Why Data Classification Isn’t Enough to Prevent Data Loss
In a world of growing data volume and diversity, protecting and keeping track of your organization’s sensitive information is increasingly complex – particularly when 63% of breaches stem from malicious insiders or human error. This blog explores how security teams can achieve visibility beyond the limits of data classification, without adding to the burden of data management.
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
Share
15
Apr 2025
Why today’s data is fundamentally difficult to protect
Data isn’t what it used to be. It’s no longer confined to neat rows in a database, or tucked away in a secure on-prem server. Today, sensitive information moves freely between cloud platforms, SaaS applications, endpoints, and a globally distributed workforce – often in real time. The sheer volume and diversity of modern data make it inherently harder to monitor, classify, and secure. And the numbers reflect this challenge – 63% of breaches stem from malicious insiders or human error.
This complexity is compounded by an outdated reliance on manual data management. While data classification remains critical – particularly to ensure compliance with regulations like GDPR or HIPAA – the burden of managing this data often falls on overstretched security teams. Security teams are expected to identify, label, and track data across sprawling ecosystems, which can be time-consuming and error-prone. Even with automation, rigid policies that depend on pre-defined data classification miss the mark.
From a data protection perspective, if manual or basic automated classification is the sole methodology for preventing data loss, critical data will likely slip through the cracks. Security teams are left scrambling to fill the gaps, facing compliance risks and increasing operational overhead. Over time, the hidden costs of these inefficiencies pile up, draining resources and reducing the effectiveness of your entire security posture.
What traditional data classification can’t cover
Data classification plays an important role in data loss prevention, but it's only half the puzzle. It’s designed to spot known patterns and apply labels, yet the most common causes of data breaches don’t follow rules. They stem from something far harder to define: human behavior.
Data classification is blind to nuance – it can’t grasp intent, context, or the subtle red flags that often precede a breach. And no amount of labeling, policy, or training can fully account for the reality that humans make mistakes. These problems require a system that sees beyond the data itself — one that understands how it’s being used, by whom, and in what context. That’s why Darktrace leans into its core strength: detecting the subtle symptoms of data loss by interpreting human behavior, not just file labels.
Achieving autonomous data protection with behavioral AI
Its understanding of business operations allows it to detect subtle anomalies around data movement for your use cases, whether that’s a misdirected email, an insecure cloud storage link, or suspicious activity from an insider. Crucially, this detection is entirely autonomous, with no need for predefined rules or static labels.
Fig 1: Darktrace uses its contextual understanding of each user to stop all types of sensitive or misdirected data from leaving the organization
Darktrace / EMAIL’s DLP add-on continuously learns in real time, enabling:
Automatic detection: Identifies risky data behavior to catch threats that traditional approaches miss – from human error to sophisticated insider threats.
A dynamic range of actions: Darktrace always aims to avoid business disruption in its blocking actions, but this can be adjusted according to the unique risk appetite of each customer – taking the most appropriate response for that business from a whole scale of possibilities.
Enhanced context: While Darktrace doesn’t require sensitivity data labeling, it integrates with Microsoft Purview to ingest sensitivity labels and enrich its understanding of the data – for even more accurate decision-making.
Beyond preventing data loss, Darktrace uses DLP activity to enhance its contextual understanding of the user itself. In other words, outbound activity can be a useful symptom in identifying a potential account compromise, or can be used to give context to that user’s inbound activity. Because Darktrace sees the whole picture of a user across their inbound, outbound, and lateral mail, as well as messaging (and into collaboration tools with Darktrace / IDENTITY), every interaction informs its continuous learning of normal.
With Darktrace, you can achieve dynamic data loss prevention for the most challenging human-related use cases – from accidental misdirected recipients to malicious insiders – that evade detection from manual classification. So don’t stand still on data protection – make the switch to autonomous, adaptive DLP that understands your business, data, and people.
[related-resource]
Interested in finding out more?
Read the full solution brief to see how Darktrace's AI-driven approach to DLP stops data loss across email and Teams
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.
