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Comparing different AI approaches to email security

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01
Feb 2021
01
Feb 2021
AI has fundamentally changed email security in recent years, but there is significant distinction to be made in the application of the technology which may determine genuine and future-proof protection from a backward-looking model incapable of catching novel attacks.

Innovations in artificial intelligence (AI) have fundamentally changed the email security landscape in recent years, but it can often be hard to determine what makes one system different to the next. In reality, under that umbrella term there exists a significant distinction in approach which may determine whether the technology provides genuine protection or simply a perceived notion of defense.

One backward-looking approach involves feeding a machine thousands of emails that have already been deemed to be malicious, and training it to look for patterns in these emails in order to spot future attacks. The second approach uses an AI system to analyze the entirety of an organization’s real-world data, enabling it to establish a notion of what is ‘normal’ and then spot subtle deviations indicative of an attack.

In the below, we compare the relative merits of each approach, with special consideration to novel attacks that leverage the latest news headlines to bypass machine learning systems trained on data sets. Training a machine on previously identified ‘known bads’ is only advantageous in certain, specific contexts that don’t change over time: to recognize the intent behind an email, for example. However, an effective email security solution must also incorporate a self-learning approach that understands ‘normal’ in the context of an organization in order to identify unusual and anomalous emails and catch even the novel attacks.

Signatures – a backward-looking approach

Over the past few decades, cyber security technologies have looked to mitigate risk by preventing previously seen attacks from occurring again. In the early days, when the lifespan of a given strain of malware or the infrastructure of an attack was in the range of months and years, this method was satisfactory. But the approach inevitably results in playing catch-up with malicious actors: it always looks to the past to guide detection for the future. With decreasing lifetimes of attacks, where a domain could be used in a single email and never seen again, this historic-looking signature-based approach is now being widely replaced by more intelligent systems.

Training a machine on ‘bad’ emails

The first AI approach we often see in the wild involves harnessing an extremely large data set with thousands or millions of emails. Once these emails have come through, an AI is trained to look for common patterns in malicious emails. The system then updates its models, rules set, and blacklists based on that data.

This method certainly represents an improvement to traditional rules and signatures, but it does not escape the fact that it is still reactive, and unable to stop new attack infrastructure and new types of email attacks. It is simply automating that flawed, traditional approach – only instead of having a human update the rules and signatures, a machine is updating them instead.

Relying on this approach alone has one basic but critical flaw: it does not enable you to stop new types of attacks that it has never seen before. It accepts that there has to be a ‘patient zero’ – or first victim – in order to succeed.

The industry is beginning to acknowledge the challenges with this approach, and huge amounts of resources – both automated systems and security researchers – are being thrown into minimizing its limitations. This includes leveraging a technique called “data augmentation” that involves taking a malicious email that slipped through and generating many “training samples” using open-source text augmentation libraries to create “similar” emails – so that the machine learns not only the missed phish as ‘bad’, but several others like it – enabling it to detect future attacks that use similar wording, and fall into the same category.

But spending all this time and effort into trying to fix an unsolvable problem is like putting all your eggs in the wrong basket. Why try and fix a flawed system rather than change the game altogether? To spell out the limitations of this approach, let us look at a situation where the nature of the attack is entirely new.

The rise of ‘fearware’

When the global pandemic hit, and governments began enforcing travel bans and imposing stringent restrictions, there was undoubtedly a collective sense of fear and uncertainty. As explained previously in this blog, cyber-criminals were quick to capitalize on this, taking advantage of people’s desire for information to send out topical emails related to COVID-19 containing malware or credential-grabbing links.

These emails often spoofed the Centers for Disease Control and Prevention (CDC), or later on, as the economic impact of the pandemic began to take hold, the Small Business Administration (SBA). As the global situation shifted, so did attackers’ tactics. And in the process, over 130,000 new domains related to COVID-19 were purchased.

Let’s now consider how the above approach to email security might fare when faced with these new email attacks. The question becomes: how can you train a model to look out for emails containing ‘COVID-19’, when the term hasn’t even been invented yet?

