Blog
/
/
February 1, 2021

Explore AI Email Security Approaches with Darktrace

Stay informed on the latest AI approaches to email security. Explore Darktrace's comparisons to find the best solution for your cybersecurity needs!
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.
Written by
Dan Fein
VP, Product
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
01
Feb 2021

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.
Written by
Dan Fein
VP, Product

More in this series

No items found.

Blog

/

Network

/

October 13, 2025

Inside Akira’s SonicWall Campaign: Darktrace’s Detection and Response

akira sonicwallDefault blog imageDefault blog image

Introduction: Background on Akira SonicWall campaign

Between July and August 2025, security teams worldwide observed a surge in Akira ransomware incidents involving SonicWall SSL VPN devices [1]. Initially believed to be the result of an unknown zero-day vulnerability, SonicWall later released an advisory announcing that the activity was strongly linked to a previously disclosed vulnerability, CVE-2024-40766, first identified over a year earlier [2].

On August 20, 2025, Darktrace observed unusual activity on the network of a customer in the US. Darktrace detected a range of suspicious activity, including network scanning and reconnaissance, lateral movement, privilege escalation, and data exfiltration. One of the compromised devices was later identified as a SonicWall virtual private network (VPN) server, suggesting that the incident was part of the broader Akira ransomware campaign targeting SonicWall technology.

As the customer was subscribed to the Managed Detection and Response (MDR) service, Darktrace’s Security Operations Centre (SOC) team was able to rapidly triage critical alerts, restrict the activity of affected devices, and notify the customer of the threat. As a result, the impact of the attack was limited - approximately 2 GiB of data had been observed leaving the network, but any further escalation of malicious activity was stopped.

Threat Overview

CVE-2024-40766 and other misconfigurations

CVE-2024-40766 is an improper access control vulnerability in SonicWall’s SonicOS, affecting Gen 5, Gen 6, and Gen 7 devices running SonicOS version 7.0.1 5035 and earlier [3]. The vulnerability was disclosed on August 23, 2024, with a patch released the same day. Shortly after, it was reported to be exploited in the wild by Akira ransomware affiliates and others [4].

Almost a year later, the same vulnerability is being actively targeted again by the Akira ransomware group. In addition to exploiting unpatched devices affected by CVE-2024-40766, security researchers have identified three other risks potentially being leveraged by the group [5]:

*The Virtual Office Portal can be used to initially set up MFA/TOTP configurations for SSLVPN users.

Thus, even if SonicWall devices were patched, threat actors could still target them for initial access by reusing previously stolen credentials and exploiting other misconfigurations.

Akira Ransomware

Akira ransomware was first observed in the wild in March 2023 and has since become one of the most prolific ransomware strains across the threat landscape [6]. The group operates under a Ransomware-as-a-Service (RaaS) model and frequently uses double extortion tactics, pressuring victims to pay not only to decrypt files but also to prevent the public release of sensitive exfiltrated data.

The ransomware initially targeted Windows systems, but a Linux variant was later observed targeting VMware ESXi virtual machines [7]. In 2024, it was assessed that Akira would continue to target ESXi hypervisors, making attacks highly disruptive due to the central role of virtualisation in large-scale cloud deployments. Encrypting the ESXi file system enables rapid and widespread encryption with minimal lateral movement or credential theft. The lack of comprehensive security protections on many ESXi hypervisors also makes them an attractive target for ransomware operators [8].

Victimology

Akira is known to target organizations across multiple sectors, most notably those in manufacturing, education, and healthcare. These targets span multiple geographic regions, including North America, Latin America, Europe and Asia-Pacific [9].

Geographical distribution of organization’s affected by Akira ransomware in 2025 [9].
Figure 1: Geographical distribution of organization’s affected by Akira ransomware in 2025 [9].

Common Tactics, Techniques and Procedures (TTPs) [7][10]

Initial Access
Targets remote access services such as RDP and VPN through vulnerability exploitation or stolen credentials.

Reconnaissance
Uses network scanning tools like SoftPerfect and Advanced IP Scanner to map the environment and identify targets.

