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June 25, 2024

Following up on our Conversation: Detecting & Containing a LinkedIn Phishing Attack with Darktrace

Darktrace/Email detected a phishing attack that had originated from LinkedIn, where the attacker impersonated a well known construction company to conduct a credential harvesting attack on the target. Darktrace’s ActiveAI Security Platform played a critical role in investigating the activity and initiating real-time responses that were outside the physical capability of human security teams.
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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25
Jun 2024

Note: Real organization, domain and user names have been modified and replaced with fictitious names to maintain anonymity.  

Social media cyber-attacks

Social media is a known breeding ground for cyber criminals to easily connect with a near limitless number of people and leverage the wealth of personal information shared on these platforms to defraud the general public.  Analysis suggests even the most tech savvy ‘digital natives’ are vulnerable to impersonation scams over social media, as criminals weaponize brands and trends, using the promise of greater returns to induce sensitive information sharing or fraudulent payments [1].

LinkedIn phishing

As the usage of a particular social media platform increases, cyber criminals will find ways to exploit the increasing user base, and this trend has been observed with the rise in LinkedIn scams in recent years [2].  LinkedIn is the dominant professional networking site, with a forecasted 84.1million users by 2027 [3].  This platform is data-driven, so users are encouraged to share information publicly, including personal life updates, to boost visibility and increase job prospects [4] [5].  While this helps legitimate recruiters to gain a good understanding of the user, an attacker could also leverage the same personal content to increase the sophistication and success of their social engineering attempts.  

Darktrace detection of LinkedIn phishing

Darktrace detected a Software-as-a-Service (SaaS) compromise affecting a construction company, where the attack vector originated from LinkedIn (outside the monitoring of corporate security tools), but then pivoted to corporate email where a credential harvesting payload was delivered, providing the attacker with credentials to access a corporate file storage platform.  

Because LinkedIn accounts are typically linked to an individual’s personal email and are most commonly accessed via the mobile application [6] on personal devices that are not monitored by security teams, it can represent an effective initial access point for attackers looking to establish an initial relationship with their target. Moreover, user behaviors to ignore unsolicited emails from new or unknown contacts are less frequently carried over to platforms like LinkedIn, where interactions with ‘weak ties’ as opposed to ‘strong ties’ are a better predictor of job mobility [7]. Had this attack been allowed to continue, the threat actor could have leveraged access to further information from the compromised business cloud account to compromise other high value accounts, exfiltrate sensitive data, or defraud the organization.

LinkedIn phishing attack details

Reconnaissance

The initial reconnaissance and social engineering occurred on LinkedIn and was thus outside the purview of corporate security tools, Darktrace included.

However, the email domain “hausconstruction[.]com” used by the attacker in subsequent communications appears to be a spoofed domain impersonating a legitimate construction company “haus[.]com”, suggesting the attacker may have also impersonated an employee of this construction company on LinkedIn.  In addition to spoofing the domain, the attacker seemingly went further to register “hausconstruction.com” on a commercial web hosting platform.  This is a technique used frequently not just to increase apparent legitimacy, but also to bypass traditional security tools since newly registered domains will have no prior threat intelligence, making them more likely to evade signature and rules-based detections [8].  In this instance, open-source intelligence (OSINT) sources report that the domain was created several months earlier, suggesting this may have been part of a targeted attack on construction companies.  

Initial Intrusion

It was likely that during the correspondence over LinkedIn, the target user was solicited into following up over email regarding a prospective construction project, using their corporate email account.  In a probable attempt to establish a precedent of bi-directional correspondence so that subsequent malicious emails would not be flagged by traditional security tools, the attacker did not initially include suspicious links, attachments or use solicitous or inducive language within their initial emails.

Example of bi-directional email correspondence between the target and the attacker impersonating a legitimate employee of the construction company haus.com.
Figure 1: Example of bi-directional email correspondence between the target and the attacker impersonating a legitimate employee of the construction company haus.com.
Cyber AI Analyst investigation into one of the initial emails the target received from the attacker.
Figure 2: Cyber AI Analyst investigation into one of the initial emails the target received from the attacker.  

To accomplish the next stage of their attack, the attacker shared a link, hidden behind the inducing text “VIEW ALL FILES”, to a malicious file using the Hightail cloud storage service. This is also a common method employed by attackers to evade detection, as this method of file sharing does not involve attachments that can be scanned by traditional security tools, and legitimate cloud storage services are less likely to be blocked.

