Blog
/
/
July 26, 2022

Self-Learning AI for Zero-Day and N-Day Attack Defense

Explore the differences between zero-day and n-day attacks on different customer servers to learn how Darktrace detects and prevents cyber threats effectively.
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
Lewis Morgan
Cyber Analyst
Default blog image
26
Jul 2022

Key Terms:

Zero-day | A recently discovered security vulnerability in computer software that has no currently available fix or patch. Its name come from the reality that vendors have “zero days” to act and respond.

N-day | A vulnerability that emerges in computer software in which a vendor is aware and may have already issued (or are currently working on) a patch or fix. Active exploits often already exist and await abuse by nefarious actors.

Traditional security solutions often apply signature-based-detection when identifying cyber threats, helping to defend against legacy attacks but consequently missing novel ones. Therefore, security teams often lend a lot of focus to ensuring that the risk of zero-day vulnerabilities is reduced [1]. As explored in this blog, however, organizations can face just as much of a risk from n-day attacks, since they invite the most attention from malicious actors [2]. This is due in part to the reduced complexity, cost and time invested in researching and finding new exploits compared with that found when attackers exploit zero-days. 

This blog will examine both a zero-day and n-day attack that two different Darktrace customers faced in the fall of 2021. This will include the activity Darktrace detected, along with the steps taken by Darktrace/Network to intervene. It will then compare the incidents, discuss the possible dangers of third-party integrations, and assess the deprecation of legacy security tools.

Revisiting zero-day attacks 

Zero-days are among the greatest concerns security teams face in the era of modern technology and networking. Defending critical systems from zero-day compromises is a task most legacy security solutions are often unable to handle. Due to the complexity of uncovering new security flaws and developing elaborate code that can exploit them, these attacks are often carried out by funded or experienced groups such as nation-state actors and APTs. One of history’s most prolific zero-days, ‘Stuxnet’, sent security teams worldwide into a global panic in 2010. This involved a widespread attack on Iranian nuclear infrastructure and was widely accepted to be a result of nation-state actors [3]. The Stuxnet worm took advantage of four zero-day exploits, compromising over 200,000 devices and physically damaging around 10% of the 9,000 critical centrifuges at the Natanz nuclear site. 

More recently, 2021 saw the emergence of several critical zero-day vulnerabilities within SonicWall’s product suite [4]. SonicWall is a security hardware manufacturer that provides hardware firewall devices, unified threat management, VPN gateways and network security solutions. Some of these vulnerabilities lie within their Secure Mobile Access (SMA) 100 series (for example, CVE-2019-7481, CVE-2021-20016 and CVE-2021-20038 to name a few). These directly affected VPN devices and often allowed attackers easy remote access to company devices. CVE-2021-20016 in particular incorporates an SQL-Injection vulnerability within SonicWall’s SSL VPN SMA 100 product line [5]. If exploited, this defect would allow an unauthenticated remote attacker to perform their own malicious SQL query in order to access usernames, passwords and other session related information. 

The N-day underdog

The shadow cast by zero-day attacks often shrouds that of n-day attacks. N-days, however, often pose an equal - if not greater - risk to the majority of organizations, particularly those in industrial sectors. Since these vulnerabilities have fixes available, all of the hard work around research is already done; malicious actors only need to view proof of concepts (POCs) or, if proficient in coding, reverse-engineer software to reveal code-changes (binary diffing) in order to exploit these security flaws in the wild. These vulnerabilities are typically attributed to opportunistic hackers and script-kiddies, where little research or heavy lifting is required.  

