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May 28, 2024

Stemming the Citrix Bleed Vulnerability with Darktrace’s ActiveAI Security Platform

This blog delves into Darktrace’s investigation into the exploitation of the Citrix Bleed vulnerability on the network of a customer in late 2023. Darktrace’s Self-Learning AI ensured the customer was well equipped to track the post-compromise activity and identify affected devices.
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
Vivek Rajan
Cyber Analyst
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28
May 2024

What is Citrix Bleed?

Since August 2023, cyber threat actors have been actively exploiting one of the most significant critical vulnerabilities disclosed in recent years: Citrix Bleed. Citrix Bleed, also known as CVE-2023-4966, remained undiscovered and even unpatched for several months, resulting in a wide range of security incidents across business and government sectors [1].

How does Citrix Bleed vulnerability work?

The vulnerability, which impacts the Citrix Netscaler Gateway and Netscaler ADC products, allows for outside parties to hijack legitimate user sessions, thereby bypassing password and multifactor authentication (MFA) requirements.

When used as a means of initial network access, the vulnerability has resulted in the exfiltration of sensitive data, as in the case of Xfinity, and even the deployment of ransomware variants including Lockbit [2]. Although Citrix has released a patch to address the vulnerability, slow patching procedures and the widespread use of these products has resulted in the continuing exploitation of Citrix Bleed into 2024 [3].

How Does Darktrace Handle Citrix Bleed?

Darktrace has demonstrated its proficiency in handling the exploitation of Citrix Bleed since it was disclosed back in 2023; its anomaly-based approach allows it to efficiently identify and inhibit post-exploitation activity as soon as it surfaces.  Rather than relying upon traditional rules and signatures, Darktrace’s Self-Learning AI enables it to understand the subtle deviations in a device’s behavior that would indicate an emerging compromise, thus allowing it to detect anomalous activity related to the exploitation of Citrix Bleed.

In late 2023, Darktrace identified an instance of Citrix Bleed exploitation on a customer network. As this customer had subscribed to the Proactive Threat Notification (PTN) service, the suspicious network activity surrounding the compromise was escalated to Darktrace’s Security Operation Center (SOC) for triage and investigation by Darktrace Analysts, who then alerted the customer’s security team to the incident.

Darktrace’s Coverage

Initial Access and Beaconing of Citrix Bleed

Darktrace’s initial detection of indicators of compromise (IoCs) associated with the exploitation of Citrix Bleed actually came a few days prior to the SOC alert, with unusual external connectivity observed from a critical server. The suspicious connection in question, a SSH connection to the rare external IP 168.100.9[.]137, lasted several hours and utilized the Windows PuTTY client. Darktrace also identified an additional suspicious IP, namely 45.134.26[.]2, attempting to contact the server. Both rare endpoints had been linked with the exploitation of the Citrix Bleed vulnerability by multiple open-source intelligence (OSINT) vendors [4] [5].

Darktrace model alert highlighting an affected device making an unusual SSH connection to 168.100.9[.]137 via port 22.
Figure 1: Darktrace model alert highlighting an affected device making an unusual SSH connection to 168.100.9[.]137 via port 22.

As Darktrace is designed to identify network-level anomalies, rather than monitor edge infrastructure, the initial exploitation via the typical HTTP buffer overflow associated with this vulnerability fell outside the scope of Darktrace’s visibility. However, the aforementioned suspicious connectivity likely constituted initial access and beaconing activity following the successful exploitation of Citrix Bleed.

Command and Control (C2) and Payload Download

Around the same time, Darktrace also detected other devices on the customer’s network conducting external connectivity to various endpoints associated with remote management and IT services, including Action1, ScreenConnect and Fixme IT. Additionally, Darktrace observed devices downloading suspicious executable files, including “tniwinagent.exe”, which is associated with the tool Total Network Inventory. While this tool is typically used for auditing and inventory management purposes, it could also be leveraged by attackers for the purpose of lateral movement.

Defense Evasion

In the days surrounding this compromise, Darktrace observed multiple devices engaging in potential defense evasion tactics using the ScreenConnect and Fixme IT services. Although ScreenConnect is a legitimate remote management tool, it has also been used by threat actors to carry out C2 communication [6]. ScreenConnect itself was the subject of a separate critical vulnerability which Darktrace investigated in early 2024. Meanwhile, CISA observed that domains associated with Fixme It (“fixme[.]it”) have been used by threat actors attempting to exploit the Citrix Bleed vulnerability [7].

