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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.
Written by
Eugene Chua
Cyber Security Analyst
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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22
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/

Written by
Eugene Chua
Cyber Security Analyst
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

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

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June 24, 2026
Justin Torres
Cyber Analyst
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June 24, 2026

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

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Introduction

Darktrace’s Threat Research team is publishing this analysis to help defenders understand an active pattern of macOS tradecraft observed in multiple customer environments. This post summarizes the behaviors observed, how they were assessed, and what defenders can do now.

Across multiple environments, Darktrace observed a consistent MacOS intrusion pattern beginning with ClickFix-style user-assisted “update” execution and transitioning into AppleScript-driven post-compromise activity and sustained outbound signaling.

While individual indicators were low-confidence, the repeated convergence of weak behavioral signals — including HTTP POST beaconing, rare or IP-only destinations, SSL anomalies, and abnormal client characteristics — provided a defensible indication of command-and-control establishment Darktrace detection and response in these cases was driven by behavior over artifacts. In the highest-confidence instances, automated containment disrupted outbound signaling before sustained tasking could occur.

Background

ClickFix-style activity typically relies on user-assisted execution and plausible “update” pretexting, followed by post-execution use of native tools to keep the footprint light. In MacOS environments, AppleScript and other built-in scripting mechanisms enable flexible post-compromise workflows while minimizing stable file-based indicators.

Following execution, affected devices exhibited a consistent behavioral pattern. AppleScript or equivalent native scripting activity was observed initiating follow-on workflows, after which outbound communications began to establish a structured rhythm.

These communications were characterized by repeated HTTP POST requests to low-prevalence or IP-only endpoints, often combined with unusual SSL properties and client identifiers that diverged from baseline device behavior. Individually, these signals were weak. When correlated across time and devices, they formed a pattern consistent with control establishment rather than benign software activity.

In higher-confidence cases, Autonomous Response actions were able to reduce or halt outbound signaling, interrupting the attacker’s ability to maintain control.

Detection Timeline

In representative cases, the sequence unfolded as follows:

Stage 1 – Initial Execution

Initial activity began with suspicious or masqueraded execution on a MacOS endpoint, consistent with ClickFix-style user deception.

Stage 2 – Post-Execution Scripting

This was followed closely by native scripting activity, most commonly AppleScript, indicating the transition into post-execution workflow.

Stage 3 – Outbound Communications

Outbound communications then emerged, initially sporadic but quickly forming a consistent cadence of HTTP POST requests to rare external endpoints.

Stage 4 – Anomaly Convergence

As activity persisted, additional anomalies became visible — unusual SSL characteristics, abnormal user agents, and connections to infrastructure with no prior network prevalence.

Stage 5 – Autonomous Response

In the most mature stages of the activity, automated containment actions disrupted outbound communications on affected devices, limiting the attacker’s ability to continue tasking while investigations progressed.

Darktrace coverage and detections

The following use-case highlights systems likely affected by malicious macOS intrusion activity linked by Microsoft to the Democratic People’s Republic of Korea (DPRK) [1], with indications of suspicious behavior observed between March 1 and May 3, 2026. The activity overlaps with patterns described in recent reporting on DPRK-nexus MacOS intrusions [1], though attribution confidence in this case remains moderate and based on behavioral alignment rather than solely infrastructure linkage.

Analyst confidence emerged through the correlation of multiple weak signals across time and devices. This included model coverage for rare external communications, sustained beaconing patterns, repeated HTTP POSTs, and anomalous client characteristics. Where enabled, Autonomous Response actions disrupted the most active outbound paths to reduce the attacker’s ability to maintain control while Darktrace’s investigation continued.

Notably, this highly anomalous behavior included:

  • Outbound connections to the rare external endpoint, zoom[.]uswebob[.]us associated with IP address, 148.72.73[.]98 [2][3] over port 443
  • Outbound connections to the rare external endpoint, check02id[.]com associated with IP address, 83.136.210[.]180 [4] over port 7365
  • Outbound connections to the rare external endpoints, 104.145.210[.]107 [5] over port 8443 and 83.136.208[.]48 [6] over port 443
  • Outbound connections to the rare external endpoint, 83.136.208[.]246 [7] over port 6783 with observed URI `/api/daemon` and a PowerShell user agent

Darktrace’s detection initially highlighted a desktop device (running MacOS) engaging in anomalous behavior as early as March 12, 2026. Starting on March 12, the source device triggered a ‘Possible Doppelganger Attack’ alert including connectivity to the hostname "zoom[.]uswebob[.]us · 148.72.73[.]98" over port 443 (TCP, HTTPS, H2). This model highlights a device connecting to a location that is rare but masquerades as legitimate software, such as Zoom in this case, a commonly used technique to blend into expected traffic [2] [3].

