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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!
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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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

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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May 21, 2026

Darktrace named a Leader in the 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR) For the Second Consecutive Year

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Continued recognition in NDR  

Darktrace has been recognized as a Leader in the 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR), marking the second consecutive year in the Leaders quadrant.

We believe this consistency reflects sustained ability to execute, adapt, and deliver outcomes as the market evolves.

While we are immensely proud to be recognized by industry analysts as a Leader in NDR, that's just part of the story. Darktrace was also Named the Only 2025 Gartner® Peer Insights™ Customers’ Choice for Network Detection and Response based on direct customer feedback and real-world experience.

We believe the combination of these two signals is important. One reflects how the market is evaluated. The other reflects how technology performs in practice.

Why Darktrace continues to be recognized as a leader

We believe our position as a Leader for the second consecutive year reflects a combination of our sustained ability to execute in NDR, continued AI innovation, and proven delivery of security outcomes for customers and partners worldwide.

We also feel that our leadership in the NDR market is a testament to our unique and multi-layered AI approach, for which we were recognized as No.7 on Fast Company’s Most Innovative AI Companies of 2026 list, plus one of the hottest AI cybersecurity companies in CRN's AI 100.

Adapting to complex, real-world environments

Organizations are no longer protecting a single network perimeter. They are securing a mix of users, devices, applications, and data that move across hybrid environments.

Darktrace has focused on maintaining visibility and detection across these conditions, allowing security teams to understand activity as it scales.

Supporting organizations globally, not just technically

Security outcomes are shaped as much by deployment and support as they are by detection capability.

Darktrace continues to invest in regional presence across 29 countries around the world, helping organizations operationalize NDR in ways that align with local requirements, internal processes, and team structures.

Continuing to push AI beyond detection

AI in cybersecurity is often positioned as a way to improve detection accuracy. But the more important shift is how AI can influence decision-making and response.

Darktrace continues to develop models that learn from both live environments and historical incident data, combining real-time behavioral analysis with insights derived from prior attack patterns.

Using technologies such as the Incident Graph and DIGEST (Darktrace Incident Graph Evaluation for Security Threats), activity is not analyzed in isolation. Instead, relationships between users, devices, connections, and events are mapped over time, allowing the system to reconstruct how an incident is unfolding and how similar incidents have progressed in the past.

By evaluating these patterns, Darktrace can assess the likelihood that an incident will escalate, prioritizing the activity that poses the greatest risk and surfacing the most relevant context for investigation.

This shifts security operations from simply identifying anomalies to understanding their trajectory, helping teams anticipate potential impact and respond earlier with greater precision.

Why NDR is shifting from reactive detection to proactive, AI-driven security

Traditional approaches to NDR have been built around reactively identifying threats once they become clearly visible. That model is increasingly difficult to rely on.

Attackers are no longer operating in ways that stand out. They use valid credentials, trusted tools, and low-and-slow techniques that blend into everyday activity. By the time something looks obviously malicious, the impact is often already underway.

This is the core limitation of reactive detection. It depends on recognizing something that already looks like a threat.

As a result, many of the most consequential incidents today fall into a gap.

Insider activity, compromised credentials, and novel attacks rarely trigger traditional alerts because they do not follow known patterns. On the surface, they often appear legitimate, making them difficult to distinguish from normal behavior without deeper context.

This is why we believe this Gartner recognition reflects a broader shift in NDR toward autonomous, proactive and pre‑emptive security operations.

By understanding normal behavior within an environment, it is possible to identify subtle deviations rather than waiting for confirmation of threats as they are taking place.

Darktrace’s Self-Learning AI is designed for behavioral understanding. By continuously learning each organization’s normal patterns, it can detect deviations in real time, enabling a proactive and pre-emptive model of NDR where security teams can respond to early signs of risk as they emerge, reducing the window in which attacks can develop.

