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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

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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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September 22, 2026

Darktrace / SECURE AI: Extending Behavioral Security for the Age of Agentic AI

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AI is moving faster than the controls built to secure it

Over 80% of Darktrace’s customers now use generative AI services, and the average organization interacted with five different AI provides in August 20261. That level of adoption reflects how quickly AI has become embedded in day-to-day business operations. But as adoption accelerates, so do the opportunities for new forms of exposure that often operate outside traditional security controls. Prompts can expose sensitive information, an over-permissioned agent can turn a routine task into a serious security concern, and an employee using an unsanctioned AI tool to get work done can quietly introduce risk long before the security team is aware of its existence.

Securing AI isn’t a nice-to-have. It's an urgent, board-level requirement for any business that wants AI adoption to be an advantage rather than a liability.

Why traditional security controls fall short

The challenge isn’t a lack of AI security tools, it’s that most security solutions weren’t built for the way AI behaves.  

AI systems are adaptive and, by nature, unpredictable. A prompt can be entirely benign in one context and a serious risk in another. An agent's permissions can look reasonable in isolation and dangerous the moment they're combined with what that agent is actually doing. Rule-based controls, built to catch known signatures and static policy violations, simply aren't designed to catch this kind of subtlety. They might be able to tell you what happened, but they can’t tell you if it mattered.  

Effective AI security requires something different: a deep understanding of what normal looks like across every human, system, and agent in an environment, so the earliest signs of drift, misuse, or compromise stand out as they emerge.

Behavioral understanding is our foundation

Darktrace isn’t reinventing itself to secure AI. We’re extending what we already do. For over a decade, Darktrace has been built on a single premise – that every organization has its own unique, evolving way of operating, shaped by how its systems, users, and devices behave. Understanding that is the only reliable way to catch what rules and signatures miss. Our Adaptive AI™ continuously learns the distinct behaviors, relationships, and operational patterns of every enterprise it protects, building a Unique Behavioral Profile that no other vendor can replicate. It's how we've spent years interpreting ambiguity, uncovering subtle intent, and spotting drift before it becomes dangerous across networks, cloud, identities, email, OT, and endpoints. AI is a new domain, but behavioral security isn't a new discipline for us.

Introducing Darktrace / SECURE AI

Darktrace / SECURE AI helps organizations embrace AI innovation without losing control of how it is used. Delivered through the Darktrace Behavioral Defense Platform™, it provides visibility into AI activity across employees, agents, and AI systems, helping security teams understand how AI is being used throughout their business.

Darktrace then applies behavioral understanding to that activity, adding the context needed to distinguish routine usage from genuine risk. By understanding the relationships between users, agents, systems, and data, / SECURE AI helps organizations move beyond simply observing AI usage to understanding risk, governing behavior against policy, and enabling AI adoption with confidence. The result is greater oversight, stronger governance, and the ability to confidently accelerate AI innovation without creating unmanaged risk.

Securing your AI ecosystem

AI risk doesn't originate from a single source, and effective AI security can't focus on just one layer of the problem. Organizations need visibility, understanding, and governance across the entire AI ecosystem, from the prompts users submit and the agents they create, to the development environments where AI is built and the unsanctioned tools operating outside approved channels. Here's how Darktrace / SECURE AI helps organizations secure each of these areas.

Shadow AI management

Darktrace / SECURE AI helps security teams discover unsanctioned AI services and track usage trends over time using Darktrace telemetry and supported SASE integrations such as Microsoft Entra Global Secure Access. It also extends visibility to Model Context Protocol (MCP) usage, helping teams understand where AI tools and agents are connecting to external services. Through Darktrace platform integrations, organizations can block unsanctioned AI usage or quarantine affected devices when needed, helping them reduce exposure and guide users toward approved options.

AI prompt analysis

Prompts reveal what users are asking AI to do, what information they are sharing, and the outcomes they are trying to produce. Darktrace / SECURE AI provides visibility into prompts, sessions, and responses across supported platforms, including Microsoft Copilot, Copilot Studio, ChatGPT Enterprise, Claude, Salesforce, and AWS Bedrock2. Behavioral analysis detects activity such as attempted jailbreaks, sensitive data exposure, and potential indirect prompt injection, while risk scoring helps analysts prioritize the sessions that need attention. Policy Manager maps organizational AI policies against prompt activity and surfaces potential violations, helping teams govern AI use with direct evidence instead of relying on fragmented logs or inferred intent.

AI agent identities and actions

AI agents have their own permissions, roles, relationships, and access to systems and data. Darktrace / SECURE AI brings agent identities together with the users interacting with them, giving security teams visibility into access, sessions, and connections across supported environments. A real-time audit trail helps teams continuously evaluate whether an agent’s activity remains aligned with its intended purpose, so they can identify excessive access or behavioral drift before it becomes a security issue.

