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August 22, 2022

Emotet Resurgence: Cross-Industry Analysis

Technical insights on the Emotet resurgence in 2022 across various client environments, industries, and regions.
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
Eugene Chua
Cyber Security Analyst
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Aug 2022

Introduction

Last year provided further evidence that the cyber threat landscape remains both complex and challenging to predict. Between uncertain attribution, novel exploits and rapid malware developments, it is becoming harder to know where to focus security efforts. One of the largest surprises of 2021 was the re-emergence of the infamous Emotet botnet. This is an example of a campaign that ignored industry verticals or regions and seemingly targeted companies indiscriminately. Only 10 months after the Emotet takedown by law enforcement agencies in January, new Emotet activities in November were discovered by security researchers. These continued into the first quarter of 2022, a period which this blog will explore through findings from the Darktrace Threat Intel Unit. 

Dating back to 2019, Emotet was known to deliver Trickbot payloads which ultimately deployed Ryuk ransomware strains on compromised devices. This interconnectivity highlighted the hydra-like nature of threat groups wherein eliminating one (even with full-scale law enforcement intervention) would not rule them out as a threat nor indicate that the threat landscape would be any more secure. 

When Emotet resurged, as expected, one of the initial infection vectors involved leveraging existing Trickbot infrastructure. However, unlike the original attacks, it featured a brand new phishing campaign.

Figure 1: Distribution of observed Emotet activities across Darktrace deployments

Although similar to the original Emotet infections, the new wave of infections has been classified into two categories: Epochs 4 and 5. These had several key differences compared to Epochs 1 to 3. Within Darktrace’s global deployments, Emotet compromises associated to Epoch 4 appeared to be the most prevalent. Affected customer environments were seen within a large range of countries (Figure 1) and industry verticals such as manufacturing and supply chain, hospitality and travel, public administration, technology and telecoms and healthcare. Company demographics and size did not appear to be a targeting factor as affected customers had varying employee counts ranging from less than 250, to over 5000.

Key differences between Epochs 1-3 vs 4-5

Based on wider security research into the innerworkings of the Emotet exploits, several key differences were identified between Epochs 4/5 and its predecessors. The newer epochs used:

·       A different Microsoft document format (OLE vs XML-based).

·       A different encryption algorithm for communication. The new epochs used Elliptic Curve Cryptograph (ECC) [1] with public encryption keys contained in the C2 configuration file [2]. This was different from the previous Rivest-Shamir-Adleman (RSA) key encryption method.

·       Control Flow Flattening was used as an obfuscation technique to make detection and reverse engineering more difficult. This is done by hiding a program’s control flow [3].

·       New C2 infrastructure was observed as C2 communications were directed to over 230 unique IPs all associated to the new Epochs 4 and 5.

In addition to the new Epoch 4 and 5 features, Darktrace detected unsurprising similarities in those deployments affected by the renewed campaign. This included self-signed SSL connections to Emotet’s new infrastructure as well as malware spam activities to multiple rare external endpoints. Preceding these outbound communications, devices across multiple deployments were detected downloading Emotet-associated payloads (algorithmically generated DLL files).

Emotet Resurgence Campaign

Figure 2: Darktrace’s Detection Timeline for Emotet Epoch 4 and 5 compromises

1. Initial Compromise

The initial point of entry for the resurgence activity was almost certainly via Trickbot infrastructure or a successful phishing attack (Figure 2). Following the initial intrusion, the malware strain begins to download payloads via macro-ladened files which are used to spawn PowerShell for subsequent malware downloads.

Following the downloads, malicious communication with Emotet’s C2 infrastructure was observed alongside activities from the spam module. Within Darktrace, key techniques were observed and documented below.

