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November 6, 2023

How PlugX Malware Has Evolved & Adapted

Discover how Darktrace effectively detected and thwarted the PlugX remote access trojan in 2023 despite its highly evasive and adaptive nature.
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
Nahisha Nobregas
SOC Analyst
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06
Nov 2023

What is PlugX Remote Access Trojan?

Understanding remote access trojans (RATs)

As malicious actors across the threat landscape continue to pursue more efficient and effective ways of compromising target networks, all while remaining undetected by security measures, it is unsurprising to see an increase in the use of remote access trojans (RATs) in recent years. RATs typically operate stealthily, evading security tools while offering threat actors remote control over infected devices, allowing attackers to execute a wide range of malicious activities like data theft or installing additional malware.

Definition and general functionality of RATs: A Remote Access Trojan (RAT) is a type of malware that enables unauthorized remote control of an infected computer. Once installed, RATs allow attackers to monitor user activities, steal sensitive information, manipulate files, and execute commands. RATs are typically distributed via phishing emails, malicious attachments, drive-by downloads, or exploiting software vulnerabilities. Due to their ability to provide comprehensive control over a compromised system, RATs pose a significant security threat to individuals and organizations.

Historical overview of PlugX

PlugX is one such example of a RAT that has attributed to Chinese threat actors such as Mustang Panda, since it first appeared in the wild back in 2008. It is known for its use in espionage, a modular and plug-in style approach to malware development. It has the ability to evolve with the latest tactics, techniques, and procedures (TTPs) that allow it to avoid the detection of traditional security tools as it implants itself target devices.

How does PlugX work?

The ultimate goal of any RAT is to remotely control affected devices with a wide range of capabilities, which in PlugX’s case has typically included rebooting systems, keylogging, managing critical system processes, and file upload/downloads. One technique PlugX heavily relies on is dynamic-link library (DLL) sideloading to infiltrate devices. This technique involves executing a malicious payload that is embedded within a benign executable found in a data link library (DLL) [1]. The embedded payload within the DLL is often encrypted or obfuscated to prevent detection.

What’s more, a new variant of PlugX was observed in the wild across Papua New Guinea, Ghana, Mongolia, Zimbabwe, and Nigeria in August 2022, that added several new capabilities to its toolbox.

Key capabilities of PlugX

The new variation is reported to continuously monitor affected environments for new USB devices to infect, allowing it to spread further through compromised networks [2]. It is then able to hide malicious files within a USB device by using a novel technique that prevents them from being viewed on Windows operating systems (OS). These hidden files can only be viewed on a Unix-like (.nix) OS, or by analyzing an affected USB devices with a forensic tool [2]. The new PlugX variant also has the ability to create a hidden directory, “RECYCLER.BIN”, containing a collection of stolen documents, likely in preparation for exfiltration via its command and control (C2) channels. [3]

Since December 2022, PlugX has been observed targeting networks in Europe through malware delivery via HTML smuggling campaigns, a technique that has been dubbed SmugX [4].

This evasive tactic allows threat actors to prepare and deploy malware via phishing campaigns by exploiting legitimate HTML5 and JavaScript features [5].

Darktrace Coverage of PlugX

Between January and March 2023, Darktrace observed activity relating to the PlugX RAT on multiple customers across the fleet. While PlugX’s TTPs may have bypassed traditional security tools, the anomaly-based detection capabilities of Darktrace allowed it to identify and alert the subtle deviations in the behavior of affected devices, while Darktrace was able to take immediate mitigative action against such anomalous activity and stop attackers in their tracks.  

C2 Communication

Between January and March 2023, Darktrace detected multiple suspicious connections related to the PlugX RAT within customer environments. When a device has been infected, it will typically communicate through C2 infrastructure established for the PlugX RAT. In most cases observed by Darktrace, affected devices exhibited suspicious C2 connections to rare endpoints that were assessed with moderate to high confidence to be linked to PlugX.

