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August 29, 2023

Analyzing Post-Exploitation on Papercut Servers

Dive into our analysis covering post-exploitation activity on PaperCut servers. Learn the details and impact of this attack and how to keep yourself safe!
Written by
Sam Lister
Specialist Security Researcher
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Sam Lister
Specialist Security Researcher
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29
Aug 2023

Introduction

Malicious cyber actors are known to exploit vulnerabilities in Internet-facing systems and services to gain entry to organizations’ digital environments. Keeping track of the vulnerabilities which malicious actors are exploiting is seemingly futile, with malicious actors continually finding new avenues of exploitation.  

In mid-April 2023, Darktrace, along with the wider security community, observed malicious cyber actors gaining entry to networks through exploitation of a critical vulnerability in the print management system, PaperCut. Darktrace observed two types of attack chain within its customer base, one involving the deployment of payloads to facilitate crypto-mining, and the other involving the deployment of a payload to facilitate Tor-based command-and-control (C2) communication.

Walking Through the Front Door

One of the most widely abused Initial Access methods attackers use to gain entry to an organization’s digital environment is the exploitation of vulnerabilities in Internet-facing systems and services [1]. The public disclosure of a critical vulnerability in a widely used, Internet-facing service, along with a proof of concept (POC) exploit for such vulnerability, provides malicious cyber actors with a key to the front door of countless organizations. Once malicious actors are in possession of such a key, security teams are in a race against time to patch all their vulnerable systems and services. But until organizations accomplish this, the doors are left open.

This year, the security community has seen malicious actors gaining entry to networks through the exploitation of vulnerabilities in a range of services. These services include familiar suspects, such as Microsoft Exchange and ManageEngine, along with less familiar suspects, such as PaperCut. PaperCut is a system for managing and tracking printing, copying, and scanning activity within organizations. In 2021, PaperCut was used in more than 50,000 sites across over 100 countries [2], making PaperCut a widely used print management system.

In January 2023, Trend Micro’s Zero Day Initiative (ZDI) notified PaperCut of a critical RCE vulnerability, namely CVE-2023–27350, in certain versions of PaperCut NG (PaperCut’s ‘print only’ variant) and PaperCut MF (PaperCut’s ‘extended feature’ variant) [3,4]. In March 2023, PaperCut released versions of PaperCut NG and PaperCut MF containing a fix for CVE-2023–27350 [4]. Despite this, security teams observed a surge in cases of malicious actors exploiting CVE-2023–27350 to compromise PaperCut servers in April 2023 [4-10]. This trend was mirrored in Darktrace’s customer base, where a surge in compromises of PaperCut servers was observed in April 2023.

Observed Attack Chains

In mid-April 2023, Darktrace identified two related clusters of attack chains. The attack chains within the first of these clusters involved Internet-facing PaperCut servers downloading payloads with crypto-mining capabilities from the external location, 50.19.48[.]59. While the attack chains within the second of the clusters involved Internet-facing PaperCut servers downloading payloads with Tor-based C2 capabilities from 192.184.35[.]216. The attack chains within the first cluster, which were observed on April 22, 2023, will be referred to as ‘50.19.48[.]59 chains’ and the attack chains in the second cluster, observed on April 24, 2023, will be called ‘192.184.35[.]216 chains’.

Both attack chains started with highly unusual external endpoints contacting the '/SetupCompleted' endpoint of an Internet-facing PaperCut server. These requests to the ‘/SetupCompleted’ endpoint likely represented attempts to exploit CVE-2023–27350 [10].  50.19.48[.]59 chains started with exploit connections from the external endpoint, 85.106.112[.]60, whereas 192.184.35[.]216 chains started with exploit connections from Tor nodes, such as 185.34.33[.]2.

Figure 1: Darktrace’s Advanced Search data showing likely CVE-2023-27350 exploitation activity from the suspicious, external endpoint, 85.106.112[.]60.

