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January 17, 2024

Detecting Trusted Network Relationship Abuse

Discover how Darktrace DETECT and the SOC team responded to a network compromise via a trusted partner relationship with this case study.
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
Adam Potter
Senior Cyber Analyst
Written by
Taylor Breland
Analyst Team Lead, San Francisco
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17
Jan 2024

Trusted relationships between organizations and third parties have become an increasingly popular target for cyber threat actors to gain access to sensitive networks. These relationships are typically granted by organizations to external or adjacent entities and allow for the access of internal resources for business purposes.1 Trusted network relations can exist between constituent elements of an overarching corporation, IT-service providers and their customers, and even implicitly between IT product vendors and their customers.

Several high-profile compromises have occurred due to the leveraging of privileged network access by such third parties. One prominent example is the 2016 DNC network attack, in which the trust between the Democratic Congressional Campaign Committee (DCCC) and the Democratic National Committee (DNC) was exploited. Supply chain attacks, which also leverage the implicit trust between IT vendors and customers, are also on the rise with some estimates projecting that by 2025, almost half of all organizations will be impact by supply chain compromises.2 These trends may also be attributed to the prevalence of remote work as well as the growth in IT-managed service providers.3

Given the nature of such network relationships and threat techniques, signatures-based detection is heavily disadvantaged in the identification and mitigation of such trust abuses; network administrators cannot as easily use firewalls to block IPs that need access to networks. However, Darktrace DETECT™, and its Self-Learning AI, has proven successful in the identification and mitigation of these compromises. In September 2023, Darktrace observed an incident involving the abuse of such a trusted relationship on the network of a healthcare provider.

Attack Overview

In early September 2023, a Darktrace customer contacted the Darktrace Security Operations Center (SOC) through the Ask the Expert™ (ATE) service requesting assistance with suspicious activity detected on their network. Darktrace had alerted the customer’s security team to an unknown device that had appeared on their network and proceeded to perform a series of unexpected activities, including reconnaissance, lateral movement, and attempted data exfiltration.

Unfortunately for this customer, Darktrace RESPOND™ was not enabled in autonomous response mode at the time of this compromise, meaning any preventative actions suggested by RESPOND had to be applied manually by the customer’s security team after the fact.  Nevertheless, Darktrace’s prompt identification of the suspicious activity and the SOC’s investigation helped to disrupt the intrusion in its early stages, preventing it from developing into a more disruptive compromise.

Initial Access

Darktrace initially observed a new device that appeared within the customers internal network with a Network Address Translated (NAT) IP address that suggested remote access from a former partner organization’s network. Further investigation carried out by the customer revealed that poor credential policies within the partner’s organization had likely been exploited by attackers to gain access to a virtual desktop interface (VDI) machine.

Using the VDI appliance of a trusted associate, the threat actor was then able to gain access to the customer’s environment by utilizing NAT remote access infrastructure. Devices within the customer’s network had previously been utilized for remote access from the partner network when such activity was permitted and expected. Since then, access to this network was thought to have been removed for all parties. However, it became apparent that the remote access functionality remained operational. While the customer also had firewalls within the environment, a misconfiguration at the time of the attack allowed inbound port access to the remote environment resulting in the suspicious device joining the network on August 29, 2023.

Internal Reconnaissance

Shortly after the device joined the network, Darktrace observed it carrying out a string of internal reconnaissance activity. This activity was initiated with internal ICMP address connectivity, followed by internal TCP connection attempts to a range of ports associated with critical services like SMB, RDP, HTTP, RPC, and SSL. The device was also detected attempting to utilize privileged credentials, which were later identified as relating to a generic multi-purpose administrative account. The threat actor proceeded to conduct further internal reconnaissance, including reverse DNS sweeps, while also attempting to use six additional user credentials.

In addition to the widespread internal connectivity, Darktrace observed persistent connection attempts focused on the RDP and SMB protocols. Darktrace also detected additional SMB enumeration during this phase of the attacker’s reconnaissance. This reconnaissance activity largely attempted to access a wide variety of SMB shares, previously unseen by the host to identify available share types and information available for aggregation. As such, the breach host conducted a large spike in SMB writes to the server service (srvsvc) endpoint on a range of internal hosts using the credential: extramedwb. SMB writes to this endpoint traditionally indicate binding attempts.

Beginning on August 31, Darktrace identified a new host associated with the aforementioned NAT IP address. This new host appeared to have taken over as the primary host conducting the reconnaissance and lateral movement on the network taking advantage of the VDI infrastructure. Like the previous host, this one was observed sustaining reconnaissance activity on August 31, featuring elevated SMB enumeration, SMB access failures, RDP connection attempts, and reverse DNS sweeps.  The attackers utilized several credentials to execute their reconnaissance, including generic and possibly default administrative credentials, including “auditor” and “administrator”.

Figure 1: Advanced Search query highlighting anomalous activity from the second observed remote access host over the course of one week surrounding the time of the breach.

Following these initial detections by Darktrace DETECT, Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the scanning and privileged internal connectivity and linked these seemingly separate events together into one wider internal reconnaissance incident.

Figure 2: Timeline of an AI Analyst investigation carried out between August 29 and August 31, 2023, during which it detected an increased volume of scanning and unusual privileged internal connectivity.

Lateral Movement

Following the reconnaissance activity performed by the new host observed exploiting the remote access infrastructure, Darktrace detected an increase in attempts to move laterally within the customer’s network, particularly via RPC commands and SMB file writes.

