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July 18, 2023

How Darktrace SOC Thwarted a BEC Attack

Discover how Darktrace's SOC detected and stopped a Business Email Compromise in a customer's SaaS environment.
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
Nicole Wong
Cyber Security Analyst
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18
Jul 2023

What is Business Email Compromise (BEC)?

Business Email Compromise (BEC) is the practice of tricking an organization into transferring funds or sensitive data to a malicious actor.

Although at face value this type of attack may not carry the same gravitas as the more blockbuster, cloak-and-dagger type of attack such as ransomware [1], the costs of BEC actually dwarf that of ransomware [2]. Moreover, among UK organizations that reported a cyber breach in 2023, attacks related to BEC – namely phishing attacks, email impersonation, attempted hacking of online back accounts, and account takeover – were reported as the most disruptive, ahead of ransomware and other types of cyber-attack [3].  

What makes a BEC attack successful?

BEC attacks are so successful and damaging due to the difficulty of detection for traditional security systems, along with their ease of execution.  BEC does not require much technical sophistication to accomplish; rather, it exploits humans’ natural trust in known correspondents, via a phishing email for example, to induce them to perform a certain action.

How does a BEC attack work?

BEC attacks typically begin with a phishing email to an employee of an organization. Traditional email gateways may be unable to block the initial phishing email, as the email often appear to have been sent by a known correspondent, or it may contain minimal payload content.

The recipient’s interaction with the initial phishing email will likely result in the attacker gaining access to the user’s identity. Once access is obtained, the attacker may abuse the identity of the compromised user to obtain details of the user’s financial relations to the rest of the organization or its customers, eventually using these details to conduct further malicious email activity, such as sending out emails containing fraudulent wire transfer requests.  Today, the continued growth in adoption of services to support remote working, such as cloud file storage and sharing, means that the compromise of a single user’s email account can also grant access to a wide range of corporate sensitive information.

How to protect against BEC attacks

The rapid uptake of cloud-based infrastructure and software-as-a-service (SaaS) outpaces the adoption of skills and expertise required to secure it, meaning that security teams are often less prepared to detect and respond to cloud-based attacks.  

Alongside the adoption of security measures that specialize in anomaly-based detection and autonomous response, like Darktrace DETECT™ and Darktrace RESPOND™, it is extremely beneficial for organizations to have an around the clock security operations center (SOC) in place to monitor and investigate ongoing suspicious activity as it emerges.

In June 2023, Darktrace’s SOC alerted a customer to an active BEC attack within their cloud environment, following the successful detection of suspicious activity by Darktrace’s AI, playing a fundamental role in thwarting the attack in its early stages.

Darktrace Mitigates BEC Attack

Figure 1: Screenshot of the SaaS Console showing location information for the compromised SaaS account.  The ability to visualize the distance between these two locations enables a SOC Analyst to deduce that the simultaneous activity from London and Derby may represent impossible travel’.

It was suspected the attack began with a phishing email, as on the previous day the user had received a highly anomalous email from an external sender with which the organization had not previously communicated. However, the customer had configured Darktrace/Email™ in passive mode, which meant that Darktrace was not able to carry out any RESPOND actions on this anomalous email to prevent it from landing in the user’s inbox. Despite this, Darktrace/Apps was able to instantly detect the subsequent unusual login to the customer’s SaaS environment; its anomaly-based approach to threat detection allowed it to recognize the anomalous behavior even though the malicious email had successfully reached the user.

Following the anomalous ExpressVPN login, Darktrace detected further account anomalies originating from another ExpressVPN IP (45.92.229[.]195), as the attacker accessed files over SharePoint.  Notably, Darktrace identified that the logins from ExpressVPN IPs were performed with the software Chrome 114, however, activity from the legitimate account owner prior to these unusual logins was performed using the software Chrome 102. It is unusual for a user to be using multiple browser versions simultaneously, therefore in addition to the observed impossible travel, this further implied the presence of different actors behind the simultaneous account activity.

Figure 2: Screenshot of the Event Log for the compromised SaaS account, showing simultaneous login and file access activity on the account from different browser versions, and thus likely from different devices.

Darktrace identified that the files observed during this anomalous activity referenced financial information and personnel schedules, suggesting that the attacker was performing internal reconnaissance to gather information about sensitive internal company procedures, in preparation for further fraudulent financial activity.

Although the actions taken by the attacker were mostly passive, Darktrace/Apps chained together the multiple anomalies to understand that this pattern of activity was indicative of movement along the cyber kill chain. The multiple model breaches generated by the ongoing unusual activity triggered an Enhanced Monitoring model breach that was escalated to Darktrace’s SOC as the customer had subscribed to Darktrace’s Proactive Threat Notification (PTN) service.  Enhanced Monitoring models detect activities that are more likely to be indicative of compromise.  