Initial connectivity observed to the rare external hostname, zoom[.]uswebob[.]us · 148.72.73[.]98, over port 443.
Figure 1: Initial connectivity observed to the rare external hostname, zoom[.]uswebob[.]us · 148.72.73[.]98, over port 443.

This was followed roughly seven later by a connection to 104.145.210[.]107 over port 8443, during which approximately 250 KiB of data of inbound data and 30 MiB of outbound data was observed, triggering the ‘Unusual Activity / Unusual External Data to New Endpoint’ in Darktrace.

Quickly after this connection, Darktrace’s Autonomous Response intervened, blocking the device’s access to the unusual external location and halting the data exfiltration attempt.

Figure 2: Darktrace’s detection of unusual data exfiltration, shortly followed by an Autonomous Response action to block it.

The device continued to consistently trigger model alerts relating to unusual external connectivity, including 'Posting HTTP to IP Without Hostname', 'Anomalous Connection / Rare External SSL Self-Signed' alerts, until well after 3 PM that day.

Figure 3: Additional external connectivity to new IP without a hostname, including connectivity to 83.136.208[.]246, alongside an anomalous ‘curl/8.7.1’ user agent and ‘/api/daemon’ URI.
Figure 4: Continued external SSL connectivity to IP 83.136.208[.]48, including connectivity to 83.136.208[.]246, alongside an anomalous ‘curl/8.7.1’ user agent and ‘/api/daemon’ URI.
Figure 5: Continued external HTTP connectivity to hostname, check02id[.]com · 83.136.210[.]180, alongside an anomalous ‘Go-http-client/1,1’ user agent.

From March 13 to March 28, the device continued exhibit unusual connectivity to various endpoints (e.g., 83.136.208[.]48, 83.136.208[.]246, check02id[.]com · 83.136.210[.]180), with the 'Multiple HTTP POSTs to Rare Hostname' model consistently triggering.

Windows OS Case

Pivoting over to an additional device, this time running Windows OS, anomalous behavior was also observed between March 30 and April 20. Notably, on March 30, the device was observed making a large number of suspicious external connection attempts to 83.136.208[.]246 over port 6783, all of which failed.

A further indicator was observed on April 1 with PowerShell connectivity to the same rare endpoint (83.136.208[.]246, port 6783), using the URI '/api/daemon' and the user agent 'Mozilla/5.0 (Windows NT; Windows NT 10.0; fr-FR) WindowsPowerShell/5.1.26100.7920'.  Additional alerts included 'New User Agent to IP Without Hostname' and 'Anomalous Github Download', alongside activity involving the same endpoint.

Figure 6 : ‘Anomalous Powershell to Rare External Destination’ and ‘Github Download’ model alerts. This behavior involved connectivity with the endpoints ‘83.136.208[.]246’ and ‘github[.]com’.

The device continued triggering 'Posting HTTP to IP Without Hostname' & 'PowerShell to External Rare' alerts between April 4 and April 20 across multiple related endpoints (i.e., 83.136.208[.]48, 83.136.208[.]246, check02id[.]com · 83.136.210[.]180).

Darktrace’s Autonomous Response capability was able to block suspicious PowerShell attempts to unusual external locations, as shown below in an example from April 20.

Figure 7:  Autonomous Response intervening to block an unusual PowerShell connection to an external destination.

Cyber AI Analyst investigations

In higher-confidence instances, Darktrace’s Cyber AI Analyst investigations helped connect otherwise separate model alerts into a single incident narrative, highlighting the attacker’s progression from post-execution scripting into sustained outbound signaling. This contextual stitching is particularly valuable in macOS scenarios where static artefacts are limited, and behavioral sequencing defines the intrusion.

Cyber AI Analyst investigations highlighted alerts on March 12, including unusual repeated connections and possible SSL command-and-control (C2) to multiple endpoints:

Figure 8: Cyber AI Analyst investigation linking events into a unified incident.

Autonomous Response

In addition to the containment actions detailed earlier, Autonomous Response implemented multiple additional measures to contain suspicious activity throughout the course of this attack. Whenever unusual external connectivity was detected, Darktrace blocked it, closing down potential C2 channels. Likewise, when data exfiltration attempts were identified, these connections were stopped to prevent the potential loss of sensitive data.

Figure 9: Autonomous Response actions implemented by Darktrace in response to suspicious connectivity in mid-March.

Furthermore, in cases where a device was deemed to have carried out a significant number of anomalous activities, Darktrace enforced a “pattern of life” on the device, preventing it from deviating from its expected behavior while allowing legitimate business operations to continue uninterrupted.

Figure 10: Autonomous Response actions implemented by Darktrace in response to suspicious connectivity in April, including the “Enforce Pattern of Life” action.

Conclusion

macOS intrusion tradecraft continues to shift toward native tooling and lightweight control channels designed to evade signature-led controls.