On the network of one Darktrace customer the observed communication was a mix of successful and unsuccessful connections at a high volume to rare endpoints on ports such as 110, 443, 5938, and 80. These ports are commonly associated with POP3, HTTPS, TeamViewer RDP / DynGate, and HTTP, respectively.  Figure 1 below showcases this pattern of activity.

Figure 1: Model Breach Event Log demonstrating various successful and unsuccessful connections to the PlugX C2 endpoint 103.56.53[.]46 via various destination ports.

On another customer’s network, Darktrace observed C2 communication involving multiple failed connection attempts to another rare external endpoint associated with PlugX. The device in this case was detected attempting connections to the endpoint, 45.142.166[.]112 on ports 110, 80, and 443 which caused the DETECT model ‘Anomalous Connection / Multiple Failed Connections to Rare Endpoint’ to breach. This model examines devices attempting connections to a rare external endpoint over a short period of time, and it breached in response to almost all PlugX C2 related activity detected by Darktrace. This highlights Darktrace DETECT’s unique ability to identify anomalous activity which appears benign or uncertain, rather than relying on traditional signature-based detections.

Figure 2: Device Event Log demonstrating various successful and unsuccessful connections to the PlugX C2 endpoint 45.142.166[.]112 via various destination on January 27, 2023.

New User Agent

Darktrace's Self-Learning AI approach to threat detection also allowed it to recognize connections to PlugX associated endpoints that utilized a new user agent. In almost all connections to PlugX endpoints detected by Darktrace, the same user agent, Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36, was observed, illustrating a clear pattern in PlugX-related activity

In one example from February 2023, an affected device successfully connected to an endpoint associated with PlugX, 45.142.166[.]112, while using the aforementioned new user agent, as depicted in Figure 3.

Figure 3: The Device Event log above showcases a successful connection to the PlugX associated IP address, 45.142.166[.]112 using the new user agent ‘Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36’.

On March 21, 2023, Darktrace observed similar activity on a separate customer’s network affected by connections to PlugX. This activity included connections to the same endpoint, 45.142.166[.]112. The connection was an HTTP POST request made via proxy with the same new user agent, ‘Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36’. When investigated further this user agent actually reveals very little about itself and appears to be missing a couple of common features that are typically contained in a user agent string, such as a web browser and its version or the mention of Safari before its build ID (‘537.36’).

Additionally, for this connection the URI observed consisted of a random string of 8 hexadecimal characters, namely ‘d819f07a’. This is a technique often used by malware to communicate with its C2 servers, while evading the detection of signature-based detection tools. Darktrace, however, recognized that this external connection to an endpoint with no hostname constituted anomalous behavior, and could have been indicative of a threat actor communicating with malicious infrastructure, thus the ‘Anomalous Connection / Possible Callback URI’ model was breached.

Figure 4: An affected device was detected using the new user agent, ‘Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36’ while connecting to the rare external endpoint 45.142.166[.]112 via proxy.

Numeric File Download

Darktrace’s detection of PlugX activity on another customer’s network, in February 2023, helped to demonstrate related patterns of activity within the C2 communication and tooling attack phases. Observed PlugX activity on this network followed the subsequent pattern; a connection to a PlugX endpoints is made, followed by a HTTP POST request to a numeric URI with a random string of 8 hexadecimal characters, as previously highlighted. Darktrace identified that this activity represented unusual ‘New Activity’ for this device, and thus treated it with suspicion.

Figure 5: New activity was identified by Darktrace in the Device Event Log shown above for connections to the endpoint 45.142.166[.]112 followed by HTTP POSTs to URIs “/8891431c” and “/ba12b866” on February 15, 2023.

The device in question continued to connect to the endpoint and make HTTP POST connections to various URIs relating to PlugX. Additionally, the user agent `Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36` was again detected for these connections. Figure 6 details the activity captured by Darktrace’s Cyber AI Analyst.