OSINT analysis on the malicious link link shows the file hosted on Hightail was a HTML file with the associated message “Following up on our LinkedIn conversation”.  Further analysis suggests the file contained obfuscated Javascript that, once opened, would automatically redirect the user to a malicious domain impersonating a legitimate Microsoft login page for credential harvesting purposes.  

The malicious HTML file containing obfuscated Javascript, where the highlighted string references the malicious credential harvesting domain.
Figure 3: The malicious HTML file containing obfuscated Javascript, where the highlighted string references the malicious credential harvesting domain.
Screenshot of fraudulent Microsoft Sign In page hosted on the malicous credential harvesting domain.
Figure 4: Screenshot of fraudulent Microsoft Sign In page hosted on the malicious credential harvesting domain.

Although there was prior email correspondence with the attacker, this email was not automatically deemed safe by Darktrace and was further analyzed for unusual properties and unusual communications for the recipient and the recipient’s peer group.  

Darktrace determined that:

  • It was unusual for this file storage solution to be referenced in communications to the user and the wider network
  • Textual properties of the email body suggested a high level of inducement from the sender, with a high level of focus on the phishing link.
  • The full link contained suspicious properties suggesting it is high risk.
Darktrace’s analysis of the phishing email, presenting key information about the unusual characteristics of this email, information on highlighted content, and an overview of actions that were initially applied.
Figure 5: Darktrace’s analysis of the phishing email, presenting key information about the unusual characteristics of this email, information on highlighted content, and an overview of actions that were initially applied.  

Based on these anomalies, Darktrace initially moved the phishing email to the junk folder and locked the link, preventing the user from directly accessing the malicious file hosted on Hightail.  However, the customer’s security team released the email, likely upon end-user request, allowing the target user to access the file and ultimately enter their credentials into that credential harvesting domain.

Darktrace alerts triggered by the malicious phishing email and the corresponding Autonomous Response actions.
Figure 6: Darktrace alerts triggered by the malicious phishing email and the corresponding Autonomous Response actions.

Lateral Movement

Correspondence between the attacker and target continued for two days after the credential harvesting payload was delivered.  Five days later, Darktrace detected an unusual login using multi-factor authentication (MFA) from a rare external IP and ASN that coincided with Darktrace/Email logs showing access to the credential harvesting link.

This attempt to bypass MFA, known as an Office365 Shell WCSS attack, was likely achieved by inducing the target to enter their credentials and legitimate MFA token into the fake Microsoft login page. This was then relayed to Microsoft by the attacker and used to obtain a legitimate session. The attacker then reused the legitimate token to log into Exchange Online from a different IP and registered their own device for MFA.

Screenshot within Darktrace/Email of the phishing email that was released by the security team, showing the recipient clicked the link to file storage where the malicious payload was stored.
Figure 7: Screenshot within Darktrace/Email of the phishing email that was released by the security team, showing the recipient clicked the link to file storage where the malicious payload was stored.

Event Log showing a malicious login and MFA bypass at 17:57:16, shortly after the link was clicked.  Highlighted in green is activity from the legitimate user prior to the malicious login, using Edge.
Figure 8: Event Log showing a malicious login and MFA bypass at 17:57:16, shortly after the link was clicked.  Highlighted in green is activity from the legitimate user prior to the malicious login, using Edge. Highlighted in orange and red is the malicious activity using Chrome.

The IP addresses used by the attacker appear to be part of anonymization infrastructure, but are not associated with any known indicators of compromise (IoCs) that signature-based detections would identify [9] [10].

In addition to  logins being observed within half an hour of each other from multiple geographically impossible locations (San Francisco and Phoenix), the unexpected usage of Chrome browser, compared to Edge browser previously used, provided Darktrace with further evidence that this activity was unlikely to originate from the legitimate user.  Although the user was a salesperson who frequently travelled for their role, Darktrace’s Self-Learning AI understood that the multiple logins from these locations was highly unusual at the user and group level, and coupled with the subsequent unexpected account modification, was a likely indicator of account compromise.  

Accomplish mission

Although the email had been manually released by the security team, allowing the attack to propagate, additional layers of defense were triggered as Darktrace's Autonomous Response initiated “Disable User” actions upon detection of the multiple unusual logins and the unauthorized registration of security information.  

However, the customer had configured Autonomous Response to require human confirmation, therefore no actions were taken until the security team manually approved them over two hours later. In that time, access to mail items and other SharePoint files from the unusual IP address was detected, suggesting a potential loss of confidentiality to business data.

