Detecting Attacks Across Email, SaaS, and Network Environments with Darktrace’s ActiveAI Security Platform
This blog explores how Darktrace’s combined AI approach enabled it to identify and connect an attack that took place over three critical areas of a customer’s digital environment, namely email, SaaS and network.
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
Zoe Tilsiter
Cyber Analyst
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30
Apr 2024
The State of AI in Cybersecurity
In a recent survey outlined in Darktrace’s State of AI Cyber Security whitepaper, 95% of cyber security professionals agree that AI-powered security solutions will improve their organization’s detection of cyber-threats [1]. Crucially, a combination of multiple AI methods is the most effective to improve cybersecurity; improving threat detection, accelerating threat investigation and response, and providing visibility across an organization’s digital environment.
In March 2024, Darktrace’s AI-led security platform was able to detect suspicious activity affecting a customer’s email, Software-as-a-Service (SaaS), and network environments, whilst its applied supervised learning capability, Cyber AI Analyst, autonomously correlated and connected all of these events together in one single incident, explained concisely using natural language processing.
Attack Overview
Following an initial email attack vector, an attacker logged into a compromised SaaS user account from the Netherlands, changed inbox rules, and leveraged the account to send thousands of phishing emails to internal and external users. Internal users fell victim to the emails by clicking on contained suspicious links that redirected them to newly registered suspicious domains hosted on same IP address as the hijacked SaaS account login. This activity triggered multiple alerts in Darktrace DETECT™ on both the network and SaaS side, all of which were correlated into one Cyber AI Analyst incident.
In this instance, Darktrace RESPOND™ was not active on any of the customer’s environments, meaning the compromise was able to escalate until their security team acted on the alerts raised by DETECT. Had RESPOND been enabled at the time of the attack, it would have been able to apply swift actions to contain the attack by blocking connections to suspicious endpoints on the network side and disabling users deviating from their normal behavior on the customer’s SaaS environment.
Nevertheless, thanks to DETECT and Cyber AI Analyst, Darktrace was able to provide comprehensive visibility across the customer’s three digital estate environments, decreasing both investigation and response time which enabled them to quickly enact remediation during the attack. This highlights the crucial role that Darktrace’s combined AI approach can play in anomaly detection cyber defense
Attack Details & Darktrace Coverage
1. Email: the initial attack vector
The initial attack vector was likely email, as on March 18, 2024, Darktrace observed a user device making several connections to the email provider “zixmail[.]net”, shortly before it connected to the first suspicious domain. Darktrace/Email identified multiple unusual inbound emails from an unknown sender that contained a suspicious link. Darktrace recognized these emails as potentially malicious and locked the link, ensuring that recipients could not directly click it.
Figure 1: Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.
2. Escalation to Network
Later that day, despite Darktrace/Email having locked the link in the suspicious email, the user proceeded to click on it and was directed to a suspicious external location, namely “rz8js7sjbef[.]latovafineart[.]life”, which triggered the Darktrace/Network DETECT model “Suspicious Domain”. Darktrace/Email was able to identify that this domain had only been registered 4 days before this activity and was hosted on an IP address based in the Netherlands, 193.222.96[.]9.
3. SaaS Account Hijack
Just one minute later, Darktrace/Apps observed the user’s Microsoft 365 account logging into the network from the same IP address. Darktrace understood that this represented unusual SaaS activity for this user, who had only previously logged into the customer’s SaaS environment from the US, triggering the “Unusual External Source for SaaS Credential Use” model.
4. SaaS Account Updates
A day later, Darktrace identified an unusual administrative change on the user’s Microsoft 365 account. After logging into the account, the threat actor was observed setting up a new multi-factor authentication (MFA) method on Microsoft Authenticator, namely requiring a 6-digit code to authenticate. Darktrace understood that this authentication method was different to the methods previously used on this account; this, coupled with the unusual login location, triggered the “Unusual Login and Account Update” DETECT model.
5. Obfuscation Email Rule
On March 20, Darktrace detected the threat actor creating a new email rule, named “…”, on the affected account. Attackers are typically known to use ambiguous or obscure names when creating new email rules in order to evade the detection of security teams and endpoints users.
This rule was seemingly created with the intention of obfuscating the sending of malicious emails, as the rule would move sent emails to the "RSS Feeds” folder, a commonly used tactic by attackers as the folder is often left unchecked by endpoint users. Interestingly, Darktrace identified that, despite the initial unusual login coming from the Netherlands, the email rule was created from a different destination IP, indicating that the attacker was using a Virtual Private Network (VPN) after gaining a foothold in the network.