Lateral Movement
Moves laterally using legitimate administrative tools, typically via RDP.

Persistence
Employs techniques such as Kerberoasting and pass-the-hash, and tools like Mimikatz to extract credentials. Known to create new domain accounts to maintain access.

Command and Control
Utilizes remote access tools including AnyDesk, RustDesk, Ngrok, and Cloudflare Tunnel.

Exfiltration
Uses tools such as FileZilla, WinRAR, WinSCP, and Rclone. Data is exfiltrated via protocols like FTP and SFTP, or through cloud storage services such as Mega.

Darktrace’s Coverage of Akira ransomware

Reconnaissance

Darktrace first detected of unusual network activity around 05:10 UTC, when a desktop device was observed performing a network scan and making an unusual number of DCE-RPC requests to the endpoint mapper (epmapper) service. Network scans are typically used to identify open ports, while querying the epmapper service can reveal exposed RPC services on the network.

Multiple other devices were also later seen with similar reconnaissance activity, and use of the Advanced IP Scanner tool, indicated by connections to the domain advanced-ip-scanner[.]com.

Lateral movement

Shortly after the initial reconnaissance, the same desktop device exhibited unusual use of administrative tools. Darktrace observed the user agent “Ruby WinRM Client” and the URI “/wsman” as the device initiated a rare outbound Windows Remote Management (WinRM) connection to two domain controllers (REDACTED-dc1 and REDACTED-dc2). WinRM is a Microsoft service that uses the WS-Management (WSMan) protocol to enable remote management and control of network devices.

Darktrace also observed the desktop device connecting to an ESXi device (REDACTED-esxi1) via RDP using an LDAP service credential, likely with administrative privileges.

Credential access

At around 06:26 UTC, the desktop device was seen fetching an Active Directory certificate from the domain controller (REDACTED-dc1) by making a DCE-RPC request to the ICertPassage service. Shortly after, the device made a Kerberos login using the administrative credential.

Figure 3: Darktrace’s detection of the of anomalous certificate download and subsequent Kerberos login.

Further investigation into the device’s event logs revealed a chain of connections that Darktrace’s researchers believe demonstrates a credential access technique known as “UnPAC the hash.”

This method begins with pre-authentication using Kerberos’ Public Key Cryptography for Initial Authentication (PKINIT), allowing the client to use an X.509 certificate to obtain a Ticket Granting Ticket (TGT) from the Key Distribution Center (KDC) instead of a password.

The next stage involves User-to-User (U2U) authentication when requesting a Service Ticket (ST) from the KDC. Within Darktrace's visibility of this traffic, U2U was indicated by the client and service principal names within the ST request being identical. Because PKINIT was used earlier, the returned ST contains the NTLM hash of the credential, which can then be extracted and abused for lateral movement or privilege escalation [11].

Flowchart of Kerberos PKINIT pre-authentication and U2U authentication [12].
Figure 4: Flowchart of Kerberos PKINIT pre-authentication and U2U authentication [12]
Figure 5: Device event log showing the Kerberos Login and Kerberos Ticket events

Analysis of the desktop device’s event logs revealed a repeated sequence of suspicious activity across multiple credentials. Each sequence included a DCE-RPC ICertPassage request to download a certificate, followed by a Kerberos login event indicating PKINIT pre-authentication, and then a Kerberos ticket event consistent with User-to-User (U2U) authentication.

Darktrace identified this pattern as highly unusual. Cyber AI Analyst determined that the device used at least 15 different credentials for Kerberos logins over the course of the attack.

By compromising multiple credentials, the threat actor likely aimed to escalate privileges and facilitate further malicious activity, including lateral movement. One of the credentials obtained via the “UnPAC the hash” technique was later observed being used in an RDP session to the domain controller (REDACTED-dc2).

C2 / Additional tooling

At 06:44 UTC, the domain controller (REDACTED-dc2) was observed initiating a connection to temp[.]sh, a temporary cloud hosting service. Open-source intelligence (OSINT) reporting indicates that this service is commonly used by threat actors to host and distribute malicious payloads, including ransomware [13].