After the exploitation step, the two attack chains took different paths. In the 50.19.48[.]59 chains, the exploitation step was followed by the affected PaperCut server making HTTP GET requests over port 82 to the rare external endpoint, 50.19.48[.]59. In the 192.184.35[.]216 chains, the exploitation step was followed by the affected PaperCut server making an HTTP GET request over port 443 to 192.184.35[.]216.

The HTTP GET requests to 50.19.48[.]59 had Target URIs such as ‘/me1.bat’, ‘/me2.bat’, ‘/dom.zip’, ‘/mazar.bat’, and ‘/mazar.zip’, whilst the HTTP GET requests to 192.184.35[.]216 had the Target URI ‘/4591187629.exe’. The User-Agent header of the GET requests to 192.184.35[.]216 indicated that that the malicious file transfers were initiated through Microsoft’s pre-installed Background Intelligent Transfer Service (BITS).

Figure 2: Darktrace’s Advanced Search data showing a PaperCut server downloading Batch and ZIP files from 50.19.48[.]59 straight after receiving likely exploit connections from 85.106.112[.]60.
Figure 3: Darktrace’s Event Log data showing a PaperCut server downloading an executable file from 192.184.35[.]216 immediately after receiving a likely exploit connection from the Tor node, 185.34.33[.]2.

Downloads from 50.19.48[.]59 were followed by cURL GET requests to 138.68.61[.]82 and then connections to external endpoints associated with the cryptocurrency miner, Mimu (as seen in Fig 4). Downloads from 192.184.35[.]216 were followed by Python-urllib GET requests to api.ipify[.]org and long connections to Tor nodes (as seen in Fig 5).  

These facts suggest that the actor behind the 50.19.48[.]59 chains were seeking to drop cryptocurrency miners on PaperCut servers, with the intention of abusing the customer’s network to carry out resource intensive and costly cryptocurrency mining activity. Meanwhile, the actors behind the 192.184.35[.]216 chains were likely attempting to establish a Tor-based C2 channel with PaperCut servers to allow actors to further communicate with compromised devices.

Figure 4: Darktrace's Event Log data showing a PaperCut contacting 50.19.48[.]59 to download payloads, and then making a cURL request to 138.68.61[.]82 before contacting a Mimu crypto-mining endpoint.
Figure 5: Darktrace’s Event Log data showing a PaperCut server contacting 192.184.35[.]216 to download a payload, and then making connections to api.ipify[.]org and several Tor nodes.

The activities ensuing from both attack chains were varied, making it difficult to ascertain whether the activities were steps of separate attack chains, or steps of the existing 50.19.48[.]59 and 192.184.35[.]216 chains. A wide variety of activities ensued from observed 50.19.48[.]59 and 192.184.35[.]216 chains, including the abuse of pre-installed tools, such as cURL, CertUtil, and PowerShell to transfer further payloads to PaperCut servers, Cobalt Strike C2 communication, Ngrok usage, Mimikatz usage, AnyDesk usage, and in one case, detonation of the LockBit ransomware strain.

Figure 6: Diagram representing the steps of observed 50.19.48[.]59 chains.
Figure 7: Diagram representing the steps of observed 192.184.35[.]215 chains.

As the PaperCut servers that were targeted by malicious actors are Internet-facing, they regularly receive connections from unusual external endpoints. The exploit connections in the 50.19.48[.]59 and 192.184.35[.]216 chains, which originated from unusual external endpoints, were therefore not detected by Darktrace DETECT™, which relies on anomaly-based methods to detect network-based steps of an intrusion.

On the other hand, the post-exploitation steps of the 50.19.48[.]59 and 192.184.35[.]216 chains yielded ample anomaly-based detections, given that they consisted of PaperCut servers displaying highly unusual behaviors. As such Darktrace DETECT was able to successfully identify multiple chains of suspicious activity, including unusual file downloads from external endpoints and beaconing activity to rare external locations.