In multiple cases, this behavioral approach has led to early threat detection where Darktrace identified completely unknown threats, including pre-CVE zero-day activity. By detecting subtle behavioral changes before vulnerabilities were publicly disclosed or widely understood, organizations can mitigate threats before they do damage.

This shift is subtle but important. Modern NDR solutions must shift from a system that explains what happened to one that helps prevent threats from developing in the first place, and Darktrace is proud to be at the forefront of this shift - helping organizations build and maintain a state of proactive network resilience.

Continuing to innovate at the forefront of NDR

In our view, recognition as a Leader reflects where the market is today. Continuing to innovate defines what comes next.

As businesses evolve, new technologies like AI tools and agents introduce new security risks and challenges; security teams need more than simple detection. They need a complete understanding of risk as it develops, the ability to investigate it in context, and to contain threats at machine speed.  

Darktrace / NETWORK is built to deliver across that full spectrum. Its Self-Learning AI continuously adapts to each organization’s environment, identifying subtle behavioral changes that signal emerging threats. Integrated investigation and autonomous response reduce the time between detection and action, allowing teams to move with greater speed and confidence.

This combination enables organizations to detect and contain known, unknown, and insider threats as they develop, while also strengthening resilience over time.

As a two-time Leader in the Gartner® Magic Quadrant™ for NDR and the only 2025 Gartner® Peer Insights™ Customers’ Choice, we feel Darktrace continues to evolve its platform to meet the demands of modern environments, delivering a more complete and adaptive approach to network security.

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Disclaimer: The 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR) ,The 2026 Gartner® Magic Quadrant™ for Network Detection and Response (NDR), Thomas Lintemuth, Charanpal Bhogal, Nahim Fazal, 18 May 2026.

Gartner does not endorse any vendor, product or service depicted in its research publications, and does not advise technology users to select only those vendors with the highest ratings or other designation. Gartner research publications consist of the opinions of Gartner’s research organization and should not be construed as statements of fact. Gartner disclaims all warranties, expressed or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose.

GARTNER is a registered trademark and service mark of Gartner, Inc. and/or its affiliates in the U.S. and internationally and is used herein with permission. All rights reserved. Magic Quadrant is a registered trademark of Gartner, Inc. and/or its affiliates and is used herein with permission. All rights reserved.

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Mikey Anderson
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May 21, 2026

Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches

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How enterprise AI Agents are changing the risk landscape  

Generative AI Agents are changing the way work gets done inside enterprises, and subsequently how security risks may emerge. Organizations have quickly realized that providing these agents with wider access to tooling, internal information, and granting permissions for the agent to perform autonomous actions can greatly increase the efficiency of employee workflows.

Early deployments of Generative AI systems led many organizations to scope individual components as self-contained applications: a chat interface, a model, and a prompt, with guardrails placed at the boundary. Research from Gartner has shown that while the volume and scope of Agentic AI deployments in enterprise environments is rapidly accelerating, many of the mechanisms required to manage risk, trust, and cost are still maturing.

The issue now resides on whether an agent can be influenced, misdirected, or manipulated in ways that leads to unsafe behavior across a broader system.

Why prompt security matters in enterprise AI

Prompt security matters in enterprise AI because prompts are the primary way users and systems interact with Agentic AI models, making them one of the earliest and most visible indicators of how these systems are being used and where risk may emerge.

For security teams, prompt monitoring is a logical starting point for understanding enterprise AI usage, providing insight into what types of questions are being asked and tasks are being given to AI Agents, how these systems are being guided, and whether interactions align with expected behavior. Complete prompt security takes this one step further, filtering out or blocking sensitive or dangerous content to prevent risks like prompt injection and data leakage.

However, visibility only at the prompt layer can create a false sense of security. Prompts show what was asked, but not always why it was asked, or what downstream actions were triggered by the agent across connected systems, data sources, or applications.

