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Email Attack Trends: How phishing attacks are becoming more sophisticated and harder to identify

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20
Mar 2024
20
Mar 2024
Using data from Darktrace's End of Year Threat Report this blog describes how advanced phishing attacks pose significant cyber risk to signature based threat detection tools and shows how AI can be leveraged by security solutions to defend against these threats.

The state of email security and phishing attacks

Employees send and receive hundreds of emails a day to keep businesses moving. Unfortunately, it just takes one employee to interact with an undetected phishing email to potentially put an entire organization at risk from cyber disruption. Attackers know this, which is why they continue to develop and improve email phishing attacks.  

Increased attack sophistication makes it harder than ever for traditional cyber security solutions like SEGs, firewalls, and spam filters to detect and mitigate increasingly novel and sophisticated email threats.

When there are tell-tale signs of a threat, these solutions can  identify an incoming message as suspicious. Pointers such as emails from unknown senders, messages which contain an unusual amount of poor spelling and grammar or encourage the receiver to respond to an unexpected but supposedly urgent request.

That is, if the phishing attacks weren’t blocked by security measures before reaching the victim’s inbox. But, this is happening more and more often as phishing campaigns are becoming more advanced. Attackers are showing signs of consistently bypassing traditional protections and getting through to exploit victims.  

Darktrace email threat reporting

In its End of Year Threat Report, Darktrace analyzed over 10 million phishing emails targeting customer environments between September 1 and December 31, 2023.  Our findings signal that attackers are starting to take advantage of advancements in artificial intelligence (AI), including using Generative AI tools such as Large Language Models (LLMs) to create more convincing and sophisticated phishing messages – and at scale.

LLMs and Phishing

With the right AI prompts, attackers can use these LLMs to help write convincing email messages designed to target specific countries, companies or even individuals – all without the suspicious hallmarks which are traditionally associated with standard phishing attacks. The attackers don’t even need to speak the language of the individuals or groups they’re targeting.  LLMs lower language barriers for attackers; using their native tongue, they can simply ask the Generative AI to write a message in the language of their choosing.  

These techniques are designed to build trust and manipulate recipients into giving up sensitive information like user credentials, intellectual property or bank information or coerce them into downloading malicious payloads which can be used to launch further attacks on business infrastructure.  With the appropriate research, attackers can tailor the messages to increase the chances of being successful, like making them look like a legitimate company email or request.

Social engineering phishing attacks

A year ago. Darktrace shared research which found a 135% increase in ‘novel social engineering attacks’ in the first two months of 2023, corresponding with the widespread adoption of ChatGPT. These novel phishing attacks showed a strong linguistic deviation compared to other phishing emails, which suggested to us that Generative AI was already providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale

We’ve seen this trend continue. Our End of Year Threat Report found 38% of these emails were identified as utilizing novel social engineering techniques.

Attackers are also deploying another technique to make phishing emails look more convincing – they’re making the emails themselves longer and more sophisticated.  

A potential victim might be suspicious of an ‘urgent’ email which prompts them to take action without an explanation - but if there’s additional context in the text, it adds an aura of legitimacy which is difficult to act against.

And threat actors know this; 28% of phishing emails analyzed by Darktrace over the period were identified as having “significant” amount of text – containing over 1,000 characters, which equates to over 200 words.  

It’s a sign that attackers are innovating and bolstering their efforts to craft sophisticated phishing campaigns, potentially leveraging Generative AI tools to automate social engineering activity by creating longer, more convincing phishing emails.  

QR code phishing

But this is far from the only innovative method which attackers are using to bypass traditional security defences. Among the 10 million plus emails analyzed during the reporting period, Darktrace/Email detected over 639,000 malicious QR codes within the messages.

Malicious QR codes placed within emails have become an increasingly common form of phishing attack, especially as QR codes have become a more common method for sharing links to information or buying links for products in recent years.

Attackers are deploying QR codes because they provide a way of directing unsuspecting victims to malicious websites or download links without needing to use a traditional phishing URL.  

