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February 29, 2024

Protecting Against AlphV BlackCat Ransomware

Learn how Darktrace AI is combating AlphV BlackCat ransomware, including the details of this ransomware and how to protect yourself from it.
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
Sam Lister
Specialist Security Researcher
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29
Feb 2024

As-a-Service malware trending

Throughout the course of 2023, “as-a-Service” strains of malware remained the most consistently observed threat type to affect Darktrace customers, mirroring their overall prominence across the cyber threat landscape. With this trend expected to continue throughout 2024, organizations and their security teams should be prepared to defend their network against increasingly versatile and tailorable malware-as-a-service (MaaS) and ransomware-as-a-service (RaaS) strains [1].

What is ALPHV ransomware?

The ALPHV ransomware, also known as ‘BlackCat’ or ‘Noberus’, is one example of a RaaS strain that has been prominent across the threat landscape over the last few years.

ALPHV is a ransomware strain coded in the Rust programming language. The ransomware is sold as part of the RaaS economy [2], with samples of the ransomware being provided and sold by a criminal group (the RaaS ‘operator’) to other cybercriminals (the RaaS ‘affiliates’) who then gain entry to organizations' networks with the intention of detonating the ransomware and demanding ransom payments.

ALPHV was likely first used in the wild back in November 2021 [3]. Since then, it has become one of the most prolific ransomware strains, with the Federal Bureau of Investigation (FBI) reporting nearly USD 300 million in ALPHV ransom payments as of September 2023 [4].

In December 2023, the FBI and the US Department of Justice announced a successful disruption campaign against the ALPHV group, which included a takedown of the their data leak site, and the release of a decryption tool for the ransomware strain [5], and in February 2024, the US Department of State announced  a reward of up to USD 10 million for information leading to the identification or location of anyone occupying a key leadership position in the group operating the ALPHV ransomware strain [6].

The disruption campaign against the ransomware group appeared to have been successful, as evidenced by the recent, significant decline in ALPHV attacks, however, it would not be surprising for the group to simply return with new branding, in a similar vein to its apparent predecessors, DarkSide and BlackMatter [7].

How does ALPHV ransomware work?

ALPHV affiliates have been known to employ a variety of methods to progress towards their objective of detonating ALPHV ransomware [4]. In the latter half of 2023, ALPHV affiliates were observed using malicious advertising (i.e, malvertising) to deliver a Python-based backdoor-dropper known as 'Nitrogen' to users' devices [8][12]. These malvertising operations consisted in affiliates setting up malicious search engine adverts for tools such as WinSCP and AnyDesk.

Users' interactions with these adverts led them to sites resembling legitimate software distribution sites. Users' attempts to download software from these spoofed sites resulted in the delivery of a backdoor-dropping malware sample dubbed 'Nitrogen' to their devices. Nitrogen has been observed dropping a variety of command-and-control (C2) implants onto users' devices, including Cobalt Strike Beacon and Sliver C2. ALPHV affiliates often used the backdoor access afforded to them by these C2 implants to conduct reconnaissance and move laterally, in preparation for detonating ALPHV ransomware payloads.

Darktrace Detection of ALPHV Ransomware

During October 2023, Darktrace observed several cases of ALPHV affiliates attempting to infiltrate organizations' networks via the use of malvertising to socially engineer users into downloading and installing Nitrogen from impersonation websites such as 'wireshhark[.]com' and wìnscp[.]net (i.e, xn--wnscp-tsa[.]net).

While the attackers managed to bypass traditional security measures and evade detection by using a device from the customer’s IT team to perform its malicious activity, Darktrace DETECT™ swiftly identified the subtle indicators of compromise (IoCs) in the first instance. This swift detection of ALPHV, along with Cyber AI Analyst™ autonomously investigating the wide array of post-compromise activity, provided the customer with full visibility over the attack enabling them to promptly initiate their remediation and recovery efforts.

Unfortunately, in this incident, Darktrace RESPOND™ was not fully deployed within their environment, hindering its ability to autonomously counter emerging threats. Had RESPOND been fully operational here, it would have effectively contained the attack in its early stages, avoiding the eventual detonation of the ALPHV ransomware.

Figure 1: Timeline of the ALPHV ransomware attack.

In mid-October, a member of the IT team at a US-based Darktrace customer attempted to install the network traffic analysis software, Wireshark, onto their desktop. Due to the customer’s configuration, Darktrace's visibility over this device was limited to its internal traffic, despite this it was still able to identify and alert for a string of suspicious activity conducted by the device.

