How Darktrace won an email security trial by learning the business, not the breach
Discover how Darktrace identified a sophisticated business email compromise (BEC) attack to successfully acquire a prospective customer in a trial alongside two other email security vendors. This case demonstrates the clear differentiator of true unsupervised machine learning applied to the right use cases, compared to miscellaneous vendor hype around AI.
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
Carlos Gray
Senior Product Marketing Manager, Email
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02
Oct 2024
Recently, Darktrace ran a customer trial of our email security product for a leading European infrastructure operator looking to upgrade its email protection.
During this prospective customer trial, Darktrace encountered several security incidents that penetrated existing security layers. Two of these incidents were Business Email Compromise (BEC) attacks, which we’re going to take a closer look at here.
Darktrace was deployed for a trial at the same time as two other email security vendors, who were also being evaluated by the prospective customer. Darktrace’s superior detection of threats in this trial laid the groundwork for the respective company to choose our product.
Let’s dig into some of the elements of this Darktrace tech win and how they came to light during this trial.
Why truly intelligent AI starts learning from scratch
Darktrace’s detection capabilities are powered by true unsupervised machine learning, which detects anomalous activity from its ever-evolving understanding of normal for every unique environment. Consequently, it learns every business from the beginning, training on an organization’s data to understand normal for its users, devices, assets and the millions of connections between them.
This learning period takes around a week, during which the AI hones its understanding of the business to a precise degree. At this stage, the system may produce some noise or lack precision, but this is a testament to our unsupervised machine learning. Unlike solutions that promise faster results by relying on preset assumptions, our AI takes the necessary time to learn from scratch, ensuring a deeper understanding and increasingly accurate detection over time.
Real threats detected by Darktrace
Attack 1: Supply chain attack
BEC and supply chain attacks are notoriously difficult to detect, as they take advantage of established, trusted senders.
This attack came from a legitimate server via a known supplier with which the prospective customer had active and ongoing communication. Using the compromised account, the attacker didn’t just send out randomized spam, they crafted four sophisticated social engineering emails with the aim of soliciting users to click on a link – directly tapping into existing conversations. Darktrace / EMAIL was configured in passive mode during this trial; it would otherwise have held the emails before they arrived in the inbox. Luckily in this instance, one user reported the email to the CISO before any other users clicked the link. Upon investigation, the link contained timed ransomware detonation.
Darktrace was the only vendor that caught any of these four emails. Our unique behavioral AI approach enables Darktrace / EMAIL to protect customers from even the most sophisticated attacks that abuse prior trust and relationships.
How did Darktrace catch this attack that other vendors missed?
With traditional email security, security teams have been obliged to allow entire organizations to eliminate false positives – on the premise that it’s easier to make a broad decision based on an entire known domain and assume that potential risk of a supply chain attack.
By contrast, Darktrace adopts a zero trust mentality, analyzing every email to understand whether communication that has previously been safe remains safe. That’s why Darktrace is uniquely positioned to detect BEC, based on its deep learning of internal and external users. Because it creates individual profiles for every account, group and business composed of multiple signals, it can detect deviations in their communication patterns based on the context and content of each message. We think of this as the ‘self-learning’ vs ‘learning the breach’ differentiator.
Fig 1: Darktrace analysis of one of four malicious emails sent by the trusted supplier. It gives it an anomaly score of 100, despite it being from a known correspondent with a known domain relationship and moderate mailing history.
If set in autonomous mode where it can apply actions, Darktrace / EMAIL would have quarantined all four emails. Using machine learning indicators such as ‘Inducement Shift’ and ‘General Behavioral Anomaly’, it deemed the four emails ‘Out of Character’. It also identified the link as highly likely to be phishing, based purely on its context. These indicators are critical because the link itself belonged to a widely used legitimate domain, leveraging their established internet reputation to appear safe.
Around an hour later the supplier regained control of the account and sent a legitimate email alerting a wide distribution list to the phishing emails sent. Darktrace was able to discern the previously sent malicious emails from the current legitimate emails and allowed these emails through. Compared to other vendors that have a static understanding of malicious which needs to be updated (in cases like this, once a supplier is de-compromised), Darktrace’s deep understanding of external entities enables further nuance and precision in determining good from bad.
Fig 2: Darktrace let through four emails (subject line: Virus E-Mail) from the supplier once they had regained control of the compromised account, with a limited anomaly score despite having held the previous malicious emails. If any actions had been taken a red icon would show on the right-hand side – in this instance Darktrace did not take action and let the emails through.
Attack 2: Microsoft 365 account takeover
As part of building behavioral profiles of every email user, Darktrace analyzes their wider account activity. Account activity, such as unusual login patterns and administrative activity, is a key variable to detect account compromise before malicious activity occurs, but it also feeds into Darktrace’s understanding of which emails should belong in every user’s inbox.