Why Organizations are Moving to Label-free, Behavioral DLP for Outbound Email
Modern data loss doesn’t always look like a regex match. It can look like everyday communication slightly out of context. Here’s how a domain specific language model paired with behavioral learning protects labeled and unlabeled data without slowing business down.
Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace
During a customer trial of Darktrace / EMAIL and Darktrace / IDENTITY, Darktrace detected an adversary-in-the-middle (AiTM) attack that compromised a user’s Office 365 account via a business email compromise (BEC) phishing email. Following the breach, the compromised account was used to launch both internal and external phishing campaigns.
How Darktrace is ending email security silos with new capabilities in cross-domain detection, DLP, and native Microsoft integrations
Darktrace is delivering a major evolution in email security, uniting true AI-powered cross-domain detection, label-free behavioral DLP, and Microsoft-native automation – to catch the 17% of threats that SEGs miss.
Under Medusa’s Gaze: How Darktrace Uncovers RMM Abuse in Ransomware Campaigns
What is Medusa Ransomware in 2025?
In 2025, the Medusa Ransomware-as-a-Service (RaaS) emerged as one of the top 10 most active ransomware threat actors [1]. Its growing impact prompted a joint advisory from the US Cybersecurity and Infrastructure Security Agency (CISA) and the Federal Bureau of Investigation (FBI) [3]. As of January 2026, more than 500 organizations have fallen victim to Medusa ransomware [2].
Darktrace previously investigated Medusa in a 2024 blog, but the group’s rapid expansion and new intelligence released in late 2025 has lead Darktrace’s Threat Research team to investigate further. Recent findings include Microsoft’s research on Medusa actors exploiting a vulnerability in Fortra’s GoAnywhere MFT License Servlet (CVE-2025-10035)[4] and Zencec’s report on Medusa’s abuse of flaws in SimpleHelp’s remote support software (CVE-2024-57726, CVE-2024-57727, CVE-2024-57728) [5].
Reports vary on when Medusa first appeared in the wild. Some sources mention June 2021 as the earliest sightings, while others point to late 2022, when its developers transitioned to the RaaS model, as the true beginning of its operation [3][11].
Madusa Ransomware history and background
The group behind Medusa is known by several aliases, including Storm-1175 and Spearwing [4] [7]. Like its mythological namesake, Medusa has many “heads,” collaborating with initial access brokers (IABs) and, according to some evidence, affiliating with Big Game Hunting (BGH) groups such as Frozen Spider, as well as the cybercriminal group UNC7885 [3][6][13].
Use of Cyrillic in its scripts, activity on Russian-language cybercrime forums, slang unique to Russian criminal subcultures, and avoidance of targets in Commonwealth of Independent States (CIS) countries suggest that Medusa operates from Russia or an allied state [11][12].
Medusa ransomware should not be confused with other similarly named malware, such as the Medusa Android Banking Trojan, the Medusa Botnet/Medusa Stealer, or MedusaLocker ransomware. It is easily distinguishable from these variants because it appends the extension .MEDUSA to encrypted files and drops the ransom note !!!READ_ME_MEDUSA!!!.txt on compromised systems [8].
Who does Madusa Ransomware target?
The group appears to show little restraint, indiscriminately attacking organizations across all sectors, including healthcare, and is known to employ triple extortion tactics whereby sensitive data is encrypted, victims are threatened with data leaks, and additional pressure is applied through DDoS attacks or contacting the victim’s customers, rather than the more common double extortion model [13].
Madusa Ransomware TTPs
To attain initial access, Medusa actors typically purchase access to already compromised devices or accounts via IABs that employ phishing, credential stuffing, or brute-force attacks, and also target vulnerable or misconfigured Internet-facing systems.
Between December 2023 and November 2025, Darktrace observed multiple cases of file encryption related to Medusa ransomware across its customer base. When enabled, Darktrace’s Autonomous Response capability intervened early in the attack chain, blocking malicious activity before file encryption could begin.
Some of the affected were based in Europe, the Middle East and Africa (EMEA), others in the Americas (AMS), and the remainder in the Asia-Pacific and Japan region. The most impacted sectors were financial services and the automotive industry, followed by healthcare, and finally organizations in arts, entertainment and recreation, ICT, and manufacturing.
