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April 10, 2023

Detecting Malicious Email Activity & AI Impersonating

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10
Apr 2023
Discover how two different phishing attempts from some known and unknown senders used a payroll diversion and credential sealing box link to harm users.

Social engineering has become widespread in the cyber threat landscape in recent years, and the near-universal use of social media today has allowed attackers to research and target victims more effectively. Social engineering involves manipulating users to carry out actions such as revealing sensitive information like login credentials or credit card details. It can also lead to user account compromises, causing huge disruption to an organization’s digital estate. 

As people use social media platforms not only for personal reasons, but also for business purposes, attackers gain information they can exploit in social engineering attacks. For example, a threat actor may attempt to impersonate a known individual or legitimate service to take advantage of a user’s established trust. This is a highly successful method of social engineering because mimicking known contacts makes it difficult for traditional security tools that rely on deny-lists to detect the attack.

In October 2022, Darktrace identified and responded to two separate malicious email campaigns in which threat actors attempted to impersonate known contacts in an effort to compromise customer devices. As it learns the normal behavior of every user in the email system, Darktrace was able to instantly detect these threats and mitigate them autonomously, preventing significant disruption to the customer networks.

Payroll Diversion Fraud Attempt Impersonating a Former Employee 

While a customer in the Canadian energy sector was trialing Darktrace in October 2022, Darktrace/Email™ identified a suspicious email seemingly sent from an employee within the organization. The email was sent to the Senior Director of Human Resources (HR) with a subject line of “Change in payroll Direct Deposit.” The email requested a change in bank account information for an employee. However, Darktrace recognized that the sender was using a free mail address that contained random letters, indicating it may have been algorithmically generated. Since this incident occurred during a trial, Darktrace/Email was not configured to take action. Otherwise, it would have prevented the email from landing in the inbox. In this case though, the email went through, bypassing all other security tools in place.

Although the email was from an unknown sender, the HR director believed the email could have been legitimate as the employee who appeared to be the sender had left the organization seven days prior and no longer had access to their corporate email account. However, after reviewing it in the Darktrace/Email dashboard, the customer grew suspicious and contacted the former employee directly to verify if the request was legitimate. The former employee validated the suspicions by confirming they had sent no such email.

Further investigation by the customer revealed that the former employee had been vocal about their departure on various social media platforms. This gave threat actors valuable information to believably impersonate the former employee and defraud the organization. 

Such attempts to target organizations’ HR departments and divert payroll are common tactics for cyber-criminals and are often identified by Darktrace/Email across the customer base. Darktrace/Email is able to instantly identify the indicators associated with these spoofing attempts and immediately bring them to the attention of the customer’s security team. 

Using Legitimate File Sharing Service to Share a Phishing Link 

On October 7, 2022, a customer in the Singaporean construction sector was targeted by a phishing campaign attempting to impersonate a law firm known to the organization. Almost 200 employees received an email with the subject line “Accepted: Valuation Agreement.” 

Figure 1: Sample of an UI view of the message held showing anomaly indicators, history, association, and validation.

Four days earlier, Darktrace observed communication between another email address associated with the law firm and an employee of the customer. Darktrace/Email noted that it was the first time this correspondent had sent emails to the customer. 

Figure 2: Metrics showing how well the sender’s domain is known within the digital environment.

The emails contained a highly unusual link to a file sharing service, (hxxps://ssvilvensstokes[.]app[.]box[.]com/notes), hidden behind the text “PREVIEW OR PRINT COPY OF DOCUMENT HERE.” Darktrace analysts investigated this event further and found that around 30 similar URLs had been identified as suspicious using OSINT security tools in October 2022, suggesting the customer was not the only target of this phishing campaign.

Figure 3: Preview of the phishing email’s body.
Figure 4: Darktrace’s evaluation of the link contained in the phishing email.

Additional OSINT work revealed that the link directed to a website which appeared to host a PDF file named “Valuation Agreement.” The recipient would then be prompted to follow another link (hulking-citrine-krypton[.]glitch[.]me), again hidden behind the text “OPEN OR ACCESS DOCUMENT HERE” to view the file. Subsequently, the user would be prompted to enter their Microsoft 365 credentials. 

Figure 5: The page displayed when the phishing link was clicked, viewed in a sandbox environment.
Figure 6: Example of a page shown when recipient clicks the second link, accessing “hulking-citrine-krypton[.]glitch[.]me”. 