Figure 6: The image above showcases activity captured by Darktrace’s AI Analyst for PlugX connections made on February 15, 2023.

Darktrace detected that during these connections, the device in question attempted to download a suspicious file named only with numbers. The use of numeric file names is a technique often used by threat actors to obfuscate the download of malicious files or programs and bypass traditional security tools. Darktrace understood that the download of a numeric file, coupled with the use of an anomalous new user agent, mean the incident should be treated with suspicion. Fortunately, Darktrace RESPOND was enabled in autonomous response mode during this attack, meaning it was able to automatically block the device from downloading the file, or any other files, from the suspicious external location for a two-hour period, potentially preventing the download of PlugX’s malicious tooling.

Conclusion

Amid the continued evolution of PlugX from an espionage tool to a more widely available malware, it is essential that threat detection does not rely on a set of characteristics or indicators, but rather is focused on anomalies. Throughout these cases, Darktrace demonstrated the efficacy of its detection and alerting on emerging activity pertaining to a particularly stealthy and versatile RAT. Over the years, PlugX has continually looked to evolve and survive in the ever-changing threat landscape by adapting new capabilities and TTPs through which it can infect a system and spread to new devices without being noticed by security teams and their tools.

However, Darktrace’s Self-Learning AI allows it to gain a strong understanding of customer networks, learning what constitutes expected network behavior which in turn allows it to recognize the subtle deviations indicative of an ongoing compromise.

Darktrace’s ability to identify emerging threats through anomaly-based detection, rather than relying on established threat intelligence, uniquely positions it to detect and respond to highly adaptable and dynamic threats, like the PlugX malware, regardless of how it may evolve in the future.

Credit to: Nahisha Nobregas, SOC Analyst & Dylan Hinz, Cyber Analyst

Appendices

MITRE ATT&CK Framework

Execution

  • T1059.003 Command and Scripting Interpreter: Windows Command Shell

Persistence and Privilege Escalation

  • T1547.001 Boot or Logon AutoStart Execution: Registry Run Keys / Startup Folder
  • T1574.001 Hijack Execution Flow: DLL Search Order Hijacking
  • T1574.002 Hijack Execution Flow: DLL Side-Loading
  • T1543.003 Create or Modify System Process: Windows Service
  • T1140 Deobfuscate / Decode Files or Information
  • T1083 File and Directory Discovery

Defense Evasion

  • T1564.001 Hide Artifacts: Hidden Files and Directories
  • T1036.004 Masquerading: Task or Service
  • T1036.005 Masquerading: Match Legitimate Name or Location
  • T1027.006 Obfuscated Files or Information: HTML Smuggling

Credential Access

  • T1056.001 Input Capture: Keylogging

Collection

  • T1105 Ingress Tool Transfer

Command and Control

  • T1573.001 Encrypted Channel: Symmetric Cryptography
  • T1070.003 Mail Protocols
  • T1071.001 Web Protocol

DETECT Model Breaches

  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / New User Agent Followed By Numeric File Download
  • Anomalous Connection / Possible Callback URL

Indicators of Compromise (IoCs)

IoC - Type - Description + Confidence

45.142.166[.]112 - IP - PlugX C2 Endpoint / moderate - high

103.56.53[.]46 - IP - PlugX C2 Endpoint / moderate - high

Mozilla/5.0 (Windows NT 10.0;Win64;x64)AppleWebKit/537.36 - User Agent - PlugX User Agent / moderate – high

/8891431c - URI - PlugX URI / moderate-high

/ba12b866 - URI - PlugX URI / moderate -high

References

1. https://www.crowdstrike.com/blog/dll-side-loading-how-to-combat-threat-actor-evasion-techniques/

2. https://unit42.paloaltonetworks.com/plugx-variants-in-usbs/

3. https://news.sophos.com/en-us/2023/03/09/border-hopping-plugx-usb-worm/

4. https://thehackernews.com/2023/07/chinese-hackers-use-html-smuggling-to.html

5. https://www.cyfirma.com/outofband/html-smuggling-a-stealthier-approach-to-deliver-malware/

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
Nahisha Nobregas
SOC Analyst

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June 24, 2026

From Click to Command: Behavioral Detection of AppleScript-Led MacOS Intrusions

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Introduction

Darktrace’s Threat Research team is publishing this analysis to help defenders understand an active pattern of macOS tradecraft observed in multiple customer environments. This post summarizes the behaviors observed, how they were assessed, and what defenders can do now.

