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August 29, 2023

Analyzing Post-Exploitation on Papercut Servers

Dive into our analysis covering post-exploitation activity on PaperCut servers. Learn the details and impact of this attack and how to keep yourself safe!
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
Aug 2023

Introduction

Malicious cyber actors are known to exploit vulnerabilities in Internet-facing systems and services to gain entry to organizations’ digital environments. Keeping track of the vulnerabilities which malicious actors are exploiting is seemingly futile, with malicious actors continually finding new avenues of exploitation.  

In mid-April 2023, Darktrace, along with the wider security community, observed malicious cyber actors gaining entry to networks through exploitation of a critical vulnerability in the print management system, PaperCut. Darktrace observed two types of attack chain within its customer base, one involving the deployment of payloads to facilitate crypto-mining, and the other involving the deployment of a payload to facilitate Tor-based command-and-control (C2) communication.

Walking Through the Front Door

One of the most widely abused Initial Access methods attackers use to gain entry to an organization’s digital environment is the exploitation of vulnerabilities in Internet-facing systems and services [1]. The public disclosure of a critical vulnerability in a widely used, Internet-facing service, along with a proof of concept (POC) exploit for such vulnerability, provides malicious cyber actors with a key to the front door of countless organizations. Once malicious actors are in possession of such a key, security teams are in a race against time to patch all their vulnerable systems and services. But until organizations accomplish this, the doors are left open.

This year, the security community has seen malicious actors gaining entry to networks through the exploitation of vulnerabilities in a range of services. These services include familiar suspects, such as Microsoft Exchange and ManageEngine, along with less familiar suspects, such as PaperCut. PaperCut is a system for managing and tracking printing, copying, and scanning activity within organizations. In 2021, PaperCut was used in more than 50,000 sites across over 100 countries [2], making PaperCut a widely used print management system.

In January 2023, Trend Micro’s Zero Day Initiative (ZDI) notified PaperCut of a critical RCE vulnerability, namely CVE-2023–27350, in certain versions of PaperCut NG (PaperCut’s ‘print only’ variant) and PaperCut MF (PaperCut’s ‘extended feature’ variant) [3,4]. In March 2023, PaperCut released versions of PaperCut NG and PaperCut MF containing a fix for CVE-2023–27350 [4]. Despite this, security teams observed a surge in cases of malicious actors exploiting CVE-2023–27350 to compromise PaperCut servers in April 2023 [4-10]. This trend was mirrored in Darktrace’s customer base, where a surge in compromises of PaperCut servers was observed in April 2023.

Observed Attack Chains

In mid-April 2023, Darktrace identified two related clusters of attack chains. The attack chains within the first of these clusters involved Internet-facing PaperCut servers downloading payloads with crypto-mining capabilities from the external location, 50.19.48[.]59. While the attack chains within the second of the clusters involved Internet-facing PaperCut servers downloading payloads with Tor-based C2 capabilities from 192.184.35[.]216. The attack chains within the first cluster, which were observed on April 22, 2023, will be referred to as ‘50.19.48[.]59 chains’ and the attack chains in the second cluster, observed on April 24, 2023, will be called ‘192.184.35[.]216 chains’.

Both attack chains started with highly unusual external endpoints contacting the '/SetupCompleted' endpoint of an Internet-facing PaperCut server. These requests to the ‘/SetupCompleted’ endpoint likely represented attempts to exploit CVE-2023–27350 [10].  50.19.48[.]59 chains started with exploit connections from the external endpoint, 85.106.112[.]60, whereas 192.184.35[.]216 chains started with exploit connections from Tor nodes, such as 185.34.33[.]2.

Figure 1: Darktrace’s Advanced Search data showing likely CVE-2023-27350 exploitation activity from the suspicious, external endpoint, 85.106.112[.]60.

After the exploitation step, the two attack chains took different paths. In the 50.19.48[.]59 chains, the exploitation step was followed by the affected PaperCut server making HTTP GET requests over port 82 to the rare external endpoint, 50.19.48[.]59. In the 192.184.35[.]216 chains, the exploitation step was followed by the affected PaperCut server making an HTTP GET request over port 443 to 192.184.35[.]216.