When the customer experienced an account compromise on day two of the trial, Darktrace began an investigation and was able to provide the full breakdown and scope of the incident.
The account was compromised via an email, which Darktrace would have blocked if it had been deployed autonomously at the time. Once the account had been compromised, detection details included:
Unusual Login and Account Update
Multiple Unusual External Sources for SaaS Credential
Unusual Activity Block
Login From Rare Endpoint While User is Active
Fig 3: Darktrace flagged the following indicators of compromise that deviated from normal behavior for the user in question, signaling an account takeover
With Darktrace / EMAIL, every user is analyzed for behavioral signals including authentication and configuration activity. Here the unusual login, credential input and rare endpoint were all clear signals a compromised account, contextualized against what is normal for that employee. Because Darktrace isn’t looking at email security merely from the perspective of the inbox. It constantly reevaluates the identity of each individual, group and organization (as defined by their behavioral signals), to determine precisely what belongs in the inbox and what doesn’t.
In this instance, Darktrace / EMAIL would have blocked the incident were it not deployed in passive mode. In the initial intrusion it would have blocked the compromising email. And once the account was compromised, it would have taken direct blocking actions on the account based on the anomalous activity it detected, providing an extra layer of defense beyond the inbox.
Account takeover protection is always part of Darktrace / EMAIL, which can be extended to fully cover Microsoft 365 SaaS with Darktrace / IDENTITY. By bringing SaaS activity into scope, security teams also benefit from an extended set of use cases including compliance and resource management.
“Darktrace was the only AI vendor that showed learning,” – CISO, Trial Customer
Throughout this trial, Darktrace evolved its understanding of the trial customer’s business and its email users. It identified attacks that other vendors did not, while allowing safe emails through. Furthermore, the CISO explicitly cited Darktrace as the only technology that demonstrated autonomous learning. As well as catching threats that other vendors did not, the CISO saw maturity areas such as how Darktrace dealt with non-productive mail and business-as-usual emails, without any user input. Because of the nature of unsupervised ML, Darktrace’s learning of right and wrong will never be static or complete – it will continue to revise its understanding and adapt to the changing business and communications landscape.
This case study highlights a key tenet of Darktrace’s philosophy – that a rules and tuning-based approach will always be one step behind. Delivering benign emails while holding back malicious emails from the same domain demonstrates that safety is not defined in a straight line, or by historical precedent. Only by analyzing every email in-depth for its content and context can you guarantee that it belongs.
While other solutions are making efforts to improve a static approach with AI, Darktrace’s AI remains truly unsupervised so it is dynamic enough to catch the most agile and evolving threats. This is what allows us to protect our customers by plugging a vital gap in their security stack that ensures they can meet the challenges of tomorrow's email attacks.
Interested in learning more about Darktrace / EMAIL? Check out our product hub.
Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.
Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
Experience 20-25% more threat blocking power with Darktrace / EMAIL
Stop the 58% of threats bypassing traditional email security
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.
Out of Character: Detecting Vendor Compromise and Trusted Relationship Abuse with Darktrace
Phishing emails from compromised vendors are increasingly difficult to distinguish from genuine correspondence. They challenge workers, security teams and traditional email SEGs alike. Anomaly detection can be a game-changer in spotting the subtle signs of these meticulous attacks.
Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision
Darktrace and Microsoft have joined forces to enhance email security through a new integration, unifying threat response and quarantine capabilities. This collaboration strengthens defenses and streamlines visibility for security teams, reflecting a shared vision for proactive cyber protection.
How a Major Civil Engineering Company Reduced MTTR across Network, Email and the Cloud with Darktrace
Asking more of the information security team
“What more can we be doing to secure the company?” is a great question for any cyber professional to hear from their Board of Directors. After successfully defeating a series of attacks and seeing the potential for AI tools to supercharge incoming threats, a UK-based civil engineering company’s security team had the answer: Darktrace.
“When things are coming at you at machine speed, you need machine speed to fight it off – it’s as simple as that,” said their Information Security Manager. “There were incidents where it took us a few hours to get to the bottom of what was going on. Darktrace changed that.”
Prevention was also the best cure. A peer organization in the same sector was still in business continuity measures 18 months after an attack, and the security team did not want to risk that level of business disruption.
Legacy tools were not meeting the team’s desired speed or accuracy
The company’s native SaaS email platform took between two and 14 days to alert on suspicious emails, with another email security tool flagging malicious emails after up to 24 days. After receiving an alert, responses often took a couple of days to coordinate. The team was losing precious time.
Beyond long detection and response times, the old email security platform was no longer performing: 19% of incoming spam was missed. Of even more concern: 6% of phishing emails reached users’ inboxes, and malware and ransomware email was also still getting through, with 0.3% of such email-borne payloads reaching user inboxes.