And while COVID-19 is the most salient example of this, the same reasoning follows for every single novel and unexpected news cycle that attackers are leveraging in their phishing emails to evade tools using this approach – and attracting the recipient’s attention as a bonus. Moreover, if an email attack is truly targeted to your organization, it might contain bespoke and tailored news referring to a very specific thing that supervised machine learning systems could never be trained on.

This isn’t to say there’s not a time and a place in email security for looking at past attacks to set yourself up for the future. It just isn’t here.

Spotting intention

Darktrace uses this approach for one specific use which is future-proof and not prone to change over time, to analyze grammar and tone in an email in order to identify intention: asking questions like ‘does this look like an attempt at inducement? Is the sender trying to solicit some sensitive information? Is this extortion?’ By training a system on an extremely large data set collected over a period of time, you can start to understand what, for instance, inducement looks like. This then enables you to easily spot future scenarios of inducement based on a common set of characteristics.

Training a system in this way works because, unlike news cycles and the topics of phishing emails, fundamental patterns in tone and language don’t change over time. An attempt at solicitation is always an attempt at solicitation, and will always bear common characteristics.

For this reason, this approach only plays one small part of a very large engine. It gives an additional indication about the nature of the threat, but is not in itself used to determine anomalous emails.

Detecting the unknown unknowns

In addition to using the above approach to identify intention, Darktrace uses unsupervised machine learning, which starts with extracting and extrapolating thousands of data points from every email. Some of these are taken directly from the email itself, while others are only ascertainable by the above intention-type analysis. Additional insights are also gained from observing emails in the wider context of all available data across email, network and the cloud environment of the organization.

Only after having a now-significantly larger and more comprehensive set of indicators, with a more complete description of that email, can the data be fed into a topic-indifferent machine learning engine to start questioning the data in millions of ways in order to understand if it belongs, given the wider context of the typical ‘pattern of life’ for the organization. Monitoring all emails in conjunction allows the machine to establish things like:

  • Does this person usually receive ZIP files?
  • Does this supplier usually send links to Dropbox?
  • Has this sender ever logged in from China?
  • Do these recipients usually get the same emails together?

The technology identifies patterns across an entire organization and gains a continuously evolving sense of ‘self’ as the organization grows and changes. It is this innate understanding of what is and isn’t ‘normal’ that allows AI to spot the truly ‘unknown unknowns’ instead of just ‘new variations of known bads.’

This type of analysis brings an additional advantage in that it is language and topic agnostic: because it focusses on anomaly detection rather than finding specific patterns that indicate threat, it is effective regardless of whether an organization typically communicates in English, Spanish, Japanese, or any other language.

By layering both of these approaches, you can understand the intention behind an email and understand whether that email belongs given the context of normal communication. And all of this is done without ever making an assumption or having the expectation that you’ve seen this threat before.

Years in the making

It’s well established now that the legacy approach to email security has failed – and this makes it easy to see why existing recommendation engines are being applied to the cyber security space. On first glance, these solutions may be appealing to a security team, but highly targeted, truly unique spear phishing emails easily skirt these systems. They can’t be relied on to stop email threats on the first encounter, as they have a dependency on known attacks with previously seen topics, domains, and payloads.

An effective, layered AI approach takes years of research and development. There is no single mathematical model to solve the problem of determining malicious emails from benign communication. A layered approach accepts that competing mathematical models each have their own strengths and weaknesses. It autonomously determines the relative weight these models should have and weighs them against one another to produce an overall ‘anomaly score’ given as a percentage, indicating exactly how unusual a particular email is in comparison to the organization’s wider email traffic flow.

It is time for email security to well and truly drop the assumption that you can look at threats of the past to predict tomorrow’s attacks. An effective AI cyber security system can identify abnormalities with no reliance on historical attacks, enabling it to catch truly unique novel emails on the first encounter – before they land in the inbox.

