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March 19, 2024

Pikabot Malware: Insights, Impact, & Attack Analysis

Learn about Pikabot malware and its rapid evolution in the wild, impacting organizations and how to defend against this growing threat.
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
Brianna Luong (Leddy)
Sr. Technical Alliances Manager
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19
Mar 2024

How does Loader Malware work?

Throughout 2023, the Darktrace Threat Research team identified and investigated multiple strains of loader malware affecting customers across its fleet. These malicious programs typically serve as a gateway for threat actors to gain initial access to an organization’s network, paving the way for subsequent attacks, including additional malware infections or disruptive ransomware attacks.

How to defend against loader malware

The prevalence of such initial access threats highlights the need for organizations to defend against multi-phase compromises, where modular malware swiftly progresses from one stage of an attack to the next. One notable example observed in 2023 was Pikabot, a versatile loader malware used for initial access and often accompanied by secondary compromises like Cobalt Strike and Black Basta ransomware.

While Darktrace initially investigated multiple instances of campaign-like activity associated with Pikabot during the summer of 2023, a new campaign emerged in October which was observed targeting a Darktrace customer in Europe. Thanks to the timely detection by Darktrace DETECT™ and the support of Darktrace’s Security Operations Center (SOC), the Pikabot compromise was quickly shut down before it could escalate into a more disruptive attack.

What is Pikabot?

Pikabot is one of the latest modular loader malware strains that has been active since the first half of 2023, with several evolutions in its methodology observed in the months since. Initial researchers noted similarities to the Qakbot aka Qbot or Pinkslipbot and Mantanbuchus malware families, and while Pikabot appears to be a new malware in early development, it shares multiple commonalities with Qakbot [1].

First, both Pikabot and Qakbot have similar distribution methods, can be used for multi-stage attacks, and are often accompanied by downloads of Cobalt Strike and other malware strains. The threat actor known as TA577, which has also been referred to as Water Curupira, has been seen to use both types of malware in spam campaigns which can lead to Black Basta ransomware attacks [2] [3].Notably, a rise in Pikabot campaigns were observed in September and October 2023, shortly after the takedown of Qakbot in Operation Duck Hunt, suggesting that Pikabot may be serving as a replacement for initial access to target network [4].

How does Pikabot malware work?

Many Pikabot infections start with a malicious email, particularly using email thread hijacking; however, other cases have been distributed via malspam and malvertising [5]. Once downloaded, Pikabot runs anti-analysis techniques and checks the system’s language, self-terminating if the language matches that of a Commonwealth of Independent States (CIS) country, such as Russian or Ukrainian. It will then gather key information to send to a command-and-control (C2) server, at which point additional payload downloads may be observed [2]. Early response to a Pikabot infection is important for organizations to prevent escalation to a significant compromise such as ransomware.

Darktrace’s Coverage of Pikabot malware

Between April and July 2023, the Darktrace Threat Research team investigated Pikabot infections affected more than 15 customer environments; these attacks primarily targeted US and European organizations spanning multiple industries, and most followed the below lifecycle:

  1. Initial access via malspam or email, often outside of Darktrace’s scope
  2. Suspicious executable download from a URI in the format /\/[a-z0-9A-Z]{3,}\/[a-z0-9A-Z]{5,}/ and using a Windows PowerShell user agent
  3. C2 connections to IP addresses on uncommon ports including 1194 and 2078
  4. Some cases involved further C2 activity to Cobalt Strike endpoints

In October 2023, a second campaign emerged that largely followed the same attack pattern, with a notable difference that cURL was used for the initial payload download as opposed to PowerShell. All the Pikabot cases that Darktrace has observed since October 2023 have used cURL, which could indicate a shift in approach from targeting Windows devices to multi-operating system environments.

Figure 1: Timeline of the Pikabot infection over a 2-hour period.

On October 17, 2023, Darktrace observed a Pikabot infection on the network of a European customer after an internal user seemingly clicked a malicious link in a phishing email, thereby compromising their device. As the customer did not have Darktrace/Email™ deployed on their network, Darktrace did not have visibility over the email. Despite this, DETECT was still able to provide full visibility over the network-based activity that ensued.

