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October 13, 2023

Protecting Brazilian Organizations from Malware

Discover how Darktrace DETECT thwarted a banking trojan targeting Brazilian organizations, preventing data theft and informing the customer.
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
Roberto Romeu
Senior SOC Analyst
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13
Oct 2023

Nationally Targeted Cyber Attacks

As the digital world becomes more and more interconnected, the threat of cyber-attacks transcends borders and presents a significant concern to security teams worldwide. Yet despite this, some malicious actors have shown a tendency to focus their attacks on specific countries. By employing highly tailored tactics, techniques, and procedures (TTPs) to target users and organizations from one nation, rather than launching more widespread campaigns, threat actors are able to maximize the efficiency and efficacy of their attacks.

What is Guildma and how does it work?

One example can be seen in the remote access trojan (RAT) and information stealer, Guildma. Guildma, also known by the demonic moniker, Astaroth, first appeared in the wild in 2017 and is a Latin America-based banking trojan known to primarily target organizations in Brazil, although has more recently been observed in North America and Europe too [1].

By concentrating their efforts on Brazil, Guildma is able to launch attacks with a high degree of specificity, focussing their language on Brazilian norms, referencing Brazilian institutions, and tailoring their social engineering accordingly. Moreover, considering that Brazilian customers likely represent a relatively small portion of security vendors’ clientele, there may be a limited pool of available indicators of compromise (IoCs). This limitation could significantly impact the efficacy of traditional security measures that rely on signature-based detection methods in identifying emerging threats.

Darktrace vs. Guildma

In June 2023, Darktrace observed a Guildma compromise on the network of a Brazilian customer in the manufacturing sector. The anomaly-based detection capabilities of Darktrace DETECT™ allowed it to identify suspicious activity surrounding the compromise, agnostic of any IoCs or specific signatures of a threat actor. Following the successful detection of the malware, the Darktrace Security Operations Center (SOC) carried out a thorough investigation into the compromise and brought it to the attention of the customer’s security team, allowing them to quickly react and prevent any further escalation.

This early detection by Darktrace effectively shut down Guildma operations on the network before any sensitive data could be gathered and stolen by malicious actors.

Attack Overview

In the case of the Guildma RAT detected by Darktrace, the affected system was a desktop device, ostensibly used by one employee. The desktop was first observed on the customer’s network in April 2023; however, it is possible that the initial compromise took place before Darktrace had visibility over the network. Guildma compromises typically start with phishing campaigns, indicating that the initial intrusion in this case likely occurred beyond the scope of Darktrace’s monitoring [2].

Early indicators

On June 23, 2023, Darktrace DETECT observed the first instance of unusual activity being performed by the affected desktop device, namely regular HTTP POST requests to a suspicious domain, indicative of command-and-control (C2) beaconing activity. The domain used an unusual Top-Level Domain (TLD), with a plausibly meaningful (in Portuguese) second-level domain and a seemingly random 11-character third-level domain, “dn00x1o0f0h.puxaofolesanfoneiro[.]quest”.

Throughout the course of this attack, Darktrace observed additional connections like this, representing something of a signature of the attack. The suspicious domains were typically registered within six months of observation, featured an uncommon TLD, and included a seemingly randomized third-level domain of 6-11 characters, followed by a plausibly legitimate second-level domain with a minimum of 15 characters. The connections to these unusual endpoints all followed a similar two-hour beaconing period, suggesting that Guildma may rotate its C2 infrastructure, using the Multi-Stage Channels TTP (MITRE ID T1104) to evade restrictions by firewalls or other signature-based security tools that rely on static lists of IoCs and “known bads”.

Figure 1: Model Breach Event Log for the “Compromise / Agent Beacon (Long Period)”. The connections at two-hour intervals, including at unreasonably late hours, is consistent with beaconing for C2.

Living-off-the-land with BITS abuse

A week later, on June 30, 2023, the affected device was observed making an unusual Microsoft BITS connection. BitsAdmin is a deprecated administrative tool available on most Windows devices and can be leveraged by attackers to transfer malicious obfuscated payloads into and around an organization’s network. The domain observed during this connection, "cwiufv.pratkabelhaemelentmarta[.]shop”, follows the previously outlined domain naming convention. Multiple open-source intelligence (OSINT) sources indicated that the endpoint had links to malware and, when visited, redirected users to the Brazilian versions of WhatsApp and Zoom. This is likely a tactic employed by threat actors to ensure users are unaware of suspicious domains, and subsequent malware downloads, by redirected them to a trusted source.

Figure 2: A screenshot of the Model Breach log summary of the “Unusual BITS Activity” model breach. The breach log contains key details such as the ASN, hostname, and user agent used in the breaching connection.

Obfuscated Tooling Downloads

Within one minute of the suspicious BITS activity, Darktrace detected the device downloading a suspicious file from the aforementioned endpoint, (cwiufv.pratkabelhaemelentmarta[.]shop). The file in question appeared to be a ZIP file with the 17-digit numeric name query, namely “?37627343830628786”, with the filename “zodzXLWwaV.zip”.