The file downloads from 50.19.48[.]59 observed in the 50.19.48[.]59 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / Application Protocol on Uncommon Port

- Anomalous File / Internet Facing System File Download

- Anomalous File / Script from Rare External Location

- Anomalous File / Zip or Gzip from Rare External Location

- Device / Internet Facing Device with High Priority Alert

Figure 8: Darktrace’s Event Log data showing a PaperCut server breaching several models immediately after contacting 50.19.48[.]59.

The file downloads from 192.184.35[.]216 observed in the 192.184.35[.]216 chains caused the following Darktrace DETECT models to breach:

- Anomalous File / EXE from Rare External Location

- Anomalous File / Numeric File Download

- Device / Internet Facing Device with High Priority Alert

Figure 9: Darktrace’s Event Log data showing a PaperCut server breaching several models immediately after contacting 192.184.35[.]216.

Subsequent C2, beaconing, and crypto-mining connections in the 50.19.48[.]59 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / New User Agent to IP Without Hostname

- Anomalous Server Activity / New User Agent from Internet Facing System

- Anomalous Server Activity / Rare External from Server

- Compromise / Crypto Currency Mining Activity

- Compromise / High Priority Crypto Currency Mining

- Compromise / High Volume of Connections with Beacon Score

- Compromise / Large Number of Suspicious Failed Connections

- Compromise / SSL Beaconing to Rare Destination

- Device / Initial Breach Chain Compromise

- Device / Large Number of Model Breaches

Figure 10: Darktrace’s Event Log data showing a PaperCut server breaching models as a result of its connections to a Mimu crypto-mining endpoint.

Subsequent C2, beaconing, and Tor connections in the 192.184.35[.]216 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / Application Protocol on Uncommon Port

- Compromise / Anomalous File then Tor

- Compromise / Beaconing Activity To External Rare

- Compromise / Possible Tor Usage

- Compromise / Slow Beaconing Activity To External Rare

- Compromise / Uncommon Tor Usage

- Device / Initial Breach Chain Compromise

Figure 11: Darktrace’s Event Log data showing a PaperCut server breaching several models as a result of its connections to Tor nodes.

Darktrace RESPOND

Darktrace RESPOND™ was not active in any of the networks affected by 192.184.35[.]216 activity, however, RESPOND was active in some of the networks affected by 50.19.48[.]59 activity.  In those environments where RESPOND was enabled in autonomous mode, observed malicious activities resulted in intervention from RESPOND, including autonomous actions like blocking connections to specific external endpoints, blocking all outgoing traffic, and restricting affected devices to a pre-established pattern of behavior.

Figure 12: Darktrace’s Event Log data showing Darktrace RESPOND automatically performing inhibitive actions on a device in response to the device’s connection to 50.19.48[.]59.
Figure 13: Darktrace’s Event Log data showing Darktrace RESPOND automatically performing inhibitive actions on a device in response to the device’s connections to a Mimu crypto-mining endpoint.

Darktrace Cyber AI Analyst

Cyber AI Analyst autonomously investigated model breaches caused by events within these 50.19.48[.]59 and 192.184.35[.]216 chains. Cyber AI Analyst created user-friendly and detailed descriptions of these events, and then linked together these descriptions into threads representing the attack chains. Darktrace DETECT thus uncovered the individual steps of the attack chains, while Cyber AI Analyst was able to piece together the individual steps and uncover the attack chains themselves.  

Figure 14: An AI Analyst Incident entry showing the first event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 15: An AI Analyst Incident entry showing the second event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 16: An AI Analyst Incident entry showing the third event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 17: An AI Analyst Incident entry showing the first event in a 192.184.35[.]216 chain uncovered by Cyber AI Analyst.
Figure 18: An AI Analyst Incident entry showing the second event in a 192.184.35[.]216 chain uncovered by Cyber AI Analyst.