The advantage of implanting QR codes for attackers is that while phishing URLs are something which traditional security solutions are actively looking to identify and mitigate, malicious QR codes are more difficult for them to detect.

Applying AI to email security

Traditional security solutions which rely heavily on previously identified malicious emails and known bad senders are struggling to identify and defend against these novel and increasingly sophisticated email threats.

But by using AI that learns the unique digital environment and patterns of each business, Darktrace/Email can recognize the subtle deviations in expected email activity to determine whether any given email could represent a threat to the business. It is then able to make highly accurate decisions to mitigate and neutralize any email attack it faces helping to keep your organization safe from cyber disruption.

It’s therefore imperative that in the battle against ever-evolving, ever more sophisticated cyber threats, defenders are also embracing AI to keep businesses safe. By effectively applying AI to cyber security challenges, defenders can take a proactive approach to cyber security, staying one step ahead of malicious attackers, with real-time detection and automated response to known and unknown threats looking to disrupt the business via the inbox.  

Darktrace/Email was recently awarded a 2024 AI Excellence Award for Machine Learning by Business Intelligence Group.

Join Darktrace on 9 April for a virtual event to explore the latest innovations needed to get ahead of the rapidly evolving threat landscape. Register today to hear more about our latest innovations coming to Darktrace’s offerings.

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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Inside the SOC

Sliver C2: How Darktrace Provided a Sliver of Hope in the Face of an Emerging C2 Framework

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17
Apr 2024

Offensive Security Tools

As organizations globally seek to for ways to bolster their digital defenses and safeguard their networks against ever-changing cyber threats, security teams are increasingly adopting offensive security tools to simulate cyber-attacks and assess the security posture of their networks. These legitimate tools, however, can sometimes be exploited by real threat actors and used as genuine actor vectors.

What is Sliver C2?

Sliver C2 is a legitimate open-source command-and-control (C2) framework that was released in 2020 by the security organization Bishop Fox. Silver C2 was originally intended for security teams and penetration testers to perform security tests on their digital environments [1] [2] [5]. In recent years, however, the Sliver C2 framework has become a popular alternative to Cobalt Strike and Metasploit for many attackers and Advanced Persistence Threat (APT) groups who adopt this C2 framework for unsolicited and ill-intentioned activities.

The use of Sliver C2 has been observed in conjunction with various strains of Rust-based malware, such as KrustyLoader, to provide backdoors enabling lines of communication between attackers and their malicious C2 severs [6]. It is unsurprising, then, that it has also been leveraged to exploit zero-day vulnerabilities, including critical vulnerabilities in the Ivanti Connect Secure and Policy Secure services.

In early 2024, Darktrace observed the malicious use of Sliver C2 during an investigation into post-exploitation activity on customer networks affected by the Ivanti vulnerabilities. Fortunately for affected customers, Darktrace DETECT™ was able to recognize the suspicious network-based connectivity that emerged alongside Sliver C2 usage and promptly brought it to the attention of customer security teams for remediation.

How does Silver C2 work?

Given its open-source nature, the Sliver C2 framework is extremely easy to access and download and is designed to support multiple operating systems (OS), including MacOS, Windows, and Linux [4].

Sliver C2 generates implants (aptly referred to as ‘slivers’) that operate on a client-server architecture [1]. An implant contains malicious code used to remotely control a targeted device [5]. Once a ‘sliver’ is deployed on a compromised device, a line of communication is established between the target device and the central C2 server. These connections can then be managed over Mutual TLS (mTLS), WireGuard, HTTP(S), or DNS [1] [4]. Sliver C2 has a wide-range of features, which include dynamic code generation, compile-time obfuscation, multiplayer-mode, staged and stageless payloads, procedurally generated C2 over HTTP(S) and DNS canary blue team detection [4].

Why Do Attackers Use Sliver C2?

Amidst the multitude of reasons why malicious actors opt for Sliver C2 over its counterparts, one stands out: its relative obscurity. This lack of widespread recognition means that security teams may overlook the threat, failing to actively search for it within their networks [3] [5].