This page contained the text “This document has been scanned for viruses by Norton Antivirus Security.” This is another example of threat actors’ employing social engineering techniques by impersonating well-known brands, such as established security vendors, to gain the trust of users and increase their likelihood of success.

It is highly probable that a real employee of the law firm had their account hijacked and that a malicious actor was exploiting it to send out these phishing emails en masse as part of a supply chain attack. In such cases, malicious actors rely on their targets’ trust of known contacts to not question departures from their normal conversations. 

Darktrace was able to instantly detect multiple anomalies in these emails, despite the fact that they were seemingly sent by known correspondents. The activity detected automatically triggered model breaches associated with unexpected and visually prominent links. As a result, Darktrace/Email responded by locking the link, stopping users from being able to click it.

Darktrace subsequently identified additional emails from this sender attempting to target other recipients within the company, triggering the model breaches associated with a surge in email sending indicative of a phishing campaign. In response, Darktrace/Email autonomously acted and filed these emails as junk. As more emails were detected across the customer’s environment, the anomaly score of the sender increased and Darktrace ultimately held back over 160 malicious emails, safeguarding recipients from potential account compromise.           

The following Darktrace/Email models were breached throughout the course of this phishing campaign:

  • Unusual/Sender Surge 
  • Unusual/Undisclosed Recipients 
  • Antigena Anomaly 
  • Association/Unlikely Recipient Association 
  • Link/Low Link Association 
  • Link/Visually Prominent Link 
  • Link/Visually Prominent Link Unexpected For Sender 
  • Unusual/New Sender Wide Distribution
  • Unusual/Undisclosed Recipients + New Address Known Domain

Conclusion

Social engineering plays a role in many of the major threats challenging current email cyber security, as attackers can use it to manipulate users into transferring money, revealing credentials, clicking malicious links, and more. 

The above threat stories happened before language generating AI became mainstream with the release of ChatGPT in December 2022. Now, it is even easier for malicious actors to generate sophisticated social engineering emails. By using social media posts as input, social engineering emails written by generative AI can be highly targeted and produced at scale. They often avoid the flags users are trained to look for, like poor grammar and spelling mistakes, and can hide payloads or forgo them entirely.

To mitigate the risk of possible social engineering attempts, it is recommended that organizations implement social media policies that advise employees to be cautious of what they post online and enact procedures to verify if fund transfer requests are legitimate.

Yet these policies are not enough on their own. Darktrace/Email can identify suspicious email traits, whether an email is sent from a known correspondent or an unknown sender. With Self-Learning AI, it knows an organization’s users better than any impersonator could. In this way, Darktrace/Email detects anomalies within emails and neutralizes malicious components at machine-speed, stopping attacks at their earliest stages, before employees fall victim. 

Appendices

List of Indicators of Compromise (IoCs)

Domain:

hxxps://ssvilvensstokes[.]app[.]box[.]com/notes/*?s=* - 1st external link (seen in email)

hxxps://hulking-citrine-krypton[.]glitch[.]me/flk.html - 2nd external link, masked behind “OPEN OR ACCESS DOCUMENT HERE”

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
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Isabelle Cheong
Cyber Security Analyst
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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 28, 2024

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Thought Leadership

Preparing for 2025: Darktrace's top 10 AI and cybersecurity predictions

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Each year, Darktrace's AI and cybersecurity experts reflect on the events of the past 12 months and predict the trends we expect to shape the cybersecurity landscape in the year ahead. In 2024, we predicted that the global elections, fast-moving AI innovations, and increasingly cloud-based IT environments would be key factors shaping the cyber threat landscape.

Looking ahead to 2025, we expect the total addressable market of cybercrime to expand as attackers add more tactics to their toolkits. Threat actors will continue to take advantage of the volatile geopolitical environment and cybersecurity challenges will increasingly move to new frontiers like space. When it comes to AI, we anticipate the innovation in AI agents in 2024 to pave the way for the rise of multi-agent systems in 2025, creating new challenges and opportunities for cybersecurity professionals and attackers alike.

Here are ten trends to watch for in 2025:

The overall Total Addressable Market (TAM) of cybercrime gets bigger

Cybercrime is a global business, and an increasingly lucrative one, scaling through the adoption of AI and cybercrime-as-a-service. Annual revenue from cybercrime is already estimated to be over $8 trillion, which we’ve found is almost 5x greater than the revenue of the Magnificent Seven stocks. There are a few key factors driving this growth.