Across multiple environments, Darktrace observed a consistent MacOS intrusion pattern beginning with ClickFix-style user-assisted “update” execution and transitioning into AppleScript-driven post-compromise activity and sustained outbound signaling.

While individual indicators were low-confidence, the repeated convergence of weak behavioral signals — including HTTP POST beaconing, rare or IP-only destinations, SSL anomalies, and abnormal client characteristics — provided a defensible indication of command-and-control establishment Darktrace detection and response in these cases was driven by behavior over artifacts. In the highest-confidence instances, automated containment disrupted outbound signaling before sustained tasking could occur.

Background

ClickFix-style activity typically relies on user-assisted execution and plausible “update” pretexting, followed by post-execution use of native tools to keep the footprint light. In MacOS environments, AppleScript and other built-in scripting mechanisms enable flexible post-compromise workflows while minimizing stable file-based indicators.

Following execution, affected devices exhibited a consistent behavioral pattern. AppleScript or equivalent native scripting activity was observed initiating follow-on workflows, after which outbound communications began to establish a structured rhythm.

These communications were characterized by repeated HTTP POST requests to low-prevalence or IP-only endpoints, often combined with unusual SSL properties and client identifiers that diverged from baseline device behavior. Individually, these signals were weak. When correlated across time and devices, they formed a pattern consistent with control establishment rather than benign software activity.

In higher-confidence cases, Autonomous Response actions were able to reduce or halt outbound signaling, interrupting the attacker’s ability to maintain control.

Detection Timeline

In representative cases, the sequence unfolded as follows:

Stage 1 – Initial Execution

Initial activity began with suspicious or masqueraded execution on a MacOS endpoint, consistent with ClickFix-style user deception.

Stage 2 – Post-Execution Scripting

This was followed closely by native scripting activity, most commonly AppleScript, indicating the transition into post-execution workflow.

Stage 3 – Outbound Communications

Outbound communications then emerged, initially sporadic but quickly forming a consistent cadence of HTTP POST requests to rare external endpoints.

Stage 4 – Anomaly Convergence

As activity persisted, additional anomalies became visible — unusual SSL characteristics, abnormal user agents, and connections to infrastructure with no prior network prevalence.

Stage 5 – Autonomous Response

In the most mature stages of the activity, automated containment actions disrupted outbound communications on affected devices, limiting the attacker’s ability to continue tasking while investigations progressed.

Darktrace coverage and detections

The following use-case highlights systems likely affected by malicious macOS intrusion activity linked by Microsoft to the Democratic People’s Republic of Korea (DPRK) [1], with indications of suspicious behavior observed between March 1 and May 3, 2026. The activity overlaps with patterns described in recent reporting on DPRK-nexus MacOS intrusions [1], though attribution confidence in this case remains moderate and based on behavioral alignment rather than solely infrastructure linkage.

Analyst confidence emerged through the correlation of multiple weak signals across time and devices. This included model coverage for rare external communications, sustained beaconing patterns, repeated HTTP POSTs, and anomalous client characteristics. Where enabled, Autonomous Response actions disrupted the most active outbound paths to reduce the attacker’s ability to maintain control while Darktrace’s investigation continued.