August 2021 gave rise to a critical vulnerability in Atlassian Confluence servers, namely CVE-2021-26084 [6]. Confluence is a widely used collaboration wiki tool and knowledge-sharing platform. As introduced and discussed a few months ago in a previous Darktrace blog (Explore Internet-Facing System Vulnerabilities), this vulnerability allows attackers to remotely execute code on internet-facing servers after exploiting injection vulnerabilities in Object-Graph Navigation Language (OGNL). Whilst Confluence had patches and fixes available to users, attackers still jumped on this opportunity and began scanning the internet for signs of critical devices serving this outdated software [7]. Once identified, they would  exploit the vulnerability, often installing crypto mining software onto the device. More recently, Darktrace explored a new vulnerability (CVE-2022-26134), disclosed midway through 2022, that affected Confluence servers and data centers using similar techniques to that found in CVE-2021-26084 [8]. 

SonicWall in the wild – 1. Zero-day attack

At the beginning of August 2021, Darktrace prevented an attack from taking place within a European automotive customer’s environment (Figure 1). The attack targeted a vulnerable internet-facing SonicWall VPN server, and while the attacker’s motive remains unclear, similar historic events suggest that they intended to perform ransomware encryption or data exfiltration. 

Figure 1: Timeline of the SonicWall attack 

Darktrace was unable to confirm the definite tactics, techniques and procedures (TTPs) used by the attacker to compromise the customer’s environment, as the device was compromised before Darktrace installation and coverage. However, from looking at recently disclosed SonicWall VPN vulnerabilities and patterns of behaviour, it is likely CVE-2021-20016 played a part. At some point after this initial infection, it is also believed the device was able to move laterally to a domain controller (DC) using administrative credentials; it was this server that then initiated the anomalous activity that Darktrace detected and alerted on. 

On August 5th 2021 , Darktrace observed this compromised domain controller engaging in unusual ICMP scanning - a protocol used to discover active devices within an environment and create a map of an organization’s network topology. Shortly after, the infected server began scanning devices for open RDP ports and enumerating SMB shares using unorthodox methods. SMB delete and HTTP requests (over port 445 and 80 respectively) were made for files named delete.me in the root directory of numerous network shares using the user agent Microsoft WebDAV. However, no such files appeared to exist within the environment. This may have been the result of an attacker probing devices in the network in an effort to see their responses and gather information on properties and vulnerabilities they could later exploit. 

Soon the infected DC began establishing RDP tunnels back to the VPN server and making requests to an internal DNS server for multiple endpoints relating to exploit kits, likely in an effort to strengthen the attacker’s foothold within the environment. Some of the endpoints requested relate to:

-       EternalBlue vulnerability 

-       Petit Potam NTLM hash attack tool

-       Unusual GitHub repositories

-       Unusual Python repositories  

The DC made outgoing NTLM requests to other internal devices, implying the successful installation of Petit Potam exploitation tools. The server then began performing NTLM reconnaissance, making over 1,000 successful logins under ‘Administrator’ to several other internal devices. Around the same time, the device was also seen making anonymous SMBv1 logins to numerous internal devices, (possibly symptomatic of the attacker probing machines for EternalBlue vulnerabilities). 

Interestingly, the device also made numerous failed authentication attempts using a spoofed credential for one of the organization’s security managers. This was likely in an attempt to hide themselves using ‘Living off the Land’ (LotL) techniques. However, whilst the attacker clearly did their research on the company, they failed to acknowledge the typical naming convention used for credentials within the environment. This ultimately backfired and made the compromise more obvious and unusual. 

In the morning of the following day, the initially compromised VPN server began conducting further reconnaissance, engaging in similar activity to that observed by the domain controller. Until now, the customer had set Darktrace RESPOND to run in human confirmation mode, meaning interventions were not made autonomously but required confirmation by a member of the internal security team. However, thanks to Proactive Threat Notifications (PTNs) delivered by Darktrace’s dedicated SOC team, the customer was made immediately aware of this unusual behaviour, allowing them to apply manual Darktrace RESPOND blocks to all outgoing connections (Figure 2). This gave the security team enough time to respond and remediate before serious damage could be done.

