Understanding a SaaS Attack and How AI Can Investigate
The Cyber AI Platform recently detected and investigated two incidents of SaaS account takeover in real-time. Learn about the importance of cyber security here!
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
Max Heinemeyer
Global Field CISO
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19
May 2020
Executive summary
Darktrace has observed a significant increase in attacks against SaaS platforms, including file storage, collaborative work, and email solutions.
This blog post details two example threats that are representative of the current threat landscape: an Office 365 business email compromise and a Box.com file sharing account compromise.
Organizations are recommended to enable multi-factor authentication to combat credential stuffing attacks and the re-use of stolen credentials from data dumps. It is further advised to actively monitor SaaS environments for in-progress cyber-attacks.
SaaS exacerbates the skill gap in security – identifying and investigating threats in SaaS environments is a different skill to traditional security operations skill-sets.
Introduction
The digital transformation – whether planned naturally or forced by the global pandemic – has increased the use of Software-as-a-Service (SaaS) solutions in modern organizations. The annual growth rate of the SaaS market is currently 18%, and as the workforce becomes increasingly remote throughout 2020, this is set to skyrocket.
Attackers have been targeting SaaS solutions for a long time – but almost nobody talks about how the Techniques, Tools & Procedures (TTPs) in SaaS attacks differ significantly from traditional TTPs seen in networks and endpoint attacks.
How do you create meaningful detections in SaaS environments that don’t have endpoint or network data? How can you investigate threats in a SaaS environment as an analyst? What does a ‘good’ SaaS event look like, and what does a threat look like? Finding skilled security analysts that can work in traditional IT environments is already hard – it gets even harder when trying to hire security people with SaaS domain knowledge.
SaaS consumers are left with only a few choices: either use the native SaaS security controls provided in each SaaS solution – and rely on the (non-)maturity of the SaaS provider – or go with a third party SaaS security solution, often in the form of Cloud Access Security Brokers (CASBs). Both cases are often not ideal.
This blog outlines two attacks we have recently observed in SaaS environments that are representative for the broader SaaS threat landscape: a Microsoft (Office) 365 business email compromise (BEC) and the compromise of a corporate Box.com account. The analysis serves to illuminate the sharp distinction between a traditional network attack and a SaaS compromise – demonstrating how using machine learning to detect anomalies in behavior offers crucial hope for defenders as SaaS applications define this new era of work.
Anonymized SaaS Threat 1: Office 365 Business Email Compromise
Figure 1: The timeline of attack for the Microsoft 365 Compromise
In this case of a classic BEC attack, a threat-actor infiltrated an employee’s Microsoft 365 account to access sensitive financial documents hosted in SharePoint, including pay slip and banking details. The attacker went on to make configuration changes to the hacked inbox, deleting items and making updates that may have allowed them to cover their tracks.
Darktrace first observed the employee’s account log in from unusual IP ranges. The particular account had never logged in from Bulgaria before, and the peer accounts belonging to those from the same department had not exhibited similar behavioral traits. This in itself was a low-level anomaly and not necessarily indicative of malicious activity – employees might change locations after all.
The unusual login location was then accompanied by an unusual login time and a new user-agent. All of these anomalies triggered Cyber AI Analyst – Darktrace’s automated threat investigation technology – to launch a deeper analysis.
Darktrace then identified that the account was starting to access highly sensitive information, including payroll information on a Sharepoint. Two examples that were highlighted by AI Analyst are shown below:
The attacker tried to gain insights about payment information and credit card details, with the likely intention of changing the payroll details to an attacker-controlled bank account. But with its ability to automatically analyze events to piece together attack narratives, Cyber AI Analyst was able to put together these weak signals of a threat and illuminate the likely account compromise. The security team was then able to lock the account and alert the user, who subsequently changed their credentials.
Anonymized SaaS Threat 2: Box.com Compromise
Figure 2: The timeline of attack for the Box.com Compromise
Darktrace observed a case of unauthorized access to a corporate Box.com file storage account belonging to an employee of a global supply company. The Box.com account login took place in the US – the same country that this organization operates in – but from an unusual IP space and ASN. Made suspicious by this low-level anomaly, Cyber AI Analyst did further, ongoing investigations into the user’s activity.
The actor behind the account logged in to Box.com successfully, and then proceeded to download expense reports, invoices, and other financial documents. It became evident that the account started accessing files that were highly unusual for the account to access. Darktrace recognized that neither the account itself, nor its peer group were usually accessing the file called ‘PASSWORD SHEET.xlsx’.