Reconnaissance and Lateral Movement

A few days after the detection of the initial beaconing communication, Darktrace identified several devices on the customer’s network carrying out reconnaissance and lateral movement activity. This included SMB writes of “PSEXESVC.exe”, network scanning, DCE-RPC binds of numerous internal devices to IPC$ shares and the transfer of compromise-related tools. It was at this point that Darktrace’s Self-Learning AI deemed the activity to be likely indicative of an ongoing compromise and several Enhanced Monitoring models alerted, triggering the aforementioned PTNs and investigation by Darktrace’s SOC.

Darktrace observed a server on the network initiating a wide range of connections to more than 600 internal IPs across several critical ports, suggesting port scanning, as well as conducting unexpected DCE-RPC service control (svcctl) activity on multiple internal devices, amongst them domain controllers. Additionally, several binds to server service (srvsvc) and security account manager (samr) endpoints via IPC$ shares on destination devices were detected, indicating further reconnaissance activity. The querying of these endpoints was also observed through RPC commands to enumerate services running on the device, as well as Security Account Manager (SAM) accounts.  

Darktrace also identified devices performing SMB writes of the WinRAR data compression tool, in what likely represented preparation for the compression of data prior to data exfiltration. Further SMB file writes were observed around this time including PSEXESVC.exe, which was ultimately used by attackers to conduct remote code execution, and one device was observed making widespread failed NTLM authentication attempts on the network, indicating NTLM brute-forcing. Darktrace observed several devices using administrative credentials to carry out the above activity.

In addition to the transfer of tools and executables via SMB, Darktrace also identified numerous devices deleting files through SMB around this time. In one example, an MSI file associated with the patch management and remediation service, Action1, was deleted by an attacker. This legitimate security tool, if leveraged by attackers, could be used to uncover additional vulnerabilities on target networks.

A server on the customer’s network was also observed writing the file “m.exe” to multiple internal devices. OSINT investigation into the executable indicated that it could be a malicious tool used to prevent antivirus programs from launching or running on a network [8].

Impact and Data Exfiltration

Following the initial steps of the breach chain, Darktrace observed numerous devices on the customer’s network engaging in data exfiltration and impact events, resulting in additional PTN alerts and a SOC investigation into data egress. Specifically, two servers on the network proceeded to read and download large volumes of data via SMB from multiple internal devices over the course of a few hours. These hosts sent large outbound volumes of data to MEGA file storage sites using TLS/SSL over port 443. Darktrace also identified the use of additional file storage services during this exfiltration event, including 4sync, file[.]io, and easyupload[.]io. In total the threat actor exfiltrated over 8.5 GB of data from the customer’s network.

Darktrace Cyber AI Analyst investigation highlighting the details of a data exfiltration attempt.
Figure 2: Darktrace Cyber AI Analyst investigation highlighting the details of a data exfiltration attempt.

Finally, Darktrace detected a user account within the customer’s Software-as-a-Service (SaaS) environment conducting several suspicious Office365 and AzureAD actions from a rare IP for the network, including uncommon file reads, creations and the deletion of a large number of files.

Unfortunately for the customer in this case, Darktrace RESPOND™ was not enabled on the network and the post-exploitation activity was able to progress until the customer was made aware of the attack by Darktrace’s SOC team. Had RESPOND been active and configured in autonomous response mode at the time of the attack, it would have been able to promptly contain the post-exploitation activity by blocking external connections, shutting down any C2 activity and preventing the download of suspicious files, blocking incoming traffic, and enforcing a learned ‘pattern of life’ on offending devices.

Conclusion

Given the widespread use of Netscaler Gateway and Netscaler ADC, Citrix Bleed remains an impactful and potentially disruptive vulnerability that will likely continue to affect organizations who fail to address affected assets. In this instance, Darktrace demonstrated its ability to track and inhibit malicious activity stemming from Citrix Bleed exploitation, enabling the customer to identify affected devices and enact their own remediation.

Darktrace’s anomaly-based approach to threat detection allows it to identify such post-exploitation activity resulting from the exploitation of a vulnerability, regardless of whether it is a known CVE or a zero-day threat. Unlike traditional security tools that rely on existing threat intelligence and rules and signatures, Darktrace’s ability to identify the subtle deviations in a compromised device’s behavior gives it a unique advantage when it comes to identifying emerging threats.