Figure 2: Darktrace RESPOND model breach showing the manually applied “Quarantine Device” action taken against the compromised VPN server. This screenshot displays the UI from Darktrace version 5.1

Confluence in the wild – 2. N-day attack

Towards the end of 2021, Darktrace saw a European broadcasting customer leave an Atlassian Confluence internet-facing server unpatched and vulnerable to crypto-mining malware using CVE-2021-26084. Thanks to Darktrace, this attack was entirely immobilized within only a few hours of the initial infection, protecting the organization from damage (Figure 3). 

Figure 3: Timeline of the Confluence attack

On midday on September 1st 2021, an unpatched Confluence server was seen receiving SSL connections over port 443 from a suspicious new endpoint, 178.238.226[.]127.  The connections were encrypted, meaning Darktrace was unable to view the contents and ascertain what requests were being made. However, with the disclosure of CVE-2021-26084 just 7 days prior to this activity, it is likely that the TTPs used involved injecting OGNL expressions to Confluence server memory; allowing the attacker to remotely execute code on the vulnerable server.

Immediately after successful exploitation of the Confluence server, the infected device was observed making outgoing HTTP GET requests to several external endpoints using a new user agent (curl/7.61.1). Curl was used to silently download and configure multiple suspicious files relating to XMRig cryptocurrency miner, including ld.sh, XMRig and config.json. Subsequent outgoing connections were then made to europe.randomx-hub.miningpoolhub[.]com · 172.105.210[.]117 using the JSON-RPC protocol, seen alongside the mining credential maillocal.confluence (Figure 4). Only 3 seconds after initial compromise, the infected device began attempting to mine cryptocurrency using the Minergate protocol but was instantly and autonomously blocked by Darktrace RESPOND. This prevented the server from abusing system resources and generating profits for the attacker.

Figure 4: A graph showing the frequency of external connections using the JSON-RPC protocol made by the breach device over a 48-hour window. The orange-red dots represent models that breached as a result of this activity, demonstrating the “waterfall” effect commonly seen when a device suffers a compromise. This screenshot displays the UI from Darktrace version 5.1

In the afternoon, the malware persisted with its infection. The compromised server began making successive HTTP GET requests to a new rare endpoint 195.19.192[.]28 using the same curl user agent (Figures 5 & 6). These requests were for executable and dynamic library files associated with Kinsing malware (but fortunately were also blocked by Darktrace RESPOND). Kinsing is a malware strain found in numerous attack campaigns which is often associated with crypto-jacking, and has appeared in previous Darktrace blogs [9].

Figure 5: Cyber AI Analyst summarising the unusual download of Kinsing software using the new curl user agent. This screenshot displays the UI from Darktrace version 5.1

The attacker then began making HTTP POST requests to an IP 185.154.53[.]140, using the same curl user agent; likely a method for the attacker to maintain persistence within the network and establish a foothold using its C2 infrastructure. The Confluence server was then again seen attempting to mine cryptocurrency using the Minergate protocol. It made outgoing JSON-RPC connections to a different new endpoint, 45.129.2[.]107, using the following mining credential: ‘42J8CF9sQoP9pMbvtcLgTxdA2KN4ZMUVWJk6HJDWzixDLmU2Ar47PUNS5XHv4Kmfdh8aA9fbZmKHwfmFo8Wup8YtS5Kdqh2’. This was once again blocked by Darktrace RESPOND (Figure 7). 

Figure 6: VirusTotal showing the unusualness of one of these external IPs [10]
Figure 7: Log data showing the action taken by Darktrace RESPOND in response to the device breaching the “Crypto Currency Mining Activity” model. This screenshot displays the UI from Darktrace version 5.1

The final activity seen from this device involved the download of additional shell scripts over HTTP associated with Kinsing, namely spre.sh and unk.sh, from 194.38.20[.]199 and 195.3.146[.]118 respectively (Figure 8). A new user agent (Wget/1.19.5 (linux-gnu)) was used when connecting to the latter endpoint, which also began concurrently initiating repeated connections indicative of C2 beaconing. These scripts help to spread the Kinsing malware laterally within the environment and may have been the attacker's last ditch efforts at furthering their compromise before Darktrace RESPOND blocked all connections from the infected Confluence server [11]. With Darktrace RESPOND's successful actions, the customer’s security team were then able to perform their own response and remediation. 