Initially, Darktrace observed the device making type A DNS requests for 'wiki.wireshark[.]org' immediately before making type A DNS requests for the domain names 'www.googleadservices[.]com', 'allpcsoftware[.]com', and 'wireshhark[.]com' (note the two 'h's). This pattern of activity indicates that the device’s user was redirected to the website, wireshhark[.]com, as a result of the user's interaction with a sponsored Google Search result pointing to allpcsoftware[.]com.

At the time of analysis, navigating to wireshhark[.]com directly from the browser search bar led to a YouTube video of Rick Astley's song "Never Gonna Give You Up". This suggests that the website, wireshhark[.]com, had been configured to redirect users to this video unless they had arrived at the website via the relevant sponsored Google Search result [8].

Although it was not possible to confirm this with certainty, it is highly likely that users who visited the website via the appropriate sponsored Google Search result were led to a fake website (wireshhark[.]com) posing as the legitimate website, wireshark[.]com. It seems that the actors who set up this fake version of wireshark[.]com were inspired by the well-known bait-and-switch technique known as 'rickrolling', where users are presented with a desirable lure (typically a hyperlink of some kind) which unexpectedly leads them to a music video of Rick Astley's "Never Gonna Give You Up".

After being redirected to wireshhark[.]com, the user unintentionally installed a malware sample which dropped what appears to be Cobalt Strike onto their device. The presence of Cobalt Strike on the user's desktop was evidenced by the subsequent type A DNS requests which the device made for the domain name 'pse[.]ac'. These DNS requests were responded to with the likely Cobalt Strike C2 server address, 194.169.175[.]132. Given that Darktrace only had visibility over the device’s internal traffic, it did not observe any C2 connections to this Cobalt Strike endpoint. However, the desktop's subsequent behavior suggests that a malicious actor had gained 'hands-on-keyboard' control of the device via an established C2 channel.

Figure 2: Advanced Search data showing an customer device being tricked into visiting the fake website, wireshhark[.]com.

Since the malicious actor had gained control of an IT member's device, they were able to abuse the privileged account credentials to spread Python payloads across the network via SMB and the Windows Management Instrumentation (WMI) service. The actor was also seen distributing the Windows Sys-Internals tool, PsExec, likely in an attempt to facilitate their lateral movement efforts. It was normal for this IT member's desktop to distribute files across the network via SMB, which meant that this malicious SMB activity was not, at first glance, out of place.

Figure 3: Advanced Search data showing that it was normal for the IT member's device to distribute files over SMB.

However, Darktrace DETECT recognized that the significant spike in file writes being performed here was suspicious, even though, on the surface, it seemed ‘normal’ for the device. Furthermore, Darktrace identified that the executable files being distributed were attempting to masquerade as a different file type, potentially in an attempt to evade the detection of traditional security tools.

Figure 4: Event Log data showing several Model Breaches being created in response to the IT member's DEVICE's SMB writes of Python-based executables.

An addition to DETECT’s identification of this unusual activity, Darktrace’s Cyber AI Analyst launched an autonomous investigation into the ongoing compromise and was able to link the SMB writes and the sharing of the executable Python payloads, viewing the connections as one lateral movement incident rather than a string of isolated events. After completing its investigation, Cyber AI Analyst was able to provide a detailed summary of events on one pane of glass, ensuring the customer could identify the affected device and begin their remediation.

Figure 5: Cyber AI Analyst investigation summary highlighting the IT member's desktop’s lateral movement activities.

C2 Activity

The Python payloads distributed by the IT member’s device were likely related to the Nitrogen malware, as evidenced by the payloads’ names and by the network behaviours which they engendered.  

Figure 6: Advanced Search data showing the affected device reaching out to the C2 endpoint, pse[.]ac, and then distributing Python-based executable files to an internal domain controller.

The internal devices to which these Nitrogen payloads were distributed immediately went on to contact C2 infrastructure associated with Cobalt Strike. These C2 connections were made over SSL on ports 443 and 8443.  Darktrace identified the attacker moving laterally to an internal SQL server and an internal domain controller.

Figure 7: Advanced Search data showing an internal SQL server contacting the Cobalt Strike C2 endpoint, 194.180.48[.]169, after receiving Python payloads from the IT member’s device.
Figure 8: Event Log data showing several DETECT model breaches triggering in response to an internal SQL server’s C2 connections to 194.180.48[.]169.

Once more, Cyber AI Analyst launched its own investigation into this activity and was able to successfully identify a series of separate SSL connections, linking them together into one wider C2 incident.

