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July 4, 2024

A Busy Agenda: Darktrace's Detection of Qilin Ransomware as a Service Operator

This blog breaks down how Darktrace detected and analyzed Qilin, a Ransomware-as-a-Service group behind recent high-impact attacks. You’ll see how Qilin affiliates customize attacks with flexible encryption, process termination, and double-extortion techniques, as well as why its cross-platform builds in Rust and Golang make it especially evasive. Darktrace highlights three real-world cases where its AI identified likely Qilin activity across customer environments, offering insights into how behavioral detection can spot novel ransomware before disruption occurs. Readers will gain a clear view of Qilin’s toolkit, tactics, and how self-learning defense adapts to these evolving threats.
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
Alexandra Sentenac
Cyber Analyst
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04
Jul 2024

Qilin ransomware has recently dominated discussions across the cyber security landscape following its deployment in an attack on Synnovis, a UK-based medical laboratory company. The ransomware attack ultimately affected patient services at multiple National Health Service (NHS) hospitals that rely on Synnovis diagnostic and pathology services. Qilin’s origins, however, date back further to October 2022 when the group was observed seemingly posting leaked data from its first known victim on its Dedicated Leak Site (DLS) under the name Agenda[1].

The Darktrace Threat Research team investigated network artifacts related to Qilin and identified three probable cases of the ransomware across the Darktrace customer base between June 2022 and May 2024.

Qilin Ransomware-as-a-Service Operator

Qilin operates as a Ransomware-as-a-Service (RaaS) that employs double extortion tactics, whereby harvested data is exfiltrated and threatened of publication on the group's DLS, which is hosted on Tor. Qilin ransomware has samples written in both the Golang and Rust programming languages, making it compilable with various operating systems, and is highly customizable. When building Qilin ransomware variants to be used on their target(s), affiliates can configure settings such as the encryption mode (i.e., skip-step, percent, and speed), the file extension being appended, files, extensions and directories to be skipped during the encryption, and the processes and services to be terminated, among others[1] [2].  

Trend Micro analysts, who were the first to discover Qilin samples in August 2022, when the name "Agenda" was still used in ransom notes, found that each analyzed sample was customized for the intended victims and that "unique company IDs were used as extensions of encrypted files" [3]. This information is configurable from within the Qilin's affiliate panel's 'Targets' section, shown below. The panel's background image features the eponym Chinese legendary chimerical creature Qilin (pronounced “Ke Lin”). Despite this Chinese mythology reference, Russian language was observed being used by a Qilin operator in an underground forum post aimed at hiring affiliates and advertising their RaaS operation[2].

Figure 1: Qilin ransomware’s affiliate panel.

Qilin's RaaS program purportedly has an attractive affiliates' payment structure, with affiliates allegedly able to earn 80% of ransom payments of USD 3m or less and 85% for payments above that figure[2], making it a possibly appealing option in the RaaS ecosystem.  Publication of stolen data and ransom payment negotiations are purportedly handled by Qilin operators. Qilin affiliates have been known to target companies located around the world and within a variety of industries, including critical sectors such as healthcare and energy.

As Qilin is a RaaS operation, the choice of targets does not necessarily reflect Qilin operators' intentions, but rather that of its affiliates.  Similarly, the tactics, techniques, procedures (TTPs) and indicators of compromise (IoC) identified by Darktrace are associated with the given affiliate deploying Qilin ransomware for their own purpose, rather than TTPs and IoCs of the Qilin group. Likewise, initial vectors of infection may vary from affiliate to affiliate. Previous studies show that initial access to networks were gained via spear phishing emails or by leveraging exposed applications and interfaces.

Differences have been observed in terms of data exfiltration and potential C2 external endpoints, suggesting the below investigations are not all related to the same group or actor(s).

Darktrace’s Threat Research Investigation

June 2022

Darktrace first detected an instance of Qilin ransomware back in June 2022, when an attacker was observed successfully accessing a customer’s Virtual Private Network (VPN) and compromising an administrative account, before using RDP to gain access to the customer’s Microsoft System Center Configuration Manager (SCCM) server

From there, an attack against the customer's VMware ESXi hosts was launched. Fortunately, a reboot of their virtual machines (VM) caught the attention of the security team who further uncovered that custom profiles had been created and remote scripts executed to change root passwords on their VM hosts. Three accounts were found to have been compromised and three systems encrypted by ransomware.  

Unfortunately, Darktrace was not configured to monitor the affected subnets at the time of the attack. Despite this, the customer was able to work directly with Darktrace analysts via the Ask the Expert (ATE) service to add the subnets in question to Darktrace’s visibility, allowing it to monitor for any further unusual behavior.

Once visibility over the compromised SCCM server was established, Darktrace observed a series of unusual network scanning activities and the use of Kali (a Linux distribution designed for digital forensics and penetration testing). Furthermore, the server was observed making connections to multiple rare external hosts, many using the “[.]ru” Top Level Domain (TLD). One of the external destinations the server was attempting to connect was found to be related to SystemBC, a malware that turns infected hosts into SOCKS5 proxy bots and provides command-and-control (C2) functionality.