With Cyber AI’s bespoke knowledge of ‘self’ for every member of the organization’s workforce, the technology was able to identify the threat immediately. The Darktrace Cyber AI Platform detected that the activity occurred at a highly unusual time for the legitimate user, and that the location of the actor’s IP address was also anomalous compared to the employee’s previous access locations for this particular SaaS service.
While accessing these documents may have been normal for the employee in another context, Darktrace Cyber AI’s deep understanding of user behavior and granular visibility within the Box.com application allowed it to spot the subtle signs of account compromise. Moreover, when Darktrace’s Cyber AI Analyst automatically investigated the threat, it was able to illuminate the wider narrative, understanding that each unauthorized file exposure was part of a connected incident and highlighted the breach as a key concern for the security team.
Conclusion
Traditional detection approaches like ‘more than X failed logins from Y’ are not enough to ensure sufficient security across SaaS applications. Keeping threat intelligence lists up to date is even more difficult, as most SaaS attacks don’t involve any Command & Control – just indiscriminate logins from remote devices. Attackers may use VPN, Tor, other compromised devices, dynamic DNS, or virtual private servers to further mask their tracks.
A more intricate and effective approach to SaaS security requires understanding the dynamic individual behind the account. SaaS applications are fundamentally platforms for humans to communicate – allowing them to exchange and store ideas and information. Abnormal, threatening behavior is therefore impossible to detect without a nuanced understanding of those unique individuals: where and when do they typically access a SaaS account, which files are they like to access, who do they typically connect with?
Cyber AI asks these questions, continuously analyzing data not only across SaaS platforms, but from the unique ‘patterns of life’ of every user and device in the organization as a whole. With this context, it can chain together seemingly disparate anomalies – unusual login times, login locations, access of new or unusual files, and hundreds of other indicators of threat. These anomalies then act as a trigger for more in-depth investigations via Cyber AI Analyst that can link the anomalies together and create a coherent attack narrative.
Both of the above SaaS attacks were comprehensively but succinctly investigated and fully reported on by the Darktrace’s Cyber AI Analyst, which then surfaced an easy-to-understand incident report, ready for executive review. For a more in-depth look at how Cyber AI Analyst investigated an emerging APT threat in the wild, read: Catching APT41 exploiting a zero-day vulnerability.
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.
Building Operational Resilience Across Mission-Critical Marine Services
Mission-Critical Marine Services
This marine organization supports offshore energy production, export infrastructure, and regional logistics, delivering critical services through its diverse fleet and a regional shorebase footprint. To power rapid mobilization and 24/7 operational readiness, the organization has embraced cloud adoption and digital transformation, reshaping how crews, contractors, and shore-based teams access services.
While technology modernization has enhanced operations, it has also introduced new security complexities.
From perimeter to identity: As access becomes more distributed, identity has become the primary security control, elevating the risk of credential compromise and privilege misuse.
From confidentiality to availability and resilience: As cloud platforms increasingly underpin fleet and operational systems, cyber incidents can disrupt services and safety.
From isolated tools to unified visibility: Because Information Technology (IT) and Operational Technology (OT) often intersect, and legacy systems coexist with modern cloud platforms, fragmented monitoring makes it harder to understand risk and respond decisively across domains.
“Our cybersecurity priorities expanded along with our business goals, placing availability and resilience at the forefront. The impact of a potential threat became an operational risk, which elevated cybersecurity from an IT issue to an operational safety and resilience enabler.” - Information and Communications Technology (ICT) Manager.
A Unified, AI-Driven Platform for IT and OT
To strengthen visibility, detection, and response across its highly distributed environment, the customer adopted the Darktrace ActiveAI Security Platform™ in 2022.
Darktrace’s contextual detection capability was a key driver. Unlike traditional tools that rely on known threat signatures, Darktrace’s Self-Learning AI learns “normal” behavior to identify emerging threats and correlate visibility across the customer's siloed on-premises and cloud domains.
Today, the customer relies on:
Darktrace / EMAIL™ to reduce phishing risk and minimize disruption from legacy mail controls and false positives
Darktrace / IDENTITY™ to support identity-centric security as cloud access expands across vessels and shore-based operations
Darktrace / NETWORK™ to strengthen oversight across the broader environment, including operational contexts where IT and OT intersect
Darktrace / CLOUD™ (Azure), added in 2024, to extend detection and response into Azure and support cloud transformation without treating cloud as a separate security silo
Darktrace / Incident Readiness & Recovery to strengthen incident readiness and recovery planning
Darktrace Managed Detection and Response Services to provide 24/7/365 monitoring and support
This combination supports a single operating model for the customer: security that can adapt as the environment changes while remaining practical for a lean team responsible for safeguarding both business operations and safety-critical services.