Figure 2: Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.
6. Outbound Phishing Emails Sent
Later that day, the attacker was observed using the compromised customer account to send out numerous phishing emails to both internal and external recipients. Darktrace/Email detected a significant spike in inbound emails on the compromised account, with the account receiving bounce back emails or replies in response to the phishing emails. Darktrace further identified that the phishing emails contained a malicious DocSend link hidden behind the text “Click Here”, falsely claiming to be a link to the presentation platform Prezi.
Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.
7. Suspicious Domains and Redirects
After the phishing emails were sent, multiple other internal users accessed the DocSend link, which directed them to another suspicious domain, “thecalebgroup[.]top”, which had been registered on the same day and was hosted on the aforementioned Netherlands-based IP, 193.222.96[.]91. At the time of the attack, this domain had not been reported by any open-source intelligence (OSINT), but it has since been flagged as malicious by multiple vendors [2].
Figure 4: External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.
8. Cyber AI Analyst’s Investigation
As this attack was unfolding, Darktrace’s Cyber AI Analyst was able to autonomously investigate the events, correlating them into one wider incident and continually adding a total of 14 new events to the incident as more users fell victim to the phishing links.
Cyber AI Analyst successfully weaved together the initial suspicious domain accessed in the initial email attack vector (Figure 5), the hijack of the SaaS account from the Netherlands IP (Figure 6), and the connection to the suspicious redirect link (Figure 7). Cyber AI Analyst was also able to uncover other related activity that took place at the time, including a potential attempt to exfiltrate data out of the customer’s network.
By autonomously analyzing the thousands of connections taking place on a network at any given time, Darktrace’s Cyber AI Analyst is able to detect seemingly separate anomalous events and link them together in one incident. This not only provides organizations with full visibility over potential compromises on their networks, but also saves their security teams precious time ensuring they can quickly scope out the ongoing incident and begin remediation.
Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Figure 7: Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.
Conclusion
In this scenario, Darktrace demonstrated its ability to detect and correlate suspicious activities across three critical areas of a customer’s digital environment: email, SaaS, and network.
It is essential that cyber defenders not only adopt AI but use a combination of AI technology capable of learning and understanding the context of an organization’s entire digital infrastructure. Darktrace’s anomaly-based approach to threat detection allows it to identify subtle deviations from the expected behavior in network devices and SaaS users, indicating potential compromise. Meanwhile, Cyber AI Analyst dynamically correlates related events during an ongoing attack, providing organizations and their security teams with the information needed to respond and remediate effectively.
Credit to Zoe Tilsiter, Analyst Consulting Lead (EMEA), Brianna Leddy, Director of Analysis
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.
Hiding in Plain Sight: Uncovering a Multi-Stage Ransomware Attack Through Behavioral Detection
Why ransomware has changed
Ransomware attacks have continued to increase globally, with 698 incidents reported in May 2026, representing a 48% rise compared to 472 incidents in May 2025 [1]. At the same time, the ransomware landscape is evolving. Several major ransomware groups, including LockBit [2], have been disrupted by successful joint law enforcement operations, resulting in a shift away from a small number of dominant actors towards a more fragmented and distributed ecosystem. This is increasingly composed of smaller groups who play a specialized role in the attack, such as initial access brokers, affiliates or developers.
As a result, ransomware tactics, techniques, and procedures (TTPs) are becoming more diverse and less predictable. On top of this, adversaries are leveraging native tools and legitimate penetration testing frameworks to evade detection. Anomaly-based detection is therefore critical to identify pre-ransomware activity, rather than relying on signatures associated with a handful of well-known ransomware groups.
As these attacks often unfold over several days, there is a critical window for defenders to act. In this context, behavioral-based detection plays a vital role in identifying suspicious pre-ransomware activity, and enabling early intervention before encryption or exfiltration occurs.
Inside a modern ransomware intrusion
In early 2026, Darktrace detected activity within a customer’s environment related to a multi-stage ransomware intrusion from the initial compromise. This activity does not appear to be attributable to a specific ransomware group, and no known ransomware payload was observed until the final stage.
The attack aligns with a broader industry trend in which compromised virtual private network (VPN) credentials are used as an entry point, followed by rapid internal reconnaissance and lateral movement using legitimate administrative tools. This growing preference for native tools and legitimate frameworks in cyber-attacks illustrates that it is increasingly unreliable to depend solely on traditional indicators of compromise such as known malware signatures or exploit detection.
