Darktrace's Cyber AI Platform swiftly detects and alerts on anomalous behavior in Microsoft 365 accounts in real-time.
Cyber-criminals are increasingly impersonating trusted SaaS platforms and suppliers with their attacks. Recently, Darktrace has detected threats leveraging QuickBooks, WeTransfer and Microsoft Teams brand names. Many of these emails attempt to coax a recipient into clicking a malicious link that leads to a page containing credential-harvesting malware. This blog post demonstrates a possible next phase in an attack – what happens after an employee enters their details on this malicious webpage and has their account compromised.
Even just one compromised internal account can greatly increase the success rate of a phishing campaign. Attackers can use a compromised Microsoft 365 account to gain access to multiple other accounts within hours.
Darktrace’s AI was monitoring over 9,000 devices at a leading technology firm in the APAC region when one employee became victim to a Microsoft 365 account takeover over the weekend. This account was then used to send hundreds of phishing emails to both internal and external contacts. Darktrace detected the early signs of account compromise and raised a high-confidence alert to the security team well before these emails were sent. If the security team had acted quickly in response to the alert, the delivery of the phishing emails – and a second account compromise – could have been avoided.
Timeline of the attack
Figure 1: A timeline of the attack
We can see in the timeline that the attacker only spent three hours performing research before acting. This raises questions on the nature of this threat. Was the attack automated? Had the attacker done preliminary research? Did they know what they were after?
A bespoke and targeted attack
Darktrace first alerted to the security incident when the AI detected that someone was logging in from an unusual geographical location, promptly setting up new inbox rules, and viewing several shared files. The attacker then proceeded to send out over 200 phishing emails to internal and external recipients.
The emails contained a link to a Microsoft OneDrive landing page titled “Contract & Proposal – Customer,” indicating the page was specifically built for this attack. The page contained a phishing link hidden under the display text “Click to Review Fax Document.” Less than one hour after the phishing emails were sent, Darktrace’s AI detected an an unusual login from the same IP to a second account in the organization, indicating this account had likely also been compromised.
How did the attack bypass the rest of the security stack?
The attacker leveraged compromised M365 credentials, with the initial entry likely via compromised credentials from a previous phishing campaign before Darktrace’s AI was deployed;
Traditional email security software trusts internal emails;
Phishing emails contained a OneDrive link, a trusted SaaS platform, so other email security products would not have identified these links as suspicious.
AI Analyst investigates
The technology firm had deployed Darktrace’s Enterprise Immune System across their network and SaaS applications, and consequently had real-time visibility across every event in this attack as it unfolded. Additionally, when the unusual login location was detected, Darktrace’s Cyber AI Analyst immediately launched an automated investigation into the malicious activity, generating a natural language summary of the events and other crucial information to help with incident review.
Figure 2: An excerpt of Cyber AI Analyst’s report of the account hijack
Darktrace’s SaaS Console also reported on the event in the context of activity on that device over the previous week.
Figure 3: Darktrace’s SaaS dashboard displaying an overview of the incident
This attack is another example of the changing nature of cyber-threats in the context of digital transformation. It is not devices, but identities that are increasingly being targeted and attacked.
Darktrace’s real-time alerting on the evolving situation could have enabled the security team to isolate the initial compromised account and change the credentials before the attack escalated further. The initial rare login destination caused Darktrace’s Cyber AI Analyst to launch an ongoing investigation into the compromised account, such that an alert was raised just three minutes after new processing rules were set up by the attacker. With eyes on the technology, a more serious breach could have been avoided, and the breach remeditated in minutes.
Thanks to Darktrace analyst Stefan Rowe for his insights on the above threat find.
For eight more case studies of cyber-threats detected within SaaS environments, read the White Paper.
IoCs:
IoCCommentcovingtonok[.]buzzUsed to host fake login page
Darktrace model detections:
SaaS / Unusual External Source for SaaS Credential Use
SaaS / New Email
SaaS / Unusual Login and New Email Rule
SaaS / Anomalous Exchange Activity
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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
Max Heinemeyer
Global Field CISO
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.