Figure 9: Cyber AI Analyst investigation summary highlighting C2 connections from the SQL server.

Darktrace observed the attacker using their 'hands-on-keyboard' access to these systems to elevate their privileges, conduct network reconnaissance (primarily port scanning), spread Python payloads further across the network, exfiltrate data from the domain controller and transfer a payload from GitHub to the domain controller.

Figure 10: Cyber AI Analyst investigation summary an IP address scan carried out by an internal domain controller.
Figure 12: Event Log data showing an internal domain controller contacting GitHub around the time that it was in communication with the C2 endpoint, 194.180.48[.]169.
Figure 13: Event Log data showing a DETECT model breach being created in response to an internal domain controller's large data upload to the C2 endpoint, 194.180.48[.]169.

After conducting extensive reconnaissance and lateral movement activities, the attacker was observed detonating ransomware with the organization's VMware environment, resulting in the successful encryption of the customer’s VMware vCenter server and VMware virtual machines. In this case, the attacker took around 24 hours to progress from initial access to ransomware detonation.  

If the targeted organization had been signed up for Darktrace's Proactive Threat Notification (PTN) service, they would have been promptly notified of these suspicious activities by the Darktrace Security Operations Center (SOC) in the first instance, allowing them to quickly identify affected devices and quarantine them before the compromise could escalate.

Additionally, given the quantity of high-severe alerts that triggered in response to this attack, Darktrace RESPOND would, under normal circumstances, have inhibited the attacker's activities as soon as they were identified by DETECT. However, due to RESPOND not being configured to act on server devices within the customer’s network, the attacker was able to seamlessly move laterally through the organization's server environment and eventually detonate the ALPHV ransomware.

Nevertheless, Darktrace was able to successfully weave together multiple Cyber AI Analyst incidents which it generated into a thread representing the chain of behavior that made up this attack. The thread of Incident Events created by Cyber AI Analyst provided a substantial account of the attack and the steps involved in it, which significantly facilitated the customer’s post-incident investigation efforts.  

Figure 14: Darktrace's AI Analyst weaved together 33 of the Incident Events it created together into a thread representing the attacker’s chain of behavior.

Conclusion

It is expected for malicious cyber actors to revise and upgrade their methods to evade organizations’ improving security measures. The continued improvement of email security tools, for example, has likely created a need for attackers to develop new means of Initial Access, such as the use of Microsoft Teams-based malware delivery.

This fast-paced ALPHV ransomware attack serves as a further illustration of this trend, with the actor behind the attack using malvertising to convince an unsuspecting user to download the Python-based malware, Nitrogen, from a fake Wireshark site. Unbeknownst to the user, this stealthy malware dropped a C2 implant onto the user’s device, giving the malicious actor the ‘hands-on-keyboard’ access they needed to move laterally, conduct network reconnaissance, and ultimately detonate ALPHV ransomware.

Despite the non-traditional initial access methods used by this ransomware actor, Darktrace DETECT was still able to identify the unusual patterns of network traffic caused by the attacker’s post-compromise activities. The large volume of alerts created by Darktrace DETECT were autonomously investigated by Darktrace’s Cyber AI Analyst, which was able to weave together related activities of different devices into a comprehensive timeline of the attacker’s operation. Given the volume of DETECT alerts created in response to this ALPHV attack, it is expected that Darktrace RESPOND would have autonomously inhibited the attacker’s operation had the capability been appropriately configured.

As the first post-compromise activities Darktrace observed in this ALPHV attack were seemingly performed by a member of the customer’s IT team, it may have looked normal to a human or traditional signature and rules-based security tools. To Darktrace’s Self-Learning AI, however, the observed activities represented subtle deviations from the device’s normal pattern of life. This attack, and Darktrace’s detection of it, is therefore a prime illustration of the value that Self-Learning AI can bring to the task of detecting anomalies within organizations’ digital estates.