Notably, this highly anomalous behavior included:

  • Outbound connections to the rare external endpoint, zoom[.]uswebob[.]us associated with IP address, 148.72.73[.]98 [2][3] over port 443
  • Outbound connections to the rare external endpoint, check02id[.]com associated with IP address, 83.136.210[.]180 [4] over port 7365
  • Outbound connections to the rare external endpoints, 104.145.210[.]107 [5] over port 8443 and 83.136.208[.]48 [6] over port 443
  • Outbound connections to the rare external endpoint, 83.136.208[.]246 [7] over port 6783 with observed URI `/api/daemon` and a PowerShell user agent

Darktrace’s detection initially highlighted a desktop device (running MacOS) engaging in anomalous behavior as early as March 12, 2026. Starting on March 12, the source device triggered a ‘Possible Doppelganger Attack’ alert including connectivity to the hostname "zoom[.]uswebob[.]us · 148.72.73[.]98" over port 443 (TCP, HTTPS, H2). This model highlights a device connecting to a location that is rare but masquerades as legitimate software, such as Zoom in this case, a commonly used technique to blend into expected traffic [2] [3].

 Initial connectivity observed to the rare external hostname, zoom[.]uswebob[.]us · 148.72.73[.]98, over port 443.
Figure 1: Initial connectivity observed to the rare external hostname, zoom[.]uswebob[.]us · 148.72.73[.]98, over port 443.

This was followed roughly seven later by a connection to 104.145.210[.]107 over port 8443, during which approximately 250 KiB of data of inbound data and 30 MiB of outbound data was observed, triggering the ‘Unusual Activity / Unusual External Data to New Endpoint’ in Darktrace.

Quickly after this connection, Darktrace’s Autonomous Response intervened, blocking the device’s access to the unusual external location and halting the data exfiltration attempt.

Figure 2: Darktrace’s detection of unusual data exfiltration, shortly followed by an Autonomous Response action to block it.

The device continued to consistently trigger model alerts relating to unusual external connectivity, including 'Posting HTTP to IP Without Hostname', 'Anomalous Connection / Rare External SSL Self-Signed' alerts, until well after 3 PM that day.

Figure 3: Additional external connectivity to new IP without a hostname, including connectivity to 83.136.208[.]246, alongside an anomalous ‘curl/8.7.1’ user agent and ‘/api/daemon’ URI.
Figure 4: Continued external SSL connectivity to IP 83.136.208[.]48, including connectivity to 83.136.208[.]246, alongside an anomalous ‘curl/8.7.1’ user agent and ‘/api/daemon’ URI.
Figure 5: Continued external HTTP connectivity to hostname, check02id[.]com · 83.136.210[.]180, alongside an anomalous ‘Go-http-client/1,1’ user agent.

From March 13 to March 28, the device continued exhibit unusual connectivity to various endpoints (e.g., 83.136.208[.]48, 83.136.208[.]246, check02id[.]com · 83.136.210[.]180), with the 'Multiple HTTP POSTs to Rare Hostname' model consistently triggering.

Windows OS Case

Pivoting over to an additional device, this time running Windows OS, anomalous behavior was also observed between March 30 and April 20. Notably, on March 30, the device was observed making a large number of suspicious external connection attempts to 83.136.208[.]246 over port 6783, all of which failed.

A further indicator was observed on April 1 with PowerShell connectivity to the same rare endpoint (83.136.208[.]246, port 6783), using the URI '/api/daemon' and the user agent 'Mozilla/5.0 (Windows NT; Windows NT 10.0; fr-FR) WindowsPowerShell/5.1.26100.7920'.  Additional alerts included 'New User Agent to IP Without Hostname' and 'Anomalous Github Download', alongside activity involving the same endpoint.

Figure 6 : ‘Anomalous Powershell to Rare External Destination’ and ‘Github Download’ model alerts. This behavior involved connectivity with the endpoints ‘83.136.208[.]246’ and ‘github[.]com’.

The device continued triggering 'Posting HTTP to IP Without Hostname' & 'PowerShell to External Rare' alerts between April 4 and April 20 across multiple related endpoints (i.e., 83.136.208[.]48, 83.136.208[.]246, check02id[.]com · 83.136.210[.]180).