Although the presence of Sliver C2 activity could be representative of authorized and expected penetration testing behavior, it could also be indicative of a threat actor attempting to communicate with its malicious infrastructure, so it is crucial for organizations and their security teams to identify such activity at the earliest possible stage.

Darktrace’s Coverage of Sliver C2 Activity

Darktrace’s anomaly-based approach to threat detection means that it does not explicitly attempt to attribute or distinguish between specific C2 infrastructures. Despite this, Darktrace was able to connect Sliver C2 usage to phases of an ongoing attack chain related to the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPN appliances in January 2024.

Around the time that the zero-day Ivanti vulnerabilities were disclosed, Darktrace detected an internal server on one customer network deviating from its expected pattern of activity. The device was observed making regular connections to endpoints associated with Pulse Secure Cloud Licensing, indicating it was an Ivanti server. It was observed connecting to a string of anomalous hostnames, including ‘cmjk3d071amc01fu9e10ae5rt9jaatj6b.oast[.]live’ and ‘cmjft14b13vpn5vf9i90xdu6akt5k3pnx.oast[.]pro’, via HTTP using the user agent ‘curl/7.19.7 (i686-redhat-linux-gnu) libcurl/7.63.0 OpenSSL/1.0.2n zlib/1.2.7’.

Darktrace further identified that the URI requested during these connections was ‘/’ and the top-level domains (TLDs) of the endpoints in question were known Out-of-band Application Security Testing (OAST) server provider domains, namely ‘oast[.]live’ and ‘oast[.]pro’. OAST is a testing method that is used to verify the security posture of an application by testing it for vulnerabilities from outside of the network [7]. This activity triggered the DETECT model ‘Compromise / Possible Tunnelling to Bin Services’, which breaches when a device is observed sending DNS requests for, or connecting to, ‘request bin’ services. Malicious actors often abuse such services to tunnel data via DNS or HTTP requests. In this specific incident, only two connections were observed, and the total volume of data transferred was relatively low (2,302 bytes transferred externally). It is likely that the connections to OAST servers represented malicious actors testing whether target devices were vulnerable to the Ivanti exploits.

The device proceeded to make several SSL connections to the IP address 103.13.28[.]40, using the destination port 53, which is typically reserved for DNS requests. Darktrace recognized that this activity was unusual as the offending device had never previously been observed using port 53 for SSL connections.

Model Breach Event Log displaying the ‘Application Protocol on Uncommon Port’ DETECT model breaching in response to the unusual use of port 53.
Figure 1: Model Breach Event Log displaying the ‘Application Protocol on Uncommon Port’ DETECT model breaching in response to the unusual use of port 53.

Figure 2: Model Breach Event Log displaying details pertaining to the ‘Application Protocol on Uncommon Port’ DETECT model breach, including the 100% rarity of the port usage.
Figure 2: Model Breach Event Log displaying details pertaining to the ‘Application Protocol on Uncommon Port’ DETECT model breach, including the 100% rarity of the port usage.

Further investigation into the suspicious IP address revealed that it had been flagged as malicious by multiple open-source intelligence (OSINT) vendors [8]. In addition, OSINT sources also identified that the JARM fingerprint of the service running on this IP and port (00000000000000000043d43d00043de2a97eabb398317329f027c66e4c1b01) was linked to the Sliver C2 framework and the mTLS protocol it is known to use [4] [5].

An Additional Example of Darktrace’s Detection of Sliver C2

However, it was not just during the January 2024 exploitation of Ivanti services that Darktrace observed cases of Sliver C2 usages across its customer base.  In March 2023, for example, Darktrace detected devices on multiple customer accounts making beaconing connections to malicious endpoints linked to Sliver C2 infrastructure, including 18.234.7[.]23 [10] [11] [12] [13].