The HTTP GET requests to 50.19.48[.]59 had Target URIs such as ‘/me1.bat’, ‘/me2.bat’, ‘/dom.zip’, ‘/mazar.bat’, and ‘/mazar.zip’, whilst the HTTP GET requests to 192.184.35[.]216 had the Target URI ‘/4591187629.exe’. The User-Agent header of the GET requests to 192.184.35[.]216 indicated that that the malicious file transfers were initiated through Microsoft’s pre-installed Background Intelligent Transfer Service (BITS).

Figure 2: Darktrace’s Advanced Search data showing a PaperCut server downloading Batch and ZIP files from 50.19.48[.]59 straight after receiving likely exploit connections from 85.106.112[.]60.
Figure 3: Darktrace’s Event Log data showing a PaperCut server downloading an executable file from 192.184.35[.]216 immediately after receiving a likely exploit connection from the Tor node, 185.34.33[.]2.

Downloads from 50.19.48[.]59 were followed by cURL GET requests to 138.68.61[.]82 and then connections to external endpoints associated with the cryptocurrency miner, Mimu (as seen in Fig 4). Downloads from 192.184.35[.]216 were followed by Python-urllib GET requests to api.ipify[.]org and long connections to Tor nodes (as seen in Fig 5).  

These facts suggest that the actor behind the 50.19.48[.]59 chains were seeking to drop cryptocurrency miners on PaperCut servers, with the intention of abusing the customer’s network to carry out resource intensive and costly cryptocurrency mining activity. Meanwhile, the actors behind the 192.184.35[.]216 chains were likely attempting to establish a Tor-based C2 channel with PaperCut servers to allow actors to further communicate with compromised devices.

Figure 4: Darktrace's Event Log data showing a PaperCut contacting 50.19.48[.]59 to download payloads, and then making a cURL request to 138.68.61[.]82 before contacting a Mimu crypto-mining endpoint.
Figure 5: Darktrace’s Event Log data showing a PaperCut server contacting 192.184.35[.]216 to download a payload, and then making connections to api.ipify[.]org and several Tor nodes.

The activities ensuing from both attack chains were varied, making it difficult to ascertain whether the activities were steps of separate attack chains, or steps of the existing 50.19.48[.]59 and 192.184.35[.]216 chains. A wide variety of activities ensued from observed 50.19.48[.]59 and 192.184.35[.]216 chains, including the abuse of pre-installed tools, such as cURL, CertUtil, and PowerShell to transfer further payloads to PaperCut servers, Cobalt Strike C2 communication, Ngrok usage, Mimikatz usage, AnyDesk usage, and in one case, detonation of the LockBit ransomware strain.

Figure 6: Diagram representing the steps of observed 50.19.48[.]59 chains.
Figure 7: Diagram representing the steps of observed 192.184.35[.]215 chains.

As the PaperCut servers that were targeted by malicious actors are Internet-facing, they regularly receive connections from unusual external endpoints. The exploit connections in the 50.19.48[.]59 and 192.184.35[.]216 chains, which originated from unusual external endpoints, were therefore not detected by Darktrace DETECT™, which relies on anomaly-based methods to detect network-based steps of an intrusion.

On the other hand, the post-exploitation steps of the 50.19.48[.]59 and 192.184.35[.]216 chains yielded ample anomaly-based detections, given that they consisted of PaperCut servers displaying highly unusual behaviors. As such Darktrace DETECT was able to successfully identify multiple chains of suspicious activity, including unusual file downloads from external endpoints and beaconing activity to rare external locations.

The file downloads from 50.19.48[.]59 observed in the 50.19.48[.]59 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / Application Protocol on Uncommon Port

- Anomalous File / Internet Facing System File Download

- Anomalous File / Script from Rare External Location

- Anomalous File / Zip or Gzip from Rare External Location

- Device / Internet Facing Device with High Priority Alert

Figure 8: Darktrace’s Event Log data showing a PaperCut server breaching several models immediately after contacting 50.19.48[.]59.

The file downloads from 192.184.35[.]216 observed in the 192.184.35[.]216 chains caused the following Darktrace DETECT models to breach:

- Anomalous File / EXE from Rare External Location

- Anomalous File / Numeric File Download

- Device / Internet Facing Device with High Priority Alert

Figure 9: Darktrace’s Event Log data showing a PaperCut server breaching several models immediately after contacting 192.184.35[.]216.

