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December 22, 2021

9 Stages of Ransomware & How AI Responds

Discover the 9 stages of ransomware attacks and how AI responds at each stage. Learn how you can protect your business from cyber threats.
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
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22
Dec 2021

Ransomware gets its name by commandeering and holding assets ransom, extorting their owner for money in exchange for discretion and full cooperation in returning exfiltrated data and providing decryption keys to allow business to resume.

Average ransom demands are skyrocketing, rising to $5.3 million in 2021, a 518% increase from the previous year. But the cost of recovering from a ransomware attack typically far exceeds the ransom payments: the average downtime after a ransomware attack is 21 days; and 66% of ransomware victims report a significant loss of revenue following a successful attack.

In this series, we break down this huge topic step by step. Ransomware is a multi-stage problem, requiring a multi-stage solution that autonomously and effectively contains the attack at any stage. Read on to discover how Self-Learning AI and Autonomous Response stops ransomware in its tracks.

1. Initial intrusion (email)

Initial entry – the first stage of a ransomware attack – can be achieved through RDP brute-forcing (exposed Internet service), malicious websites and drive-by downloads, an insider threat with company credentials, system and software vulnerabilities, or any number of other attack vectors.

But the most common initial attack vector is email. An organization’s biggest security weakness is often their people – and attackers are good at finding ways of exploiting this. Well-researched, targeted, legitimate-looking emails are aimed at employees attempting to solicit a reaction: a click of a link, an opening of an attachment, or persuading them to divulge credentials or other sensitive information.

Gateways: Stops what has been seen before

Most conventional email tools rely on past indicators of attack to try and spot the next threat. If an email comes in from a blocklisted IP address or email domain, and uses known malware that has previously been seen in the wild, the attack may be blocked.

But the reality is, attackers know the majority of defenses take this historical approach, and so constantly update their attack infrastructure to bypass these tools. By buying new domains for a few pennies each, or creating bespoke malware with just small adaptions to the code, they can outpace and outsmart the legacy approach taken by a typical email gateway.

Real-world example: Supply chain phishing attack

By contrast, Darktrace’s evolving understanding of ‘normal’ for every email user in the organization enables it to detect subtle deviations that point to a threat – even if the sender or any malicious contents of the email are unknown to threat intelligence. This is what enabled the technology to stop an attack that recently targeted McLaren Racing, with emails sent to a dozen employees in the organization each containing a malicious link. This possible precursor to ransomware bypassed conventional email tools – largely because it was sent from a known supplier – however Darktrace recognized the account hijack and held the email back.

Figure 1: A snapshot of Darktrace’s Threat Visualizer surfacing the malicious email

Read the full case study

2. Initial intrusion (server-side)

With organizations rapidly expanding their Internet-facing perimeter, this increased attack surface has paved the way for a surge in brute-force and server-side attacks.

A number of vulnerabilities against such Internet-facing servers and systems have been disclosed this year, and for attackers, targeting and exploiting public-facing infrastructure is easier than ever – scanning the Internet for vulnerable systems is made simple with tools like Shodan or MassScan.

Attackers may also achieve initial intrusion via RDP brute-forcing or stolen credentials, with attackers often reusing legitimate credentials from previous data dumps. This has much higher precision and is less noisy than a classic brute-force attack.

A lot of ransomware attacks use RDP as an entry vector. This is part of a wider trend of ‘Living off the Land’: using legitimate off-the-shelf tools (abusing RDP, SMB1 protocol, or various command line tools WMI or Powershell) to blur detection and attribution by blending in with typical administrator activity. Ensuring that backups are isolated, configurations are hardened, and systems are patched is not enough – real-time detection of every anomalous action is needed.

Antivirus, firewalls and SIEMs

In cases of malware downloads, endpoint antivirus will detect these if, and only if, the malware has been seen and fingerprinted before. Firewalls typically require configuration on a per-organization basis, and often need to be modified based on the needs of the business. If the attack hits the firewall where a rule or signature does not match it, again, it will bypass the firewall.

SIEM and SOAR tools also look for known malware being downloaded, leverage pre-programmed rules and use pre-programmed responses. While these tools do look for patterns, these patterns are defined in advance, and this approach relies on a new attack to have sufficiently similar traits to attacks that have been seen before.

Real-world example: Dharma ransomware

Darktrace detected a targeted Dharma ransomware attack against a UK organization exploiting an open RDP connection through Internet-facing servers. The RDP server began receiving a large number of incoming connections from rare IP addresses on the Internet. It is highly likely that the RDP credential used in this attack had been compromised at a previous stage – either via common brute-force methods, credential stuffing attacks, or phishing. Indeed, a technique growing in popularity is to buy RDP credentials on marketplaces and skip to initial access.