Conclusion

The existence of critical vulnerabilities in third-party software leaves organizations at constant risk of malicious actors breaching the perimeters of their networks. This risk can be mitigated through attack surface management and regular patching. However, this does not eliminate cyber risk entirely, meaning that organizations must be prepared for the eventuality of malicious actors getting inside their digital estate.

In April 2023, Darktrace observed malicious actors breaching the perimeters of several customer networks through exploitation of a critical vulnerability in PaperCut. Darktrace DETECT observed actors exploiting PaperCut servers to conduct a wide variety of post-exploitation activities, including downloading malicious payloads associated with cryptocurrency mining or payloads with Tor-based C2 capabilities. Darktrace DETECT created numerous model breaches based on this activity which alerted then customer’s security teams early in their development, providing them with ample time to take mitigative steps.

The successful detection of this payload delivery activity, along with the crypto-mining, beaconing, and Tor C2 activities which followed, elicited Darktrace RESPOND to take autonomous inhibitive action against the ongoing activity in those environments where it was operating in autonomous response mode.

If left to unfold, these intrusions developed in a variety of ways, in some cases leading to Cobalt Strike and ransomware activity. The detection of these intrusions in their early stages thus played a vital role in preventing malicious cyber actors from causing significant disruption.

Credit to: Sam Lister, Senior SOC Analyst, Zoe Tilsiter, Senior Cyber Analyst.

Appendices

MITRE ATT&CK Mapping

Initial Access techniques:

- Exploit Public-Facing Application (T1190)

Execution techniques:

- Command and Scripting Interpreter: PowerShell (T1059.001)

Discovery techniques:

- System Network Configuration Discovery (T1016)

Command and Control techniques

- Application Layer Protocol: Web Protocols (T1071.001)

- Encrypted Channel: Asymmetric Cryptography (T1573.002)

- Ingress Tool Transfer (T1105)

- Non-Standard Port (T1571)

- Protocol Tunneling (T1572)

- Proxy: Multi-hop Proxy (T1090.003)

- Remote Access Software (T1219)

Defense Evasion techniques:

- BITS Jobs (T1197)

Impact techniques:

- Data Encrypted for Impact (T1486)

List of Indicators of Compromise (IoCs)

IoCs from 50.19.48[.]59 attack chains:

- 85.106.112[.]60

- http://50.19.48[.]59:82/me1.bat

- http://50.19.48[.]59:82/me2.bat

- http://50.19.48[.]59:82/dom.zip

- 138.68.61[.]82

- update.mimu-me[.]cyou • 102.130.112[.]157

- 34.195.77[.]216

- http://50.19.48[.]59:82/mazar.bat

- http://50.19.48[.]59:82/mazar.zip

- http://50.19.48[.]59:82/prx.bat

- http://50.19.48[.]59:82/lol.exe  

- http://77.91.85[.]117/122.exe

- windows.n1tro[.]cyou • 176.28.51[.]151

- 77.91.85[.]117

- 91.149.237[.]76

- kernel-mlclosoft[.]site • 104.21.29[.]206

- tunnel.us.ngrok[.]com • 3.134.73[.]173

- 212.113.116[.]105

- c34a54599a1fbaf1786aa6d633545a60 (JA3 client fingerprint of crypto-mining client)

IoCs from 192.184.35[.]216 attack chains:

- 185.56.83[.]83

- 185.34.33[.]2

- http://192.184.35[.]216:443/4591187629.exe

- api.ipify[.]org • 104.237.62[.]211

- www.67m4ipctvrus4cv4qp[.]com • 192.99.43[.]171

- www.ynbznxjq2sckwq3i[.]com • 51.89.106[.]29

- www.kuo2izmlm2silhc[.]com • 51.89.106[.]29

- 148.251.136[.]16

- 51.158.231[.]208

- 51.75.153[.]22

- 82.66.61[.]19

- backmainstream-ltd[.]com • 77.91.72[.]149

- 159.65.42[.]223

- 185.254.37[.]236

- http://137.184.56[.]77:443/for.ps1

- http://137.184.56[.]77:443/c.bat

- 45.88.66[.]59

- http://5.8.18[.]237/download/Load64.exe

- http://5.8.18[.]237/download/sdb64.dll

- 140e0f0cad708278ade0984528fe8493 (JA3 client fingerprint of Tor-based client)