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
ABOUT ThE AUTHOR
Dan Fein
VP, Product

Based in New York, Dan joined Darktrace’s technical team in 2015, helping customers quickly achieve a complete and granular understanding of Darktrace’s product suite. Dan has a particular focus on Darktrace/Email, ensuring that it is effectively deployed in complex digital environments, and works closely with the development, marketing, sales, and technical teams. Dan holds a Bachelor’s degree in Computer Science from New York University.

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Gootloader Malware: Detecting and Containing Multi-Functional Threats with Darktrace

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15
Feb 2024

What is multi-functional malware?

While traditional malware variants were designed with one specific objective in mind, the emergence of multi-functional malware, such as loader malware, means that organizations are likely to be confronted with multiple malicious tools and strains of malware at once. These threats often have non-linear attack patterns and kill chains that can quickly adapt and progress quicker than human security teams are able to react. Therefore, it is more important than ever for organizations to adopt an anomaly approach to combat increasingly versatile and fast-moving threats.

Example of Multi-functional malware

One example of a multi-functional malware recently observed by Darktrace can be seen in Gootloader, a multi-payload loader variant that has been observed in the wild since 2020. It is known to primarily target Windows-based systems across multiple industries in the US, Canada, France, Germany, and South Korea [1].  

How does Gootloader malware work?

Once installed on a target network, Gootloader can download additional malicious payloads that allow threat actors to carry out a range of harmful activities, such as stealing sensitive information or encrypting files for ransom.

The Gootloader malware is known to infect networks via search engine optimization (SEO) poisoning, directing users searching for legitimate documents to compromised websites hosting a malicious payload masquerading as the desired file.

If the malware remains undetected, it paves the way for a second stage payload known as Gootkit, which functions as a banking trojan and information-stealer, or other malware tools including Cobalt Strike and Osiris [2].

Darktrace detection of Gootloader malware

In late 2023, Darktrace observed one instance of Gootloader affecting a customer in the US. Thanks to its anomaly-focused approach, Darktrace DETECT™ quickly identified the anomalous activity surrounding this emerging attack and brought it to the immediate attention of the customer’s security team. All the while, Darktrace RESPOND™ was in place and able to autonomously intervene, containing the suspicious activity and ensuring the Gootloader compromise could not progress any further.

In September 2023, Darktrace identified an instance of the Gootloader malware attempting to propagate within the network of a customer in the US. Darktrace identified the first indications of the compromise when it detected a device beaconing to an unusual external location and performing network scanning. Following this, the device was observed making additional command-and-control (C2) connections, before finally downloading an executable (.exe) file which likely represented the download of a further malicious payload.

As this customer had subscribed to the Proactive Notification Service (PTN), the suspicious activity was escalated to the Darktrace Security Operations Center (SOC) for further investigation by Darktrace’s expert analysts. The SOC team were able to promptly triage the incident and advise urgent follow-up actions.

Gootloader Attack Overview

Figure 1: Timeline of Anomalous Activities seen on the breach device.

Initial Beaconing and Scanning Activity

On September 21, 2023, Darktrace observed the first indications of compromise on the network when a device began to make regular connections to an external endpoint that was considered extremely rare for the network, namely ‘analyzetest[.]ir’.

Although the endpoint did not overtly seem malicious in nature (it appeared to be related to laboratory testing), Darktrace recognized that it had never previously been seen on the customer’s network and therefore should be treated with caution.  This initial beaconing activity was just the beginning of the malicious C2 communications, with several additional instances of beaconing detected to numerous suspicious endpoints, including funadhoo.gov[.]mv, tdgroup[.]ru’ and ‘army.mil[.]ng.

Figure 2: Initial beaconing activity detected on the breach device.

Soon thereafter, Darktrace detected the device performing internal reconnaissance, with an unusually large number of connections to other internal locations observed. This scanning activity appeared to primarily be targeting the SMB protocol by scanning port 445.