Darktrace’s Autonomous Response capability was able to block suspicious PowerShell attempts to unusual external locations, as shown below in an example from April 20.

Figure 7:  Autonomous Response intervening to block an unusual PowerShell connection to an external destination.

Cyber AI Analyst investigations

In higher-confidence instances, Darktrace’s Cyber AI Analyst investigations helped connect otherwise separate model alerts into a single incident narrative, highlighting the attacker’s progression from post-execution scripting into sustained outbound signaling. This contextual stitching is particularly valuable in macOS scenarios where static artefacts are limited, and behavioral sequencing defines the intrusion.

Cyber AI Analyst investigations highlighted alerts on March 12, including unusual repeated connections and possible SSL command-and-control (C2) to multiple endpoints:

Figure 8: Cyber AI Analyst investigation linking events into a unified incident.

Autonomous Response

In addition to the containment actions detailed earlier, Autonomous Response implemented multiple additional measures to contain suspicious activity throughout the course of this attack. Whenever unusual external connectivity was detected, Darktrace blocked it, closing down potential C2 channels. Likewise, when data exfiltration attempts were identified, these connections were stopped to prevent the potential loss of sensitive data.

Figure 9: Autonomous Response actions implemented by Darktrace in response to suspicious connectivity in mid-March.

Furthermore, in cases where a device was deemed to have carried out a significant number of anomalous activities, Darktrace enforced a “pattern of life” on the device, preventing it from deviating from its expected behavior while allowing legitimate business operations to continue uninterrupted.

Figure 10: Autonomous Response actions implemented by Darktrace in response to suspicious connectivity in April, including the “Enforce Pattern of Life” action.

Conclusion

macOS intrusion tradecraft continues to shift toward native tooling and lightweight control channels designed to evade signature-led controls.

The repeated convergence of rare destinations, POST-based signaling, and anomalous client behavior — observed across time and across devices — provided sufficient evidence to act early and with confidence.

As macOS tradecraft continues to evolve, the defender advantage increasingly lies not in signatures, but in the ability to reason from behavior.

Credit to Justin Torres (Senior Cyber Analyst), Nathaniel Jones (VP, Security & AI Strategy, FCISO)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Alert Coverage:

/ NETWORK-based model alerts:

·       Anomalous Connection::Multiple HTTP POSTs to Rare Hostname

·       Anomalous Connection::Rare External SSL Self-Signed

·       Anomalous Connection::Powershell to Rare External

·       Anomalous Connection::New User Agent to IP Without Hostname

·       Anomalous Connection::Posting HTTP to IP Without Hostname

·       Compromise::Fast Beaconing to DGA

·       Compromise::Large Number of Suspicious Failed Connections

·       Device::Anomalous Github Download

·       Device::New PowerShell User Agent

·       Unusual Activity::Unusual External Data to New Endpoint

/ NETWORK-based Autonomous Response model alerts:

·       Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block

·       Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach

·       Antigena / Network::Significant Anomaly::Antigena Breaches Over Time Block

Indicators of Compromise (IoCs)

IP/Hostname:

·       zoom[.]uswebob[.]us · 148.72.73[.]98

·       83.136.208[.]246

·       check02id[.]com · 83.136.210[.]180

·       83.136.208[.]48

·       104.145.210[.]107

URIs:

·       /api/daemon

Destination Port Usage:

·       6783

·       5202

·       443

·       7365

·       8443

ASN:

·       AS400897 PETROSKY

·       AS398256 AS-ULTAHOST

User agents:

·       Mozilla/5.0 (Windows NT; Windows NT 10.0; fr-FR) WindowsPowerShell/5.1.26100.7920

·       Go-http-client/1.1

·       curl/8.7.1

MITRE ATT&CK Mapping

(Technique Name - Tactic - ID - Sub-Technique of)