Shortly afterward, the ESXi device was observed downloading an executable named “vmwaretools” from the rare external endpoint 137.184.243[.]69, using the user agent “Wget.” The repeated outbound connections to this IP suggest potential command-and-control (C2) activity.

Cyber AI Analyst investigation into the suspicious file download and suspected C2 activity between the ESXI device and the external endpoint 137.184.243[.]69.
Figure 6: Cyber AI Analyst investigation into the suspicious file download and suspected C2 activity between the ESXI device and the external endpoint 137.184.243[.]69.
Packet capture (PCAP) of connections between the ESXi device and 137.184.243[.]69.
Figure 7: Packet capture (PCAP) of connections between the ESXi device and 137.184.243[.]69.

Data exfiltration

The first signs of data exfiltration were observed at around 7:00 UTC. Both the domain controller (REDACTED-dc2) and a likely SonicWall VPN device were seen uploading approximately 2 GB of data via SSH to the rare external endpoint 66.165.243[.]39 (AS29802 HVC-AS). OSINT sources have since identified this IP as an indicator of compromise (IoC) associated with the Akira ransomware group, known to use it for data exfiltration [14].

Cyber AI Analyst incident view highlighting multiple unusual events across several devices on August 20. Notably, it includes the “Unusual External Data Transfer” event, which corresponds to the anomalous 2 GB data upload to the known Akira-associated endpoint 66.165.243[.]39.
Figure 8: Cyber AI Analyst incident view highlighting multiple unusual events across several devices on August 20. Notably, it includes the “Unusual External Data Transfer” event, which corresponds to the anomalous 2 GB data upload to the known Akira-associated endpoint 66.165.243[.]39.

Cyber AI Analyst

Throughout the course of the attack, Darktrace’s Cyber AI Analyst autonomously investigated the anomalous activity as it unfolded and correlated related events into a single, cohesive incident. Rather than treating each alert as isolated, Cyber AI Analyst linked them together to reveal the broader narrative of compromise. This holistic view enabled the customer to understand the full scope of the attack, including all associated activities and affected assets that might otherwise have been dismissed as unrelated.

Overview of Cyber AI Analyst’s investigation, correlating all related internal and external security events across affected devices into a single pane of glass.
Figure 9: Overview of Cyber AI Analyst’s investigation, correlating all related internal and external security events across affected devices into a single pane of glass.

Containing the attack

In response to the multiple anomalous activities observed across the network, Darktrace's Autonomous Response initiated targeted mitigation actions to contain the attack. These included:

  • Blocking connections to known malicious or rare external endpoints, such as 137.184.243[.]69, 66.165.243[.]39, and advanced-ip-scanner[.]com.
  • Blocking internal traffic to sensitive ports, including 88 (Kerberos), 3389 (RDP), and 49339 (DCE-RPC), to disrupt lateral movement and credential abuse.
  • Enforcing a block on all outgoing connections from affected devices to contain potential data exfiltration and C2 activity.
Autonomous Response actions taken by Darktrace on an affected device, including the blocking of malicious external endpoints and internal service ports.
Figure 10: Autonomous Response actions taken by Darktrace on an affected device, including the blocking of malicious external endpoints and internal service ports.

Managed Detection and Response

As this customer was an MDR subscriber, multiple Enhanced Monitoring alerts—high-fidelity models designed to detect activity indicative of compromise—were triggered across the network. These alerts prompted immediate investigation by Darktrace’s SOC team.

Upon determining that the activity was likely linked to an Akira ransomware attack, Darktrace analysts swiftly acted to contain the threat. At around 08:05 UTC, devices suspected of being compromised were quarantined, and the customer was promptly notified, enabling them to begin their own remediation procedures without delay.

A wider campaign?

Darktrace’s SOC and Threat Research teams identified at least three additional incidents likely linked to the same campaign. All targeted organizations were based in the US, spanning various industries, and each have indications of using SonicWall VPN, indicating it had likely been targeted for initial access.