Darktrace identified that the observed connections to this endpoint contained the unusual URI ‘/NIS-[REDACTED]’ which contained 125 characters, including numbers, lower and upper case letters, and special characters like “_”, “/”, and “-“, as well as various other URIs which suggested attempted data exfiltration:

‘/upload/api.html?c=[REDACTED] &fp=[REDACTED]’

  • ‘/samples.html?mx=[REDACTED] &s=[REDACTED]’
  • ‘/actions/samples.html?l=[REDACTED] &tc=[REDACTED]’
  • ‘/api.html?gf=[REDACTED] &x=[REDACTED]’
  • ‘/samples.html?c=[REDACTED] &zo=[REDACTED]’

This anomalous external connectivity was carried out through multiple destination ports, including the key ports 443 and 8888.

Darktrace additionally observed devices on affected customer networks performing TLS beaconing to the IP address 44.202.135[.]229 with the JA3 hash 19e29534fd49dd27d09234e639c4057e. According to OSINT sources, this JA3 hash is associated with the Golang TLS cipher suites in which the Sliver framework is developed [14].

Conclusion

Despite its relative novelty in the threat landscape and its lesser-known status compared to other C2 frameworks, Darktrace has demonstrated its ability effectively detect malicious use of Sliver C2 across numerous customer environments. This included instances where attackers exploited vulnerabilities in the Ivanti Connect Secure and Policy Secure services.

While human security teams may lack awareness of this framework, and traditional rules and signatured-based security tools might not be fully equipped and updated to detect Sliver C2 activity, Darktrace’s Self Learning AI understands its customer networks, users, and devices. As such, Darktrace is adept at identifying subtle deviations in device behavior that could indicate network compromise, including connections to new or unusual external locations, regardless of whether attackers use established or novel C2 frameworks, providing organizations with a sliver of hope in an ever-evolving threat landscape.

Credit to Natalia Sánchez Rocafort, Cyber Security Analyst, Paul Jennings, Principal Analyst Consultant

Appendices

DETECT Model Coverage

  • Compromise / Repeating Connections Over 4 Days
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Anomalous Server Activity / Server Activity on New Non-Standard Port
  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compromise / Quick and Regular Windows HTTP Beaconing
  • Compromise / High Volume of Connections with Beacon Score
  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Compromise / Slow Beaconing Activity To External Rare
  • Compromise / HTTP Beaconing to Rare Destination
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Large Number of Suspicious Failed Connections
  • Compromise / SSL or HTTP Beacon
  • Compromise / Possible Malware HTTP Comms
  • Compromise / Possible Tunnelling to Bin Services
  • Anomalous Connection / Low and Slow Exfiltration to IP
  • Device / New User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Numeric File Download
  • Anomalous Connection / Powershell to Rare External
  • Anomalous Server Activity / New Internet Facing System

List of Indicators of Compromise (IoCs)

18.234.7[.]23 - Destination IP - Likely C2 Server

103.13.28[.]40 - Destination IP - Likely C2 Server

44.202.135[.]229 - Destination IP - Likely C2 Server

References

[1] https://bishopfox.com/tools/sliver

[2] https://vk9-sec.com/how-to-set-up-use-c2-sliver/

[3] https://www.scmagazine.com/brief/sliver-c2-framework-gaining-traction-among-threat-actors

[4] https://github[.]com/BishopFox/sliver

[5] https://www.cybereason.com/blog/sliver-c2-leveraged-by-many-threat-actors

[6] https://securityaffairs.com/158393/malware/ivanti-connect-secure-vpn-deliver-krustyloader.html

[7] https://www.xenonstack.com/insights/out-of-band-application-security-testing

[8] https://www.virustotal.com/gui/ip-address/103.13.28.40/detection

[9] https://threatfox.abuse.ch/browse.php?search=ioc%3A107.174.78.227

[10] https://threatfox.abuse.ch/ioc/1074576/

[11] https://threatfox.abuse.ch/ioc/1093887/

[12] https://threatfox.abuse.ch/ioc/846889/

[13] https://threatfox.abuse.ch/ioc/1093889/

[14] https://github.com/projectdiscovery/nuclei/issues/3330

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About the author
Natalia Sánchez Rocafort
Cyber Security Analyst

Blog

Email

Looking Beyond Secure Email Gateways with the Latest Innovations to Darktrace/Email

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09
Apr 2024

Organizations Should Demand More from their Email Security

In response to a more intricate threat landscape, organizations should view email security as a critical component of their defense-in-depth strategy, rather than defending the inbox alone with a traditional Secure Email Gateway (SEG). Organizations need more than a traditional gateway – that doubles, instead of replaces, the capabilities provided by native security vendor – and require an equally granular degree of analysis across all messaging, including inbound, outbound, and lateral mail, plus Teams messages.  