Choosing Darktrace
“When evaluating tools in 2023, only Darktrace had what I was looking for: an existing, mature, AI-based cybersecurity solution. ChatGPT had just come out and a lot of companies were saying ‘AI this’ and ‘AI that’. Then you’d take a look, and it was all rules- and cases-based, not AI at all,” their Information Security Manager.
The team knew that, with AI-enabled attacks on the horizon, a cybersecurity company that had already built, fielded, and matured an AI-powered cyber defense would give the security team the ability to fend off machine-speed attacks at the same pace as the attackers.
Darktrace accomplishes this with multi-layered AI that learns each organization’s normal business operations. With this detailed level of understanding, Darktrace’s Self-Learning AI can recognize unusual activity that may indicate a cyber-attack, and works to neutralize the threat with precise response actions. And it does this all at machine speed and with minimal disruption.
On the morning the team was due to present its findings, the session was cancelled – for a good reason. The Board didn’t feel further discussion was necessary because the case for Darktrace was so conclusive. The CEO described the Darktrace option as ‘an insurance policy we can’t do without’.
Saving time with Darktrace / EMAIL
Darktrace / EMAIL reduced the discovery, alert, and response process from days or weeks to seconds .
Darktrace / EMAIL automates what was originally a time-consuming and repetitive process. The team has recovered between eight and 10 working hours a week by automating much of this process using / EMAIL.
Today, Darktrace / EMAIL prevents phishing emails from reaching employees’ inboxes. The volume of hostile and unsolicited email fell to a third of its original level after Darktrace / EMAIL was set up.
Further savings with Darktrace / NETWORK and Darktrace / IDENTITY
Since its success with Darktrace / EMAIL, the company adopted two more products from the Darktrace ActiveAI Security Platform – Darktrace / NETWORK and Darktrace / IDENTITY.
These have further contributed to cost savings. An initial plan to build a 24/7 SOC would have required hiring and retaining six additional analysts, rather than the two that currently use Darktrace, costing an additional £220,000 per year in salary. With Darktrace, the existing analysts have the tools needed to become more effective and impactful.
An additional benefit: Darktrace adoption has lowered the company’s cyber insurance premiums. The security team can reallocate this budget to proactive projects.
Detection of novel threats provides reassurance
Darktrace’s unique approach to cybersecurity added a key benefit. The team’s previous tool took a rules-based approach – which was only good if the next attack featured the same characteristics as the ones on which the tool was trained.
“Darktrace looks for anomalous behavior, and we needed something that detected and responded based on use cases, not rules that might be out of date or too prescriptive,” their Information Security Manager. “Our existing provider could take a couple of days to update rules and signatures, and in this game, speed is of the essence. Darktrace just does everything we need - without delay.”
Where rules-based tools must wait for a threat to emerge before beginning to detect and respond to it, Darktrace identifies and protects against unknown and novel threats, speeding identification, response, and recovery, minimizing business disruption as a result.
Looking to the future
With Darktrace in place, the UK-based civil engineering company team has reallocated time and resources usually spent on detection and alerting to now tackle more sophisticated, strategic challenges. Darktrace has also equipped the team with far better and more regularly updated visibility into potential vulnerabilities.
“One thing that frustrates me a little is penetration testing; our ISO accreditation mandates a penetration test at least once a year, but the results could be out of date the next day,” their Information Security Manager. “Darktrace / Proactive Exposure Management will give me that view in real time – we can run it daily if needed - and that’s going to be a really effective workbench for my team.”
As the company looks to further develop its security posture, Darktrace remains poised to evolve alongside its partner.
Inside Akira’s SonicWall Campaign: Darktrace’s Detection and Response
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].
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].
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.
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.
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].
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.
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.
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
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![Geographical distribution of organization’s affected by Akira ransomware in 2025 [9].](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68e684a90c107be86fa5c2e0_Screenshot%202025-10-08%20at%207.53.20%E2%80%AFAM.png)
![Flowchart of Kerberos PKINIT pre-authentication and U2U authentication [12].](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68e53a2b5e9394d5a5cbebb7_Screenshot%202025-10-07%20at%209.04.43%E2%80%AFAM.png)
![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.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68e53a8ea01e348d5a62a6c3_Screenshot%202025-10-07%20at%209.06.31%E2%80%AFAM.png)
![Packet capture (PCAP) of connections between the ESXi device and 137.184.243[.]69.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68e53ae5304f84a4192967db_Screenshot%202025-10-07%20at%209.07.53%E2%80%AFAM.png)
![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.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68e53b26d90343a0a6ab3bb2_Screenshot%202025-10-07%20at%209.09.02%E2%80%AFAM.png)