Subsequently, Darktrace’s SOC triaged the activity detected on the SaaS account and sent a PTN alert to the customer, advising urgent follow up action.  The encrypted alert contained relevant technical details of the incident that were summarized by an expert Darktrace Analyst, along with recommendations to the customer’s internal SOC team to take immediate action.  Upon receipt and validation of the alert, the customer used Darktrace RESPOND to perform a manual force logout and block access from the external ExpressVPN IP.

Had Darktrace RESPOND been enabled in autonomous response mode, it would have immediately taken action to disable the account after ongoing anomalies were detected from it. However, as the customer only had RESPOND configured in the manual human confirmation model, the expertise of Darktrace’s SOC team was critical in enabling the customer to react and prevent further escalation of post-compromise activity.  Evidence of further attempts to access the compromised account were observed hours after RESPOND actions were taken, including failed login attempts from another rare external IP, this time associated with the VPN service NordVPN.

Figure 3: Timeline of attack and response actions from Darktrace SOC and Darktrace RESPOND.

Because the customer had subscribed to Darktrace’s PTN service, they were able to further leverage the expertise of Darktrace’s global team of cyber analysts and request further analysis of which files were accessed by the legitimate account owner versus the attacker.  This information was shared securely within the same Customer Portal ticket that was automatically opened on behalf of the customer when the PTN was alerted, allowing the customer’s security team to submit further queries and feedback, and request assistance to further investigate this alert within Darktrace. A similar service called Ask the Expert (ATE) exists for customers to draw from the expertise of Darktrace’s analysts at any time, not just when PTNs are alerted.

Conclusion

The growing prevalence and impact of BEC attacks amid the shift to cloud-based infrastructure means that already stretched internal security teams may not have the sufficient human capacity to detect and respond to these threats.

Darktrace’s round-the-clock SOC thwarted a BEC attack that had the potential to result in significant financial and reputational damage to the legal services company, by alerting the customer to high priority activity during the early stages of the attack and sharing actionable insights that the customer could use to prevent further escalation.  Following the confirmed compromise, the support and in-depth analysis provided by Darktrace’s SOC on the files accessed by the attacker enabled the customer to effectively report this breach to the Information Commissioner’s Office, to maintain compliance with UK data protection regulations. [4].  

Although the attacker used IP addresses that were local to the customer’s country of operations and did not perform overtly noisy actions during reconnaissance, Darktrace was able to identify that this activity deviated from the legitimate user’s typical pattern of life, triggering model breaches at each stage of the attack as it progressed from initial access to internal reconnaissance. While Darktrace RESPOND triggered an action that would have prevented the attack autonomously, the customer’s configuration meant that Darktrace’s SOC had an even more significant role in alerting the customer directly to take manual action.

Credit to: Sam Lister, Senior Analyst, for his contributions to this blog.

Appendices

Darktrace DETECT/Apps Models Breached:

  • SaaS / Access / Unusual External Source for SaaS Credential Use
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active
  • SaaS / Unusual Activity / Activity from Multiple Unusual IPs
  • SaaS / Unusual Activity / Multiple Unusual SaaS Activities
  • SaaS / Access / Suspicious Login Attempt
  • SaaS / Compromise / SaaS Anomaly Following Anomalous Login (Enhanced Monitoring Model)

Darktrace RESPOND/Apps Models Breached:

  • Antigena / SaaS / Antigena Unusual Activity Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Tactic Techniques
Reconnaissance • T1598 – Phishing for Information
Initial Access • T1078.004 – Valid Accounts: Cloud Accounts
Collection • T1213.002 – Data from Information Repositories: Sharepoint

References

[1] Rand, D. (2022, November 10). Why Business Email Compromise Costs Companies More Than Ransomware Attacks. Retrieved from Tanium: https://www.tanium.com/blog/whybusiness-email-compromise-costs-companies-more-than-ransomware-attacks/

[2] Federal Bureau of Investigation. (2022). 2022 IC3 Report. Retrieved from IC3.gov: https://www.ic3.gov/Media/PDF/AnnualReport/2022_IC3Report.pdf

[3] Department for Science, Innovation & Technology. (2023, April 19). Cyber security breaches survey 2023. Retrieved from gov.uk: https://www.gov.uk/government/statistics/cyber-security-breaches-survey-2023/cybersecurity-breaches-survey-2023

[4] ICO. (2023). Personal data breaches: a guide. Retrieved from Information Commissioner's Office: https://ico.org.uk/for-organisations/report-a-breach/personal-data-breach/personal-data-breaches-a-guide/#whatbreachesdo

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
Nicole Wong
Cyber Security 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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