Darktrace/Email is the industry’s most advanced cloud email security, powered by Self-Learning AI. It combines AI techniques to exceed the accuracy and efficiency of leading security solutions, and is the only security built to elevate, not duplicate, native email security.  

With its largest update ever, Darktrace/Email introduces the following innovations, finally allowing security teams to look beyond secure email gateways with autonomous AI:

  • AI-augmented data loss prevention to stop the entire spectrum of outbound mail threats
  • an easy way to deploy DMARC quickly with AI
  • major enhancements to streamline SOC workflows and increase the detection of sophisticated phishing links
  • expansion of Darktrace’s leading AI prevention to lateral mail, account compromise and Microsoft Teams

What’s New with Darktrace/Email  

Data Loss Prevention  

Block the entire spectrum of outbound mail threats with advanced data loss prevention that builds on tags in native email to stop unknown, accidental, and malicious data loss

Darktrace understands normal at individual user, group and organization level with a proven AI that detects abnormal user behavior and dynamic content changes. Using this understanding, Darktrace/Email actions outbound emails to stop unknown, accidental and malicious data loss.  

Traditional DLP solutions only take into account classified data, which relies on the manual input of labelling each data piece, or creating rules to catch pattern matches that try to stop data of certain types leaving the organization. But in today’s world of constantly changing data, regular expression and fingerprinting detection are no longer enough.

  • Human error – Because it understands normal for every user, Darktrace/Email can recognize cases of misdirected emails. Even if the data is correctly labelled or insensitive, Darktrace recognizes when the context in which it is being sent could be a case of data loss and warns the user.  
  • Unclassified data – Whereas traditional DLP solutions can only take action on classified data, Darktrace analyzes the range of data that is either pending labels or can’t be labeled with typical capabilities due to its understanding of the content and context of every email.  
  • Insider threat – If a malicious actor has compromised an account, data exfiltration may still be attempted on encrypted, intellectual property, or other forms of unlabelled data to avoid detection. Darktrace analyses user behaviour to catch cases of unusual data exfiltration from individual accounts.

And classification efforts already in place aren’t wasted – Darktrace/Email extends Microsoft Purview policies and sensitivity labels to avoid duplicate workflows for the security team, combining the best of both approaches to ensure organizations maintain control and visibility over their data.

End User and Security Workflows

Achieve more than 60% improvement in the quality of end-user phishing reports and detection of sophisticated malicious weblinks1

Darktrace/Email improves end-user reporting from the ground up to save security team resource. Employees will always be on the front line of email security – while other solutions assume that end-user reporting is automatically of poor quality, Darktrace prioritizes improving users’ security awareness to increase the quality of end-user reporting from day one.  

Users are empowered to assess and report suspicious activity with contextual banners and Cyber AI Analyst generated narratives for potentially suspicious emails, resulting in 60% fewer benign emails reported.  

Out of the higher-quality emails that end up being reported, the next step is to reduce the amount of emails that reach the SOC. Darktrace/Email’s Mailbox Security Assistant automates their triage with secondary analysis combining additional behavioral signals – using x20 more metrics than previously – with advanced link analysis to detect 70% more sophisticated malicious phishing links.2 This directly alleviates the burden of manual triage for security analysts.

For the emails that are received by the SOC, Darktrace/Email uses automation to reduce time spent investigating per incident. With live inbox view, security teams gain access to a centralized platform that combines intuitive search capabilities, Cyber AI Analyst reports, and mobile application access. Analysts can take remediation actions from within Darktrace/Email, eliminating console hopping and accelerating incident response.