Credit to Vivek Rajan, Cyber Analyst, Adam Potter, Cyber Analyst

Appendices

Darktrace Model Coverage

Device / Suspicious SMB Scanning Activity

Device / ICMP Address Scan

Device / Possible SMB/NTLM Reconnaissance

Device / Network Scan

Device / SMB Lateral Movement

Device / Possible SMB/NTLM Brute Force

Device / Suspicious Network Scan Activity

User / New Admin Credentials on Server

Anomalous File / Internal::Unusual Internal EXE File Transfer

Compliance / SMB Drive Write

Device / New or Unusual Remote Command Execution

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Rare WinRM Incoming

Anomalous Connection / Unusual Admin SMB Session

Device / Unauthorised Device

User / New Admin Credentials on Server

Anomalous Server Activity / Outgoing from Server

Device / Long Agent Connection to New Endpoint

Anomalous Connection / Multiple Connections to New External TCP Port

Device / New or Uncommon SMB Named Pipe

Device / Multiple Lateral Movement Model Breaches

Device / Large Number of Model Breaches

Compliance / Remote Management Tool On Server

Device / Anomalous RDP Followed By Multiple Model Breaches

Device / SMB Session Brute Force (Admin)

Device / New User Agent

Compromise / Large Number of Suspicious Failed Connections

Unusual Activity / Unusual External Data Transfer

Unusual Activity / Enhanced Unusual External Data Transfer

Device / Increased External Connectivity

Unusual Activity / Unusual External Data to New Endpoints

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Uncommon 1 GiB Outbound

Anomalous Connection / Active Remote Desktop Tunnel

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Compliance / Possible Unencrypted Password File On Server

Anomalous Connection / Suspicious Read Write Ratio and Rare External

Device / Reverse DNS Sweep]

Unusual Activity / Possible RPC Recon Activity

Anomalous File / Internal::Executable Uploaded to DC

Compliance / SMB Version 1 Usage

Darktrace AI Analyst Incidents

Scanning of Multiple Devices

Suspicious Remote Service Control Activity

SMB Writes of Suspicious Files to Multiple Devices

Possible SSL Command and Control to Multiple Devices

Extensive Suspicious DCE-RPC Activity

Suspicious DCE-RPC Activity

Internal Downloads and External Uploads

Unusual External Data Transfer

Unusual External Data Transfer to Multiple Related Endpoints

MITRE ATT&CK Mapping

Technique – Tactic – ID – Sub technique of

Network Scanning – Reconnaissance - T1595 - T1595.002

Valid Accounts – Defense Evasion, Persistence, Privilege Escalation, Initial Access – T1078 – N/A

Remote Access Software – Command and Control – T1219 – N/A

Lateral Tool Transfer – Lateral Movement – T1570 – N/A

Data Transfers – Exfiltration – T1567 – T1567.002

Compressed Data – Exfiltration – T1030 – N/A

NTLM Brute Force – Brute Force – T1110 - T1110.001

AntiVirus Deflection – T1553 - NA

Ingress Tool Transfer   - COMMAND AND CONTROL - T1105 - NA

Indicators of Compromise (IoCs)

204.155.149[.]37 – IP – Possible Malicious Endpoint

199.80.53[.]177 – IP – Possible Malicious Endpoint

168.100.9[.]137 – IP – Malicious Endpoint

45.134.26[.]2 – IP – Malicious Endpoint

13.35.147[.]18 – IP – Likely Malicious Endpoint

13.248.193[.]251 – IP – Possible Malicious Endpoint

76.223.1[.]166 – IP – Possible Malicious Endpoint

179.60.147[.]10 – IP – Likely Malicious Endpoint

185.220.101[.]25 – IP – Likely Malicious Endpoint

141.255.167[.]250 – IP – Malicious Endpoint

106.71.177[.]68 – IP – Possible Malicious Endpoint

cat2.hbwrapper[.]com – Hostname – Likely Malicious Endpoint

aj1090[.]online – Hostname – Likely Malicious Endpoint

dc535[.]4sync[.]com – Hostname – Likely Malicious Endpoint

204.155.149[.]140 – IP - Likely Malicious Endpoint

204.155.149[.]132 – IP - Likely Malicious Endpoint

204.155.145[.]52 – IP - Likely Malicious Endpoint

204.155.145[.]49 – IP - Likely Malicious Endpoint

References

  1. https://www.axios.com/2024/01/02/citrix-bleed-security-hacks-impact
  2. https://www.csoonline.com/article/1267774/hackers-steal-data-from-millions-of-xfinity-customers-via-citrix-bleed-vulnerability.html
  3. https://www.cybersecuritydive.com/news/citrixbleed-security-critical-vulnerability/702505/
  4. https://www.virustotal.com/gui/ip-address/168.100.9.137
  5. https://www.virustotal.com/gui/ip-address/45.134.26.2
  6. https://www.trendmicro.com/en_us/research/24/b/threat-actor-groups-including-black-basta-are-exploiting-recent-.html
  7. https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-325a
  8. https://www.file.net/process/m.exe.html
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
Vivek Rajan
Cyber 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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