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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 25, 2026

Shadow AI Detection: The First Step Toward Securing AI

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Why shadow AI is emerging  

Imagine you’re an employee under pressure, deadlines stacking up, repetitive tasks piling higher by the day. You find a free AI tool online that promises to automate the work in seconds; no approvals are needed. It feels like a simple win, paste in some data, write a quick prompt, and move faster.

But in that moment, something changed.  

Sensitive customer information is entered into a tool your organization doesn’t monitor, doesn’t govern, and can’t see and suddenly, that data is no longer where it should be, and no one knows where it’s gone.

This is the reality of Shadow AI: employees using unsanctioned AI tools to move faster, while unintentionally creating risk that exists entirely outside visibility and control.  

This is not just a one off case, research across businesses indicate that nearly half of employees report using unsanctioned AI tools, often prioritizing speed and productivity over security. Additionally, 51% of employees report connecting AI tools to work systems or apps without IT approval, creating significant operational risk where the average cost of security incidents in organizations with a high level of shadow AI usage can reach $670k.

While shadow AI is often top of mind for security professionals, it is just one component of how AI use can increase risk. Understanding and managing shadow AI use should be considered as part of a broader, comprehensive risk management strategy that aims to secure AI systems, including human and agent identities, interactions, human-AI partnerships, and behaviors operating across the digital enterprise from visibility and governance through detection, response, and recovery.  

Effective risk management calls for a layered and interdisciplinary strategy. It requires addressing issues across governance and visibility; identity, access and agent control, data security and privacy, secure MLOps / LLMOps, runtime security, behavior-based detection, autonomous response and recovery.  

This blog explores a specific governance and visibility use case linked to shadow AI and reveals the challenges it presents as well as the defensive strategies that security teams can adopt.

Why shadow AI is hard to detect  

When it comes to AI, what organizations can easily see does not always reflect the full scope of AI activity occurring within the tools, applications, and workflows used across an enterprise. As a result, organizations using traditional rule-based methods to flag unusual activity may struggle to distinguish unsanctioned AI usage from legitimate operational behavior, particularly as SaaS applications, APIs, and orchestration layers increasingly have AI embedded into normal business workflows. Identifying threats using previously observed intelligence or depending on hard to maintain allow and block lists does not provide a dynamic enough strategy to manage risk. Also, many organizations are focusing on identifying Shadow AI in their governed infrastructure, like gateways, endpoints, or SASE, which is foundational. But, organizations require visibility and Shadow AI detection across all networked infrastructure from on-prem, hybrid, data centers, and cloud infrastructure that may not have endpoint agent visibility. This uncovers the utilization of MCP, data flows, and autonomous agents across these domains.

For example, employees interact with AI assistants across approved SaaS platforms every day. However, browser extensions and other types of plug-ins can route prompts that include enterprise data to embedded AI services in ways that are not visible to the security team. AI enabled workflows may invoke multiple APIs, orchestration layers, and cloud services behind the scenes, making it difficult for traditional security tooling to determine where data is processed, stored, or retransmitted. Because much of this activity occurs within trusted browser sessions and encrypted SaaS traffic, conventional network monitoring, DLP, and application allowlisting controls often lack the context needed to accurately identify or govern these interactions

Identifying AI tools in the environment is one part of the equation. Understanding the behavior surrounding their use is where the real challenge lies. An AI application is not inherently risky, but the way users or other assets interact with it may be. Sensitive data exposure, abnormal access patterns, and misuse of AI-assisted workflows often appear legitimate in isolation and only become visible through behavioral analysis across the broader environment.  

What Shadow AI visibility does and doesn’t show

Comprehensive Shadow AI visibility allows organizations to answer several important questions:

  • What types of AI are we using? What AI platforms, agents, MCP clients/servers, and services are active across the enterprise?  
  • Who is using AI services? Which users, business units, or systems are interacting with those AI services?  
  • Is our data safe? Is sensitive or regulated data being exposed through prompts, workflows, or integrations?  
  • Are AI systems behaving as expected? Are AI systems behaving anomalously or operating outside approved governance processes?  
  • Are our AI systems under attack? Is an attacker attempting to manipulate prompts, influence agent behavior, or abuse AI-enabled workflows?