·       Browser Session Hijacking - COLLECTION - T1185

·       Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

·       Install Digital Certificate - RESOURCE DEVELOPMENT - T1608.003 - T1608

·       PowerShell - EXECUTION - T1059.001 - T1059

·       Domain Generation Algorithms - COMMAND AND CONTROL - T1568.002 - T1568

·       Non-Standard Port - COMMAND AND CONTROL - T1571

·       Malware - RESOURCE DEVELOPMENT - T1588.001 - T1588

·       Web Service - COMMAND AND CONTROL - T1102

·       Code Repositories - COLLECTION - T1213.003 - T1213

·       Exploitation of Remote Services - LATERAL MOVEMENT - T1210

·       Exfiltration Over C2 Channel - EXFILTRATION - T1041

·       Exfiltration to Cloud Storage - EXFILTRATION - T1567.002 - T1567

References:

[1] https://www.microsoft.com/en-us/security/blog/2026/04/16/dissecting-sapphire-sleets-macos-intrusion-from-lure-to-compromise/

[2] https://radar.securityalliance.org/advisory-on-dprk-unc1069-fake-microsoft-teams-and-zoom-calls/

[3] https://www.virustotal.com/gui/domain/uswebob.us

[4] https://www.virustotal.com/gui/ip-address/83.136.210.180/community

[5] https://www.virustotal.com/gui/ip-address/104.145.210.107/community

[6] https://www.virustotal.com/gui/ip-address/83.136.208.48/community

[7] https://www.virustotal.com/gui/ip-address/83.136.208.246/community

[8] https://www.darktrace.com/blog/applescript-abuse-unpacking-a-macos-phishing-campaign

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About the author
Justin Torres
Cyber Analyst

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June 24, 2026

A New Security Challenge: The Curious Case of Prompt Language Analysis

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Why prompt analysis is emerging as a key AI security challenge

If securing AI has been one of the defining cybersecurity conversations of the past year, prompt analysis is quickly becoming one of its most interesting frontiers.

Security leaders are under pressure to understand how AI is being used across the business. In some organizations, that means governing employee use of chatbots. In others, it means overseeing copilots embedded into SaaS platforms, monitoring coding assistants, or assessing the growing footprint of autonomous agents. However different these use cases may appear on the surface, they share a common factor: humans and machines are usually interacting with enterprise systems through language.  

How prompt language differs from traditional security telemetry

For years, defenders have become used to working with familiar forms of telemetry: email traffic, network connections, API calls, endpoint processes, authentication events. Prompt language is different. It is not simply another log source. It is an expression of intent, instruction, curiosity, urgency, and sometimes manipulation. It reflects the end-goal of a user or agent, but not always with enough surrounding context to interpret the risk correctly.

Why existing security approaches only partially explain prompt risk

A growing number of vendors are approaching the task of securing AI from the angle they know best. Perimeter vendors are extending web or browser controls into AI usage. Identity vendors are emphasizing agent permissions and access governance. Data security and DLP providers are focusing on content inspection and exfiltration risk. All of these perspectives matter, but individually can’t fully explain the problem.

The challenge with securing AI is not just that a new application category has emerged. It is that language has become a new operating layer in the enterprise.

Employees now use prompts to summarize documents, generate code, analyze spreadsheets, query internal knowledge, and trigger multi-step actions through agents. In each case, prompt language acts as the interface between human intent and machine execution. That makes prompts incredibly valuable from a security perspective as they can hint at misuse, policy violations, data exposure, or attempts to circumvent controls. However, they can also be deeply ambiguous when viewed in isolation. That ambiguity is the heart of the issue.

Prompts as behavioral signals, not just text to classify

A prompt by itself tells you what was asked. It does not necessarily tell you whether the request is expected, risky, accidental, or entirely legitimate in context. Two nearly identical prompts can carry very different meanings depending on the role and function of who issued them, what systems they can access, and what actions followed. In other words, prompts are not just text to classify. They are behavioral signals to interpret.