Figure 8: Cyber AI Analyst revealing the last ditch efforts made by the threat actor to download further malicious software. This screenshot displays the UI from Darktrace version 5.1

Darktrace Coverage: N- vs Zero-days

In the SonicWall case the attacker was unable to achieve their actions on objectives (thanks to Darktrace's intervention). However, this incident displayed tactics of a more stealthy and sophisticated attacker - they had an exploited machine but waited for the right moment to execute their malicious code and initiate a full compromise. Due to the lack of visibility over attacker motive, it is difficult to deduce what type of actor led to this intrusion. However, with the disclosure of a zero-day vulnerability (CVE-2021-20016) not long before this attack, along with a seemingly dormant initially compromised device, it is highly possible that it was carried out by a sophisticated cyber criminal or gang. 

On the other hand, the Confluence case engaged in a slightly more noisy approach; it dropped crypto mining malware on vulnerable devices in the hope that the target’s security team did not maintain visibility over their network or would merely turn a blind eye. The files downloaded and credentials observed alongside the mining activity heavily imply the use of Kinsing malware [11]. Since this vulnerability (CVE-2021-26084) emerged as an n-day attack with likely easily accessible POCs, as well as there being a lack of LotL techniques and the motive being long term monetary gain, it is possible this attack was conducted by a less sophisticated or amateur actor (script-kiddie); one that opportunistically exploits known vulnerabilities in internet-facing devices in order to make a quick profit [12].

Whilst Darktrace RESPOND was enabled in human confirmation mode only during the start of the SonicWall attack, Darktrace’s Cyber AI Analyst still offered invaluable insight into the unusual activity associated with the infected machines during both the Confluence and SonicWall compromises. SOC analysts were able to see these uncharacteristic behaviours and escalate the incident through Darktrace’s PTN and ATE services. Analysts then worked through these tickets with the customers, providing support and guidance and, in the SonicWall case, quickly helping to configure Darktrace RESPOND. In both scenarios, Darktrace RESPOND was able to block abnormal connections and enforce a device’s pattern of life, affording the security team enough time to isolate the infected machines and prevent further threats such as ransomware detonation or data exfiltration. 

Concluding thoughts and dangers of third-party integrations 

Organizations with internet-facing devices will inevitably suffer opportunistic zero-day and n-day attacks. While little can be done to remove the risk of zero-days entirely, ensuring that organizations keep their systems up to date will at the very least help prevent opportunistic and script-kiddies from exploiting n-day vulnerabilities.  

However, it is often not always possible for organizations to keep their systems up to date, especially for those who require continuous availability. This may also pose issues for organizations that rely on, and put their trust in, third party integrations such as those explored in this blog (Confluence and SonicWall), as enforcing secure software is almost entirely out of their hands. Moreover, with the rising prevalence of remote working, it is essential now more than ever that organizations ensure their VPN devices are shielded from external threats, guidance on which has been released by the NSA/CISA [13].

These two case studies have shown that whilst organizations can configure their networks and firewalls to help identify known indicators of compromise (IoC), this ‘rearview mirror’ approach will not account for, or protect against, any new and undisclosed IoCs. With the aid of Self-Learning AI and anomaly detection, Darktrace can detect the slightest deviation from a device’s normal pattern of life and respond autonomously without the need for rules and signatures. This allows for the disruption and prevention of known and novel attacks before irreparable damage is caused- reassuring security teams that their digital estates are secure. 

Thanks to Paul Jennings for his contributions to this blog.