Specifically, the threat actor was observed attempting RPC binds to several destination devices, which can be used in the calling of commands and/or the creation of services on destination devices. This activity was highlighted in repeated failed attempts to bind to the ntsvcs named pipe on several destination devices within the network. However, given the large number of connection attempts, Darktrace did also detect a number of successful RPC connections.

Darktrace also detected a spike in uncommon service control (SVCCTL) ExecMethod, Create, and Start service operations from the breach device.

Figure 3: Model breach details noting the affected device performing unsuccessful RPC binds to endpoints not supported on the destination device.

Additional lateral movement activity was performed using the SMB/NTLM protocols. The affected device also conducted a series of anonymous NTLM logins, whereby NTLM authentication attempts occurred without a named client principal, to a range of internal hosts. Such activity is highly indicative of malicious or unauthorized activity on the network. The host also employed the outdated SMB version 1 (SMBv1) protocol during this phase of the kill chain. The use of SMBv1 often represents a compliance issue for most networks due to the high number of exploitable vulnerabilities associated with this version of the protocol.

Lastly, Darktrace identified the internal transfer of uncommon executables, such as ‘TRMtZSqo.exe’, via SMB write. The breach device was observed writing this file to the hidden administrative share (ADMIN$) on a destination server. Darktrace recognized that this activity was highly unusual for the device and may have represented the threat actor transferring a malicious payload to the destination server for further persistence, data aggregation, and/or command and control (C2) operations. Further SMB writes of executable files, and the subsequent delete of these binaries, were observed from the device at this time. For example, the additional executable ‘JAqfhBEB.exe’ was seen being deleted by the breach device. This deletion, paired with the spike in SVCCTL Create and Start operations occurring, suggests the transfer, execution, and removal of persistence and data harvesting binaries within the network.

Figure 4: AI Analyst details highlighting the SMB file writes of the unusual executable from the remote access device during the compromise.

Conclusion

Ultimately, Darktrace was able to successfully identify and alert for suspicious activity being performed by a threat actor who had gained unauthorized access to the customer’s network by abusing one of their trusted relationships.

The identification of scanning, RPC commands and SMB sessions directly assisted the customer in their response to contain and mitigate this intrusion. The investigation carried out by the Darktrace SOC enabled the customer to promptly triage and remediate the attack, mitigating the potential damage and preventing the compromise from escalating further. Had Darktrace RESPOND been enabled in autonomous response mode at the time of the attack, it would have been able to take swift action to inhibit the scanning, share enumerations and file write activity, thereby thwarting the attacker’s network reconnaissance and lateral movement attempts.

By exploiting trusted relationships between organizations, threat actors are often able to bypass traditional signatured-based security methods that have previously been reconfigured to allow and trust connections from and to specific endpoints. Rather than relying on the configurations of specific rules and permitted IP addresses, ports, and devices, Darktrace DETECT’s anomaly-based approach to threat detection meant it was able to identify suspicious network activity at the earliest stage, irrespective of the offending device and whether the domain or relationship was trusted.

Credit to Adam Potter, Cyber Security Analyst, Taylor Breland, Analyst Team Lead, San Francisco.

Darktrace DETECT Model Breach Coverage:

  • Device / ICMP Address Scan
  • Device / Network Scan
  • Device / Suspicious SMB Scanning Activity
  • Device / RDP Scan
  • Device / Possible SMB/NTLM Reconnaissance
  • Device / Reverse DNS Sweep
  • Anomalous Connection / SMB Enumeration
  • Device / Large Number of Model Breaches
  • Anomalous Connection / Suspicious Activity On High Risk Device
  • Unusual Activity / Possible RPC Recon Activity
  • Device / Anonymous NTLM Logins
  • Anomalous Connection / Unusual SMB Version 1 Connectivity
  • Device / Repeated Unknown RPC Service Bind Errors
  • Anomalous Connection / New or Uncommon Service Control
  • Compliance / SMB Drive Write
  • Anomalous File / Internal / Unusual Internal EXE File Transfer
  • Device / Multiple Lateral Movement Model Breaches

AI Analyst Incidents:

  • Scanning of Multiple Devices
  • Extensive Unusual RDPConnections
  • SMB Write of Suspicious File
  • Suspicious DCE-RPC Activity

MITRE ATT&CK Mapping

  • Tactic: Initial Access
  • Technique: T1199 - Trusted Relationship
  • Tactic: Discovery
  • Technique:
  • T1018 - Remote System Discovery
  • T1046 - Network Service Discovery
  • T1135 - Network Share Discovery
  • T1083 - File and Directory Discovery
  • Tactic: Lateral Movement
  • Technique:
  • T1570 - Lateral Tool Transfer
  • T1021 - Remote Services
  • T1021.002 - SMB/Windows Admin Shares
  • T1021.003 - Distributed Component Object Model
  • T1550 - Use Alternate Authentication Material

References

1https://attack.mitre.org/techniques/T1199/

2https://www.cloudflare.com/learning/insights-supply-chain-attacks/

3https://newsroom.cisco.com/c/r/newsroom/en/us/a/y2023/m09/companies-reliance-on-it-managed-services-increases-in-2023-sector-valued-at-us-472-billion-globally.html#:~:text=IT%20channel%20partners%20selling%20managed,US%24419%20billion%20in%202022.

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
Adam Potter
Senior Cyber Analyst
Written by
Taylor Breland
Analyst Team Lead, San Francisco

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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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Justin Torres
Cyber Analyst
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