rare domains regardless of how well they may be disguised to the unsuspecting user.
SaaS security solutions
From social engineering attacks to insider threats to stolen credentials, the inherent risks are largely user-dependent. As a consequence, any security tool up to the task of defending these applications must understand how these users work, evolve, and collaborate.
Indeed, it is precisely the sought-after interconnectedness and collaborative nature of cloud platforms which makes the potential reward for attackers so great, as a single breach could allow them to compromise an entire company. Yet the efficiencies promised need not come at the cost of security, since the latest AI cyber defenses shine a light on even the most remote corners of the cloud.
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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.
Author
Justin Fier
SVP, Red Team Operations
Justin is one of the US’s leading cyber intelligence experts, and holds the position of SVP, Red Team Operations at Darktrace. His insights on cyber security and artificial intelligence have been widely reported in leading media outlets, including the Wall Street Journal, CNN, The Washington Post, and VICELAND. With over 10 years’ experience in cyber defense, Justin has supported various elements in the US intelligence community, holding mission-critical security roles with Lockheed Martin, Northrop Grumman Mission Systems and Abraxas. Justin is also a highly-skilled technical specialist, and works with Darktrace’s strategic global customers on threat analysis, defensive cyber operations, protecting IoT, and machine learning.
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)