References

[1] https://www.cisa.gov/news-events/cybersecurity-advisories/aa22-137a

[2] https://www.papercut.com/kb/Main/PaperCutMFSolutionBrief/

[3] https://www.zerodayinitiative.com/advisories/ZDI-23-233/

[4] https://www.papercut.com/kb/Main/PO-1216-and-PO-1219

[5] https://www.trendmicro.com/en_us/research/23/d/update-now-papercut-vulnerability-cve-2023-27350-under-active-ex.html

[6] https://www.huntress.com/blog/critical-vulnerabilities-in-papercut-print-management-software

[7] https://news.sophos.com/en-us/2023/04/27/increased-exploitation-of-papercut-drawing-blood-around-the-internet/

[8] https://twitter.com/MsftSecIntel/status/1651346653901725696

[9] https://twitter.com/MsftSecIntel/status/1654610012457648129

[10] https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-131a

‍

執筆者
Sam Lister
Specialist Security Researcher
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Sam Lister
Specialist Security Researcher

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June 26, 2026

How Darktrace Transformed Cybersecurity at Our Health Center: A CIO’s Perspective

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How Darktrace Transformed Cybersecurity at Our Health Center: A CIO’s Perspective

In my role as CIO, I bring years of experience leading IT for healthcare organizations. I’ve seen firsthand the unique cybersecurity challenges that nonprofit health centers face: limited budgets, small IT teams, and the constant pressure to prioritize patient care over technology investments. Yet, the threat landscape for health is relentless, and the stakes for protecting patient data and ensuring operational continuity have never been higher. It’s a balancing act.

The search for a better solution

Like many nonprofits, organizations I work at start with Microsoft’s security stack. The discounted pricing for nonprofits makes it an obvious choice, and Microsoft Defender provided a solid foundation for endpoint and email security. However, I quickly realized that relying on a single vendor, even one as robust as Microsoft, left gaps in our defenses. Cybersecurity is never one-size-fits-all, which is why my preference was to layer an additional solution on top of our native security to improve our security posture.

Teams needed a solution that could layer seamlessly on top of Microsoft, without adding complexity or draining limited resources. That’s when I found Darktrace. I had heard of their reputation after seeing how other organizations used Darktrace to secure their infrastructure and was impressed by their AI-native, agentless approach and agreed to a proof of value (POV).

Our goal was to elavate Microsoft with an additional layer of intelligence- one that could seamlessly integrate, operate autonomously, and support a small team without increasing overhead. We turned to Darktrace because its AI-native, agentless approach offered a fundamentally different way to detect and respond to threats, learning our environment in real time and filling gaps that traditional tools can miss. With a quick POV, we were able to validate how effectively Darktrace works alongside Microsoft to deliver a more complete and resilient security architecture.

Why Darktrace stood out

From the start, Darktrace differentiated itself in several critical ways:

  • Deep visibility: Unlike other solutions that rely simply on host-based monitoring with endpoint agents, Darktrace operates passively at the network layer and integrates via APIs for email and identity security. This gave full visibility into network traffic that we previously didn’t have, going beyond our existing endpoint-based tools without adding additional maintenance overhead for our small IT team.
  • AI-native from the ground up: Darktrace wasn’t just layering AI on top of an existing product; it was built with AI at its core. Their autonomous detection and response to threats immediately reduced the need for constant human supervision. In a world where cyber-attacks are increasingly sophisticated and subtle, having an AI that learns our environment and adapts in real time is invaluable.
  • Comprehensive coverage: We started with a POV focused on email security, but quickly expanded to full deployment across our entire infrastructure. Darktrace’s products now protect our email, network, and identity layers, providing visibility and defense against lateral movement and abnormal behavior that traditional tools often miss.