Across these incidents, similar patterns emerged. In each case, a suspicious executable named “vmwaretools” was downloaded from the endpoint 85.239.52[.]96 using the user agent “Wget”, bearing some resemblance to the file downloads seen in the incident described here. Data exfiltration was also observed via SSH to the endpoints 107.155.69[.]42 and 107.155.93[.]154, both of which belong to the same ASN also seen in the incident described in this blog: S29802 HVC-AS. Notably, 107.155.93[.]154 has been reported in OSINT as an indicator associated with Akira ransomware activity [15]. Further recent Akira ransomware cases have been observed involving SonicWall VPN, where no similar executable file downloads were observed, but SSH exfiltration to the same ASN was. These overlapping and non-overlapping TTPs may reflect the blurring lines between different affiliates operating under the same RaaS.

Lessons from the campaign

This campaign by Akira ransomware actors underscores the critical importance of maintaining up-to-date patching practices. Threat actors continue to exploit previously disclosed vulnerabilities, not just zero-days, highlighting the need for ongoing vigilance even after patches are released. It also demonstrates how misconfigurations and overlooked weaknesses can be leveraged for initial access or privilege escalation, even in otherwise well-maintained environments.

Darktrace’s observations further reveal that ransomware actors are increasingly relying on legitimate administrative tools, such as WinRM, to blend in with normal network activity and evade detection. In addition to previously documented Kerberos-based credential access techniques like Kerberoasting and pass-the-hash, this campaign featured the use of UnPAC the hash to extract NTLM hashes via PKINIT and U2U authentication for lateral movement or privilege escalation.

Credit to Emily Megan Lim (Senior Cyber Analyst), Vivek Rajan (Senior Cyber Analyst), Ryan Traill (Analyst Content Lead), and Sam Lister (Specialist Security Researcher)

Appendices

Darktrace Model Detections

Anomalous Connection / Active Remote Desktop Tunnel

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous Connection / Possible Data Staging and External Upload

Anomalous Connection / Rare WinRM Incoming

Anomalous Connection / Rare WinRM Outgoing

Anomalous Connection / Uncommon 1 GiB Outbound

Anomalous Connection / Unusual Admin RDP Session

Anomalous Connection / Unusual Incoming Long Remote Desktop Session

Anomalous Connection / Unusual Incoming Long SSH Session

Anomalous Connection / Unusual Long SSH Session

Anomalous File / EXE from Rare External Location

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Server Activity / Outgoing from Server

Anomalous Server Activity / Rare External from Server

Compliance / Default Credential Usage

Compliance / High Priority Compliance Model Alert

Compliance / Outgoing NTLM Request from DC

Compliance / SSH to Rare External Destination

Compromise / Large Number of Suspicious Successful Connections

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Device / Anomalous Certificate Download Activity

Device / Anomalous SSH Followed By Multiple Model Alerts

Device / Anonymous NTLM Logins

Device / Attack and Recon Tools

Device / ICMP Address Scan

Device / Large Number of Model Alerts

Device / Network Range Scan

Device / Network Scan

Device / New User Agent To Internal Server

Device / Possible SMB/NTLM Brute Force

Device / Possible SMB/NTLM Reconnaissance

Device / RDP Scan

Device / Reverse DNS Sweep

Device / Suspicious SMB Scanning Activity

Device / UDP Enumeration

Unusual Activity / Unusual External Data to New Endpoint

Unusual Activity / Unusual External Data Transfer

User / Multiple Uncommon New Credentials on Device

User / New Admin Credentials on Client

User / New Admin Credentials on Server

Enhanced Monitoring Models

Compromise / Anomalous Certificate Download and Kerberos Login

Device / Initial Attack Chain Activity

Device / Large Number of Model Alerts from Critical Network Device

Device / Multiple Lateral Movement Model Alerts

Device / Suspicious Network Scan Activity

Unusual Activity / Enhanced Unusual External Data Transfer

Antigena/Autonomous Response Models

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

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

Antigena / Network / Insider Threat / Antigena Network Scan Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block

Antigena / Network / Manual / Quarantine Device

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

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

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

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

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

Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

Antigena / Network / Significant Anomaly / Repeated Antigena Alerts

List of Indicators of Compromise (IoCs)