Additionally, the server was observed making external connections over ports 993 and 143 (typically associated with the use of the Interactive Message Access Protocol (IMAP) to multiple rare external endpoints. This was likely due to the presence of Tofsee malware on the device.

After the compromise had been contained, Darktrace identified several ransom notes following the naming convention “README-RECOVER-<extension/company_id>.txt”” on the network. This naming convention, as well as the similar “<company_id>-RECOVER-README.txt” have been referenced by open-source intelligence (OSINT) providers as associated with Qilin ransom notes[5] [6] [7].

April 2023

The next case of Qilin ransomware observed by Darktrace took place in April 2023 on the network of a customer in the manufacturing sector in APAC. Unfortunately for the customer in this instance, Darktrace RESPOND™ was not active on their environment and no autonomous response actions were taken to contain the compromise.

Over the course of two days, Darktrace identified a wide range of malicious activity ranging from extensive initial scanning and lateral movement attempts to the writing of ransom notes that followed the aforementioned naming convention (i.e., “README-RECOVER-<extension/company_id>.txt”).

Darktrace observed two affected devices attempting to move laterally through the SMB, DCE-RPC and RDP network protocols. Default credentials (e.g., UserName, admin, administrator) were also observed in the large volumes of SMB sessions initiated by these devices. One of the target devices of these SMB connections was a domain controller, which was subsequently seen making suspicious WMI requests to multiple devices over DCE-RPC and enumerating SMB shares by binding to the ‘server service’ (srvsvc) named pipe to a high number of internal devices within a short time frame. The domain controller was further detected establishing an anomalously high number of connections to several internal devices, notably using the RDP administrative protocol via a default admin cookie.  

Repeated connections over the HTTP and SSL protocol to multiple newly observed IPs located in the 184.168.123.0/24 range were observed, indicating C2 connectivity.  WebDAV user agent and a JA3 fingerprint potentially associated with Cobalt Strike were notably observed in these connections. A few hours later, Darktrace detected additional suspicious external connections, this time to IPs associated with the MEGA cloud storage solution. Storage solutions such as MEGA are often abused by attackers to host stolen data post exfiltration. In this case, the endpoints were all rare for the network, suggesting this solution was not commonly used by legitimate users. Around 30 GB of data was exfiltrated over the SSL protocol.

Darktrace did not observe any encryption-related activity on this customer’s network, suggesting that encryption may have taken place locally or within network segments not monitored by Darktrace.

May 2024

The most recent instance of Qilin observed by Darktrace took place in May 2024 and involved a customer in the US. In this case, Darktrace initially detected affected devices using unusual administrative and default credentials, before additional internal systems were observed making extensive suspicious DCE-RPC requests to a range of internal locations, performing network scanning, making unusual internal RDP connections, and transferring suspicious executable files like 'a157496.exe' and '83b87b2.exe'.  SMB writes of the file "LSM_API_service" were also observed, activity which was considered 100% unusual by Darktrace; this is an RPC service that can be abused to enumerate logged-in users and steal their tokens. Various repeated connections likely representative of C2 communications were detected via both HTTP and SSL to rare external endpoints linked in OSINT to Cobalt Strike use. During these connections, HTTP GET requests for the following URIs were observed:

/asdffHTTPS

/asdfgdf

/asdfgHTTP

/download/sihost64.dll

Notably, this included a GET request a DLL file named "sihost64.dll" from a domain controller using PowerShell.  

Over 102 GB of data may have been transferred to another previously unseen endpoint, 194.165.16[.]13, via the unencrypted File Transfer Protocol (FTP). Additionally, many non-FTP connections to the endpoint could be observed, over which more than 783 GB of data was exfiltrated. Regarding file encryption activity, a wide range of destination devices and shares were targeted.

Figure 2: Advanced Search graph displaying the total volume of data transferred over FTP to a malicious IP.

During investigations, Darktrace’s Threat Research team identified an additional customer, also based in the United States, where similar data exfiltration activity was observed in April 2024. Although no indications of ransomware encryption were detected on the network, multiple similarities were observed with the case discussed just prior. Notably, the same exfiltration IP and protocol (194.165.16[.]13 and FTP, respectively) were identified in both cases. Additional HTTP connectivity was further observed to another IP using a self-signed certificate (i.e., CN=ne[.]com,OU=key operations,O=1000,L=,ST=,C=KM) located within the same ASN (i.e., AS48721 Flyservers S.A.). Some of the URIs seen in the GET requests made to this endpoint were the same as identified in that same previous case.

Information regarding another device also making repeated connections to the same IP was described in the second event of the same Cyber AI Analyst incident. Following this C2 connectivity, network scanning was observed from a compromised domain controller, followed by additional reconnaissance and lateral movement over the DCE-RPC and SMB protocols. Darktrace again observed SMB writes of the file "LSM_API_service", as in the previous case, activity which was also considered 100% unusual for the network. These similarities suggest the same actor or affiliate may have been responsible for activity observed, even though no encryption was observed in the latter case.

Figure 3: First event of the Cyber AI Analyst investigation following the compromise activity.