Within seconds of DETECT’s detection of this suspicious SMB scanning activity, Darktrace RESPOND moved to contain the compromise by blocking the device from connecting to port 445 and enforcing its ‘pattern of life’. Darktrace’s Self-Learning AI enables it to learn a device’s normal behavior and recognize if it deviates from this; by enforcing a pattern of life on an affected device, malicious activity is inhibited but the device is allowed to continue its expected activity, minimizing disruption to business operations.

Figure 3: The breach device Model Breach Event Log showing Darktrace DETECT identifying suspicious SMB scanning activity and the corresponding RESPOND actions.

Following the initial detection of this anomalous activity, Darktrace’s Cyber AI Analyst launched an autonomous investigation into the beaconing and scanning activity and was able to connect these seemingly separate events into one incident. AI Analyst analyzes thousands of connections to hundreds of different endpoints at machine speed and then summarizes its findings in a single pane of glass, giving customers the necessary information to assess the threat and begin remediation if necessary. This significantly lessens the burden for human security teams, saving them previous time and resources, while ensuring they maintain full visibility over any suspicious activity on their network.

Figure 4: Cyber AI Analyst incident log summarizing the technical details of the device’s beaconing and scanning behavior.

Beaconing Continues

Darktrace continued to observe the device carrying out beaconing activity over the next few days, likely representing threat actors attempting to establish communication with their malicious infrastructure and setting up a foothold within the customer’s environment. In one such example, the device was seen connecting to the suspicious endpoint ‘fysiotherapie-panken[.]nl’. Multiple open-source intelligence (OSINT) vendors reported this endpoint to be a known malware delivery host [3].

Once again, Darktrace RESPOND was in place to quickly intervene in response to these suspicious external connection attempts. Over the course of several days, RESPOND blocked the offending device from connecting to suspicious endpoints via port 443 and enforced its pattern of life. These autonomous actions by RESPOND effectively mitigated and contained the attack, preventing it from escalating further along the kill chain and providing the customer’s security team crucial time to take act and employ their own remediation.

Figure 5: A sample of the autonomous RESPOND actions that was applied on the affected device.

Possible Payload Retrieval

A few days later, on September 26, 2023, Darktrace observed the affected device attempting to download a Windows Portable Executable via file transfer protocol (FTP) from the external location ‘ftp2[.]sim-networks[.]com’, which had never previously been seen on the network. This download likely represented the next step in the Gootloader infection, wherein additional malicious tooling is downloaded to further cement the malicious actors’ control over the device. In response, Darktrace RESPOND immediately blocked the device from making any external connections, ensuring it could not download any suspicious files that may have rapidly escalated the attackers’ efforts.

Figure 6: DETECT’s identification of the offending device downloading a suspicious executable file via FTP.

The observed combination of beaconing activity and a suspicious file download triggered an Enhanced Monitoring breach, a high-fidelity DETECT model designed to detect activities that are more likely to be indicative of compromise. These models are monitored by the Darktrace SOC round the clock and investigated by Darktrace’s expert team of analysts as soon as suspicious activity emerges.

In this case, Darktrace’s SOC triaged the emerging activity and sent an additional notice directly to the customer’s security team, informing them of the compromise and advising on next steps. As this customer had subscribed to Darktrace’s Ask the Expert (ATE) service, they also had a team of expert analysts available to them at any time to aid their investigations.

Figure 7: Enhanced Monitoring Model investigated by the Darktrace SOC.

Conclusion

Loader malware variants such as Gootloader often lay the groundwork for further, potentially more severe threats to be deployed within compromised networks. As such, it is crucial for organizations and their security teams to identify these threats as soon as they emerge and ensure they are effectively contained before additional payloads, like information-stealing malware or ransomware, can be downloaded.

In this instance, Darktrace demonstrated its value when faced with a multi-payload threat by detecting Gootloader at the earliest stage and responding to it with swift targeted actions, halting any suspicious connections and preventing the download of any additional malicious tooling.

Darktrace DETECT recognized that the beaconing and scanning activity performed by the affected device represented a deviation from its expected behavior and was indicative of a potential network compromise. Meanwhile, Darktrace RESPOND ensured that any suspicious activity was promptly shut down, buying crucial time for the customer’s security team to work with Darktrace’s SOC to investigate the threat and quarantine the compromised device.