Integration and workflow: Smooth and simple

One of the most impressive aspects of Darktrace is how easy it was to integrate into an existing environment. For network security, it was as simple as plugging an appliance into our top-of-rack switch – no downtime, no complex configuration. For email and identity, API integrations meant we could be up and running in hours, not weeks.

This simplicity extended to day-to-day operations. Our IT team received regular security reports, and any time we had questions or needed to adjust policies, Darktrace’s support team was there with white-glove service. Their responsiveness- even in the middle of the night- gave us confidence that we had true partners, not just a vendor.

Real-world impact: Threats stopped, time saved

The results spoke for themselves. During the time with Darktrace, I did not experience any security incidents. The team slept better at night knowing that Darktrace was monitoring for anomalies and proactively blocking suspicious activity, alerting us even before we noticed anything was wrong.

A memorable example was during an Electronic Health Record (EHR) upgrade, when my team forgot to adjust the policy in advance. Darktrace’s autonomous response was so effective that it blocked our upgrade activities- proof that nothing, not even internal changes, could slip by unnoticed. This level of vigilance meant that ransomware, data exfiltration attempts, or insider threats would be detected and contained before causing harm.

While I can’t share specific ROI numbers, the value was clear: we’ve avoided costly breaches, reduced the time spent investigating alerts, and eliminated the performance drag of agent-based tools. With Darktrace layered on top of Microsoft, I’ve hit the right balance of maximum protection with minimal spending. The cost of Darktrace / EMAIL was competitive, especially when factoring in the included Managed Detection and Response (MDR) service, which provides expert human oversight on top of the AI.

Key differentiators over the competition

  • Extending visibility beyond the endpoint: Traditional host-based monitoring solutions, such as EDR, play a critical role in securing individual devices. By adding a network detection and response (NDR) layer, we gained visibility into activity across our wider digital environment, surfacing threats that move laterally, operate between devices, or bypass endpoint controls. Darktrace also stood out for its ability to learn our normal patterns of behavior and identify subtle deviations in real time, not just known indicators of compromise. Because this is delivered through passive, non-disruptive monitoring, we were able to strengthen our defenses without adding complexity or impacting performance.
  • Layered security without complexity: Darktrace elevated our Microsoft foundation without creating conflicts or requiring us to disable existing protections. This layered approach maximized our security posture without adding operational burden.
  • Expert partnership: Beyond technology, Darktrace’s team acted as true partners, guiding us through deployment, providing ongoing support, and helping us interpret findings. This partnership was as valuable as the technology itself.

Advice for other nonprofits

If you’re an IT leader in a nonprofit, my advice is simple: look for solutions that are easy to deploy, intelligent in their response, and cost-effective. Don’t settle for more endpoint based tools that overlap with what you already have. Seek out a layered approach that covers your blind spots – especially at the network and email layers- at a price point that suits your organization.

Most importantly, don’t be afraid to evaluate new solutions. Even if you’re inundated with vendor pitches, you owe it to your organization to explore options that could save you time, money, and sleepless nights.

For organizations I work at, combining Microsoft’s security stack with Darktrace’s AI-native, platform struck the right balance between protection and practicality. We gained enterprise-grade security without sacrificing performance or stretching our budget. In the end, that meant more resources for what matters most: delivering care to our patients. If you’re facing similar challenges, I encourage you to consider how Darktrace could transform your security posture, and give your team the peace of mind they deserve.

For the organization I work in, combining Microsoft with Darktrace delivered a clear step-change in our security posture. Microsoft provided the foundation, while Darktrace’s behavioral intelligence added visibility into the unknown, surfacing emerging threats based on deviations in real-time activity, not just known indicators.

The result was enterprise-grade protection without added overhead, allowing us to stay focused on patient outcomes, not security operations. For organizations facing similar pressures, this layered approach offers a smarter, more efficient path to securing modern environments.