According to researchers at Microsoft, some of the IoCs observed on both affected accounts are associated with Pistachio Tempest, a threat actor reportedly associated with ransomware distribution. The Microsoft threat actor naming convention uses the term "tempest" to reference criminal organizations with motivations of financial gain that are not associated with high confidence to a known non-nation state or commercial entity. While Pistachio Tempest’s TTPs have changed over time, their key elements still involve ransomware, exfiltration, and extortion. Once they've gained access to an environment, Pistachio Tempest typically utilizes additional tools to complement their use of Cobalt Strike; this includes the use of the SystemBC RAT and the SliverC2 framework, respectively. It has also been reported that Pistacho Tempest has experimented with various RaaS offerings, which recently included Qilin ransomware[4].

Conclusion

Qilin is a RaaS group that has gained notoriety recently due to high-profile attacks perpetrated by its affiliates. Despite this, the group likely includes affiliates and actors who were previously associated with other ransomware groups. These individuals bring their own modus operandi and utilize both known and novel TTPs and IoCs that differ from one attack to another.

Darktrace’s anomaly-based technology is inherently threat-agnostic, treating all RaaS variants equally regardless of the attackers’ tools and infrastructure. Deviations from a device’s ‘learned’ pattern of behavior during an attack enable Darktrace to detect and contain potentially disruptive ransomware attacks.

Credit to: Alexandra Sentenac, Emma Foulger, Justin Torres, Min Kim, Signe Zaharka for their contributions.

References

[1] https://www.sentinelone.com/anthology/agenda-qilin/  

[2] https://www.group-ib.com/blog/qilin-ransomware/

[3] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[4] https://www.microsoft.com/en-us/security/security-insider/pistachio-tempest

[5] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[6] https://www.bleepingcomputer.com/forums/t/790240/agenda-qilin-ransomware-id-random-10-char;-recover-readmetxt-support/

[7] https://github.com/threatlabz/ransomware_notes/tree/main/qilin

Darktrace Model Detections

Internal Reconnaissance

Device / Suspicious SMB Scanning Activity

Device / Network Scan

Device / RDP Scan

Device / ICMP Address Scan

Device / Suspicious Network Scan Activity

Anomalous Connection / SMB Enumeration

Device / New or Uncommon WMI Activity

Device / Attack and Recon Tools

Lateral Movement

Device / SMB Session Brute Force (Admin)

Device / Large Number of Model Breaches from Critical Network Device

Device / Multiple Lateral Movement Model Breaches

Anomalous Connection / Unusual Admin RDP Session

Device / SMB Lateral Movement

Compliance / SMB Drive Write

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Anomalous DRSGetNCChanges Operation

Anomalous Server Activity / Domain Controller Initiated to Client

User / New Admin Credentials on Client

C2 Communication

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Connection / Anomalous SSL without SNI to New External

Anomalous Connection / Rare External SSL Self-Signed

Device / Increased External Connectivity

Unusual Activity / Unusual External Activity

Compromise / New or Repeated to Unusual SSL Port

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Device / Suspicious Domain

Device / Increased External Connectivity

Compromise / Sustained SSL or HTTP Increase

Compromise / Botnet C2 Behaviour

Anomalous Connection / POST to PHP on New External Host

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

Anomalous File / EXE from Rare External Location

Exfiltration

Unusual Activity / Enhanced Unusual External Data Transfer

Anomalous Connection / Data Sent to Rare Domain

Unusual Activity / Unusual External Data Transfer

Anomalous Connection / Uncommon 1 GiB Outbound

Unusual Activity / Unusual External Data to New Endpoint

Compliance / FTP / Unusual Outbound FTP

File Encryption

Compromise / Ransomware / Suspicious SMB Activity

Anomalous Connection / Sustained MIME Type Conversion

Anomalous File / Internal / Additional Extension Appended to SMB File

Compromise / Ransomware / Possible Ransom Note Write

Compromise / Ransomware / Possible Ransom Note Read

Anomalous Connection / Suspicious Read Write Ratio

IoC List

IoC – Type – Description + Confidence

93.115.25[.]139 IP C2 Server, likely associated with SystemBC

194.165.16[.]13 IP Probable Exfiltration Server

91.238.181[.]230 IP C2 Server, likely associated with Cobalt Strike

ikea0[.]com Hostname C2 Server, likely associated with Cobalt Strike

lebondogicoin[.]com Hostname C2 Server, likely associated with Cobalt Strike

184.168.123[.]220 IP Possible C2 Infrastructure

184.168.123[.]219 IP Possible C2 Infrastructure

184.168.123[.]236 IP Possible C2 Infrastructure

184.168.123[.]241 IP Possible C2 Infrastructure

184.168.123[.]247 IP Possible C2 Infrastructure

184.168.123[.]251 IP Possible C2 Infrastructure

184.168.123[.]252 IP Possible C2 Infrastructure

184.168.123[.]229 IP Possible C2 Infrastructure

184.168.123[.]246 IP Possible C2 Infrastructure

184.168.123[.]230 IP Possible C2 Infrastructure

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

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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
Alexandra Sentenac
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
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