Example: How context changes prompt risk entirely

Consider a common enterprise scenario. An employee is pulled into a new project with an aggressive deadline. Almost overnight, their use of AI tools spikes. They begin prompting more frequently, working across unfamiliar documents, querying new data sources, and interacting with more systems than usual to accelerate delivery. Viewed narrowly, this may look suspicious. Prompt volume increases, file access patterns change, API and SaaS activity rise. From some vantage points, it may resemble insider risk or unmanaged AI usage.

But now add context. Imagine that, earlier that day, the employee received instructions from a senior leader asking them to support a time-sensitive initiative. Their communication history shows that this leader is a legitimate reporting-line superior. Their recent collaboration patterns align with the new project team. Their subsequent activity, while unusual for that individual’s baseline, is consistent with the business task they were assigned.

What initially looked like a risk event may actually be a normal response to business pressure. Without the surrounding context of communication, organizational relationships, and broader behavioral patterns, prompt activity alone could generate more noise than insight.

The reverse is also true. A prompt may appear benign on the surface while the context around it suggests elevated risk. A request that seems routine could originate from a compromised user, a newly connected external agent, a shadow AI workflow, or a user acting outside their normal role. The language itself may not contain anything obviously malicious, but the surrounding conditions may tell a very different story.

What security teams need to analyze prompts effectively

The future of prompt analysis is not just about understanding language. It is about understanding language in context.

To do that well, security teams need more than prompt inspection. They need to understand:

  • Who is issuing the prompt, whether human or agent
  • How that identity normally behaves across the enterprise
  • What systems, data, and workflows are connected to the interaction
  • Which relationships and communications explain the surrounding activity
  • Whether the downstream actions align with expected business behavior

When those layers are absent, prompt analysis can become another isolated control surface: useful in theory, but limited in practice. Security teams may detect unusual wording but miss the operational function behind it, overreact to benign changes in behavior, or miss subtle misuse because the prompt itself did not appear dangerous.

How organizations should think about prompt analysis going forward

Security teams have seen this pattern before. In the cloud, posture without runtime context left important gaps. In identity, access control without behavioral understanding missed misuse that looked legitimate on paper. In data security, content inspection without business context often created friction without resolving risk. AI is exposing the same lesson again: controls are strongest when they are coordinated, not isolated. As organizations work to secure AI and identify gaps across their security operations, prompt analysis will become an increasingly important source of insight, but only as part of a broader strategy.

Prompt analysis will undoubtedly become more common, as prompts are one of the clearest windows into how people and agents are using AI systems. However, what matters most is not simply collecting prompts or filtering dangerous phrases, but being able to place that language inside a wider behavioral and operational picture.

Organizations that already have a broader understanding of how work gets done across the enterprise will be better positioned to make sense of prompt language as this category matures. They will be better able to distinguish urgency from abuse, experimentation from exfiltration, and productive AI adoption from hidden risk.

Figure 1: Darktrace / SECURE AI reconstructs the full sequence of events, showing every user and agent interaction in context, with risky prompts highlighted and categorized, including PII, sensitive data, and other policy violations.

At Darktrace, this is the key lesson emerging from the market: prompt language does matter, but it does not stand alone. It is most valuable when treated as a new behavioral input that can enrich understanding across the enterprise, not as a self-contained source of truth.

Why prompts become less useful when analyzed in isolation

The curious case of prompt language analysis, then, is this: the more important prompts become, the less useful they are in a vacuum.

The real opportunity is not just to see what was asked. It is to understand why it was asked, what it meant in that moment, and what happened next.

For a deeper look at how organizations are approaching this challenge from the strengths of prompt analysis to its limitations in isolation see Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches, which expands on the role prompt-level controls play within a broader, context-driven security strategy.

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About the author
Nabil Zoldjalali
VP, Field CISO
Your data. Our AI.
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