Answering these questions is foundational to broader AI governance efforts. However, it is limited to helping teams understand initial interactions and fails to offer insight into dependencies and outcomes that are critical to securing AI across an enterprise.  

Deeper visibility that includes the ability to understand dependencies and outcomes are not always available in AI security point products. Answering the questions below requires understanding runtime behavior and operational outcomes:  

  • What actions did the AI interaction trigger?  
  • What systems, applications, or data did it access? Did the AI operate beyond its intended permissions or scope?  
  • Could a low-risk interaction lead to high-risk outcomes?  
  • What is the risk and context understanding of an anomalous activity to assist in prioritization of analysis and autonomous response action?

The distinction between these two sets of questions offers two different layers of AI security. The first set of questions focuses on discovery and interaction visibility. The second set focuses on providing visibility that includes the context and outcomes that are critical for managing follow-on risks associated with obfuscated downstream activities.  

Together, these layers help organizations move beyond simply identifying AI usage toward understanding how AI behaves operationally across the enterprise.

How organizations are addressing shadow AI

Most organizations still approach shadow AI as an application control problem, relying on policies, browser restrictions, and allow/block lists. However, AI adoption is evolving faster than most governance processes can realistically keep pace with. New assistants, plugins, and embedded AI features appear continuously, creating pressure to enable business productivity while simultaneously containing risk.  

Existing governance processes were designed for a more traditional SaaS adoption cycle, where new applications could be reviewed, approved, and monitored over longer time horizons. AI adoption operates differently. New capabilities can appear overnight inside existing platforms employees already use, making it difficult for security and governance teams to maintain an accurate understanding of enterprise AI exposure. This means that many organizations are experiencing significant operational overhead, particularly in large environments where AI usage is decentralized across teams, departments, and third-party services.  

Where should organizations start when securing their AI systems?

Shadow AI identification is an on-going critical component for AI Risk/Governance Boards as well as security organizations. As organizations seek AI certifications like ISO 42001 AI Management Systems, visibility into all AI adoption from enterprise use to custom innovation and development is crucial. Shadow AI identification provides organizations with the visibility needed to decide whether an AI tool should be brought into governed environments to reduce data loss (DLP) risks or whether policies should be established and enforced to restrict their use.

As organizations rapidly innovate and adopt AI, they are taking on more and more risk. Organizations need to have a strategy in place to mitigate the assumed risk, especially with third-party adoption. Visibility, monitoring, governance enforcement, behavioral-based detection of non-deterministic systems, and autonomous investigation and containment becomes critical to mitigating the risk of AI systems.  

How Darktrace secures AI and shadow AI

Attackers are using AI to move faster, scale tactics, and make threats more adaptive and convincing. Internally, organizations are grappling with new forms of risk created by generative AI, autonomous agents, shadow AI, and increasingly complex digital environments.

Darktrace helps organizations protect both people and AI in a world where AI is now central to how business gets done. Darktrace / SECURE AI helps organizations discover and control shadow AI by surfacing unsanctioned or unexpected AI activity where it appears – including MCP detections, distinguishing misuse of legitimate tools and unapproved services, and applying policy to contain data exposure while guiding users toward sanctioned options.

Stay up to date on AI security

Sign up for the Secure AI Readiness Program here: This gives you exclusive access to the latest news on the latest AI threats, updates on emerging approaches shaping AI security, and insights into the latest innovations, including Darktrace’s ongoing work in this area.

Ready to talk with a Darktrace expert on securing AI? Register here to receive practical guidance on the AI risks that matter most to your business, paired with clarity on where to focus first across governance, visibility, risk reduction, and long-term readiness.  

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June 25, 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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