The intrusion also involved the use of Sliver, an open-source adversary emulation framework, which is increasingly observed in real-world attacks. Originally designed for penetration testing and red teaming, Sliver has gained traction among threat actors as a stealthier alternative to more heavily signatured frameworks such as Cobalt Strike. As a legitimate framework, its use further complicates detection for security tools that rely on known malicious signatures.
Darktrace’s detection of a ransomware event in a customer’s environment
The initial compromise appears to have occurred via compromised credentials used over the VPN shortly before, or at the onset of the first indicators of suspicious activity. While it remains unclear as to how or when the threat actors gained access to these credentials, the use of initial access brokers (IABs) is a common feature of modern ransomware operations. This suggests that access to the environment may have been established several days or weeks beforehand.
The intrusion unfolded over three days, presenting multiple opportunities for early detection and intervention before ransomware deployment. The attack progressed through a compressed but structured sequence: initial access and reconnaissance were completed within hours, followed by privilege escalation and lateral movement the next day, and culminating in data exfiltration and encryption shortly thereafter. Throughout each stage, distinct behavioral anomalies emerged across the network providing clear indicators of malicious activity well before the ransomware was deployed.
While Darktrace’s Autonomous Response capability was enabled within the customer’s environment, it was not fully configured across the impacted devices, allowing the attack to progress to ransomware deployment. Had Autonomous Response been fully deployed across the affected systems, it could have taken targeted action against the earliest stages of malicious activity, potentially disrupting the intrusion before it escalated.
Figure 1: Timeline of the attack progression.
Day 1: Reconnaissance and privilege escalation
The threat actor gained access via compromised VPN credentials and initiated internal reconnaissance. Darktrace detected anomalous scanning behavior, including unusual port scanning activity and widespread network enumeration.
Specifically, Darktrace detected a high volume of east-west scanning activity across a broad range of ports, with TCP connections targeting ports 21, 80, 445, 4899 and 8080. Associated URIs suggested the use of Nmap, a widely used penetration testing tool. This highlights how attackers often leverage legitimate penetration testing tools for malicious reconnaissance, enabling them to blend into normal network activity and evade traditional signature-based detection methods.
Figure 2: Darktrace's detection of a sharp increase in anomalous internal connections, triggering multiple high-severity model alerts associated with reconnaissance activity.
Several devices were observed using administrative credentials to carry out privileged actions in a manner that was highly anomalous for the environment. This activity was accompanied by behavior consistent with SMB authentication scanning, suggesting efforts to identify and access additional systems. As the activity intensified, an increasing number of devices became involved, signalling lateral movement and further spread across the network.
Darktrace also identified privilege escalation through active directory (AD) replication abuse, specifically via the drsuapi::DRSGetNCChanges function. This technique allows an attacker with sufficient privileges to request directory replication data from a domain controller (DC), enabling them to extract credentials, including password hashes, without directly interacting with user accounts. Commonly associated with ‘DCSync’ attacks, this technique is frequently used to obtain highly privileged credentials and enable further escalation within an environment.
Figure 3: Darktrace’s detection of anomalous AD replication activity indicative of privilege escalation.
This activity was seen alongside the use of the now obsolete SMBv1, repeated NTLM authentication attempts using multiple variations of ‘Administrator’ credentials, reverse DNS scanning, and large-scale network scanning. Darktrace observed widespread use of SMBv1 across the customer’s environment, exposing a significant security weakness. As a legacy protocol with well-documented weaknesses, SMBv1 can be exploited to facilitate lateral movement, allowing the attackers to expand their access following initial compromise.
Day 3: Lateral Movement, Command & Control, and Exfiltration
Two days later, the attacker escalated privileges and expanded their foothold using living-off-the-land (LOTL) techniques such as PSExec, WMI, and RDP. Concurrently, Darktrace identified command-and-control (C2)-style communications consistent with the Sliver framework, alongside rare outbound connections to cloud infrastructure indicating potential data exfiltration. The volume and severity of observed activity increased as attack behavior intensified.
The device was observed conducting extensive lateral movement, leveraging LOTL techniques to evade detection. Activity included WMI execution (e.g. ExecQuery), DCE-RPC activity, SMB sessions and file writes, most of which were successful, as well as the deployment of PSEXESVC.exe via ADMIN$ shares and prolonged RDP sessions. Darktrace identified this behavior as highly anomalous for the environment. Such activity is commonly associated with the transfer of attacker tooling, remote command execution, and the establishment of persistent access across compromised systems.