Figure 2: The model breaches that fired over the course of this attack, including anomalous RDP activity

Unfortunately, in this case, without Autonomous Response installed, the Dharma ransomware attack continued until its final stages, where the security team were forced into the heavy-handed and disruptive action of pulling the plug on the RDP server midway through encryption.

Read the full case study

3. Establish foothold and C2

Whether through a successful phish, a brute-force attack, or some other method, the attacker is in. Now, they make contact with the breached device(s) and establish a foothold.

This stage allows attackers to control subsequent stages of the attack remotely. During these command and control (C2) communications, further malware may also pass from the attacker to the devices. This helps them to establish an even greater foothold within the organization and readies them for lateral movement.

Attackers can adapt malware functionality with an assortment of ready-made plug-ins, allowing them to lie low inside the business undetected. More modern and sophisticated ransomware is able to adapt by itself to the surrounding environment, and operate autonomously, blending in to regular activity even when cut off from its command and control server. These ‘self-sufficient’ ransomware strains pose a big problem for traditional defenses reliant on stopping threats solely on the grounds of its malicious external connections.

Viewing connections in isolation vs understanding the business

Conventional security tools like IDS and firewalls tend to look at connections in isolation rather than in the context of previous and potentially relevant connections, making command and control very difficult to spot.

IDS and firewalls may block ‘known-bad’ domains or use some geo-blocking, but this is where an attacker would likely leverage new infrastructure.

These tools also don’t tend to analyze for things like the periodicity, such as whether a connection is beaconing at a regular or irregular interval, or the age and rarity of the domain in the context of the environment.

With Darktrace’s evolving understanding of the digital enterprise, suspicious C2 connections and the downloads which follow them are spotted, even when conducted using regular programs or methods. The AI technology correlates multiple subtle signs of threat – a small subset of which includes anomalous connections to young and/or unusual endpoints, anomalous file downloads, incoming remote desktop, and unusual data uploads and downloads.

Once they are detected as a threat, Darktrace's Autonomous Response halts these connections and downloads, while allowing normal business activity to continue.

Real-world example: WastedLocker attack

When a WastedLocker ransomware attack hit a US agricultural organization, Darktrace immediately detected the initial unusual SSL C2 activity (based on a combination of destination rarity, JA3 unusualness and frequency analysis). Antigena (on this occasion configured in passive mode, and therefore not granted permission to take autonomous action) suggested instantly blocking the C2 traffic on port 443 and parallel internal scanning on port 135.

Figure 3: The Threat Visualizer reveals the action Antigena would have taken

When beaconing was later observed to bywce.payment.refinedwebs[.]com, this time over HTTP to /updateSoftwareVersion, Antigena escalated its response by blocking the further C2 channels.

Figure 4: Antigena escalates its response

Read the full case study

4. Lateral movement

Once an attacker has established a foothold within an organization, they begin to increase their knowledge of the wider digital estate and their presence within it. This is how they will find and access the files which they will ultimately attempt to exfiltrate and encrypt. It begins reconnaissance: scanning the network; building up a picture of its component devices; identifying the location of the most valuable assets.

Then the attacker begins moving laterally. They infect more devices and look to escalate their privileges – for instance, by obtaining admin credentials – thereby increasing their control over the environment. Once they have obtained authority and presence within the digital estate, they can progress to the final stages of the attack.

Modern ransomware has built-in functions that allow it to search automatically for stored passwords and spread through the network. More sophisticated strains are designed to build themselves differently in different environments, so the signature is constantly changing and it’s harder to detect.

Legacy tools: A blunt response to known threats

Because they rely upon static rules and signatures, legacy solutions struggle to prevent lateral movement and privilege escalation without also impeding essential business operations. Whilst in theory, an organization leveraging firewalls and NAC internally with proper network segmentation and a perfect configuration could prevent cross-network lateral movement, maintaining a perfect balance between protective and disruptive controls is near impossible.

Some organizations rely on Intrusion Prevent Systems (IPS) to deny network traffic when known threats are detected in packets, but as with previous stages, novel malware will evade detection, and this requires the database to be constantly updated. These solutions also sit at the ingress/egress points, limiting their network visibility. An Intrusion Detection System (IDS) may sit out-of-line, but doesn’t have response capabilities.

A self-learning approach

Darktrace’s AI learns ‘self’ for the organization, enabling it to detect suspicious activity indicative of lateral movement, regardless of whether the attacker uses new infrastructure or ‘lives off the land’. Potential unusual activity that Darktrace detects includes unusual scanning activity, unusual SMB, RDP, and SSH activity. Other models that fire at this stage include:

  • Suspicious Activity on High-Risk Device
  • Numeric EXE in SMB Write
  • New or Uncommon Service Control

Autonomous Response then takes targeted action to stop the threat at this stage, blocking anomalous connections, enforcing the infected device’s ‘pattern of life’, or enforcing the group ‘pattern of life’ – automatically clustering devices into peer groups and preventing a device from doing anything its peer group hasn’t done.