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)
Senior Cyber Analyst and Deputy Analyst Team Lead, Singapore
Blog
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January 14, 2025
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Email
Why AI-powered Email Protection Became Essential for this Global Financial Services Leader
When agile cyber-attackers don’t stop, but pivot
When he first joined this leading financial services provider, it was clear to the CISO that email security needed to be a top priority. The organization provides transfer services to millions of consumers via a network of thousands of agent locations across the US. Those agents are connected to hundreds of thousands of global payers to complete consumer transfers, ranging from leading financial institutions to small local businesses.
With this vast network of agents and payers, the provider relies on email as its primary communications channel. Transmitting billions of dollars every year, the organization is a prime target for cyber criminals looking to steal credentials, financial assets, and sensitive data.
Vulnerable to attacks with gaps in email security and visibility
The CISO discovered that employees were under constant attack by phishing emails impersonating his company’s own executives. The business email compromise (BEC) attacks were designed to deceive employees into sharing credentials or clicking on malicious links.
Upon discovering that their Microsoft 365 tenant lacked secure configuration, the CISO implemented necessary changes to strengthen the service, including enabling authentication controls. While his efforts significantly reduced BEC attacks, cyber criminals changed their tactics, sending employees malicious phishing emails from seemingly valid email accounts from trusted domains like Google and Yahoo. The emails passed through the organization’s native email filters without detection.
The CISO also sought to strengthen defenses against third-party supply chain attacks that could originate with any of the hundreds of thousands of third-party agents and payers the company works with around the world. While the larger institutions typically have sophisticated email security strategies in place, the smaller businesses may lack the cybersecurity expertise needed to effectively secure and manage their data, putting the organization at risk.
While the CISO knew the company was vulnerable to phishing and third-party threats, he didn’t have visibility across the flow of email. Without access to key metrics and valuable data, he couldn’t get the crucial insights needed to quickly identify possible threats and adjust security protocols.
Skilled analysts bogged down with low-level tasks
Like many enterprise organizations, this leading financial services provider relied on a crew of highly skilled analysts to respond to alerts and analyze and triage emails most of their workday. “That shouldn’t be how we operate,” said the CISO. “My role and the role of my staff should be to focus on more strategic projects, support the business, and work on important new product development.”
Balancing user experience with mitigating threats
Enabling greater email security measures without negatively impacting the business, user experience, and customer satisfaction was a daunting challenge the CISO and his security team faced. Imposing restrictions that are too stringent could restrict communication, delay the delivery of important messages, or block legitimate emails – potentially slowing down money transfers, frustrating customers, affecting employee productivity, and impacting revenue. However, maintaining controls that are too permissive could result in serious outcomes like data theft, financial fraud, operational disruption, compliance penalties, and customer attrition.
Self-Learning AI is a game changer
After conducting a thorough POC with several modern security solution providers, this global financial services provider chose the Darktrace / EMAIL an AI-driven email security platform. The CISO said they chose the solution for two key reasons:
Self-Learning AI uses business data to recognize anomalies in communication patterns and user behavior to stop known and unknown threats
Secures the organization’s entire mailflow across all inbound, outbound, and lateral email
Protects against account takeover attacks by identifying subtle anomalies in cloud SaaS
Catches sophisticated threats like impersonations, session token misuse, adversary-in-the-middle attacks, credential theft, and data exfiltration
Second, they pointed to Darktrace’s experience, innovation, and expertise
Deep cybersecurity and industry knowledge
Demonstrated customers successes worldwide
At the forefront of innovation and research, establishing new thresholds in cybersecurity, with technology advances backed by over 200 patents and pending applications
Moreover, and most importantly, this organization trusted Darktrace to deliver on its promises. And according to the CISO, that’s just what happened.
Significantly reduced phishing threats and business risk
Since implementing Darktrace / EMAIL, the threat posed by BEC attacks has dropped sharply. “Phishing is not an issue that concerns me anymore. I estimate we are now identifying and blocking more than 85% of threats our previous solution was missing,” said the CISO. The biggest factor contributing to this success? The power of AI.