However, Darktrace DETECT recognized that the file extension did not match its true file type and identified that it was, in fact, an executable (.exe) file masquerading as a ZIP file. By masquerading files downloads, threat actors are able to make their malicious files seem legitimate and benign to security teams and traditional security tools, thereby evading detection. In this case, the suspicious file in question was indeed identified as malicious by multiple OSINT sources.

Following the initial download of this masqueraded file, Darktrace also detected subsequent downloads of additional executable files from the same endpoint.  It is possible that these downloads represented Guildma actors attempting to download additional tooling, including the information-stealer widely known as Astaroth, in order to begin its data collection and exfiltration operations.

Figure 3: A screenshot of a graph produced by the Threat Visualizer of the affected device's external connections. The visual aid marks breaches with red and orange dots, creating a more intuitive explanation of observed behavior.

Darktrace SOC

The successful detection of the masqueraded file transfer triggered an Enhanced Monitoring model breach, a high-fidelity model designed to detect activity that is more likely indicative of an ongoing compromise.  

This breach was immediately escalated to the Darktrace SOC for analysis by Darktrace’s team of expert analysts who were able to complete a thorough investigation and notify the customer’s security team of the compromise in just over half an hour. The investigation carried out by Darktrace’s analysts confirmed that the activity was, indeed, malicious, and provided the customer’s security team with details around the extent of the compromise, the specific IoCs, and risks this compromise posed to their digital environment. This information empowered the customer’s security team to promptly address the issue, having a significant portion of the investigative burden reduced and resolved by the round-the-clock Darktrace analyst team.

In addition to this, Cyber AI Analyst™ launched an investigation into the ongoing compromise and was able to connect the anomalous HTTP connections to the subsequent suspicious file downloads, viewing them as one incident rather than two isolated events. AI Analyst completed its investigation in just three minutes, upon which it provided a detailed summary of events of the activity, further aiding the customer’s remediation process.

Figure 4: CyberAI Analyst summary of the suspicious activity. A prose summary of the breach activity and the meaning of the technical details is included to maintain an easily digestible stream of information.

Conclusion

While the combination of TTPs observed in this Guildma RAT compromise is not uncommon globally, the specificity to targeting organizations in Brazil allows it to be incredibly effective. By focussing on just one country, malicious actors are able to launch highly specialized attacks, adapting the language used and tailoring the social engineering effectively to achieve maximum success. Moreover, as Brazil likely represents a smaller segment of security vendors’ customers, therefore leading to a limited pool of IoCs, attackers are often able to evade traditional signature-based detections.

Darktrace DETECT’s anomaly-based approach to threat detection allows for effective detection, mitigation, and response to emerging threats, regardless of the specifics of the attack and without relying on threat intelligence or previous IoCs. Ultimately in this case, Darktrace was able to identify the suspicious activity surrounding the Guildma compromise and swiftly bring it to the attention of the customer’s security team, before any data gathering, or exfiltration activity took place.

Darktrace’s threat detection capabilities coupled with its expert analyst team and round-the-clock SOC response is a highly effective addition to an organization’s defense-in-depth, whether in Brazil or anywhere else around the world.

Credit to Roberto Romeu, Senior SOC Analyst, Taylor Breland, Analyst Team Lead, San Francisco

References

https://malpedia.caad.fkie.fraunhofer.de/details/win.astaroth

https://www.welivesecurity.com/2020/03/05/guildma-devil-drives-electric/  

Appendices

Darktrace DETECT Model Breaches

  • Compromise / Agent Beacon (Long Period)
  • Device / Unusual BITS Activity
  • Anomalous File / Anomalous Octet Stream (No User Agent)
  • Anomalous File / Masqueraded File Transfer (Enhanced Monitoring Model)
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations

List of IoCs

IoC Type - Description + Confidence

5q710e1srxk.broilhasoruikaliventiladorrta[.]shop - Domain - Likely C2 server

m2pkdlse8md.roilhasohlcortinartai[.]hair - Domain - Likely C2 server

cwiufv.pratkabelhaemelentmarta[.]shop - Domain - C2 server

482w5pct234.jaroilcasacorkalilc[.]ru[.]com - Domain - C2 server

dn00x1o0f0h.puxaofolesanfoneiro[.]quest - Domain - Likely C2 server

10v7mybga55.futurefrontier[.]cyou - Domain - Likely C2 server

f788gbgdclp.growthgenerator[.]cyou - Domain - Likely C2 server

6nieek.satqabelhaeiloumelsmarta[.]shop - Domain - Likely C2 server

zodzXLWwaV.zip (SHA1 Hash: 2a4062e10a5de813f5688221dbeb3f3ff33eb417 ) - File hash - Malware

IZJQCAOXQb.zip (SHA1 Hash: eaec1754a69c50eac99e774b07ef156a1ca6de06 ) - File hash - Likely malware

MITRE ATT&CK Mapping

ATT&CK Technique - Technique ID

Multi-Stage Channels - T1104

BITS Jobs - T1197

Application Layer Protocol: Web Protocols - T1071.001

Acquire Infrastructure: Web Services - T1583.006

Obtain Capabilities: Malware - T1588.001

Masquerading - T1036

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
Roberto Romeu
Senior SOC Analyst

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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.  

Research indicates 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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