Subsequent C2, beaconing, and crypto-mining connections in the 50.19.48[.]59 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / New User Agent to IP Without Hostname

- Anomalous Server Activity / New User Agent from Internet Facing System

- Anomalous Server Activity / Rare External from Server

- Compromise / Crypto Currency Mining Activity

- Compromise / High Priority Crypto Currency Mining

- Compromise / High Volume of Connections with Beacon Score

- Compromise / Large Number of Suspicious Failed Connections

- Compromise / SSL Beaconing to Rare Destination

- Device / Initial Breach Chain Compromise

- Device / Large Number of Model Breaches

Figure 10: Darktrace’s Event Log data showing a PaperCut server breaching models as a result of its connections to a Mimu crypto-mining endpoint.

Subsequent C2, beaconing, and Tor connections in the 192.184.35[.]216 chains caused the following Darktrace DETECT models to breach:

- Anomalous Connection / Application Protocol on Uncommon Port

- Compromise / Anomalous File then Tor

- Compromise / Beaconing Activity To External Rare

- Compromise / Possible Tor Usage

- Compromise / Slow Beaconing Activity To External Rare

- Compromise / Uncommon Tor Usage

- Device / Initial Breach Chain Compromise

Figure 11: Darktrace’s Event Log data showing a PaperCut server breaching several models as a result of its connections to Tor nodes.

Darktrace RESPOND

Darktrace RESPOND™ was not active in any of the networks affected by 192.184.35[.]216 activity, however, RESPOND was active in some of the networks affected by 50.19.48[.]59 activity.  In those environments where RESPOND was enabled in autonomous mode, observed malicious activities resulted in intervention from RESPOND, including autonomous actions like blocking connections to specific external endpoints, blocking all outgoing traffic, and restricting affected devices to a pre-established pattern of behavior.

Figure 12: Darktrace’s Event Log data showing Darktrace RESPOND automatically performing inhibitive actions on a device in response to the device’s connection to 50.19.48[.]59.
Figure 13: Darktrace’s Event Log data showing Darktrace RESPOND automatically performing inhibitive actions on a device in response to the device’s connections to a Mimu crypto-mining endpoint.

Darktrace Cyber AI Analyst

Cyber AI Analyst autonomously investigated model breaches caused by events within these 50.19.48[.]59 and 192.184.35[.]216 chains. Cyber AI Analyst created user-friendly and detailed descriptions of these events, and then linked together these descriptions into threads representing the attack chains. Darktrace DETECT thus uncovered the individual steps of the attack chains, while Cyber AI Analyst was able to piece together the individual steps and uncover the attack chains themselves.  

Figure 14: An AI Analyst Incident entry showing the first event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 15: An AI Analyst Incident entry showing the second event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 16: An AI Analyst Incident entry showing the third event in a 50.19.48[.]59 chain uncovered by Cyber AI Analyst.
Figure 17: An AI Analyst Incident entry showing the first event in a 192.184.35[.]216 chain uncovered by Cyber AI Analyst.
Figure 18: An AI Analyst Incident entry showing the second event in a 192.184.35[.]216 chain uncovered by Cyber AI Analyst.

Conclusion

The existence of critical vulnerabilities in third-party software leaves organizations at constant risk of malicious actors breaching the perimeters of their networks. This risk can be mitigated through attack surface management and regular patching. However, this does not eliminate cyber risk entirely, meaning that organizations must be prepared for the eventuality of malicious actors getting inside their digital estate.

In April 2023, Darktrace observed malicious actors breaching the perimeters of several customer networks through exploitation of a critical vulnerability in PaperCut. Darktrace DETECT observed actors exploiting PaperCut servers to conduct a wide variety of post-exploitation activities, including downloading malicious payloads associated with cryptocurrency mining or payloads with Tor-based C2 capabilities. Darktrace DETECT created numerous model breaches based on this activity which alerted then customer’s security teams early in their development, providing them with ample time to take mitigative steps.

The successful detection of this payload delivery activity, along with the crypto-mining, beaconing, and Tor C2 activities which followed, elicited Darktrace RESPOND to take autonomous inhibitive action against the ongoing activity in those environments where it was operating in autonomous response mode.