·      66.165.243[.]39 – IP Address – Data exfiltration endpoint

·      107.155.69[.]42 – IP Address – Probable data exfiltration endpoint

·      107.155.93[.]154 – IP Address – Likely Data exfiltration endpoint

·      137.184.126[.]86 – IP Address – Possible C2 endpoint

·      85.239.52[.]96 – IP Address – Likely C2 endpoint

·      hxxp://85.239.52[.]96:8000/vmwarecli  – URL – File download

·      hxxp://137.184.126[.]86:8080/vmwaretools – URL – File download

MITRE ATT&CK Mapping

Initial Access – T1190 – Exploit Public-Facing Application

Reconnaissance – T1590.002 – Gather Victim Network Information: DNS

Reconnaissance – T1590.005 – Gather Victim Network Information: IP Addresses

Reconnaissance – T1592.004 – Gather Victim Host Information: Client Configurations

Reconnaissance – T1595 – Active Scanning

Discovery – T1018 – Remote System Discovery

Discovery – T1046 – Network Service Discovery

Discovery – T1083 – File and Directory Discovery

Discovery – T1135 – Network Share Discovery

Lateral Movement – T1021.001 – Remote Services: Remote Desktop Protocol

Lateral Movement – T1021.004 – Remote Services: SSH

Lateral Movement – T1021.006 – Remote Services: Windows Remote Management

Lateral Movement – T1550.002 – Use Alternate Authentication Material: Pass the Hash

Lateral Movement – T1550.003 – Use Alternate Authentication Material: Pass the Ticket

Credential Access – T1110.001 – Brute Force: Password Guessing

Credential Access – T1649 – Steal or Forge Authentication Certificates

Persistence, Privilege Escalation – T1078 – Valid Accounts

Resource Development – T1588.001 – Obtain Capabilities: Malware

Command and Control – T1071.001 – Application Layer Protocol: Web Protocols

Command and Control – T1105 – Ingress Tool Transfer

Command and Control – T1573 – Encrypted Channel

Collection – T1074 – Data Staged

Exfiltration – T1041 – Exfiltration Over C2 Channel

Exfiltration – T1048 – Exfiltration Over Alternative Protocol

References

[1] https://thehackernews.com/2025/08/sonicwall-investigating-potential-ssl.html

[2] https://www.sonicwall.com/support/notices/gen-7-and-newer-sonicwall-firewalls-sslvpn-recent-threat-activity/250804095336430

[3] https://psirt.global.sonicwall.com/vuln-detail/SNWLID-2024-0015

[4] https://arcticwolf.com/resources/blog/arctic-wolf-observes-akira-ransomware-campaign-targeting-sonicwall-sslvpn-accounts/

[5] https://www.rapid7.com/blog/post/dr-akira-ransomware-group-utilizing-sonicwall-devices-for-initial-access/

[6] https://www.ic3.gov/AnnualReport/Reports/2024_IC3Report.pdf

[7] https://www.cisa.gov/news-events/cybersecurity-advisories/aa24-109a

[8] https://blog.talosintelligence.com/akira-ransomware-continues-to-evolve/

[9] https://www.ransomware.live/map?year=2025&q=akira

[10] https://attack.mitre.org/groups/G1024/
[11] https://labs.lares.com/fear-kerberos-pt2/#UNPAC

[12] https://www.thehacker.recipes/ad/movement/kerberos/unpac-the-hash

[13] https://www.s-rminform.com/latest-thinking/derailing-akira-cyber-threat-intelligence)

[14] https://fieldeffect.com/blog/update-akira-ransomware-group-targets-sonicwall-vpn-appliances

[15] https://arcticwolf.com/resources/blog/arctic-wolf-observes-july-2025-uptick-in-akira-ransomware-activity-targeting-sonicwall-ssl-vpn/

Continue reading
About the author
Emily Megan Lim
Cyber Analyst

Blog

/

Email

/

September 30, 2025

Out of Character: Detecting Vendor Compromise and Trusted Relationship Abuse with Darktrace

vendor email compromiseDefault blog imageDefault blog image

What is Vendor Email Compromise?