Credit to: Ashiq Shafee, Cyber Security Analyst, Qing Hong Kwa, Senior Cyber Analyst and Deputy Analyst Team Lead, Singapore

Appendices

Darktrace DETECT Model Detections

Anomalous Connection / Rare External SSL Self-Signed

Device / Suspicious SMB Scanning Activity

Anomalous Connection / Young or Invalid Certificate SSL Connections to Rare

Compromise / High Volume of Connections with Beacon Score

Compromise / Beacon to Young Endpoint

Compromise / Beaconing Activity To External Rare

Compromise / Slow Beaconing Activity To External Rare

Compromise / Beacon for 4 Days

Anomalous Connection / Suspicious Expired SSL

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Compromise / Sustained SSL or HTTP Increase

Compromise / Large Number of Suspicious Successful Connections

Compromise / Large Number of Suspicious Failed Connections

Device / Large Number of Model Breaches

Anomalous File / FTP Executable from Rare External Location

Device / Initial Breach Chain Compromise

RESPOND Models

Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

Antigena / Network/Insider Threat/Antigena Network Scan Block

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / External Threat / Antigena File then New Outbound Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

List of Indicators of Compromise (IoCs)

Type

Hostname

IoCs + Description

explorer[.]ee - C2 Endpoint

fysiotherapie-panken[.]nl- C2 Endpoint

devcxp2019.theclearingexperience[.]com- C2 Endpoint

campsite.bplaced[.]net- C2 Endpoint

coup2pompes[.]fr- C2 Endpoint

analyzetest[.]ir- Possible C2 Endpoint

tdgroup[.]ru- C2 Endpoint

ciedespuys[.]com- C2 Endpoint

fi.sexydate[.]world- C2 Endpoint

funadhoo.gov[.]mv- C2 Endpoint

geying.qiwufeng[.]com- C2 Endpoint

goodcomix[.]fun- C2 Endpoint

ftp2[.]sim-networks[.]com- Possible Payload Download Host

MITRE ATT&CK Mapping

Tactic – Technique

Reconnaissance - Scanning IP blocks (T1595.001, T1595)

Command and Control - Web Protocols , Application Layer Protocol, One-Way Communication, External Proxy, Non-Application Layer Protocol, Non-Standard Port (T1071.001/T1071, T1071, T1102.003/T1102, T1090.002/T1090, T1095, T1571)

Collection – Man in the Browser (T1185)

Resource Development - Web Services, Malware (T1583.006/T1583, T1588.001/T1588)

Persistence - Browser Extensions (T1176)

References

1.     https://www.blackberry.com/us/en/solutions/endpoint-security/ransomware-protection/gootloader

2.     https://redcanary.com/threat-detection-report/threats/gootloader/

3.     https://www.virustotal.com/gui/domain/fysiotherapie-panken.nl

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Ashiq Shafee
Cyber Security Analyst

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Seven Cyber Security Predictions for 2024

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13
Feb 2024

2024 Cyber Threat Predictions

After analyzing the observed threats and trends that have affected customers across the Darktrace fleet in the second half of 2023, the Darktrace Threat Research team have made a series of predictions. These assessments highlight the threats that are expected to impact Darktrace customers and the wider threat landscape in 2024.  

1. Initial access broker malware, especially loader malware, is likely to be a prominent threat.  

Initial access malware such as loaders, information stealers, remote access trojans (RATs), and downloaders, will probably remain some of the most relevant threats to most organizations, especially when noted in the context that many are interoperable, tailorable Malware-as-a-Service (MaaS) tools.  

These types of malware often serve as a gateway for threat actors to compromise a target network before launching subsequent, and often more severe, attacks. Would-be cyber criminals are now able to purchase and deploy these malware without the need for technical expertise.  

