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July 9, 2024

How Darktrace Detects NTLM Hash Theft

Explore Darktrace's innovative methods for detecting NTLM hash theft and safeguarding your organization from cyber threats.
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
Charlotte Thompson
Cyber Analyst
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09
Jul 2024

What is credential theft and how does it work?

What began as a method to achieve unauthorized access to an account, often driven by the curiosity of individual attackers, credentials theft become a key tactic for malicious actors and groups, as stolen login credentials can be abused to gain unauthorized access to accounts and systems. This access can be leveraged to carry out malicious activities such as data exfiltration, fraud, espionage and malware deployment.

It is therefore no surprise that the number of dark web marketplaces selling privileged credentials has increased in recent years, making it easier for malicious actors to monetize stolen credentials [1]. This, in turn, has created new opportunities for threat actors to use increasingly sophisticated tactics such as phishing, social engineering and credential stuffing in their attacks, targeting individuals, organizations and government entities alike [1].

Credential theft example

TA577 Threat Actor

TA577 is a threat actor known to leverage stolen credentials, also known as Hive0118 [2], an initial access broker (IAB) group that was previously known for delivering malicious payloads [2]. On March 4, 2024, Proofpoint reported evidence of TA577 using a new attack chain with a different aim in mind: stealing NT LAN Manager (NTLM) hashes that can be used to authenticate to systems without needing to know plaintext passwords [3].

How does TA577 steal credentials?

Proofpoint reported that this new attack chain, which was first observed on February 26 and 27, was made up of two distinct campaigns. The first campaign consisted of a phishing attack featuring tens of thousands of emails targeting hundreds of organizations globally [3]. These phishing emails often appeared as replies to previous messages (thread hijacking) and contained zipped HTML attachments that each contained a unique file hash, customized for each recipient [3]. These attached files also contained a HTTP Meta refresh function, which triggered an automatic connection to a text file hosted on external IP addresses running as SMB servers [3].

When attempting to access the text file, the server requires an SMB session authentication via NTLM. This session is initiated when a client sends an ‘SMB_COM_NEGOTIATE’ request to the server, which answers with a ‘SMB_COM_NEGOTIATE’ response.

The client then proceeds to send a ‘SMB_COM_SESSION_SETUP_ANDX’ request to start the SMB session setup process, which includes initiating the NTLM authentication process. The server responds with an ‘SMB_COM_SESSION_SETUP_ANDX’ response, which includes an NTLM challenge message [6].

The client can then use the challenge message and its own credentials to generate a response by hashing its password using an NTLM hash algorithm. The response is sent to the server in an ‘SMB_COM_SESSION_SETUP_ANDX’ request. The server validates the response and, if the authentication is successful, the server answers with a final ‘SMB_COM_SESSION_SETUP_ANDX’ response, which completes the session setup process and allows the client to access the file listed on the server [6].

What is the goal of threat actor TA577?

As no malware delivery was detected during these sessions, researchers have suggested that the aim of TA577 was not to deliver malware, but rather to take advantage of the NTLMV2 challenge/response to steal NTLM authentication hashes [3] [4]. Hashes stolen by attackers can be exploited in pass-the-hash attacks to authenticate to a remote server or service [4]. They can also be used for offline password cracking which, if successful, could be utilized to escalate privileges or perform lateral movement through a target network [4]. Under certain circumstances, these hashes could also permit malicious actors to hijack accounts, access sensitive information and evade security products [4].

The open-source toolkit Impacket, which includes modules for password cracking [5] and which can be identified by the default NTLM server challenge “aaaaaaaaaaaaaaaa”[3], was observed during the SMB sessions. This indicates that TA577 actor aim to use stolen credentials for password cracking and pass-the-hash attacks.

TA577 has previously been associated with Black Basta ransomware infections and Qbot, and has been observed delivering various payloads including IcedID, SystemBC, SmokeLoader, Ursnif, and Cobalt Strike [2].This change in tactic to follow the current trend of credential theft may indicate that not only are TA577 actors aware of which methods are most effective in the current threat landscape, but they also have monetary and time resources needed to create new methods to bypass existing detection tools [3].  

Darktrace’s Coverage of TA577 Activity

On February 26 and 27, coinciding with the campaign activity reported by Proofpoint, Darktrace/Email™ observed a surge of inbound emails from numerous suspicious domains targeting multiple customer environments. These emails consistently included zip files with seemingly randomly generated names, containing HTLM content and links to an unusual external IP address [3].

A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Figure 1: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.
Figure 2: Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.

The URL of these links contained an unusually named .txt file, which corresponds with Proofpoint reports of the automatic connection to a text file hosted on an external SMB server made when the attachment is opened [3].

A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.
Figure 3: A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.

Darktrace identified devices on multiple customer networks connecting to external SMB servers via the SMB protocol. It understood this activity was suspicious as the SMB protocol is typically reserved for internal connections and the endpoint in question had never previously been observed on the network.

The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
Figure 4: The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
External Sites Summary highlighting the rarity of the external SMB server.
Figure 5: External Sites Summary highlighting the rarity of the external SMB server.
External Sites Summary highlightin that the SMB server is geolocated in Moldova.
Figure 6: External Sites Summary highlightin that the SMB server is geolocated in Moldova.