Remote Monitoring and Management (RMM) tool abuse
In most customer environments where Medusa file encryption attempts were observed, and in one case where the compromise was contained before encryption, unusual external HTTP connections associated with JWrapper were also detected. JWrapper is a legitimate tool designed to simplify the packaging, distribution, and management of Java applications, enabling the creation of executables that run across different operating systems. Many of the destination IP addresses involved in this activity were linked to SimpleHelp servers or associated with Atera.
Medusa actors appear to favor RMM tools such as SimpleHelp. Unpatched or misconfigured SimpleHelp RMM servers can serve as an initial access vector to the victims’ infrastructure. After gaining access to SimpleHelp management servers, the threat actors edit server configuration files to redirect existing SimpleHelp RMM agents to communicate with unauthorized servers under their control.
The SimpleHelp tool is not only used for command-and-control (C2) and enabling persistence but is also observed during lateral movement within the network, downloading additional attack tools, data exfiltration, and even ransomware binary execution. Other legitimate remote access tools abused by Medusa in a similar manner to evade detection include Atera, AnyDesk, ScreenConnect, eHorus, N-able, PDQ Deploy/Inventory, Splashtop, TeamViewer, NinjaOne, Navicat, and MeshAgent [4][5][15][16][17].
Data exfiltration
Another correlation among Darktrace customers affected by Medusa was observed during the data exfiltration phase. In several environments, data was exfiltrated to the endpoints erp.ranasons[.]com or pruebas.pintacuario[.]mx (143.110.243[.]154, 144.217.181[.]205) over ports 443, 445, and 80. erp.ranasons[.]com was seemingly active between November 2024 and September 2025, while pruebas.pintacuario[.]mx was seen from November 2024 to March 2025. Evidence suggests that pruebas.pintacuario[.]mx previously hosted a SimpleHelp server [22][23].
Apart from RMM tools, Medusa is also known to use Rclone and Robocopy for data exfiltration [3][19]. During one Medusa compromise detected in mid-2024, the customer’s data was exfiltrated to external destinations associated with the Ngrok proxy service using an SSH-2.0-rclone client.
Medusa Compromise Leveraging SimpleHelp
In Q4 2025, Darktrace assisted a European company impacted by Medusa ransomware. The organization had partial Darktrace / NETWORK coverage and had configured Darktrace’s Autonomous Response capability to require manual confirmation for all actions. Despite these constraints, data received through the customer’s security integration with CrowdStrike Falcon enabled Darktrace analysts to reconstruct the attack chain, although the initial access vector remains unclear due to limited visibility.
In late September 2025, a device out of the scope of Darktrace's visibility began scanning the network and using RDP, NTLM/SMB, DCE_RPC, and PowerShell for lateral movement.
CrowdStrike “Defense Evasion: Disable or Modify Tools” alerts related to a suspicious driver (c:\windows\[0-9a-b]{4}.exe) and a PDQ Deploy executable (share=\\<device_hostname>\ADMIN$ file=AdminArsenal\PDQDeployRunner\service-1\exec\[0-9a-b]{4}.exe) suggest that the attackers used the Bring Your Own Vulnerable Driver (BYOVD) technique to terminate antivirus processes on network devices, leveraging tools such as KillAV or AbyssWorker along with the PDQ Software Deployment solution [19][26].
A few hours later, Darktrace observed the same device that had scanned the network writing Temp\[a-z]{2}.exe over SMB to another device on the same subnet. According to data from the CrowdStrike alert, this executable was linked to an RMM application located at C:\Users\<compromised_user>\Documents\[a-z]{2}.exe. The same compromised user account later triggered a CrowdStrike “Command and Control: Remote Access Tools” alert when accessing C:\ProgramData\JWrapper-Remote Access\JWrapper-Remote Access Bundle-[0-9]{11}\JWrapperTemp-[0-9]{10}-[0-9]{1}-app\bin\windowslauncher.exe [27].