What prompt security reveals  

The primary function of prompt security is to minimize risks associated with generative and agentic AI use, but monitoring and analysis of prompts can also grant insight into use cases for particular agents and model. With comprehensive prompt security, security teams should be able to answer the following questions for each prompt:

  • What task was the user attempting to complete?
  • What data was included in the request, and was any of the data high-risk or confidential?
  • Was the interaction high-risk, potentially malicious, or in violation of company policy?
  • Was the prompt anomalous (in comparison to previous prompts sent to the agent / model)?

Improving visibility at this layer is a necessary first step, allowing organizations to establish a baseline for how AI systems are being used and where potential risks may exist.  

Prompt security alone does not provide a complete view of risk. Further data is needed to understand how the prompt is interpreted, how context is applied, what autonomous actions the agent takes (if any), or what downstream systems are affected. Understanding the outcome of a query is just as important for complete prompt security as understanding the input prompt itself – for example, a perfectly normal, low-risk prompt may inadvertently result in an agent taking a high-risk action.

Comprehensive AI security systems like Darktrace / SECURE AI can monitor and analyze both the prompt submitted to a Generative AI system, as well as the responses and chain-of-thought of the system, providing greater insight into the behavior of the system. Darktrace / SECURE AI builds on the core Darktrace methodology, learning the expected behaviors of your organization and identifying deviations from the expected pattern of life.

How organizations address prompt security today

As prompt-level visibility has become a focus, a range of approaches have emerged to make this activity more observable and controllable. Various monitoring and logging tools aim to capture prompt inputs to be analyzed after the fact.  

Input validation and filtering systems attempt to intervene earlier, inspecting prompts before they reach the model. These controls look for known jailbreak patterns, language indicative of adversarial attacks, or ambiguous instructions which could push the system off course.

Importantly, for a prompt security solution to be accurate and effective, prompts must be continually observed and governed, rather than treated as a point-in-time snapshot.  

Where prompt security breaks down in real environments

In more complex environments, especially those involving multiple agents or extensive tool use, AI security becomes harder to define and control.

Agent-to-Agent communications can be harder to monitor and trace as these happen without direct user interaction. Communication between agents can create routes for potential context leakage between agents, unintentional privilege escalation, or even data leakage from a higher privileged agent to a lower privileged one.

Risk is shaped not just by what is asked, but by the conditions in which that prompt operates and the actions an agent takes. Controls at the orchestration layer are starting to reflect this reality. Techniques such as context isolation, scoped memory, and role-based boundaries aim to limit how far a prompt’s influence can extend.  

Furthermore, Shadow AI usage can be difficult to monitor. AI systems that are deployed outside of formal governance structures and Generative AI systems hosted on unknown endpoints can fly under the radar and can go unseen by monitoring tools, leaving a critical opening where adversarial prompts may go undetected. Darktrace / SECURE AI features comprehensive detection of Shadow AI usage, helping organizations identify potential risk areas.

How prompt security fits in a broader AI risk model

Prompt security is an important starting point, but it is not a complete security strategy. As AI systems become more integrated into enterprise environments, the risks extend to what resources the system can access, how it interprets context, and what actions it is allowed to take across connected tools and workflows.

This creates a gap between visibility and control. Prompt security alone allows security teams to observe prompt activity but falls short of creating a clear understanding of how that activity translates into real-world impact across the organization.

Closing that gap requires a broader approach, one that connects signals across human and AI agent identities, SaaS, cloud, and endpoint environments. It means understanding not just how an AI system is being used, but how that usage interacts with the rest of the digital estate.

Prompt security, in that sense, is less of a standalone solution and more of an entry point into a larger problem: securing AI across the enterprise as a whole.

Explore how Darktrace / SECURE AI brings prompt security to enterprises

Darktrace brings more than a decade of AI expertise, built on an enterprise‑wide platform designed to operate in and understand the behaviors of the complex, ambiguous environments where today’s AI now lives. With Darktrace / SECURE AI, enterprises can safely adopt, manage, monitor, and build AI within their business.  

Learn about Darktrace / SECURE AI here.

Sign up today to stay informed about innovations across securing AI.

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Jamie Bali
Technical Author (AI) Developer
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