Figure 4: Darktrace’s detection of a spike in RPC binding events indicative of potential lateral movement.
On the same day, Darktrace detected C2-style SSL communications originating from multiple internal devices to rare external endpoints. These connections exhibited anomalous characteristics, including invalid SSL certificates and repeated connection patterns resembling beaconing. Analysis of the observed JA3 fingerprint further linked the activity to Sliver, the adversary simulation framework referenced earlier, as the hash has previously been associated with Sliver-related infrastructure [3]. The use of this framework reflects a broader trend of attackers repurposing legitimate offensive security tools for stealthy C2 communications. Connections to 137[.]220[.]59[.]55 (ASN AS20473 AS-VULTR) indicated that the communications were likely routed via a virtual private server (VPS) hosted by Vultr. Attackers often utilize VPS infrastructure from legitimate cloud providers like Vultr to obscure their true origin, blend into benign traffic, and evade IP-based detection mechanisms [4].
Figure 5: Darktrace’s Cyber AI Analyst detection of two linked unusual connections to Vultr infrastructure.
Darktrace also observed a device initiating SSL connections to safedata.s3[.]wasabisys[.]com, an endpoint associated with Wasabi cloud storage. Darktrace recognized that neither the destination nor the associated IP address had previously been observed within the environment. More than 200 MB of data was subsequently uploaded externally to endpoints sharing the same JA3 client hash, indicating a sustained transfer session and potential data exfiltration to third-party storage. The apparent exfiltration prior to encryption is consistent with a double-extortion ransomware strategy.
Figure 6: Darktrace’s Cyber AI Analyst detection of more than 30 rare outbound connections to a Wasabi cloud storage endpoint, indicative of potential data exfiltration
Day 4: Encryption
The attack culminated in ransomware deployment, marking the transition from suspicious network activity to a business-impacting incident. Using SMB-based propagation, the threat actor encrypted thousands of files across the network, affecting multiple systems and disrupting normal operations. Throughout the encryption event, the legacy SMBv1 protocol was used extensively across multiple internal systems, resulting in a significant increase in newly encrypted files.
Figure 7: Darktrace’s detection of abnormal spikes in SMB activity and associated model alerts, indicative of ransomware encryption and propagation.
Darktrace’s Cyber AI Analyst automatically investigated and correlated the encryption activity and related events into a single incident narrative, providing the customer with real-time visibility into the attack while significantly reducing investigation time.
Figure 8: Darktrace’s Cyber AI Analyst’s investigation into the encryption activity. AI Analyst incident detailing example encryption activity in real time. Related events are automatically correlated and summarized into a clear narrative, reducing investigation time.
Defender action recommendations
What Could Have Stopped the Attack Earlier?
Although the attack ultimately resulted in ransomware deployment, there were multiple opportunities to detect, contain, and disrupt the intrusion before encryption occurred. The following actions could have significantly reduced the overall impact:
Detect and investigate indicators of reconnaissance and lateral movement
Unusual scanning
Active Directory replication anomalies consistent with DCSync activity
Anomalous use of native tools and processes indicative of LOTL attacks
Unusual use of common reconnaissance tools such as Nmap and NetScan
Contain compromised credentials and affected devices
Disable and reset compromised VPN credentials
Isolate devices performing anomalous scanning and lateral movement activity
Block suspicious external communications and data exfiltration
Use anomaly-based detection to detect and block repeated outbound connections to rare external infrastructure
Prevent data exfiltration to unauthorized cloud storage services such as Wasabi
Conclusion
The incident highlights the importance of anomaly-based detection, particularly against attacks that primarily use native or legitimate tools to evade traditional security measures. Darktrace identified suspicious activity from the first day of the compromise, providing multiple opportunities to disrupt the intrusion before it progressed to lateral movement and data exfiltration.
In this instance, detection was not the limiting factor; response time was. Prompt investigation and containment of devices exhibiting anomalous behavior could have prevented lateral movement, data exfiltration, and ultimately ransomware deployment.
As adversaries increasingly prioritize stealth over custom malware, relying instead on legitimate tools, valid credentials, and trusted infrastructure, traditional signature-based detection becomes less effective. Identifying subtle behavioral deviations early remains critical to disrupting attacks before they escalate into full-scale ransomware incidents.