2. Establish Foothold: Binary Dynamic-link library (.dll) with algorithmically generated filenames 

Emotet payloads are polymorphic and contain algorithmically generated filenames . Within deployments, HTTP GET requests involving a suspicious hostname, www[.]arkpp[.]com, and Emotet related samples such as those seen below were observed:

·       hpixQfCoJb0fS1.dll (SHA256 hash: 859a41b911688b00e104e9c474fc7aaf7b1f2d6e885e8d7fbf11347bc2e21eaa)

·       M0uZ6kd8hnzVUt2BNbRzRFjRoz08WFYfPj2.dll (SHA256 hash: 9fbd590cf65cbfb2b842d46d82e886e3acb5bfecfdb82afc22a5f95bda7dd804)

·       TpipJHHy7P.dll (SHA256 hash: 40060259d583b8cf83336bc50cc7a7d9e0a4de22b9a04e62ddc6ca5dedd6754b)

These DLL files likely represent the distribution of Emotet loaders which depends on windows processes such as rundll32[.]exe and regsvr32[.]exe to execute. 

3. Establish Foothold: Outbound SSL connections to Emotet C2 servers 

A clear network indicator of compromise for Emotet’s C2 communication involved self-signed SSL using certificate issuers and subjects which matched ‘CN=example[.]com,OU=IT Department,O=Global Security,L=London,ST=London,C=GB’ , and a common JA3 client fingerprint (72a589da586844d7f0818ce684948eea). The primary C2 communications were seen involving infrastructures classified as Epoch 4 rather than 5. Despite encryption in the communication content, network contextual connection details were sufficient for the detection of the C2 activities (Figure 3).

Figure 3: UI Model Breach logs on download and outbound SSL activities.

Outbound SSL and SMTP connections on TCP ports 25, 465, 587 

An anomalous user agent such as, ‘Microsoft Outlook 15.0’, was observed being used for SMTP connections with some subject lines of the outbound emails containing Base64-encoded strings. In addition, this JA3 client fingerprint (37cdab6ff1bd1c195bacb776c5213bf2) was commonly seen from the SSL connections. Based on the set of malware spam hostnames observed across at least 10 deployments, the majority of the TLDs were .jp, .com, .net, .mx, with the Japanese TLD being the most common (Figure 4).

Figure 4: Malware Spam TLDs observed in outbound SSL and SMTP

 Plaintext spam content generated from the spam module were seen in PCAPs (Figure 5). Examples of clear phishing or spam indicators included 1) mismatched personal header and email headers, 2) unusual reply chain and recipient references in the subject line, and 3) suspicious compressed file attachments, e.g. Electronic form[.]zip.

Figure 5: Example of PCAP associated to SPAM Module

4. Accomplish Mission

 The Emotet resurgence also showed through secondary compromises involving anomalous SMB drive writes related to CobaltStrike. This consistently included the following JA3 hash (72a589da586844d7f0818ce684948eea) seen in SSL activities as well as SMB writes involving the svchost.exe file.

Darktrace Detection

 The key DETECT models used to identify Emotet Resurgence activities were focused on determining possible C2. These included:

·       Suspicious SSL Activity

·       Suspicious Self-Signed SSL

·       Rare External SSL Self-Signed

·       Possible Outbound Spam

File-focused models were also beneficial and included:

·       Zip or Gzip from Rare External Location

·       EXE from Rare External Location

Darktrace’s detection capabilities can also be shown through a sample of case studies identified during the Threat Research team’s investigations.

Case Studies 

Darktrace’s detection of Emotet activities was not limited by industry verticals or company sizing. Although there were many similar features seen across the new epoch, each incident displayed varying techniques from the campaign. This is shown in two client environments below:

When investigating a large customer environment within the public administration sector, 16 different devices were detected making 52,536 SSL connections with the example[.]com issuer. Devices associated with this issuer were mainly seen breaching the same Self-Signed and Spam DETECT models. Although anomalous incoming octet-streams were observed prior to this SSL, there was no clear relation between the downloads and the Emotet C2 connections. Despite the total affected devices occupying only a small portion of the total network, Darktrace analysts were able to filter against the much larger network ‘noise’ and locate detailed evidence of compromise to notify the customer.

Darktrace also identified new Emotet activities in much smaller customer environments. Looking at a company in the healthcare and pharmaceutical sector, from mid-March 2022 a single internal device was detected making an HTTP GET request to the host arkpp[.]com involving the algorithmically-generated DLL, TpipJHHy7P.dll with the SHA256 hash: 40060259d583b8cf83336bc50cc7a7d9e0a4de22b9a04e62ddc6ca5dedd6754b (Figure 6). 