Advanced Search query showing several FilePreviewed and MailItemsAccessed events from either the IPs used by the attacker, or using the software Chrome.  Note some of the activity originated from Microsoft IPs which may be whitelisted by traditional security tools.
Figure 9: Advanced Search query showing several FilePreviewed and MailItemsAccessed events from either the IPs used by the attacker, or using the software Chrome.  Note some of the activity originated from Microsoft IPs which may be whitelisted by traditional security tools.

However, it appears that the attacker was able to maintain access to the compromised account, as login and mail access events from 199.231.85[.]153 continued to be observed until the afternoon of the next day.  

Conclusion

This incident demonstrates the necessity of AI to security teams, with Darktrace’s ActiveAI Security Platform detecting a sophisticated phishing attack where human judgement fell short and initiated a real-time response when security teams could not physically respond as fast.  

Security teams are very familiar with social engineering and impersonation attempts, but these attacks remain highly prevalent due to the widespread adoption of technologies that enable these techniques to be deployed with great sophistication and ease.  In particular, the popularity of information-rich platforms like LinkedIn that are geared towards connecting with unknown people make it an attractive initial access point for malicious attackers.

In the second half of 2023 alone, over 200 thousand fake profiles were reported by members on LinkedIn [11].  Fake profiles can be highly sophisticated, use professional images, contain compelling descriptions, reference legitimate company listings and present believable credentials.  

It is unrealistic to expect end users to defend themselves against such sophisticated impersonation attempts. Moreover, it is extremely difficult for human defenders to recognize every fraudulent interaction amidst a sea of fake profiles. Instead, defenders should leverage AI, which can conduct autonomous investigations without human biases and limitations. AI-driven security can ensure successful detection of fraudulent or malicious activity by learning what real users and devices look like and identifying deviations from their learned behaviors that may indicate an emerging threat.

Appendices

Darktrace Model Detections

DETECT/ Apps

SaaS / Compromise / SaaS Anomaly Following Anomalous Login

SaaS / Compromise / Unusual Login and Account Update

SaaS / Unusual Activity / Multiple Unusual External Sources For SaaS Credential

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Compliance / M365 Security Information Modified

RESPOND/ Apps

Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Antigena / SaaS / Antigena Unusual Activity Block

DETECT & RESPOND/ Email

·      Link / High Risk Link + Low Sender Association

·      Link / New Correspondent Classified Link

·      Link / Watched Link Type

·      Antigena Anomaly

·      Association / Unknown Sender

·      History / New Sender

·      Link / Link to File Storage

·      Link / Link to File Storage + Unknown Sender

·      Link / Low Link Association

List of IoCs

·      142.252.106[.]251 - IP            - Possible malicious IP used by attacker during cloud account compromise

·      199.231.85[.]153 – IP - Probable malicious IP used by attacker during cloud account compromise

·      vukoqo.hebakyon[.]com – Endpoint - Credential harvesting endpoint

MITRE ATT&CK Mapping

·      Resource Development - T1586 - Compromise Accounts

·      Resource Development - T1598.003 – Spearphishing Link

·      Persistence - T1078.004 - Cloud Accounts

·      Persistence - T1556.006 - Modify Authentication Process: Multi-Factor Authentication

·      Reconnaissance - T1593.001 – Social Media

·      Reconnaissance - T1598 – Phishing for Information

·      Reconnaissance - T1589.001 – Credentials

·      Reconnaissance - T1591.002 – Business Relationships

·      Collection - T1111 – Multifactor Authentication Interception

·      Collection - T1539 – Steal Web Session Cookie

·      Lateral Movement - T1021.007 – Cloud Services

·      Lateral Movement - T1213.002 - Sharepoint

References

[1] Jessica Barker, Hacked: The secrets behind cyber attacks, (London: Kogan Page, 2024), p. 130-146.

[2] https://www.bitdefender.co.uk/blog/hotforsecurity/5-linkedin-scams-and-how-to-avoid-them/

[3] https://www.washingtonpost.com/technology/2023/08/31/linkedin-personal-posts/

[4] https://www.forbes.com/sites/joshbersin/2012/05/21/facebook-vs-linkedin-whats-the-difference/

[5] https://thelinkedblog.com/2022/3-reasons-why-you-should-make-your-profile-public-1248/

[6] https://www.linkedin.com/pulse/50-linkedin-statistics-every-professional-should-ti9ue

[7] https://www.nytimes.com/2022/09/24/business/linkedin-social-experiments.html

[8] https://darktrace.com/blog/the-domain-game-how-email-attackers-are-buying-their-way-into-inboxes

[9] https://spur.us/context/142.252.106[.]251

[10] https://spur.us/context/199.231.85[.]153

[11]https://www.statista.com/statistics/1328849/linkedin-number-of-fake-accounts-detected-and-removed

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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