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Mice Chen
Chief Information Security Officer

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June 25, 2026

Shadow AI Detection: The First Step Toward Securing AI

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Why shadow AI is emerging  

Imagine you’re an employee under pressure, deadlines stacking up, repetitive tasks piling higher by the day. You find a free AI tool online that promises to automate the work in seconds; no approvals are needed. It feels like a simple win, paste in some data, write a quick prompt, and move faster.

But in that moment, something changed.  

Sensitive customer information is entered into a tool your organization doesn’t monitor, doesn’t govern, and can’t see and suddenly, that data is no longer where it should be, and no one knows where it’s gone.

This is the reality of Shadow AI: employees using unsanctioned AI tools to move faster, while unintentionally creating risk that exists entirely outside visibility and control.  

This is not just a one off case, research across businesses indicate that nearly half of employees report using unsanctioned AI tools, often prioritizing speed and productivity over security. Additionally, 51% of employees report connecting AI tools to work systems or apps without IT approval, creating significant operational risk where the average cost of security incidents in organizations with a high level of shadow AI usage can reach $670k.

While shadow AI is often top of mind for security professionals, it is just one component of how AI use can increase risk. Understanding and managing shadow AI use should be considered as part of a broader, comprehensive risk management strategy that aims to secure AI systems, including human and agent identities, interactions, human-AI partnerships, and behaviors operating across the digital enterprise from visibility and governance through detection, response, and recovery.  

Effective risk management calls for a layered and interdisciplinary strategy. It requires addressing issues across governance and visibility; identity, access and agent control, data security and privacy, secure MLOps / LLMOps, runtime security, behavior-based detection, autonomous response and recovery.  

This blog explores a specific governance and visibility use case linked to shadow AI and reveals the challenges it presents as well as the defensive strategies that security teams can adopt.

Why shadow AI is hard to detect  

When it comes to AI, what organizations can easily see does not always reflect the full scope of AI activity occurring within the tools, applications, and workflows used across an enterprise. As a result, organizations using traditional rule-based methods to flag unusual activity may struggle to distinguish unsanctioned AI usage from legitimate operational behavior, particularly as SaaS applications, APIs, and orchestration layers increasingly have AI embedded into normal business workflows. Identifying threats using previously observed intelligence or depending on hard to maintain allow and block lists does not provide a dynamic enough strategy to manage risk. Also, many organizations are focusing on identifying Shadow AI in their governed infrastructure, like gateways, endpoints, or SASE, which is foundational. But, organizations require visibility and Shadow AI detection across all networked infrastructure from on-prem, hybrid, data centers, and cloud infrastructure that may not have endpoint agent visibility. This uncovers the utilization of MCP, data flows, and autonomous agents across these domains.

For example, employees interact with AI assistants across approved SaaS platforms every day. However, browser extensions and other types of plug-ins can route prompts that include enterprise data to embedded AI services in ways that are not visible to the security team. AI enabled workflows may invoke multiple APIs, orchestration layers, and cloud services behind the scenes, making it difficult for traditional security tooling to determine where data is processed, stored, or retransmitted. Because much of this activity occurs within trusted browser sessions and encrypted SaaS traffic, conventional network monitoring, DLP, and application allowlisting controls often lack the context needed to accurately identify or govern these interactions

Identifying AI tools in the environment is one part of the equation. Understanding the behavior surrounding their use is where the real challenge lies. An AI application is not inherently risky, but the way users or other assets interact with it may be. Sensitive data exposure, abnormal access patterns, and misuse of AI-assisted workflows often appear legitimate in isolation and only become visible through behavioral analysis across the broader environment.  

What Shadow AI visibility does and doesn’t show

Comprehensive Shadow AI visibility allows organizations to answer several important questions:

  • What types of AI are we using? What AI platforms, agents, MCP clients/servers, and services are active across the enterprise?  
  • Who is using AI services? Which users, business units, or systems are interacting with those AI services?  
  • Is our data safe? Is sensitive or regulated data being exposed through prompts, workflows, or integrations?  
  • Are AI systems behaving as expected? Are AI systems behaving anomalously or operating outside approved governance processes?  
  • Are our AI systems under attack? Is an attacker attempting to manipulate prompts, influence agent behavior, or abuse AI-enabled workflows?