Appendices: SonicWall (Zero-day)

Darktrace model detections

·      AIA / Suspicious Chain of Administrative Credentials

·      Anomalous Connection / Active Remote Desktop Tunnel

·      Anomalous Connection / SMB Enumeration

·      Anomalous Connection / Unusual Internal Remote Desktop

·      Compliance / High Priority Compliance Model Breach

·      Compliance / Outgoing NTLM Request from DC

·      Device / Anomalous RDP Followed By Multiple Model Breaches

·      Device / Anomalous SMB Followed By Multiple Model Breaches

·      Device / ICMP Address Scan

·      Device / Large Number of Model Breaches

·      Device / Large Number of Model Breaches from Critical Network Device

·      Device / Multiple Lateral Movement Model Breaches (PTN/Enhanced Monitoring model)

·      Device / Network Scan

·      Device / Possible SMB/NTLM Reconnaissance

·      Device / RDP Scan

·      Device / Reverse DNS Sweep

·      Device / SMB Session Bruteforce

·      Device / Suspicious Network Scan Activity (PTN/Enhanced Monitoring model)

·      Unusual Activity / Possible RPC Recon Activity

Darktrace RESPOND (Antigena) actions (as displayed in example)

·      Antigena / Network / Manual / Quarantine Device

MITRE ATT&CK Techniques Observed
IoCs

Appendices: Confluence (N-day)

Darktrace model detections

·      Anomalous Connection / New User Agent to IP Without Hostname

·      Anomalous Connection / Posting HTTP to IP Without Hostname

·      Anomalous File / EXE from Rare External Location

·      Anomalous File / Script from Rare Location

·      Compliance / Crypto Currency Mining Activity

·      Compromise / High Priority Crypto Currency Mining (PTN/Enhanced Monitoring model)

·      Device / Initial Breach Chain Compromise (PTN/Enhanced Monitoring model)

·      Device / Internet Facing Device with High Priority Alert

·      Device / New User Agent

Darktrace RESPOND (Antigena) actions (displayed in example)

·      Antigena / Network / Compliance / Antigena Crypto Currency Mining Block

·      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 Block Enhanced Monitoring

MITRE ATT&CK Techniques Observed
IOCs

References:

[1] https://securitybrief.asia/story/why-preventing-zero-day-attacks-is-crucial-for-businesses

[2] https://electricenergyonline.com/energy/magazine/1150/article/Security-Sessions-More-Dangerous-Than-Zero-Days-The-N-Day-Threat.htm

[3] https://www.wired.com/2014/11/countdown-to-zero-day-stuxnet/

[4] https://cve.mitre.org/cgi-bin/cvekey.cgi?keyword=SonicWall+2021 

[5] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-20016

[6] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-26084

[7] https://www.zdnet.com/article/us-cybercom-says-mass-exploitation-of-atlassian-confluence-vulnerability-ongoing-and-expected-to-accelerate/

[8] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2022-26134

[9] https://attack.mitre.org/software/S0599/

[10] https://www.virustotal.com/gui/ip-address/195.19.192.28/detection 

[11] https://sysdig.com/blog/zoom-into-kinsing-kdevtmpfsi/

[12] https://github.com/alt3kx/CVE-2021-26084_PoC

[13] https://www.nsa.gov/Press-Room/Press-Releases-Statements/Press-Release-View/Article/2791320/nsa-cisa-release-guidance-on-selecting-and-hardening-remote-access-vpns/

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
Lewis Morgan
Cyber Analyst

More in this series

No items found.

Blog

/

/

June 25, 2026

Shadow AI Detection: The First Step Toward Securing AI

shadow aiDefault blog imageDefault blog image

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.  

Continue reading
About the author

Blog

/

Network

/

June 25, 2026

From Click to Command: Behavioral Detection of AppleScript-Led MacOS Intrusions

applescript-led mac os intrusionDefault blog imageDefault blog image

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

Continue reading
About the author
Justin Torres
Cyber Analyst
Your data. Our AI.
Elevate your network security with Darktrace AI