The ongoing growth of devices and systems means that existing malware families will continue to be successful. As of October 2024, it’s estimated that more than 5.52 billion people (~67%) have access to the internet and sources estimate 18.8 billion connected devices will be online by the end of 2024. The increasing adoption of AI is poised to drive even more interconnected systems as well as new data centers and infrastructure globally.

At the same time, more sophisticated capabilities are available for low-level attackers – we’ve already seen the trickle-down economic benefits of living off the land, edge infrastructure exploitation, and identity-focused exploitation. The availability of Ransomware-as-a-Service (RaaS) and Malware-as-a-Service (MaaS) make more advanced tactics the norm. The subscription income that these groups can generate enables more adversarial innovation, so attacks are getting faster and more effective with even bigger financial ramifications.

While there has also been an increasing trend in the last year of improved cross-border law enforcement, the efficacy of these efforts remains to be seen as cybercriminal gangs are also getting more resilient and professionalized. They are building better back-up systems and infrastructure as well as more multi-national networks and supply chains.

Security teams need to prepare for the rise of AI agents and multi-agent systems

Throughout 2024, we’ve seen major announcements about advancements in AI agents from the likes of OpenAI, Microsoft, Salesforce, and more. In 2025, we’ll see increasing innovation in and adoption of AI agents as well as the emergence of multi-agent systems (or “agent swarms”), where groups of autonomous agents work together to tackle complex tasks.

The rise of AI agents and multi-agent systems will introduce new challenges in cybersecurity, including new attack vectors and vulnerabilities. Security teams need to think about how to protect these systems to prevent data poisoning, prompt injection, or social engineering attacks.

One benefit of multi-agent systems is that agents can autonomously communicate, collaborate, and interact. However without clear and distinct boundaries and explicit permissions, this can also pose a major data privacy risk and avenue for manipulation. These issues cannot be addressed by traditional application testing alone. We must ensure these systems are secure by design, where robust protective mechanisms and data guardrails are built into the foundations.

Threat actors will be the earliest adopters of AI agents and multi-agent systems

We’ve already seen how quickly threat actors have been able to adopt generative AI for tasks like email phishing and reconnaissance. The next frontier for threat actors will be AI agents and multi-agent systems that are specialized in autonomous tasks like surveillance, initial access brokering, privilege escalation, vulnerability exploitation, data summarization for smart exfiltration, and more. Because they have no concern for safe, secure, accurate, and responsible use, adversaries will adopt these systems faster than cyber defenders.

We could also start to see use cases emerge for multi-agent systems in cyber defense – with potential for early use cases in incident response, application testing, and vulnerability discovery. On the whole, security teams will be slower to adopt these systems than adversaries because of the need to put in place proper security guardrails and build trust over time.

There is heightened supply chain risk for Large Language Models (LLMs)

Training LLMs requires a lot of data, and many experts have warned that world is running out of quality data for that training. As a result, there will be an increasing reliance on synthetic data, which can introduce new issues of accuracy and efficacy. Moreover, data supply chain risks will be an Achilles heel for organizations, with the potential interjection of vulnerabilities through the data and machine learning providers that they rely on. Poisoning one data set could have huge trickle-down impacts across many different systems. Data security will be paramount in 2025.

The race to identify software vulnerabilities intensifies

The time it takes for threat actors to exploit newly published CVEs is getting shorter, giving defenders an even smaller window to apply patches and remediations. A 2024 report from Cloudflare found that threat actors quickly weaponized proof of concept exploits in attacks as quickly as 22 minutes after the exploits were made public.

At the same time, 2024 also saw the first reports from researchers across academia and the tech industry using AI for vulnerability discovery in real-world code. With threat actors getting faster at exploiting vulnerabilities, defenders will need to use AI to identify vulnerabilities in their software stack and to help identify and prioritize remediations and patches.

Insider threat risks will force organizations to evolve zero trust strategies

In 2025, an increasingly volatile geopolitical situation and the intensity of the AI race will make insider threats an even bigger risk for businesses, forcing organizations to expand zero-trust strategies. The traditional zero-trust model provides protection from external threats to an organization’s network by requiring continuous verification of the devices and users attempting to access critical business systems, services, and information from multiple sources. However, as we have seen in the more recent Jack Teixeira case, malicious insiders can still do significant damage to an organization within their approved and authenticated boundary.

To circumvent the remaining security gaps in a zero-trust architecture and mitigate increasing risk of insider threats, organizations will need to integrate a behavioral understanding dimension to their zero-trust approaches. The zero-trust best practice of “never trust, always verify” needs to evolve to become “never trust, always verify, and continuously monitor.”