AI agent development risk management

Many AI risks are introduced during development, when agents are created, permissions are assigned, and connections to data sources are established. Darktrace / SECURE AI provides visibility across both low-code and high-code environments. In platforms such as AWS Bedrock, teams can examine AI architecture and the agent identities involved in development and deployment. In low-code environments, such as Copilot Studio, they can observe agents as they are created, monitor whether behavior stays aligned with their intended purpose, and connect prompt activity during development with behavior in production. This helps organizations address misconfigurations and excessive permissions before they reach production.

The promise of AI, secured

The question isn't whether to adopt AI, it's whether security teams can enable secure adoption that allows every business to benefit from AI’s potential.

Darktrace / SECURE AI is built to solve this problem – extending a decade of behavioral understanding to the newest, fastest-moving part of the enterprise, using the same principles which already protect people and hybrid infrastructure.

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Darktrace / SECURE AI is generally available now. Discover the product, or get a demo today.

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[1] Based on aggregated Darktrace product telemetry across a fleet of ~8,200 observed deployments, measuring generative AI service usage across accounts monitored in August 2026. The 80%+ figure reflects the share of monitored accounts with any generative AI service usage during the same period.

[2] Microsoft, Copilot, ChatGPT, Claude, Salesforce, and Amazon Bedrock are trademarks of their respective owners.

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Brittany Woodsmall
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September 17, 2026

The Problem of Re-defining Human Value in the Agentic Age

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Newsfeeds are constantly informing us about the rapid escalation of agentic AI systems. These systems move far beyond simple machine-based computations, and  the focused, defined and bounded assistance that most AI systems started out as.

The next evolution of AI will harness the agentic properties of orchestration, automation, and heightened value-chains in IT, taking on the burden of workflow management, not just workflow delivery.

In nearly all of these instances, promises are made such as ‘this will free up human time’ or ‘this will allow people to focus on higher-order strategy’. However that message is delivered, one thing is clear: in ceding the orchestration and management of work to increasingly sophisticated AI agents and agentic systems, human value will be elevated to a particular and specific layer: the ability to judge its outputs.  As AI takes on more tasks, humans should be able to focus on a higher level of governance; making sure the decisions that AI offers us are ethical, responsible and worthwhile.  

But there are two major problems with that approach.

This blog discusses the problem of how Agentic systems are re-shaping how we review information, where we fit in, and when we make decisions.  It also discusses the problem of how the increased flow of confident, generated information affects the way we make judgement.  This blog considers how human judgement needs to adapt, and how a behavioral defense approach – using techniques pioneered by Darktrace – can help us do that.

The challenge of knowing where human judgement belongs

As we confer more automated decision-making to agentic systems, it might look increasingly less like ‘granting permissions’, and more like ‘surrendering authority’.  

The judgement layer for AI-generated work is not a fixed boundary. We have become used to the idea of a ‘human in the loop’ (HITL) and, historically, relationships between humans and IT systems were reasonably clear and bounded.  Computer and software systems were programmed to carry out certain tasks or automated functions, and humans could control the gates and decision points where actions were undertaken. Even across highly complex computational workflows, human interaction was a controllable node within the process; we were able to configure and regulate. But in the agentic age, where that human interaction sits, and what it can influence shifts every time AI systems are granted autonomy.  

This leads us to the first problem: if humans are moving themselves (or are being moved) into the ‘judgement’ part of the value chain, exactly where and when do we exercise that judgement?  

Humans are no longer the sole shepherds of computer-based or software-controlled outputs.  We are at times at least one step further (and slower) behind the new agentic shepherds.  We might also be blind to what they are doing.  Not only might we be removed and blind to the actions of our AI shepherds, but with the challenge of unknown, unapproved AI systems operating beyond our control, humans might not even know that our work is being shepherded by an AI at all.  Simply put, with the advent of greater levels of autonomy and orchestration, humans are at risk of not even knowing where to apply our newly-extended powers of strategic judgement.

Shadow AI – the use of unapproved AI systems or processes – is a growing threat to the role of effective governance and oversight. Shadow AI isn't just the AI you can't see. Its the AI you already know about being used in an unapproved way. The ability to generate effective oversight of the AI systems you use (or that are used on your behalf) will be increasingly important to ensure that human judgement in the AI value chain is effective, and deliberately placed.

The problem of what makes good judgement

The second problem lies in how flawed human judgement can be.  Humans are historically, notoriously, and, sometimes dangerously, unreliable when it comes to exercising judgement.  Humans are prone to the worst kinds of bias, the seduction of malign influence, and the sometimes-overwhelming urge to succeed. AI has long had a known flaw of operating with sycophancy, providing outputs that tend to agree with or flatter the human user.  But as AI grows ever more effective, there is a risk of both hyper-enablement (where humans increasingly and knowingly enable AI despite potential harm), as well as the greater risk of suggestion. Both of these aspects could skew the newly-elevated input of human judgement.