Answering these questions is foundational to broader AI governance efforts. However, it is limited to helping teams understand initial interactions and fails to offer insight into dependencies and outcomes that are critical to securing AI across an enterprise.  

Deeper visibility that includes the ability to understand dependencies and outcomes are not always available in AI security point products. Answering the questions below requires understanding runtime behavior and operational outcomes:  

  • What actions did the AI interaction trigger?  
  • What systems, applications, or data did it access? Did the AI operate beyond its intended permissions or scope?  
  • Could a low-risk interaction lead to high-risk outcomes?  
  • What is the risk and context understanding of an anomalous activity to assist in prioritization of analysis and autonomous response action?

The distinction between these two sets of questions offers two different layers of AI security. The first set of questions focuses on discovery and interaction visibility. The second set focuses on providing visibility that includes the context and outcomes that are critical for managing follow-on risks associated with obfuscated downstream activities.  

Together, these layers help organizations move beyond simply identifying AI usage toward understanding how AI behaves operationally across the enterprise.

How organizations are addressing shadow AI

Most organizations still approach shadow AI as an application control problem, relying on policies, browser restrictions, and allow/block lists. However, AI adoption is evolving faster than most governance processes can realistically keep pace with. New assistants, plugins, and embedded AI features appear continuously, creating pressure to enable business productivity while simultaneously containing risk.  

Existing governance processes were designed for a more traditional SaaS adoption cycle, where new applications could be reviewed, approved, and monitored over longer time horizons. AI adoption operates differently. New capabilities can appear overnight inside existing platforms employees already use, making it difficult for security and governance teams to maintain an accurate understanding of enterprise AI exposure. This means that many organizations are experiencing significant operational overhead, particularly in large environments where AI usage is decentralized across teams, departments, and third-party services.  

Where should organizations start when securing their AI systems?

Shadow AI identification is an on-going critical component for AI Risk/Governance Boards as well as security organizations. As organizations seek AI certifications like ISO 42001 AI Management Systems, visibility into all AI adoption from enterprise use to custom innovation and development is crucial. Shadow AI identification provides organizations with the visibility needed to decide whether an AI tool should be brought into governed environments to reduce data loss (DLP) risks or whether policies should be established and enforced to restrict their use.

As organizations rapidly innovate and adopt AI, they are taking on more and more risk. Organizations need to have a strategy in place to mitigate the assumed risk, especially with third-party adoption. Visibility, monitoring, governance enforcement, behavioral-based detection of non-deterministic systems, and autonomous investigation and containment becomes critical to mitigating the risk of AI systems.  

How Darktrace secures AI and shadow AI

Attackers are using AI to move faster, scale tactics, and make threats more adaptive and convincing. Internally, organizations are grappling with new forms of risk created by generative AI, autonomous agents, shadow AI, and increasingly complex digital environments.

Darktrace helps organizations protect both people and AI in a world where AI is now central to how business gets done. Darktrace / SECURE AI helps organizations discover and control shadow AI by surfacing unsanctioned or unexpected AI activity where it appears – including MCP detections, distinguishing misuse of legitimate tools and unapproved services, and applying policy to contain data exposure while guiding users toward sanctioned options.

Stay up to date on AI security

Sign up for the Secure AI Readiness Program here: This gives you exclusive access to the latest news on the latest AI threats, updates on emerging approaches shaping AI security, and insights into the latest innovations, including Darktrace’s ongoing work in this area.

Ready to talk with a Darktrace expert on securing AI? Register here to receive practical guidance on the AI risks that matter most to your business, paired with clarity on where to focus first across governance, visibility, risk reduction, and long-term readiness.  

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