Figure 1: An executable file associated with the SimpleHelp RMM tool being written to other devices using the SMB protocol, as detected by Darktrace.
Soon after, the destination device and multiple other network devices began establishing connections to 31.220.45[.]120 and 213.183.63[.]41, both of which hosted malicious SimpleHelp RMM servers. These C2 connections continued for more than 20 days after the initial compromise.
CrowdStrike integration alerts for the execution of robocopy . "c:\windows\\" /COPY:DT /E /XX /R:0 /W:0 /NP /XF RunFileCopy.cmd /IS /IT commands on several Windows servers, suggested that this utility was likely used to stage files in preparation for data exfiltration [19].
Around two hours later, Darktrace detected another device connecting to the attacker’s SimpleHelp RMM servers. This internal server had ‘doc’ in its hostname, indicating it was likely a file server. It was observed downloading documents from another internal server over SMB and uploading approximately 70 GiB of data to erp.ranasons[.]com (143.110.243[.]154:443).
Figure 2: Data uploaded to erp.ranasons[.]com and the number of model alerts from the exfiltrating device, represented by yellow and orange dots.
Darktrace’s Cyber AI Analyst autonomously investigated the unusual connectivity, correlating the separate C2 and data exfiltration events into a single incident, providing greater visibility into the ongoing attack.
Figure 3: Cyber AI Analyst identified a file server making C2 connections to an attacker-controlled SimpleHelp server (213.183.63[.]41) and exfiltrating data to erp.ranasons[.]com.
Figure 4: The same file server that connected to 213.183.63[.]41 and exfiltrated data to erp.ranasons[.]com was also observed attempting to connect to an IP address associated with Moscow, Russia (193.37.69[.]154:7070).
One of the devices connecting to the attacker's SimpleHelp RMM servers was also observed downloading 35 MiB from [0-9]{4}.filemail[.]com. Filemail, a legitimate file-sharing service, has reportedly been abused by Medusa actors to deliver additional malicious payloads [11].
Figure 5: A device controlled remotely via SimpleHelp downloading additional tooling from the Filemail file-sharing service.
Finally, integration alerts related to the ransomware binary, such as c:\windows\system32\gaze.exe and <device_hostname>\ADMIN$ file=AdminArsenal\PDQDeployRunner\service-1\exec\gaze.exe, along with “!!!READ_ME_MEDUSA!!!.txt” ransom notes were observed on network devices. This indicates that file encryption in this case was most likely carried out directly on the victim hosts rather than via the SMB protocol [3].
Conclusion
Threat actors, including nation-state actors and ransomware groups like Medusa, have long abused legitimate commercial RMM tools, typically used by system administrators for remote monitoring, software deployment, and device configuration, instead of relying on remote access trojans (RATs).
Attackers employ existing authorized RMM tools or install new remote administration software to enable persistence, lateral movement, data exfiltration, and ingress tool transfer. By mimicking legitimate administrative behavior, RMM abuse enables attackers to evade detection, as security software often implicitly trusts these tools, allowing attackers to bypass traditional security controls [28][29][30].
To mitigate such risks, organizations should promptly patch publicly exposed RMM servers and adopt anomaly-based detection solutions, like Darktrace / NETWORK, which can distinguish legitimate administrative activity from malicious behavior, applying rapid response measures through its Autonomous Response capability to stop attacks in their tracks.
Darktrace delivers comprehensive network visibility and Autonomous Response capabilities, enabling real-time detection of anomalous activity and rapid mitigation, even if an organization fall under Medusa’s gaze.