Imagine a highly competent AI system that has just orchestrated and managed a dizzying array of processes and workflows.  The AI is designed to present the human decision-maker with recommendations; based on analysis, comparison and other programmed factors.  This is where the human judgement layer is enabled.  But what if that judgement is summarily diffused by an AI-based recommendation that emulates the decision, provides plausible but unattractive alternatives, then suggests (or, worse, directs) the human end-user to take a particular course of action.

The risk here is that you are given a recommendation, tailored to your preferences (which the AI has learned, or which you have divulged), and which appears to make perfect sense.  It appears to be a well-weighted recommendation, with sound arguments that tap into our inherent biases or inclinations so that a specific decision-path is followed. With the growth of agentic systems specifically designed to match user profiles (from Cowork agents to ‘digital twin’ models), the likelihood of agentic influence could badly skew human judgement or, at the least, devalue the proposition that humans are taking a higher-layer of strategic control over AI-based decisions.

If AI convincingly recommends something that may be problematic, it can be difficult to discern both accurate data, and the context required to make the right judgement.

Given the two problems described above, the job of exercising valuable human judgement in the agentic age can draw down to these two questions:

  • When should humans intervene in the agentic process?  
  • How can we make the best possible judgement calls?

What humans contribute that AI cannot

For all the flaws that make human judgement unreliable, people have the edge over even the most sophisticated and powerful AI systems when it comes to issues such as ethics and social context.  An AI system can, with startling granularity, rank the value of adopting a new business proposal: offering predictive metrics on costs, returns, market value, time-to-deliver operations, conformance with legal registers, etc.  But it can’t tell if the business proposal is ethically sound, or if the business venture will potentially affect groups outside of the analyzed proposal. It can’t tell you if the CEO has a ‘bad feeling’ about this effort.  It can’t tell you if this is the right thing to do.  

The ability to add social context, balance complex interpersonal dynamics, understand nuance, and to go beyond what seems economically reasonable is where human judgement can add value.  

Human judgement is difficult to encapsulate in metrics. And the way we train our development may need to adapt too. Rather than building up a gradual, experiential knowledge base, we should think about training the skill of judgement itself; especially for an agentic age.

How behavioral security strengthens AI governance

If this all feels like a vicious circle (‘I need AI help to make good judgements’ / ‘AI can twist what I need to judge’) it needn’t be. The key to this is having a defense-in-depth approach, with tools that can actually help.

This is precisely where behavioral security becomes important. The complex and nuanced way that humans exercise judgement is often rooted in our ability to recognize behavior that doesn't look right. We may not always be able to articulate it immediately, but we can often identify when an action, recommendation, or outcome feels inconsistent with the context around it. As AI systems take on more responsibility across the decision chain, preserving that ability to recognize meaningful deviations becomes increasingly important.

Darktrace’s / SECURE AI is designed to do exactly that. It applies behavioral security to AI ecosystems, helping organizations understand how people, AI tools, identities, and agents interact across the business. By learning the patterns of normal AI usage and surfacing activity that deviates from those patterns, it provides security teams with the context needed to investigate risk, understand unusual behavior, and make informed governance decisions. Rather than relying solely on predefined rules or assumptions, this behavioral understanding helps organizations distinguish between expected AI activity and behavior that warrants closer scrutiny.

This matters because we are already in an era of information overload. If humans are expected to elevate their value through strategic judgement, the ability to do this without being overwhelmed by data (good or bad) will be critical.  

We need the ability to discern when we're being misled by AI, and whether our judgement calls are being made on the basis of accurate, contextual information. Darktrace / SECURE AI provides that additional layer of defensive security for activity we cannot easily see. Whether it is suspected Shadow AI or skewed recommendations, the net result is a protected organization, where users can more effectively use AI to make positive judgements.

For those where that judgement is a critical skill (both individuals, as well as those working in security teams), improving our metacognition - the ability to understand information in a broader context - will supercharge the value of human judgement. When those judgements are grounded in context rather than assumptions we have better information to make sound decisions.

Conclusion

Human judgement is a skill that is honed over time and experience.  Darktrace’s / SECURE AI employs the same principles, but at machine-speed. Rather than influencing or directing, Darktrace / SECURE AI offers AI-enabled assurance; providing human-based judgement with the right context to make a balanced decision.  

What we judge can be valued by the legitimacy of its outputs. For AI, those outputs are valued on the speed and accuracy of the information provided.  Increasingly for humans, the value of our outputs will be based on the validity of our judgement, and how we justify our decisions in ways that engineer confidence.  

Humans often know more than we can express, while AI is prone to expressing more than it truly understands. Humans can bridge the context AI often fails to appreciate. When that judgement is supported by relevant, impartial AI systems, this is the future space where good AI governance will be exercised.

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Discover Darktrace / SECURE AI.

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About the author
Jason Lusted
AI Governance Advisor
Your data. Our AI.
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