Extending cloud protection without complexity
As the customer accelerated cloud adoption, it expanded coverage in 2024 with Darktrace / CLOUD for Azure to bring cloud workloads under the same AI-driven visibility and response model – without adding operational burden. “This matters in hybrid environments because attacks rarely stay in one place,” explains the ICT Manager. “A compromised identity can trigger activity in the cloud, which can open pathways back into on-premises systems.”
In parallel, Darktrace / CLOUD’s posture management capabilities support governance and audit readiness by surfacing misconfigurations and exposure risks earlier, before they become incidents.
A Stronger, Faster, More Resilient Business
Since adopting Darktrace, the customer has strengthened cyber resilience while reducing operational burden on its small ICT team.
Darktrace continuously analyzes millions of individual events that can contribute to a wider incident. Within a single month, the solution autonomously investigated 88% of all potential threats, taking appropriate action within just 39.4 seconds on average.
Autonomous capabilities ensure threats are stopped and contained until the ICT team can investigate. In one standout instance, Darktrace autonomously blocked malicious links during a mass phishing/spam event before other controls flagged the threat. the ICT Manager later confirmed Microsoft reported the link as malicious, but Darktrace had already acted to prevent delivery and reduce exposure.
“Whether something happens during off hours, while we’re on vacation, or when our attention is focused elsewhere, we’re confident Darktrace will take control and stop a threat before it spreads,” says the ICT Manager.
Darktrace’s Self-Learning AI combines multiple AI methods and advanced techniques to improve threat detection, investigation, and response dramatically reducing alert overload and manual triage. Within a single month, the solution saved the customer's IT group 411 equivalent human investigation hours.
“For a lean team supporting a 24/7 operational footprint, this autonomous action eliminates the constant firefighting and stress, giving us the space to focus on higher-value priorities.”- Information and Communications Technology (ICT) Manager.
Protecting communications without disruption
the customer experienced friction from legacy email and network controls prior to Darktrace, which generated high false positive rates, disrupted legitimate communications, created operational drag, and added workload for ICT. With Darktrace / EMAIL learning normal email behavior and applying context-aware actions, the team reduced unnecessary interruptions while maintaining protection.
“That shift matters in marine services, where business communications directly support coordination across vessels, shore bases, clients, ports, and regulators,” says the ICT Manager. “Darktrace doesn’t just block more threats, it autonomously makes decisions that preserve operational continuity and enable my team to focus on credible threats instead of chasing volume.”
Delivering clarity and confidence
Darktrace has reduced manual triage by correlating activity across email, identity, network, and cloud, providing the context needed to prioritize what matters without requiring the ICT team to stitch together evidence across multiple tools.
“With unified visibility we can identify patterns across domains, make informed decisions about where risk actually exists, and align security actions with operational impact rather than theoretical threats,” explains the ICT Manager. “I can now prioritize effort and investment across our ICT landscape with far greater confidence.”
Regular Executive Threat Reports reinforce operational confidence by giving leadership clear visibility into threats Darktrace has handled autonomously, supporting decisive action when needed and confidence to avoid unnecessary disruption when it isn’t.
Scaling Securely in a Hybrid World
As the customer advances its cloud transformation, the ICT Manager sees the Darktrace partnership evolving into a foundational layer of resilience and assurance, supporting scale, governance, and operational confidence in an increasingly cloud-centric environment.
Key priorities include:
Shifting from hybrid visibility to cloud-first resilience, using continuous monitoring and posture insights to reduce exposure earlier
Strengthening governance and audit readiness, especially as critical workloads and sensitive data expand in Azure and expectations rise under regulatory and client assurance requirements
Increasing reliance on autonomous response and AI investigation as the number of identities, workloads, and access paths grows faster than headcount
Deepening cross-domain correlation so cloud signals further enrich decision-making, supporting faster containment and more confident prioritization
“As we accelerate our cloud strategy, Darktrace will play an even more strategic role,” says the ICT Manager, “providing the guidance, technology, and expertise that allow us to grow with confidence and innovate securely.”
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)