Credit to Alexandra Evzona (Cyber Analyst), Priya Thapa (Senior Cyber Analyst) Edited by Ryan Traill (Content Manager)
Darktrace / EMAIL Expands Behavioral Defense Across Email and Collaboration Workflows
Email and collaboration tools do more than carry messages. They are where organizations approve payments, share sensitive data, reset credentials, and make thousands of everyday decisions. Increasingly, they are interfaces through which humans direct AI agents in their daily activity. Email, Slack and Teams are high volume, rich with sensitive data, and an easy place to hide malicious activity.
The opportunity isn’t lost on bad actors. Darktrace / EMAIL detected more than 32 million high-confidence phishing emails globally in 2025, and 70% of those messages passed DMARC authentication. Phishing is increasingly difficult to detect and familiar trust signals alone are not enough. People and security teams need to understand how a message fits the normal behavior of the sender, recipient, and organization. They also need to correlate activity across platforms to spot threats that span multiple channels.
To effectively secure against today’s evolved threats, security teams need to act at two levels: they need to help each employee make a safer decision ‘in the moment’, and they need to understand the wider patterns that may expose the business to risk.
Darktrace is introducing four new capabilities in Darktrace / EMAIL to address both challenges. The new features explain suspicious content more clearly to end users, strengthen the capabilities of Darktrace / Adaptive Human Defense with richer guidance, let organizations define their own patterns for detecting sensitive data in messages, and give security teams a process-level view of risk across email and collaboration workflows.
Darktrace / EMAIL Inbox Analysis highlights risky content within your emails
A warning is more useful when it explains what the user should look at. To help do that, we’ve expanded Darktrace / EMAIL’s Inbox Analysis Add-In to highlight potentially dangerous content within the body of emails that Darktrace / EMAIL flags as potentially suspicious or high risk.
The add-in can highlight language designed to create urgency, financial references, requests for payment, suspicious links, and content that is unusual for the sender. Each highlighted element includes a pop up that explains why it may be suspicious. Instead of asking an employee to accept a verdict without context, the analysis helps them examine the message and make a more informed decision.
Enhanced Just-In-Time Training Banners in Darktrace / Adaptive Human Defense
Enhanced Just-In-Time Training Banners build on the same principle. The banners now include a contextual header, actionable advice, and specific detection context. This gives employees more useful guidance at the point of risk without adding unnecessary information or cognitive load.
Together, the capabilities help turn a warning into a short learning moment. Employees can see what looks unusual, understand what action to take, and build their judgment.
Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention
Sensitive data is different for every business. Standard categories such as payment card details or government identifiers matter, but organizations also have their own customer codes, project names, research formats, account structures, and internal identifiers.
Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention allows administrators to write custom expressions for the data their organization needs to protect. Matched content can trigger existing model actions and data loss prevention (DLP) workflows, extending Darktrace's DLP capabilities.
This extends data loss detection beyond a fixed library of common data types. Security teams can apply controls to information that is sensitive in the context of their own organization and adapt those controls as the business changes.
Introducing Email and Collaboration Workflow Risk Posture Dashboards
Some of the most important risks are not isolated events. They are repeated ways of working that create an opening for error, misuse, or attack. For example, a payment request may be one suspicious message, but a recurring approval workflow that relies on weak verification is a business process risk.
The new Email and Collaboration Workflow Risk Posture Dashboard analyzes email and collaboration data across Email, Microsoft Teams, Slack and Zoom to provide a process-level view of risk in the organization. These may include financial authorization workflows, sensitive data sharing patterns, and activity that could expose credentials.
The dashboard brings these patterns into a view and provides actionable recommendations. This helps security teams determine where to investigate or strengthen controls, where ownership needs to be clarified, and where the business may need to change a risky process. It gives CISOs a clearer view of how human and communication risk is embedded in everyday operations, not only where individual alerts occur.
Behavior connects the individual decision to the wider risk
These capabilities build on Darktrace’s unique behavioral approach to security. We use Adaptive AI to learn how people and AI normally behave within an organization, creating the context needed to recognize when activity changes.
Within the Darktrace Behavioral Defense Platform, Darktrace / EMAIL helps protect people against phishing, account takeover, data exfiltration, and human risk across email and collaboration tools. The new capabilities extend that protection in both directions. They give employees clearer context for the decision in front of them, while giving security leaders a broader view of the workflows and behavior that create risk across the organization.
The result is not simply more alerts. It is a better understanding of why something is risky, what action to take, and where the organization can reduce risk before a familiar process becomes an easy route for an attacker.
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