If left to unfold, these intrusions developed in a variety of ways, in some cases leading to Cobalt Strike and ransomware activity. The detection of these intrusions in their early stages thus played a vital role in preventing malicious cyber actors from causing significant disruption.

Credit to: Sam Lister, Senior SOC Analyst, Zoe Tilsiter, Senior Cyber Analyst.

Appendices

MITRE ATT&CK Mapping

Initial Access techniques:

- Exploit Public-Facing Application (T1190)

Execution techniques:

- Command and Scripting Interpreter: PowerShell (T1059.001)

Discovery techniques:

- System Network Configuration Discovery (T1016)

Command and Control techniques

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

- Encrypted Channel: Asymmetric Cryptography (T1573.002)

- Ingress Tool Transfer (T1105)

- Non-Standard Port (T1571)

- Protocol Tunneling (T1572)

- Proxy: Multi-hop Proxy (T1090.003)

- Remote Access Software (T1219)

Defense Evasion techniques:

- BITS Jobs (T1197)

Impact techniques:

- Data Encrypted for Impact (T1486)

List of Indicators of Compromise (IoCs)

IoCs from 50.19.48[.]59 attack chains:

- 85.106.112[.]60

- http://50.19.48[.]59:82/me1.bat

- http://50.19.48[.]59:82/me2.bat

- http://50.19.48[.]59:82/dom.zip

- 138.68.61[.]82

- update.mimu-me[.]cyou • 102.130.112[.]157

- 34.195.77[.]216

- http://50.19.48[.]59:82/mazar.bat

- http://50.19.48[.]59:82/mazar.zip

- http://50.19.48[.]59:82/prx.bat

- http://50.19.48[.]59:82/lol.exe  

- http://77.91.85[.]117/122.exe

- windows.n1tro[.]cyou • 176.28.51[.]151

- 77.91.85[.]117

- 91.149.237[.]76

- kernel-mlclosoft[.]site • 104.21.29[.]206

- tunnel.us.ngrok[.]com • 3.134.73[.]173

- 212.113.116[.]105

- c34a54599a1fbaf1786aa6d633545a60 (JA3 client fingerprint of crypto-mining client)

IoCs from 192.184.35[.]216 attack chains:

- 185.56.83[.]83

- 185.34.33[.]2

- http://192.184.35[.]216:443/4591187629.exe

- api.ipify[.]org • 104.237.62[.]211

- www.67m4ipctvrus4cv4qp[.]com • 192.99.43[.]171

- www.ynbznxjq2sckwq3i[.]com • 51.89.106[.]29

- www.kuo2izmlm2silhc[.]com • 51.89.106[.]29

- 148.251.136[.]16

- 51.158.231[.]208

- 51.75.153[.]22

- 82.66.61[.]19

- backmainstream-ltd[.]com • 77.91.72[.]149

- 159.65.42[.]223

- 185.254.37[.]236

- http://137.184.56[.]77:443/for.ps1

- http://137.184.56[.]77:443/c.bat

- 45.88.66[.]59

- http://5.8.18[.]237/download/Load64.exe

- http://5.8.18[.]237/download/sdb64.dll

- 140e0f0cad708278ade0984528fe8493 (JA3 client fingerprint of Tor-based client)

References

[1] https://www.cisa.gov/news-events/cybersecurity-advisories/aa22-137a

[2] https://www.papercut.com/kb/Main/PaperCutMFSolutionBrief/

[3] https://www.zerodayinitiative.com/advisories/ZDI-23-233/

[4] https://www.papercut.com/kb/Main/PO-1216-and-PO-1219

[5] https://www.trendmicro.com/en_us/research/23/d/update-now-papercut-vulnerability-cve-2023-27350-under-active-ex.html

[6] https://www.huntress.com/blog/critical-vulnerabilities-in-papercut-print-management-software

[7] https://news.sophos.com/en-us/2023/04/27/increased-exploitation-of-papercut-drawing-blood-around-the-internet/

[8] https://twitter.com/MsftSecIntel/status/1651346653901725696

[9] https://twitter.com/MsftSecIntel/status/1654610012457648129

[10] https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-131a

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

applescript-led mac os intrusionDefault blog imageDefault blog image

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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