Where malicious behavior persists, and only if necessary, Darktrace will quarantine an infected device.

Real-world example: Unusual chain of RDP connections

At an organization in Singapore, one compromised server led to the creation of a botnet, which began moving laterally, predominantly by establishing chains of unusual RDP connections. The server then started making external SMB and RPC connections to rare endpoints on the Internet, in an attempt to find further vulnerable hosts.

Other lateral movement activities detected by Darktrace included the repeated failing attempts to access multiple internal devices over the SMB file-sharing protocol with a range of different usernames, implying brute-force network access attempts.

Figure 5: Darktrace’s Cyber AI Analyst reveals suspicious TCP scanning followed by a suspicious chain of administrative RDP connections

Read the full case study

5. Data exfiltration

In the past, ransomware was simply about encrypting an operating system and network files.

In a modern attack, as organizations insure against malicious encryption by becoming increasingly diligent with data backups, threat actors have moved towards ‘double extortion’, where they exfiltrate key data and destroy backups before the encryption takes place. Exfiltrated data is used to blackmail organizations, with attackers threatening to publish sensitive information online or sell it on to the organization’s competitors if they are not paid.

Modern ransomware variants also look for cloud file storage repositories such as Box, Dropbox, and others.

Many of these incidents aren’t public, because if IP is stolen, organizations are not always legally required to disclose it. However, in the case of customer data, organizations are obligated by law to disclose the incident and face the additional burden of compliance files – and we’ve seen these mount in recent years (Marriot, $23.8 million; British Airways, $26 million; Equifax, $575 million). There’s also the reputational blow associated with having to inform customers that a data breach has occurred.

Legacy tools: The same old story

For those that have been following, the narrative by now will sound familiar: to stop a ransomware attack at this stage, most defenses rely on either pre-programmed definitions of 'bad' or have rules constructed to combat different scenarios put organizations in a risky, never-ending game of cat and mouse.

A firewall and proxy might block connections based on pre-programmed policies based on specific endpoints or data volumes, but it’s likely an attacker will ‘live off the land’ and utilize a service that is generally allowed by the business.

The effectiveness of these tools will vary according to data volumes: they might be effective for ‘smash and grab’ attacks using known malware, and without employing any defense evasion techniques, but are unlikely to spot ‘low and slow’ exfiltration and novel or sophisticated strains.

On the other hand, because by nature it involves a break from expected behavior, even less conspicuous, low and slow data exfiltration is detected by Darktrace and stopped with Darktrace's Autonomos Response. No confidential files are lost, and attackers are unable to extort a ransom payment through blackmail.

Real-world example: Unusual chain of RDP connections

It becomes more difficult to find examples of Darktrace stopping ransomware at these later stages, as the threat is usually contained before it gets this far. This is the double-edged sword of effective security – early containment makes for bad storytelling! However, we can see the effects of a double extortion ransomware attack on an energy company in Canada. The organization had the Enterprise Immune System but no Antigena, and without anyone actively monitoring Darktrace’s AI detections, the attack was allowed to unfold.

The attacker managed to connect to an internal file server and download 1.95TB of data. The device was also seen downloading Rclone software – an open-source tool, which was likely applied to sync data automatically to the legitimate file storage service pCloud. Following the completion of the data exfiltration, the device ‘serverps’ finally began encrypting files on 12 devices with the extension *.06d79000. As with the majority of ransomware incidents, the encryption happened outside of office hours – overnight in local time – to minimize the chance of the security team responding quickly.

Read the full details of the attack

It should be noted that the exact order of the stages 3–5 above is not set in stone, and varies according to attack. Sometimes data is exfiltrated and then there is further lateral movement, and additional C2 beaconing. This entire period is known as the ‘dwell time’. Sometimes it takes place over only a few days, other times attackers may persist for months, slowly gathering more intel and exfiltrating data in a ‘low and slow’ fashion so as to avoid detection from rule-based tools that are configured to flag any single data transfer over a certain threshold. Only through a holistic understanding of malicious activity over time can a technology spot this level of activity and allow the security team to remove the threat before it reaches the latter and most damaging stages of ransomware.

6. Data encryption

Using either symmetric encryption, asymmetric encryption, or a combination of the two, attackers attempt to render as much data unusable in the organization’s network as they can before the attack is detected.

As the attackers alone have access to the relevant decryption keys, they are now in total control of what happens to the organization’s data.