Credit to Signe Zaharka (Principal Cyber Analyst) and Emma Foulger (Global Threat Research Operations Lead
Edited by Ryan Traill (Analyst Content Lead)
Appendices
List of Indicators of Compromise (IoCs)
IoC - Type - Description + Confidence + Time Observed
185.108.129[.]62 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - March 7, 2023
185.126.238[.]119 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - November 26-27, 2024
213.183.63[.]41 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - November 28, 2024 - Sep 30, 2025
213.183.63[.]42 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - July 4 -9 , 2024
31.220.45[.]120 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - September 12 - Oct 20 , 2025
91.92.246[.]110 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - May 24, 2024
45.9.149[.]112:15330 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - June 21, 2024
89.36.161[.]12 IP address Malicious SimpleHelp server observed during Medusa attacks (High confidence) - June 26-28, 2024
193.37.69[.]154:7070 IP address Suspicious RU IP seen on a device being controlled via SimpleHelp and exfiltrating data to a Medusa related endpoint - September 30 - October 20, 2025
erp.ranasons[.]com·143.110.243[.]154 Hostname Data exfiltration destination - November 27, 2024 - September 30, 2025
pruebas.pintacuario[.]mx·144.217.181[.]205 - Hostname Data exfiltration destination - November 27, 2024 - March 26, 2025
lirdel[.]com · 44.235.83[.]125/a.msi (1b9869a2e862f1e6a59f5d88398463d3962abe51e19a59) File & hash Atera related file downloaded with PowerShell - June 20, 2024
wizarr.manate[.]ch/108.215.180[.]161:8585/$/1dIL5 File Suspicious file observed on one of the devices exhibiting unusual activity during a Medusa compromise - February 28, 2024
!!!READ_ME_MEDUSA!!!.txt" File - Ransom note
*.MEDUSA - File extension File extension added to encrypted files
gaze.exe – File - Ransomware binary
Darktrace Model Coverage
Darktrace / NETWORK model detections triggered during connections to attacker controlled SimpleHelp servers:
Anomalous Connection/Anomalous SSL without SNI to New External
Anomalous Connection/Multiple Connections to New External UDP Port
Anomalous Connection/New User Agent to IP Without Hostname
How a leading bank is prioritizing risk management to power a resilient future
As one of the region’s most established financial institutions, this bank sits at the heart of its community’s economic life – powering everything from daily transactions to business growth and long-term wealth planning. Its blend of physical branches and advanced digital services gives customers the convenience they expect and the personal trust they rely on. But as the financial world becomes more interconnected and adversaries more sophisticated, safeguarding that trust requires more than traditional cybersecurity. It demands a resilient, forward-leaning approach that keeps pace with rising threats and tightening regulatory standards.
A complex risk landscape demands a new approach
The bank faced a challenge familiar across the financial sector: too many tools, not enough clarity. Vulnerability scans, pen tests, and risk reports all produced data, yet none worked together to show how exposures connected across systems or what they meant for day-to-day operations. Without a central platform to link and contextualize this data, teams struggled to see how individual findings translated into real exposure across the business.
Fragmented risk assessments: Cyber and operational risks were evaluated in silos, often duplicated across teams, and lacked the context needed to prioritize what truly mattered.
Limited executive visibility: Leadership struggled to gain a complete, real-time view of trends or progress, making risk ownership difficult to enforce.
Emerging compliance pressure: This gap also posed compliance challenges under the EU’s Digital Operational Resilience Act (DORA), which requires financial institutions to demonstrate continuous oversight, effective reporting, and the ability to withstand and recover from cyber and IT disruptions.
“The issue wasn’t the lack of data,” recalls the bank’s Chief Technology Officer. “The challenge was transforming that data into a unified, contextualized picture we could act on quickly and decisively.”
As the bank advanced its digital capabilities and embraced cloud services, its risk environment became more intricate. New pathways for exploitation emerged, human factors grew harder to quantify, and manual processes hindered timely decision-making. To maintain resilience, the security team sought a proactive, AI-powered platform that could consolidate exposures, deliver continuous insight, and ensure high-value risks were addressed before they escalated.
Choosing Darktrace to unlock proactive cyber resilience
To reclaim control over its fragmented risk landscape, the bank selected Darktrace / Proactive Exposure Management™ for cyber risk insight. The solution’s ability to consolidate scanner outputs, pen test results, CVE data, and operational context into one AI-powered view made it the clear choice. Darktrace delivered comprehensive visibility the team had long been missing.