Vendor Email Compromise (VEC) refers to an attack where actors breach a third-party provider to exploit their access, relationships, or systems for malicious purposes. The initially compromised entities are often the target’s existing partners, though this can extend to any organization or individual the target is likely to trust.

It sits at the intersection of supply chain attacks and business email compromise (BEC), blending technical exploitation with trust-based deception. Attackers often infiltrate existing conversations, leveraging AI to mimic tone and avoid common spelling and grammar pitfalls. Malicious content is typically hosted on otherwise reputable file sharing platforms, meaning any shared links initially seem harmless.

While techniques to achieve initial access may have evolved, the goals remain familiar. Threat actors harvest credentials, launch subsequent phishing campaigns, attempt to redirect invoice payments for financial gain, and exfiltrate sensitive corporate data.

Why traditional defenses fall short

These subtle and sophisticated email attacks pose unique challenges for defenders. Few busy people would treat an ongoing conversation with a trusted contact with the same level of suspicion as an email from the CEO requesting ‘URGENT ASSISTANCE!’ Unfortunately, many traditional secure email gateways (SEGs) struggle with this too. Detecting an out-of-character email, when it does not obviously appear out of character, is a complex challenge. It’s hardly surprising, then, that 83% of organizations have experienced a security incident involving third-party vendors [1].  

This article explores how Darktrace detected four different vendor compromise campaigns for a single customer, within a two-week period in 2025.  Darktrace / EMAIL successfully identified the subtle indicators that these seemingly benign emails from trusted senders were, in fact, malicious. Due to the configuration of Darktrace / EMAIL in this customer’s environment, it was unable to take action against the malicious emails. However, if fully enabled to take Autonomous Response, it would have held all offending emails identified.

How does Darktrace detect vendor compromise?

The answer lies at the core of how Darktrace operates: anomaly detection. Rather than relying on known malicious rules or signatures, Darktrace learns what ‘normal’ looks like for an environment, then looks for anomalies across a wide range of metrics. Despite the resourcefulness of the threat actors involved in this case, Darktrace identified many anomalies across these campaigns.

Different campaigns, common traits

A wide variety of approaches was observed. Individuals, shared mailboxes and external contractors were all targeted. Two emails originated from compromised current vendors, while two came from unknown compromised organizations - one in an associated industry. The sender organizations were either familiar or, at the very least, professional in appearance, with no unusual alphanumeric strings or suspicious top-level domains (TLDs). Subject line, such as “New Approved Statement From [REDACTED]” and “[REDACTED] - Proposal Document” appeared unremarkable and were not designed to provoke heightened emotions like typical social engineering or BEC attempts.

All emails had been given a Microsoft Spam Confidence Level of 1, indicating Microsoft did not consider them to be spam or malicious [2]. They also passed authentication checks (including SPF, and in some cases DKIM and DMARC), meaning they appeared to originate from an authentic source for the sender domain and had not been tampered with in transit.  

All observed phishing emails contained a link hosted on a legitimate and commonly used file-sharing site. These sites were often convincingly themed, frequently featuring the name of a trusted vendor either on the page or within the URL, to appear authentic and avoid raising suspicion. However, these links served only as the initial step in a more complex, multi-stage phishing process.

A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Figure 1: A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.
Figure 2: Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.

If followed, the recipient would be redirected, sometimes via CAPTCHA, to fake Microsoft login pages designed to capturing credentials, namely http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html and https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html#.

The latter made use of homoglyphs to deceive the user, with a link referencing ‘s3cure0line’, rather than ‘secureonline’. Post-incident investigation using open-source intelligence (OSINT) confirmed that the domains were linked to malicious phishing endpoints [3] [4].

Fake Microsoft login page designed to harvest credentials.
Figure 3: Fake Microsoft login page designed to harvest credentials.
Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.
Figure 4: Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.

Darktrace Anomaly Detection

Some senders were unknown to the network, with no previous outbound or inbound emails. Some had sent the email to multiple undisclosed recipients using BCC, an unusual behavior for a new sender.  

Where the sender organization was an existing vendor, Darktrace recognized out-of-character behavior, in this case it was the first time a link to a particular file-sharing site had been shared. Often the links themselves exhibited anomalies, either being unusually prominent or hidden altogether - masked by text or a clickable image.