2. Infrastructure complexity will increase SaaS attacks and leave cloud environments vulnerable.

The increasing reliance on SaaS solutions and platforms for business operations, coupled with larger attack surfaces than ever before, make it likely that attackers will continue targeting organizations’ cloud environments with account takeovers granting unauthorized access to privileged accounts. These account hijacks can be further exploited to perform a variety of nefarious activities, such as data exfiltration or launching phishing campaigns.  

It is paramount for organizations to not only fortify their SaaS environments with security strategies including multifactor authentication (MFA), regular monitoring of credential usage, and strict access control, but moreover augment SaaS security using anomaly detection.  

3. The prevalence and evolution of ransomware will surge.

The Darktrace Threat Research team anticipates a surge in Ransomware-as-a-Service (RaaS) attacks, marking a shift away from conventional ransomware. The uptick in RaaS observed in 2023 evidences that ransomware itself is becoming increasingly accessible, lowering the barrier to entry for threat actors. This surge also demonstrates how lucrative RaaS is for ransomware operators in the current threat landscape, further reinforcing a rise in RaaS.  

This development is likely to coincide with a pivot away from traditional encryption-centric ransomware tactics towards more sophisticated and advanced extortion methods. Rather than relying solely on encrypting a target’s data for ransom, malicious actors are expected to employ double or even triple extortion strategies, encrypting sensitive data but also threatening to leak or sell stolen data unless their ransom demands are met.  

4. Threat actors will continue to rely on living-off-the-land techniques.

With evolving sophistication of security tools and greater industry adoption of AI techniques, threat actors have focused more and more on living-off-the-land. The extremely high volume of vulnerabilities discovered in 2023 highlights threat actors’ persistent need to compromise trusted organizational mechanisms and infrastructure to gain a foothold in networks. Although inbox intrusions remain prevalent, the exploitation of edge infrastructure has demonstrably expanded compared to previously endpoint-focused attacks.

Given the prevalence of endpoint evasion techniques and the high proportion of tactics utilizing native programs, threat actors will likely progressively live off the land, even utilizing new techniques or vulnerabilities to do so, rather than relying on unidentified malicious programs which evade traditional detection.

5. The “as-a-Service” marketplace will contribute to an increase in multi-phase compromises.

With the increasing “as-a-Service” marketplaces, it is likely that organizations will face more multi-phase compromises, where one strain of malware is observed stealing information and that data is sold to additional threat actors or utilized for second and/or third-stage malware or ransomware.  

This trend builds on the concept of initial access brokers but utilizes basic browser scraping and data harvesting to make as much profit throughout the compromise process as possible. This will likely result in security teams observing multiple malicious tools and strains of malware during incident response and/or multi-functional malware, with attack cycles and kill chains morphing into less linear and more abstract chains of activity. This makes it more essential than ever for security teams to apply an anomaly approach to stay ahead of asymmetric threats.  

6. Generative AI will let attackers phish across language barriers.

Classic phishing scams play a numbers game, targeting as many inboxes as possible and hoping that some users take the bait, even if there are spelling and grammar errors in the email. Now, Generative AI has reduced the barrier for entry, so malicious actors do not have to speak English to produce a convincing phishing email.  

In 2024, we anticipate this to extend to other languages and regions. For example, many countries in Asia have not yet been greatly impacted by phishing. Yet Generative AI continues to develop, with improved data input yielding improved output. More phishing emails will start to be generated in various languages with increasing sophistication.    

7. AI regulation and data privacy rules will stifle AI adoption.

AI regulation, like the European Union’s AI Act and NIS2, is starting to be implemented around the world. As policies continue to come out about AI and data privacy, practical and pragmatic AI adoption becomes more complex.  

Businesses will likely have to take a second look at AI they are adopting into their tech stacks to consider what may happen if a tool is suddenly deprecated because it is no longer fit for purpose or loses the approvals in place. Many will also have to use completely different supply chain evaluations from their usual ones based on developing compliance registrars. This increased complication may make businesses reticent to adopt innovative AI solutions as legislation scrambles to keep up.  

Learn more about observed threat trends and future predictions in the 2023 End of Year Threat Report

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The Darktrace Threat Research Team

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