Credit to Sam Lister, Senior Cyber Analyst, Emma Foulger, Principal Cyber Analyst

Appendices

Darktrace DETECT Model Breaches

- Compliance / SMB Drive Write

- Compliance / High Priority Compliance Model Breach

- Anomalous File / Internal / Masqueraded Executable SMB Write

- Device / New or Uncommon WMI Activity

- Anomalous Connection / New or Uncommon Service Control

- Anomalous Connection / High Volume of New or Uncommon Service Control

- Device / New or Uncommon SMB Named Pipe

- Device / Multiple Lateral Movement Model Breaches

- Device / Large Number of Model Breaches  

- SMB Writes of Suspicious Files (Cyber AI Analyst)

- Suspicious Remote WMI Activity (Cyber AI Analyst)

- Suspicious DCE-RPC Activity (Cyber AI Analyst)

- Compromise / Connection to Suspicious SSL Server

- Compromise / High Volume of Connections with Beacon Score

- Anomalous Connection / Suspicious Self-Signed SSL

- Anomalous Connection / Anomalous SSL without SNI to New External

- Compromise / Suspicious TLS Beaconing To Rare External

- Compromise / Beacon to Young Endpoint

- Compromise / SSL or HTTP Beacon

- Compromise / Agent Beacon to New Endpoint

- Device / Long Agent Connection to New Endpoint

- Compromise / SSL Beaconing to Rare Destination

- Compromise / Large Number of Suspicious Successful Connections

- Compromise / Slow Beaconing Activity To External Rare

- Anomalous Server Activity / Outgoing from Server

- Device / Multiple C2 Model Breaches

- Possible SSL Command and Control (Cyber AI Analyst)

- Unusual Repeated Connections (Cyber AI Analyst)

- Device / ICMP Address Scan

- Device / RDP Scan

- Device / Network Scan

- Device / Suspicious Network Scan Activity

- Scanning of Multiple Devices (Cyber AI Analyst)

- ICMP Address Scan (Cyber AI Analyst)

- Device / Anomalous Github Download

- Unusual Activity / Unusual External Data Transfer

- Device / Initial Breach Chain Compromise

MITRE ATT&CK Mapping

Resource Development techniques:

- Acquire Infrastructure: Malvertising (T1583.008)

Initial Access techniques:

- Drive-by Compromise (T1189)

Execution techniques:

- User Execution: Malicious File (T1204.002)

- System Services: Service Execution (T1569.002)

- Windows Management Instrumentation (T1047)

Defence Evasion techniques:

- Masquerading: Match Legitimate Name or Location (T1036.005)

Discovery techniques:

- Remote System Discovery (T1018)

- Network Service Discovery (T1046)

Lateral Movement techniques:

- Remote Services: SMB/Windows Admin Shares

- Lateral Tool Transfer (T1570)

Command and Control techniques:

- Application Layer Protocol: Web Protocols (T1071.001)

- Encrypted Channel: Asymmetric Cryptography (T1573.002)

- Non-Standard Port (T1571)

- Ingress Tool Channel (T1105)

Exfiltration techniques:

- Exfiltration Over C2 Channel (T1041)

Impact techniques:

- Data Encrypted for Impact (T1486)

List of Indicators of Compromise

- allpcsoftware[.]com

- wireshhark[.]com

- pse[.]ac • 194.169.175[.]132

- 194.180.48[.]169

- 193.42.33[.]14

- 141.98.6[.]195

References  

[1] https://darktrace.com/threat-report-2023

[2] https://www.microsoft.com/en-us/security/blog/2022/05/09/ransomware-as-a-service-understanding-the-cybercrime-gig-economy-and-how-to-protect-yourself/

[3] https://www.bleepingcomputer.com/news/security/alphv-blackcat-this-years-most-sophisticated-ransomware/

[4] https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-353a

[5] https://www.justice.gov/opa/pr/justice-department-disrupts-prolific-alphvblackcat-ransomware-variant

[6] https://www.state.gov/u-s-department-of-state-announces-reward-offers-for-criminal-associates-of-the-alphv-blackcat-ransomware-variant/

[7] https://www.bleepingcomputer.com/news/security/blackcat-alphv-ransomware-linked-to-blackmatter-darkside-gangs/

[8] https://www.trendmicro.com/en_us/research/23/f/malvertising-used-as-entry-vector-for-blackcat-actors-also-lever.html

[9] https://news.sophos.com/en-us/2023/07/26/into-the-tank-with-nitrogen/

[10] https://www.esentire.com/blog/persistent-connection-established-nitrogen-campaign-leverages-dll-side-loading-technique-for-c2-communication

[11] https://www.esentire.com/blog/nitrogen-campaign-2-0-reloads-with-enhanced-capabilities-leading-to-alphv-blackcat-ransomware

[12] https://www.esentire.com/blog/the-notorious-alphv-blackcat-ransomware-gang-is-attacking-corporations-and-public-entities-using-google-ads-laced-with-malware-warns-esentire

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
Sam Lister
Specialist Security Researcher

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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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