With Darktrace / EMAIL, this leadingglobal financial services provider is identifying and blocking more than 85% ofthe phishing email threats its previous solution missed.
AI wasn’t originally on the financial service provider’s list of criteria. But after seeing AI in action and understanding its potential to vastly scale their detection and response capabilities–without adding headcount, the CISO determined AI wasn’t an option but an imperative. “AI is essential when it comes to email security, it’s an absolute necessity,” he said.
Darktrace / EMAIL’s Self-Learning AI is uniquely powerful because it learns the content and context of every internal and external user and can spot the subtle differences in behavioral patterns that point to possible social engineering attacks. Through patented behavioral anomaly detection, Darktrace / EMAIL continuously learns about the organization’s business and users, based on its own operations and data, adjusting security protocols accordingly.
For example, when clients are transferring large amounts of money, they are required to send photos of their driver’s licenses and passports via email to the organization for verification – accounting for a large percentage of its’ inbound email. Darktrace / EMAIL recognizes that it’s normal for customers to send this sensitive information, and it also knows that it’s not normal for that same sensitive information to leave the organization via outbound mail. In addition, Darktrace identifies patterns in user behavior, including who employees communicate with and what kind of information they share. When user behavior falls outside of established norms, such as an email sent from the CFO to employees the CEO would not typically communicate with, Darktrace can take the appropriate action to remove the threat.
“After the implementation, we gave the solution two weeks to ingest our data and learn the specifics of our business. After that, it was perfect, just amazing,” said the CISO.
Boosted team productivity and elevated value to the business
With Darktrace / EMAIL, the organization has successfully scaled its detection and response efforts without scaling personnel. The security team has reduced the number of emails requiring manual investigation by 90%. And because analysts now have the benefit of Darktrace / EMAIL’s analytics and reporting, the investigation process is much easier and faster. “The impact of this solution on my team has been very positive,” said the CISO. “Darktrace / EMAIL essentially manages itself, freeing up time for our skilled analysts–and for myself–to focus on more important projects.”
The security team has scaled its detection and response efforts without scaling personnel,reducing the number of emails it manually investigates by 90%
You can’t control what you can’t see, and with zero visibility into critical data and metrics, this financial services provider was at a serious disadvantage. That has all changed. “Something that I love about Darktrace / EMAIL is the visibility that it provides into key metrics from a single dashboard. We can now understand the behavior of our email flow and data traffic and can make insight-driven decisions to continuously optimize our email security. It’s awesome,” said the CISO.
An efficient user interface also improves productivity and reduces mean time to action by enabling teams to easily visualize key data points and quickly evaluate what actions need to be taken. Darktrace / EMAIL was developed with that experience in mind, allowing users to access data and take quick action without having to constantly log into the solution.
Keeping the business focused on cybersecurity
The leadership of this global organization takes information security very seriously, understanding that cyber-attacks aren’t just an IT problem but a business problem. When it came to evaluating Darktrace, the CISO said numerous stakeholders were involved including C-level executives, infrastructure, and IT, which operates separately from information security. The CISO initially identified the need, conducted the market research, engaged the target vendors, and then brought the other decision makers into the process for the solution evaluation and final decision. “Our IT group, infrastructure team, CTO and CEO are all involved when it comes to making major cybersecurity investments. We always try to make these decisions jointly to ensure we are taking everything into consideration.”
The organization has reached a higher level of maturity when it comes to email cybersecurity. The ability to automate routine email detection and investigation tasks has both strengthened the organization’s cyber resilience and enabled the CISO and his team to contribute more to the business. His advice for other IT leaders facing the same email security and visibility challenges he once experienced: “For those companies that need greater insight and control over their email but have limited resources and people, AI is the answer.”
Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.
Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
Experience 20-25% more threat blocking power with Darktrace / EMAIL
Stop the 58% of threats bypassing traditional email security