During these connections, Darktrace observed multiple devices establishing an SMB session to this server via a NTLM challenge/response, representing the potential theft of the credentials used in this session. During this session, some devices also attempted to access an unusually named .txt file, further indicating that the affected devices were trying to access the .txt file hosted on external SMB servers [3].

Packet captures (PCAPs) of these sessions show the default NTLM server challenge, indicating the use of Impacket, suggesting that the captured NTLM hashes were to be used for password cracking or pass-the-hash-attacks [3]

PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.
Figure 7: PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.

Conclusions

Ultimately, Darktrace’s suite of products effectively detected and alerted for multiple aspects of the TA577 attack chain and NTLM hash data theft activity across its customer base. Darktrace/Email was able to uncover the inbound phishing emails that served as the initial access vector for TA577 actors, while Darktrace DETECT identified the subsequent external connections to unusual external locations and suspicious SMB sessions.

Furthermore, Darktrace’s anomaly-based approach enabled it to detect suspicious TA577 activity across the customer base on February 26 and 27, prior to Proofpoint’s report on their new attack chain. This showcases Darktrace’s ability to identify emerging threats based on the subtle deviations in a compromised device’s behavior, rather than relying on a static list of indicators of compromise (IoCs) or ‘known bads’.

This approach allows Darktrace to remain one step ahead of increasingly adaptive threat actors, providing organizations and their security teams with a robust AI-driven solution able to safeguard their networks in an ever-evolving threat landscape.

Credit to Charlotte Thompson, Cyber Analyst, Anna Gilbertson, Cyber Analyst.

References

1)    https://www.sentinelone.com/cybersecurity-101/what-is-credential-theft/

2)    https://malpedia.caad.fkie.fraunhofer.de/actor/ta577

3)    https://www.proofpoint.com/us/blog/threat-insight/ta577s-unusual-attack-chain-leads-ntlm-data-theft

4)    https://www.bleepingcomputer.com/news/security/hackers-steal-windows-ntlm-authentication-hashes-in-phishing-attacks/

5)    https://pawanjswal.medium.com/the-power-of-impacket-a-comprehensive-guide-with-examples-1288f3a4c674

6)    https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-nlmp/c083583f-1a8f-4afe-a742-6ee08ffeb8cf

7)    https://www.hivepro.com/threat-advisory/ta577-targeting-windows-ntlm-hashes-in-global-campaigns/

Darktrace Model Detections

Darktrace/Email

·       Attachment / Unsolicited Archive File

·       Attachment / Unsolicited Attachment

·       Link / New Correspondent Classified Link

·       Link / New Correspondent Rare Link

·       Spoof / Internal User Similarities

Darktrace DETECT

·       Compliance / External Windows Communications

Darktrace RESPOND

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

IoCs

IoC - Type - Description

176.123.2[.]146 - IP address -Likely malicious SMB Server

89.117.2[.]33 - IP address - Likely malicious SMB Server

89.117.1[.]161 - IP address - Likely malicious SMB Server

104.129.20[.]167 - IP address - Likely malicious SMB Server

89.117.1[.]160 - IP address - Likely malicious SMB Server

85.239.33[.]149 - IP address - Likely malicious SMB Server

89.117.2[.]34 - IP address - Likely malicious SMB Server

146.19.213[.]36 - IP address - Likely malicious SMB Server

66.63.188[.]19 - IP address - Likely malicious SMB Server

103.124.104[.]76 - IP address - Likely malicious SMB Server

103.124.106[.]224 - IP address - Likely malicious SMB Server

\5aohv\9mn.txt - SMB Path and File - SMB Path and File

\hvwsuw\udrh.txt - SMB Path and File - SMB Path and File

\zkf2rj4\VmD.txt = SMB Path and File - SMB Path and File

\naams\p3aV.txt - SMB Path and File - SMB Path and File

\epxq\A.txt - SMB Path and File - SMB Path and File

\dbna\H.txt - SMB Path and File - SMB Path and File

MAGNAMSB.zip – Filename - Phishing Attachment

e751f9dddd24f7656459e1e3a13307bd03ae4e67 - SHA1 Hash - Phishing Attachment

OMNIS2C.zip  - Filename - Phishing Attachment

db982783b97555232e28d5a333525118f10942e1 - SHA1 Hash - Phishing Attachment

aaaaaaaaaaaaaaaa - NTLM Server Challenge -Impacket Default NTLM Challenge

MITRE ATT&CK Tactics, Techniques and Procedures (TTPs)

Tactic - Technique

TA0001            Initial Access

TA0002            Execution

TA0008            Lateral Movement

TA0003            Persistence

TA0005            Defense Evasion

TA0006            Credential Access

T1021.002       SMB/Windows Admin Shares

T1021  Remote Services

T1566.001       Spearfishing Attachment

T1566  Phishing

T1204.002       Malicious File

T1204  User Execution

T1021.002       SMB/Windows Admin Shares

T1574  Hijack Execution Flow

T1021  Remote Services

T1555.004       Windows Credential Manager

T1555  Credentials from Password Stores

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
Charlotte Thompson
Cyber 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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