Figure 6: A screenshot from VirusTotal, showing that the SHA256 hash has been flagged as malicious by other security vendors.

After the sample was downloaded, the device contacted a large number of endpoints that had never been contacted by devices on the network. The endpoints were contacted over ports 443, 8080, and 7080 involving Emotet related IOCs and the same SSL certificate mentioned previously. Malware spam activities were also observed during a similar timeframe.

 The Emotet case studies above demonstrate how autonomous detection of an anomalous sequence of activities - without depending on conventional rules and signatures - can reveal significant threat activities. Though possible staged payloads were only seen in a proportion of the affected environments, the following outbound C2 and malware spam activities involving many endpoints and ports were sufficient for the detection of Emotet.

 If present, in both instances Darktrace’s Autonomous Response technology, RESPOND, would recommend or implement surgical actions to precisely target activities associated with the staged payload downloads, outgoing C2 communications, and malware spam activities. Additionally, restriction to the devices’ normal pattern of life will prevent simultaneously occurring malicious activities while enabling the continuity of normal business operations.

 Conclusion 

·       The technical differences between past and present Emotet strains emphasizes the versatility of malicious threat actors and the need for a security solution that is not reliant on signatures.

·       Darktrace’s visibility and unique behavioral detection continues to provide visibility to network activities related to the novel Emotet strain without reliance on rules and signatures. Key examples include the C2 connections to new Emotet infrastructure.

·       Looking ahead, detection of C2 establishment using suspicious DLLs will prevent further propagation of the Emotet strains across networks.

·       Darktrace’s AI detection and response will outpace conventional post compromise research involving the analysis of Emotet strains through static and dynamic code analysis, followed by the implementation of rules and signatures.

Thanks to Paul Jennings and Hanah Darley for their contributions to this blog.

Appendices

Model breaches

·       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 / Multiple Failed Connections to Rare Endpoint 

·       Anomalous Connection / Multiple HTTP POSTs to Rare Hostname 

·       Anomalous Connection / Possible Outbound Spam 

·       Anomalous Connection / Rare External SSL Self-Signed 

·       Anomalous Connection / Repeated Rare External SSL Self-Signed      

·       Anomalous Connection / Suspicious Expired SSL 

·       Anomalous Connection / Suspicious Self-Signed SSL

·       Anomalous File / Anomalous Octet Stream (No User Agent) 

·       Anomalous File / Zip or Gzip from Rare External Location 

·       Anomalous File / EXE from Rare External Location

·       Compromise / Agent Beacon to New Endpoint 

·       Compromise / Beacon to Young Endpoint 

·       Compromise / Beaconing Activity To External Rare 

·       Compromise / New or Repeated to Unusual SSL Port 

·       Compromise / Repeating Connections Over 4 Days 

·       Compromise / Slow Beaconing Activity To External Rare 

·       Compromise / SSL Beaconing to Rare Destination 

·       Compromise / Suspicious Beaconing Behaviour 

·       Compromise / Suspicious Spam Activity 

·       Compromise / Suspicious SSL Activity 

·       Compromise / Sustained SSL or HTTP Increase 

·       Device / Initial Breach Chain Compromise 

·       Device / Large Number of Connections to New Endpoints 

·       Device / Long Agent Connection to New Endpoint 

·       Device / New User Agent 

·       Device / New User Agent and New IP 

·       Device / SMB Session Bruteforce 

·       Device / Suspicious Domain 

·       Device / Suspicious SMB Scanning Activity 

For Darktrace customers who want to know more about using Darktrace to triage Emotet, refer here for an exclusive supplement to this blog.

References

[1] https://blog.lumen.com/emotet-redux/

[2] https://blogs.vmware.com/security/2022/03/emotet-c2-configuration-extraction-and-analysis.html

[3] https://news.sophos.com/en-us/2022/05/04/attacking-emotets-control-flow-flattening/

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
Eugene Chua
Cyber Security 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.  

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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