Pre-programmed response and disruption

There are many families of tools that claim to stop encryption in this manner, but each contain blind spots which enable a sophisticated attacker to evade detection at this crucial stage. Where they do take action, it is often highly disruptive, causing major shutdowns and preventing a business from continuing its usual operations.

Internal firewalls prevent clients from accessing servers, so once an attacker has penetrated to servers using any of the techniques outlined above, they have complete freedom to act as they want.

Similarly, antivirus tools look only for known malware. If the malware has not been detected until this point, it is highly unlikely the antivirus will act here.

Stopping encryption autonomously

Even if familiar tools and methods are used to conduct it, Autonomous Response can enforce the normal ‘pattern of life’ for devices attempting encryption, without using static rules or signatures. This action can be taken independently or via integrations with native security controls, maximizing the return on other security investments. With a targeted Autonomous Response, normal business operations can continue while encryption is prevented.

7. Ransom note

It is important to note that in the stages before encryption, this ransomware attack is not yet “ransomware”. Only at this stage does it gets its name.

A ransom note is deployed. The attackers request payment in return for a decryption key and threaten the release of sensitive exfiltrated data. The organization must decide whether to pay the ransom or lose their data, possibly to their competition or the public. The average demand made by ransomware threat actors rose in 2021 to $5.3 million, with meat processing company JBS paying out $11 million and DarkSide receiving over $90 million in Bitcoin payments following the Colonial Pipeline incident.

All of the stages up until this point represent a typical, traditional ransomware attack. But ransomware is shifting from indiscriminate encryption of devices to attackers targeting business disruption in general, using multiple techniques to hold their victims to ransom. Additional methods of extortion include not only data exfiltration, but corporate domain hijack, deletion or encryption of backups, attacks against systems close to industrial control systems, targeting company VIPs… the list goes on.

Sometimes, attackers will just skip straight from stage 2 to 6 and jump straight to extortion. Darktrace recently stopped an email attack which showed an attacker bypassing the hard work and attempting to jump straight to extortion in an email. The attacker claimed to have compromised the organization’s sensitive data, requesting payment in bitcoin for its same return. Whether or not the claims were true, this attack shows that encryption is not always necessary for extortion, and this type of harassment exists in multiple forms.

Figure 6: Darktrace holds back the offending email, protecting the recipient and organization from harm

As with the email example we explored in the first post of this series, Darktrace/Email was able to step in and stop this email where other email tools would have let it through, stopping this potentially costly extortion attempt.

Whether through encryption or some other kind of blackmail, the message is the same every time. Pay up, or else. At this stage, it’s too late to start thinking about any of the options described above that were available to the organization, that would have stopped the attack in its earliest stages. There is only one dilemma. “To pay or not to pay” – that is the question.

Often, people believe their payment troubles are over after the ransom payment stage, but unfortunately, it’s just beginning to scratch the surface…

8. Clean-up

Efforts are made to try to secure the vulnerabilities which allowed the attack to happen initially – the organization should be conscious that approximately 80% of ransomware victims will in fact be targeted again in the future.

Legacy tools largely fail to shed light on the vulnerabilities which allowed the initial breach. Like searching for a needle in an incomplete haystack, security teams will struggle to find useful information within the limited logs offered by firewalls and IDSs. Antivirus solutions may reveal some known malware but fail to spot novel attack vectors.

With Darktrace’s Cyber AI Analyst, organizations are given full visibility over every stage of the attack, across all coverage areas of their digital estate, taking the mystery out of ransomware attacks. They are also able to see the actions that would have been taken to halt the attack by Darktrace RESPOND.

9. Recovery

The organization begins attempts to return its digital environment to order. Even if it has paid for a decryption key, many files may remain encrypted or corrupted. Beyond the costs of the ransom payment, network shutdowns, business disruption, remediation efforts, and PR setbacks all incur hefty financial losses.

The victim organization may also suffer additional reputation costs, with 66% of victims reporting a significant loss of revenue following a ransomware attack, and 32% reporting losing C-level talent as a direct result from ransomware.

Conclusion

While the high-level stages described above are common in most ransomware attacks, the minute you start looking at the details, you realize every ransomware attack is different.

As many targeted ransomware attacks come through ransomware affiliates, the Tools, Techniques and Procedures (TTPs) displayed during intrusions vary widely, even when the same ransomware malware is used. This means that even comparing two different ransomware attacks using the same ransomware family, you are likely to encounter completely different TTPs. This makes it impossible to predict what tomorrow’s ransomware will look like.

This is the nail in the coffin for traditional tooling which is based on historic attack data. The above examples demonstrate that Self-Learning technology and Autonomous Response is the only solution that stops ransomware at every stage, across email and network.

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

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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/

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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

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