Darktrace observed the device using a cURL user agent when initiating the download of an unusual executable (.exe) file from an IP address that had never previously been observed on the network. Darktrace further recognized that the executable file was attempting to masquerade as a different file type, likely to evade the detection of security teams and their security tools. Within one minute, the device began to communicate with additional unusual IP addresses on uncommon ports (185.106.94[.]174:5000 and 80.85.140[.]152:5938), both of which have been noted by open-source intelligence (OSINT) vendors as Pikabot C2 servers [6] [7].

Figure 2: Darktrace model breach Event Log showing the initial file download, immediately followed by a connection attempt to a Pikabot C2 server.

Around 40 minutes after the initial download, Darktrace detected the device performing suspicious DNS tunneling using a pattern that resembled the Cobalt Strike Beacon. This was accompanied by beaconing activity to a rare domain, ‘wordstt182[.]com’, which was registered only 4 days prior to this activity [8]. Darktrace observed additional DNS connections to the endpoint, ‘building4business[.]net’, which had been linked to Black Basta ransomware [2].

Figure 3: The affected device making successful TXT DNS requests to known Black Basta endpoints.

As this customer had integrated Darktrace with the Microsoft Defender, Defender was able to contextualize the DETECT model breaches with endpoint insights, such as known threats and malware, providing customers with unparalleled visibility of the host-level detections surrounding network-level anomalies.

In this case, the behavior of the affected device triggered multiple Microsoft Defender alerts, including one alert which linked the activity to the threat actor Storm-0464, another name for TA577 and Water Curupira. These insights were presented to the customer in the form of a Security Integration alert, allowing them to build a full picture of the ongoing incident.

Figure 4: Security Integration alert from Microsoft Defender in Darktrace, linking the observed activity to the threat group Storm-0464.

As the customer had subscribed to Darktrace’s Proactive Threat Notification (PTN) service, the customer received timely alerts from Darktrace’s SOC notifying them of the suspicious activity associated with Pikabot. This allowed the customer’s security team to quickly identify the affected device and remove it from their environment for remediation.

Although the customer did have Darktrace RESPOND™ enabled on their network, it was configured in human confirmation mode, requiring manual application for any RESPOND actions. RESPOND had suggested numerous actions to interrupt and contain the attack, including blocking connections to the observed Pikabot C2 addresses, which were manually actioned by the customer’s security team after the fact. Had RESPOND been enabled in autonomous response mode during the attack, it would have autonomously blocked these C2 connections and prevented the download of any suspicious files, effectively halting the escalation of the attack.

Nonetheless, Darktrace DETECT’s prompt identification and alerting of this incident played a crucial role in enabling the customer to mitigate the threat of Pikabot, preventing it from progressing into a disruptive ransomware attack.

Figure 5: Darktrace RESPOND actions recommended from the initial file download and throughout the C2 traffic, ranging from blocking specific connections to IP addresses and ports to enforcing a normal pattern of life for the source device.

Conclusion

Pikabot is just one recent example of a modular strain of loader known for its adaptability and speed, seamlessly changing tactics from one campaign to the next and utilizing new infrastructure to initiate multi-stage attacks. Leveraging commonly used tools and services like Windows PowerShell and cURL, alongside anti-analysis techniques, this malware can evade the detection and often bypass traditional security tools.

In this incident, Darktrace detected a Pikabot infection in its early stages, identifying an anomalous file download using a cURL user agent, a new tactic for this particular strain of malware. This timely detection, coupled with the support of Darktrace’s SOC, empowered the customer to quickly identify the compromised device and act against it, thwarting threat actors attempting to connect to malicious Cobalt Strike and Black Basta servers. By preventing the escalation of the attack, including potential ransomware deployment, the customer’s environment remained safeguarded.

Had Darktrace RESPOND been enabled in autonomous response mode at the time of this attack, it would have been able to further support the customer by applying targeted mitigative actions to contain the threat of Pikabot at its onset, bolstering their defenses even more effectively.