Crucially, Darktrace / EMAIL is able to identify malicious links at the time of processing the emails, without needing to visit the URLs or analyze the destination endpoints, meaning even the most convincing phishing pages cannot evade detection – meaning even the most convincing phishing emails cannot evade detection. This sets it apart from many competitors who rely on crawling the endpoints present in emails. This, among other things, risks disruption to user experience, such as unsubscribing them from emails, for instance.

Darktrace was also able to determine that the malicious emails originated from a compromised mailbox, using a series of behavioral and contextual metrics to make the identification. Upon analysis of the emails, Darktrace autonomously assigned several contextual tags to highlight their concerning elements, indicating that the messages contained phishing links, were likely sent from a compromised account, and originated from a known correspondent exhibiting out-of-character behavior.

A summary of the anomalous email, confirming that it contained a highly suspicious link.
Figure 5: Tags assigned to offending emails by Darktrace / EMAIL.

Figure 6: A summary of the anomalous email, confirming that it contained a highly suspicious link.

Out-of-character behavior caught in real-time

In another customer environment around the same time Darktrace / EMAIL detected multiple emails with carefully crafted, contextually appropriate subject lines sent from an established correspondent being sent to 30 different recipients. In many cases, the attacker hijacked existing threads and inserted their malicious emails into an ongoing conversation in an effort to blend in and avoid detection. As in the previous, the attacker leveraged a well-known service, this time ClickFunnels, to host a document containing another malicious link. Once again, they were assigned a Microsoft Spam Confidence Level of 1, indicating that they were not considered malicious.

The legitimate ClickFunnels page used to host a malicious phishing link.
Figure 7: The legitimate ClickFunnels page used to host a malicious phishing link.

This time, however, the customer had Darktrace / EMAIL fully enabled to take Autonomous Response against suspicious emails. As a result, when Darktrace detected the out-of-character behavior, specifically, the sharing of a link to a previously unused file-sharing domain, and identified the likely malicious intent of the message, it held the email, preventing it from reaching recipients’ inboxes and effectively shutting down the attack.

Figure 8: Darktrace / EMAIL’s detection of malicious emails inserted into an existing thread.*

*To preserve anonymity, all real customer names, email addresses, and other identifying details have been redacted and replaced with fictitious placeholders.

Legitimate messages in the conversation were assigned an Anomaly Score of 0, while the newly inserted malicious emails identified and were flagged with the maximum score of 100.

Key takeaways for defenders

Phishing remains big business, and as the landscape evolves, today’s campaigns often look very different from earlier versions. As with network-based attacks, threat actors are increasingly leveraging legitimate tools and exploiting trusted relationships to carry out their malicious goals, often staying under the radar of security teams and traditional email defenses.

As attackers continue to exploit trusted relationships between organizations and their third-party associates, security teams must remain vigilant to unexpected or suspicious email activity. Protecting the digital estate requires an email solution capable of identifying malicious characteristics, even when they originate from otherwise trusted senders.

Credit to Jennifer Beckett (Cyber Analyst), Patrick Anjos (Senior Cyber Analyst), Ryan Traill (Analyst Content Lead), Kiri Addison (Director of Product)

Appendices

IoC - Type - Description + Confidence  

- http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html#p – fake Microsoft login page

- https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html# - link to domain used in homoglyph attack

MITRE ATT&CK Mapping  

Tactic – Technique – Sub-Technique  

Initial Access - Phishing – (T1566)  

References

1.     https://gitnux.org/third-party-risk-statistics/

2.     https://learn.microsoft.com/en-us/defender-office-365/anti-spam-spam-confidence-level-scl-about

3.     https://www.virustotal.com/gui/url/5df9aae8f78445a590f674d7b64c69630c1473c294ce5337d73732c03ab7fca2/detection

4.     https://www.virustotal.com/gui/url/695d0d173d1bd4755eb79952704e3f2f2b87d1a08e2ec660b98a4cc65f6b2577/details

The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.

Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.

Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.

The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI