November 7, 2022

[Part 1] Analysis of a Raccoon Stealer v1 Infection

Darktrace’s SOC team observed a fast-paced compromise involving Raccoon Stealer v1. See which steps the Raccoon Stealer v1 took to extract company data!

Written by

Mark Turner

SOC Shift Supervisor

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

Mark Turner

SOC Shift Supervisor

Written by

Sam Lister

Specialist Security Researcher

Nov 2022

Introduction

Towards the end of March 2022, the operators of Raccoon Stealer announced the closure of the Raccoon Stealer project [1]. In May 2022, Raccoon Stealer v2 was unleashed onto the world, with huge numbers of cases being detected across Darktrace’s client base. In this series of blog posts, we will follow the development of Raccoon Stealer between March and September 2022. We will first shed light on how Raccoon Stealer functioned before its demise, by providing details of a Raccoon Stealer v1 infection which Darktrace’s SOC saw within a client network on the 18^th March 2022. In the follow-up post, we will provide details about the surge in Raccoon Stealer v2 cases that Darktrace’s SOC has observed since May 2022.

What is Raccoon Stealer?

The misuse of stolen account credentials is a primary method used by threat actors to gain initial access to target environments [2]. Threat actors have several means available to them for obtaining account credentials. They may, for example, distribute phishing emails which trick their recipients into divulging account credentials. Alternatively, however, they may install information-stealing malware (i.e, info-stealers) onto users’ devices. The results of credential theft can be devastating. Threat actors may use the credentials to gain access to an organization’s SaaS environment, or they may use them to drain users’ online bank accounts or cryptocurrency wallets.

Raccoon Stealer is a Malware-as-a-Service (MaaS) info-stealer first publicized in April 2019 on Russian-speaking hacking forums.

Figure 1: One of the first known mentions of Raccoon Stealer on a Russian-speaking hacking forum named ‘Hack Forums’ on the 13th April 2019

The team of individuals behind Raccoon Stealer provide a variety of services to their customers (known as ‘affiliates’), including access to the info-stealer, an easy-to-use automated backend panel, hosting infrastructure, and 24/7 customer support [3].

Once Raccoon Stealer affiliates gain access to the info-stealer, it is up to them to decide how to distribute it. Since 2019, affiliates have been observed distributing the info-stealer via a variety of methods, such as exploit kits, phishing emails, and fake cracked software websites [3]/[4]. Once affiliates succeed in installing Raccoon Stealer onto target systems, the info-stealer will typically seek to obtain sensitive information saved in browsers and cryptocurrency wallets. The info-stealer will then exfiltrate the stolen data to a Command and Control (C2) server. The affiliate can then use the stolen data to conduct harmful follow-up activities.

Towards the end of March 2022, the team behind Raccoon Stealer publicly announced that they would be suspending their operations after one of their core developers was killed during the Russia-Ukraine conflict [5].

Figure 2: Raccoon Stealer resignation post on March 25th 2022

Recent details shared by the US Department of Justice [6]/[7] indicate that it was in fact the arrest, rather than the death, of a key Raccoon Stealer operator which led the Raccoon Stealer team to suspend their operations [8].

The closure of the Raccoon Stealer project, which ultimately resulted from the FBI-backed dismantling of Raccoon Stealer’s infrastructure in March 2022, did not last long, with the completion of Raccoon Stealer v2 being announced on the Raccoon Stealer Telegram channel on the 17^th May 2022 [9].

Figure 3: Telegram post about new version of Raccoon Stealer

In the second part of this blog series, we will provide details of the recent surge in Raccoon Stealer v2 activity. In this post, however, we will provide insight into how the old version of Raccoon Stealer functioned just before its demise, by providing details of a Raccoon Stealer v1 infection which occurred on the 18^th March 2022.

Attack Details

On the 18^th March, at around 13:00 (UTC), a user’s device within a customer’s network was seen contacting several websites providing fake cracked software.

Figure 4: The above figure — obtained from the Darktrace Event Log for the infected device — highlights its connections to cracked software websites such as ‘licensekeysfree[.]com’ and ‘hdlicense[.]com’ before contacting ‘lion-files[.]xyz’ and ‘www.mediafire[.]com’

The user’s attempt to download cracked software from one of these websites resulted in their device making an HTTP GET request with a URI string containing ‘autodesk-revit-crack-v2022-serial-number-2022’ to an external host named ‘lion-filez[.]xyz’

Figure 5: Screenshot from hdlicense[.]com around the time of the infection shows a “Download” button linking to the ‘lion-filez[.]xyz’ endpoint

The device’s HTTP GET request to lion-filez[.]xyz was immediately followed by an HTTPS connection to the file hosting service, www.mediafire[.]com. Given that threat actors are known to abuse platforms such as MediaFire and Discord CDN to host their malicious payloads, it is likely that the user’s device downloaded the Raccoon Stealer v1 sample over its HTTPS connection to www.mediafire[.]com.

After installing the info-stealer sample, the user’s device was seen making an HTTP GET request with the URI string ‘/g_shock_casio_easy’ to 194.180.191[.]185. The endpoint responded to the request with data related to a Telegram channel named ‘G-Shock’.

Figure 6: Telegram channel ‘@g_shock_casio_easy’

The returned data included the Telegram channel’s description, which in this case, was a base64 encoded and RC4 encrypted string of characters [10]/[11]. The Raccoon Stealer sample decoded and decrypted this string of characters to obtain its C2 IP address, 188.166.49[.]196. This technique used by Raccoon Stealer v1 closely mirrors the espionage method known as ‘dead drop’ — a method in which an individual leaves a physical object such as papers, cash, or weapons in an agreed hiding spot so that the intended recipient can retrieve the object later on without having to come in to contact with the source. In this case, the operators of Raccoon Stealer ‘left’ the malware’s C2 IP address within the description of a Telegram channel. Usage of this method allowed the operators of Raccoon Stealer to easily change the malware’s C2 infrastructure.

After obtaining the C2 IP address from the ‘G-Shock’ Telegram channel, the Raccoon Stealer sample made an HTTP POST request with the URI string ‘/’ to the C2 IP address, 188.166.49[.]196. This POST request contained a Windows GUID, a username, and a configuration ID. These details were RC4 encrypted and base64 encoded [12]. The C2 server responded to this HTTP POST request with JSON-formatted configuration information [13], including an identifier string, URL paths for additional files, along with several other fields. This configuration information was also concealed using RC4 encryption and base64 encoding.

Figure 7- Fields within the JSON-formatted configuration data [13]

In this case, the server’s response included the identifier string ‘hv4inX8BFBZhxYvKFq3x’, along with the following URL paths:

/l/f/hv4inX8BFBZhxYvKFq3x/77d765d8831b4a7d8b5e56950ceb96b7c7b0ed70
/l/f/hv4inX8BFBZhxYvKFq3x/0cb4ab70083cf5985b2bac837ca4eacb22e9b711
/l/f/hv4inX8BFBZhxYvKFq3x/5e2a950c07979c670b1553b59b3a25c9c2bb899b
/l/f/hv4inX8BFBZhxYvKFq3x/2524214eeea6452eaad6ea1135ed69e98bf72979

After retrieving configuration data, the user’s device was seen making HTTP GET requests with the above URI strings to the C2 server. The C2 server responded to these requests with legitimate library files such as sqlite3.dll. Raccoon Stealer uses these libraries to extract data from targeted applications.

Once the Raccoon Stealer sample had collected relevant data, it made an HTTP POST request with the URI string ‘/’ to the C2 server. This posted data likely included a ZIP file (named with the identifier string) containing stolen credentials [13].