Credit to Brianna Leddy, Director of Analysis, Signe Zaharka, Senior Cyber Security Analyst

Appendix

Darktrace DETECT Models

Anomalous Connection / Anomalous SSL without SNI to New External

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous Connection / Powershell to Rare External

Anomalous Connection / Rare External SSL Self-Signed

Anomalous Connection / Repeated Rare External SSL Self-Signed

Anomalous File / EXE from Rare External Location

Anomalous File / Masqueraded File Transfer

Anomalous File / Multiple EXE from Rare External Locations

Compromise / Agent Beacon to New Endpoint

Compromise / Beacon to Young Endpoint

Compromise / Beaconing Activity To External Rare

Compromise / DNS / DNS Tunnel with TXT Records

Compromise / New or Repeated to Unusual SSL Port

Compromise / SSL Beaconing to Rare Destination

Compromise / Suspicious Beaconing Behaviour

Compromise / Suspicious File and C2

Device / Initial Breach Chain Compromise

Device / Large Number of Model Breaches

Device / New PowerShell User Agent

Device / New User Agent

Device / New User Agent and New IP

Device / Suspicious Domain

Security Integration / C2 Activity and Integration Detection

Security Integration / Egress and Integration Detection

Security Integration / High Severity Integration Detection

Security Integration / High Severity Integration Incident

Security Integration / Low Severity Integration Detection

Security Integration / Low Severity Integration Incident

Antigena / Network / External Threat / Antigena File then New Outbound Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

Antigena / Network / Significant Anomaly / Antigena Significant Security Integration and Network Activity Block

List of Indicators of Compromise (IoC)

IOC - TYPE - DESCRIPTION + CONFIDENCE

128.140.102[.]132 - IP Address - Pikabot Download

185.106.94[.]174:5000 - IP Address: Port - Pikabot C2 Endpoint

80.85.140[.]152:5938 - IP Address: Port - Pikabot C2 Endpoint

building4business[.]net - Hostname - Cobalt Strike DNS Beacon

wordstt182[.]com - Hostname - Cobalt Strike Server

167.88.166[.]109 - IP Address - Cobalt Strike Server

192.9.135[.]73 - IP - Pikabot C2 Endpoint

192.121.17[.]68 - IP - Pikabot C2 Endpoint

185.87.148[.]132 - IP - Pikabot C2 Endpoint

129.153.22[.]231 - IP - Pikabot C2 Endpoint

129.153.135[.]83 - IP - Pikabot C2 Endpoint

154.80.229[.]76 - IP - Pikabot C2 Endpoint

192.121.17[.]14 - IP - Pikabot C2 Endpoint

162.252.172[.]253 - IP - Pikabot C2 Endpoint

103.124.105[.]147 - IP - Likely Pikabot Download

178.18.246[.]136 - IP - Pikabot C2 Endpoint

86.38.225[.]106 - IP - Pikabot C2 Endpoint

198.44.187[.]12 - IP - Pikabot C2 Endpoint

154.12.233[.]66 - IP - Pikabot C2 Endpoint

MITRE ATT&CK Mapping

TACTIC - TECHNIQUE

Defense Evasion - Masquerading: Masquerade File Type (T1036.008)

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

Command and Control - Non-Standard Port (T1571)

Command and Control - Application Layer Protocol: DNS (T1071.004)

Command and Control - Protocol Tunneling (T1572)

References

[1] https://news.sophos.com/en-us/2023/06/12/deep-dive-into-the-pikabot-cyber-threat/?&web_view=true  

[2] https://www.trendmicro.com/en_be/research/24/a/a-look-into-pikabot-spam-wave-campaign.html

[3] https://thehackernews.com/2024/01/alert-water-curupira-hackers-actively.html

[4] https://www.darkreading.com/cyberattacks-data-breaches/pikabot-malware-qakbot-replacement-black-basta-attacks

[5] https://www.redpacketsecurity.com/pikabot-distributed-via-malicious-ads-6/

[6] https://www.virustotal.com/gui/ip-address/185.106.94.174/detection

[7] https://www.virustotal.com/gui/ip-address/80.85.140.152/detection

[8] https://www.domainiq.com/domain?wordstt182.com

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
Brianna Luong (Leddy)
Sr. Technical Alliances Manager

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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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