By shifting from a reactive model to proactive security, the bank aimed to:
Improve resilience and compliance with DORA
Prioritize remediation efforts with greater accuracy
Eliminate duplicated work across teams
Provide leadership with a complete view of risk, updated continuously
Reduce the overall likelihood of attack or disruption
The CTO explains: “We needed a solution that didn’t just list vulnerabilities but showed us what mattered most for our business – how risks connected, how they could be exploited, and what actions would create the biggest reduction in exposure. Darktrace gave us that clarity.”
Targeting the risks that matter most
Darktrace / Proactive Exposure Management offered the bank a new level of visibility and control by continuously analyzing misconfigurations, critical attack paths, human communication patterns, and high-value assets. Its AI-driven risk scoring allowed the team to understand which vulnerabilities had meaningful business impact, not just which were technically severe.
Unifying exposure across architectures
Darktrace aggregates and contextualizes data from across the bank’s security stack, eliminating the need to manually compile or correlate findings. What once required hours of cross-team coordination now appears in a single, continuously updated dashboard.
Revealing an adversarial view of risk
The solution maps multi-stage, complex attack paths across network, cloud, identity systems, email environments, and endpoints – highlighting risks that traditional CVE lists overlook.
Identifying misconfigurations and controlling gaps
Using Self-Learning AI, Darktrace / Proactive Exposure Management spots misconfigurations and prioritizes them based on MITRE adversary techniques, business context, and the bank’s unique digital environment.
Enhancing red-team and pen test effectiveness
By directing testers to the highest-value targets, Darktrace removes guesswork and validates whether defenses hold up against realistic adversarial behavior.
Supporting DORA compliance
From continuous monitoring to executive-ready reporting, the solution provides the transparency and accountability the bank needs to demonstrate operational resilience frameworks.
Proactive security delivers tangible outcomes
Since deploying Darktrace / Proactive Exposure Management, the bank has significantly strengthened its cybersecurity posture while improving operational efficiency.
Security teams are now saving more than four hours per week previously spent aggregating and analyzing risk data. With a unified view of their exposure, they can focus directly on remediation instead of manually correlating multiple reports.
Because risks are now prioritized based on business impact and real-time operational context, they no longer waste time on low-value tasks. Instead, critical issues are identified and resolved sooner, reducing potential windows for exploitation and strengthening the bank’s ongoing resilience against both known and emerging threats.
“Our goal was to move from reactive to proactive security,” the CTO says. “Darktrace didn’t just help us achieve that, it accelerated our roadmap. We now understand our environment with a level of clarity we simply didn’t have before.”
Leadership clarity and stronger governance
Executives and board stakeholders now receive clear, organization-wide visibility into the bank’s risk posture, supported by consistent reporting that highlights trends, progress, and areas requiring attention. This transparency has strengthened confidence in the bank’s cyber resilience and enabled leadership to take true ownership of risk across the institution.
Beyond improved visibility, the bank has also deepened its overall governance maturity. Continuous monitoring and structured oversight allow leaders to make faster, more informed decisions that strategically align security efforts with business priorities. With a more predictable understanding of exposure and risk movement over time, the organization can maintain operational continuity, demonstrate accountability, and adapt more effectively as regulatory expectations evolve.
Trading stress for control
With Darktrace, leaders now have the clarity and confidence they need to report to executives and regulators with accuracy. The ability to see organization-wide risk in context provides assurance that the right issues are being addressed at the right time. That clarity is also empowering security analysts who no longer shoulder the anxiety of wondering which risks matter most or whether something critical has slipped through the cracks. Instead, they’re working with focus and intention, redirecting hours of manual effort into strategic initiatives that strengthen the bank’s overall resilience.
Prioritizing risk to power a resilient future
For this leading financial institution, Darktrace / Proactive Exposure Management has become the foundation for a more unified, data-driven, and resilient cybersecurity program. With clearer, business-relevant priorities, stronger oversight, and measurable efficiency gains, the bank has strengthened its resilience and met demanding regulatory expectations without adding operational strain.
Most importantly, it shifted the bank’s security posture from a reactive stance to a proactive, continuous program. Giving teams the confidence and intelligence to anticipate threats and safeguard the people and services that depend on them.