The observed infection chain, which lasted around 20 minutes, consisted of the following steps:

1. User’s device installs Raccoon Stealer v1 samples from the user attempting to download cracked software

2. User’s device obtains the info-stealer’s C2 IP address from the description text of a Telegram channel

3. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains a Windows GUID, a username, and a configuration ID. The response to the request contains configuration details, including an identifier string and URL paths for additional files

4. User’s device downloads library files from the C2 server

5. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains stolen data

Darktrace Coverage

Although RESPOND/Network was not enabled on the customer’s deployment, DETECT picked up on several of the info-stealer’s activities. In particular, the device’s downloads of library files from the C2 server caused the following DETECT/Network models to breach:

Anomalous File / Masqueraded File Transfer
Anomalous File / EXE from Rare External Location
Anomalous File / Zip or Gzip from Rare External Location
Anomalous File / EXE from Rare External Location
Anomalous File / Multiple EXE from Rare External Locations

Figure 8: Event Log for the infected device shows 'Anomalous File / Masqueraded File Transfer' model breach after the device's download of a library file from the C2 server

Since the customer was subscribed to the Darktrace Proactive Threat Notification (PTN) service, they were proactively notified of the info-stealer’s activities. The quick response by Darktrace’s 24/7 SOC team helped the customer to contain the infection and to prevent further damage from being caused. Having been alerted to the info-stealer activity by the SOC team, the customer would also have been able to change the passwords for the accounts whose credentials were exfiltrated.

If RESPOND/Network had been enabled on the customer’s deployment, then it would have blocked the device’s connections to the C2 server, which would have likely prevented any stolen data from being exfiltrated.

Conclusion

Towards the end of March 2022, the team behind Raccoon Stealer announced that they would be suspending their operations. Recent developments suggest that the arrest of a core Raccoon Stealer developer was responsible for this suspension. Just before the Raccoon Stealer team were forced to shut down, Darktrace’s SOC team observed a Raccoon Stealer infection within a client’s network. In this post, we have provided details of the network-based behaviors displayed by the observed Raccoon Stealer sample. Since these v1 samples are no longer active, the details provided here are only intended to provide historical insight into the development of Raccoon Stealer’s operations and the activities carried out by Raccoon Stealer v1 just before its demise. In the next post of this series, we will discuss and provide details of Raccoon Stealer v2 — the new and highly prolific version of Raccoon Stealer.

Thanks to Stefan Rowe and the Threat Research Team for their contributions to this blog.

References

[1] https://twitter.com/3xp0rtblog/status/1507312171914461188

[2] https://www.gartner.com/doc/reprints?id=1-29OTFFPI&ct=220411&st=sb

[3] https://www.cybereason.com/blog/research/hunting-raccoon-stealer-the-new-masked-bandit-on-the-block

[4] https://www.cyberark.com/resources/threat-research-blog/raccoon-the-story-of-a-typical-infostealer

[5] https://www.bleepingcomputer.com/news/security/raccoon-stealer-malware-suspends-operations-due-to-war-in-ukraine/

[6] https://www.justice.gov/usao-wdtx/pr/newly-unsealed-indictment-charges-ukrainian-national-international-cybercrime-operation

[7] https://www.youtube.com/watch?v=Fsz6acw-ZJY

[8] https://riskybiznews.substack.com/p/raccoon-stealer-dev-didnt-die-in

[9] https://medium.com/s2wblog/raccoon-stealer-is-back-with-a-new-version-5f436e04b20d

[10] https://blog.cyble.com/2021/10/21/raccoon-stealer-under-the-lens-a-deep-dive-analysis/

[11] https://decoded.avast.io/vladimirmartyanov/raccoon-stealer-trash-panda-abuses-telegram/

[12] https://blogs.blackberry.com/en/2021/09/threat-thursday-raccoon-infostealer

[13] https://cyberint.com/blog/research/raccoon-stealer/

Appendices

Specialist Security Researcher

Inside the SOC

Written by

Mark Turner

SOC Shift Supervisor

Written by

Sam Lister

Specialist Security Researcher

Watch the NIS2 Webinar

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Network

June 24, 2026

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

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].

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.

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

About the author

Justin Torres

Cyber Analyst

Blog

June 24, 2026

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

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.

About the author

Nabil Zoldjalali

VP, Field CISO

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

Why prompt analysis is emerging as a key AI security challenge

How prompt language differs from traditional security telemetry

Why existing security approaches only partially explain prompt risk

Prompts as behavioral signals, not just text to classify

Example: How context changes prompt risk entirely

What security teams need to analyze prompts effectively

How organizations should think about prompt analysis going forward

Why prompts become less useful when analyzed in isolation