Darktrace takes a user-focused and business-centric approach to email security, in contrast to the attack-centric rules and signatures approach of secure email gateways

Microsoft Teams

Detect threats within your Teams environment such as account compromise, phishing, malware and data loss

Around 83% of Fortune 500 companies rely on Microsoft Office products and services, particularly Teams and SharePoint.3

Darktrace now leverages the same behavioral AI techniques for Microsoft customers across 365 and Teams, allowing organizations to detect threats and signals of account compromise within their Teams environment including social engineering, malware and data loss.  

The primary use case for Microsoft Teams protection is as a potential entry vector. While messaging has traditionally been internal only, as organizations open up it is becoming an entry vector which needs to be treated with the same level of caution as email. That’s why we’re bringing our proven AI approach to Microsoft Teams, that understands the user behind the message.  

Anomalous messaging behavior is also a highly relevant indicator of whether a user has been compromised. Unlike other solutions that analyze Microsoft Teams content which focus on payloads, Darktrace goes beyond basic link and sandbox analysis and looks at actual user behavior from both a content and context perspective. This linguistic understanding isn’t bound by the requirement to match a signature to a malicious payload, rather it looks at the context in which the message has been delivered. From this analysis, Darktrace can spot the early symptoms of account compromise such as early-stage social engineering before a payload is delivered.

Lateral Mail Analysis

Detect and respond to internal mailflow with multi-layered AI to prevent account takeover, lateral phishing and data leaks

The industry’s most robust account takeover protection now prevents lateral mail account compromise. Darktrace has always looked at internal mail to inform inbound and outbound decisions, but will now elevate suspicious lateral mail behaviour using the same AI techniques for inbound, outbound and Teams analysis.

Darktrace integrates signals from across the entire mailflow and communication patterns to determine symptoms of account compromise, now including lateral mailflow

Unlike other solutions which only analyze payloads, Darktrace analyzes a whole range of signals to catch lateral movement before a payload is delivered. Contributing yet another layer to the AI behavioral profile for each user, security teams can now use signals from lateral mail to spot the early symptoms of account takeover and take autonomous actions to prevent further compromise.

DMARC

Gain in-depth visibility and control of 3rd parties using your domain with an industry-first AI-assisted DMARC

Darktrace has created the easiest path to brand protection and compliance with the new Darktrace/DMARC. This new capability continuously stops spoofing and phishing from the enterprise domain, while automatically enhancing email security and reducing the attack surface.

Darktrace/DMARC helps to upskill businesses by providing step by step guidance and automated record suggestions provide a clear, efficient road to enforcement. It allows organizations to quickly achieve compliance with requirements from Google, Yahoo, and others, to ensure that their emails are reaching mailboxes.  

Meanwhile, Darktrace/DMARC helps to reduce the overall attack surface by providing visibility over shadow-IT and third-party vendors sending on behalf of an organization’s brand, while informing recipients when emails from their domains are sent from un-authenticated DMARC source.

Darktrace/DMARC integrates with the wider Darktrace product platform, sharing insights to help further secure your business across Email Attack Path and Attack Surface management.

Conclusion

To learn more about the new innovations to Darktrace/Email download the solution brief here.

All of the new updates to Darktrace/Email sit within the new Darktrace ActiveAI Security Platform, creating a feedback loop between email security and the rest of the digital estate for better protection. Click to read more about the Darktrace ActiveAI Security Platform or to hear about the latest innovations to Darktrace/OT, the most comprehensive prevention, detection, and response solution purpose built for critical infrastructures.  

Learn about the intersection of cyber and AI by downloading the State of AI Cyber Security 2024 report to discover global findings that may surprise you, insights from security leaders, and recommendations for addressing today’s top challenges that you may face, too.

References

[1] Internal Darktrace Research

[2] Internal Darktrace Research

[3] Essential Microsoft Office Statistics in 2024

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About the author
Carlos Gray
Product Manager
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