Identity remains an expensive problem for businesses

2024 saw some of the biggest and costliest attacks – all because the attacker had access to compromised credentials. Essentially, they had the key to the front door. Businesses still struggle with identity and access management (IAM), and it’s getting more complex now that we’re in the middle of a massive Software-as-a-Service (SaaS) migration driven by increasing rates of AI and cloud use across businesses.

This challenge is going to be exacerbated in 2025 by a few global and business factors. First, there is an increasing push for digital identities, such as the rollout of the EU Digital Identity Framework that is underway, which could introduce additional attack vectors. As they scale, businesses are turning more and more to centralized identity and access solutions with decentralized infrastructure and relying on SaaS and application-native security.

Increasing vulnerabilities at the edge

During the COVID-19 pandemic, many organizations had to stand-up remote access solutions quickly – in a matter of days or weeks – without the high level of due diligence that they require to be fully secured. In 2025, we expect to see continued fall-out as these quickly spun-up solutions start to present genuine vulnerability to businesses. We’ve already seen this start to play out in 2024 with the mass-exploitation of internet-edge devices like firewalls and VPN gateway products.

By July 2024, Darktrace’s threat research team observed that the most widely exploited edge infrastructure devices were those related to Ivanti Connect Secure, JetBrains TeamCity, FortiClient Enterprise Management Server, and Palo Alto Networks PAN-OS. Across the industry, we’ve already seen many zero days and vulnerabilities exploiting these internet-connected devices, which provide inroads into the network and store/cache credentials and passwords of other users that are highly valuable for threat actors.

Hacking Operational Technology (OT) gets easier

Hacking OT is notoriously complex – causing damage requires an intimate knowledge of the specific systems being targeted and historically was the reserve of nation states. But as OT has become more reliant and integrated with IT systems, attackers have stumbled on ways to cause disruption without having to rely on the sophisticated attack-craft normally associated with nation-state groups. That’s why some of the most disruptive attacks of the last year have come from hacktivist and financially-motivated criminal gangs – such as the hijacking of internet-exposed Programmable Logic Controllers (PLCs) by anti-Israel hacking groups and ransomware attacks resulting in the cancellation of hospital operations.  

In 2025, we expect to see an increase in cyber-physical disruption caused by threat groups motivated by political ideology or financial gain, bringing the OT threat landscape closer in complexity and scale to that of the IT landscape. The sectors most at risk are those with a strong reliance on IoT sensors, including healthcare, transportation, and manufacturing sectors.

Securing space infrastructure and systems becomes a critical imperative

The global space industry is growing at an incredibly fast pace, and 2025 is on track to be another record-breaking year for spaceflight with major missions and test flights planned by NASA, ESA, CNSA as well as the expected launch of the first commercial space station from Vast and programs from Blue Origin, Amazon and more. Research from Analysis Mason suggests that 38,000 additional satellites will be built and launched by 2033 and the global space industry revenue will reach $1.7 trillion by 2032. Space has also been identified as a focus area for the incoming US administration.

In 2025, we expect to see new levels of tension emerge as private and public infrastructure increasingly intersect in space, shining a light on the lack of agreed upon cyber norms and the increasing challenge of protecting complex and remote space systems against modern cyber threats.  Historically focused on securing earth-bound networks and environments, the space industry will face challenges as post-orbit threats rise, with satellites moving up the target list.

The EU’s NIS2 Directive now recognizes the space sector as an essential entity that is subject to its most strict cybersecurity requirements. Will other jurisdictions follow suit? We expect global debates about cyber vulnerabilities in space to come to the forefront as we become more reliant on space-based technology.

Preparing for the future

Whatever 2025 brings, Darktrace is committed to providing robust cybersecurity leadership and solutions to enterprises around the world. Our team of subject matter experts will continue to monitor emerging threat trends, advising both our customers and our product development teams.

And for day-to-day security, our multi-layered AI cybersecurity platform can protect against all types of threats, whether they are known, unknown, entirely novel, or powered by AI. It accomplishes this by learning what is normal for your unique organization, therefore identifying unusual and suspicious behavior at machine speed, regardless of existing rules and signatures. In this way, organizations with Darktrace can be ready for any developments in the cybersecurity threat landscape that the new year may bring.

Discover more about Darktrace's predictions on the AI and cybersecurity landscape for 2025 by joining the upcoming webinar on December 12, 2024 at 10:00am EST/3:00pm GMT. Register here.

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