The repeated convergence of rare destinations, POST-based signaling, and anomalous client behavior — observed across time and across devices — provided sufficient evidence to act early and with confidence.

As macOS tradecraft continues to evolve, the defender advantage increasingly lies not in signatures, but in the ability to reason from behavior.

‍

Credit to Justin Torres (Senior Cyber Analyst), Nathaniel Jones (VP, Security & AI Strategy, FCISO)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Alert Coverage:

/ NETWORK-based model alerts:

·       Anomalous Connection::Multiple HTTP POSTs to Rare Hostname

·       Anomalous Connection::Rare External SSL Self-Signed

·       Anomalous Connection::Powershell to Rare External

·       Anomalous Connection::New User Agent to IP Without Hostname

·       Anomalous Connection::Posting HTTP to IP Without Hostname

·       Compromise::Fast Beaconing to DGA

·       Compromise::Large Number of Suspicious Failed Connections

·       Device::Anomalous Github Download

·       Device::New PowerShell User Agent

·       Unusual Activity::Unusual External Data to New Endpoint

/ NETWORK-based Autonomous Response model alerts:

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

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

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

Indicators of Compromise (IoCs)

IP/Hostname:

·       zoom[.]uswebob[.]us · 148.72.73[.]98

·       83.136.208[.]246

·       check02id[.]com · 83.136.210[.]180

·       83.136.208[.]48

·       104.145.210[.]107

URIs:

·       /api/daemon

Destination Port Usage:

·       6783

·       5202

·       443

·       7365

·       8443

ASN:

·       AS400897 PETROSKY

·       AS398256 AS-ULTAHOST

User agents:

·       Mozilla/5.0 (Windows NT; Windows NT 10.0; fr-FR) WindowsPowerShell/5.1.26100.7920

·       Go-http-client/1.1

·       curl/8.7.1

MITRE ATT&CK Mapping

(Technique Name - Tactic - ID - Sub-Technique of)

·       Browser Session Hijacking - COLLECTION - T1185

·       Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

·       Install Digital Certificate - RESOURCE DEVELOPMENT - T1608.003 - T1608

·       PowerShell - EXECUTION - T1059.001 - T1059

·       Domain Generation Algorithms - COMMAND AND CONTROL - T1568.002 - T1568

·       Non-Standard Port - COMMAND AND CONTROL - T1571

·       Malware - RESOURCE DEVELOPMENT - T1588.001 - T1588

·       Web Service - COMMAND AND CONTROL - T1102

·       Code Repositories - COLLECTION - T1213.003 - T1213

·       Exploitation of Remote Services - LATERAL MOVEMENT - T1210

·       Exfiltration Over C2 Channel - EXFILTRATION - T1041

·       Exfiltration to Cloud Storage - EXFILTRATION - T1567.002 - T1567

References:

[1] https://www.microsoft.com/en-us/security/blog/2026/04/16/dissecting-sapphire-sleets-macos-intrusion-from-lure-to-compromise/

[2] https://radar.securityalliance.org/advisory-on-dprk-unc1069-fake-microsoft-teams-and-zoom-calls/

[3] https://www.virustotal.com/gui/domain/uswebob.us

[4] https://www.virustotal.com/gui/ip-address/83.136.210.180/community

[5] https://www.virustotal.com/gui/ip-address/104.145.210.107/community

[6] https://www.virustotal.com/gui/ip-address/83.136.208.48/community

[7] https://www.virustotal.com/gui/ip-address/83.136.208.246/community

[8] https://www.darktrace.com/blog/applescript-abuse-unpacking-a-macos-phishing-campaign

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Justin Torres
Cyber Analyst

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June 24, 2026

A New Security Challenge: The Curious Case of Prompt Language Analysis

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Why prompt analysis is emerging as a key AI security challenge

If securing AI has been one of the defining cybersecurity conversations of the past year, prompt analysis is quickly becoming one of its most interesting frontiers.

Security leaders are under pressure to understand how AI is being used across the business. In some organizations, that means governing employee use of chatbots. In others, it means overseeing copilots embedded into SaaS platforms, monitoring coding assistants, or assessing the growing footprint of autonomous agents. However different these use cases may appear on the surface, they share a common factor: humans and machines are usually interacting with enterprise systems through language.  

How prompt language differs from traditional security telemetry

For years, defenders have become used to working with familiar forms of telemetry: email traffic, network connections, API calls, endpoint processes, authentication events. Prompt language is different. It is not simply another log source. It is an expression of intent, instruction, curiosity, urgency, and sometimes manipulation. It reflects the end-goal of a user or agent, but not always with enough surrounding context to interpret the risk correctly.

Why existing security approaches only partially explain prompt risk

A growing number of vendors are approaching the task of securing AI from the angle they know best. Perimeter vendors are extending web or browser controls into AI usage. Identity vendors are emphasizing agent permissions and access governance. Data security and DLP providers are focusing on content inspection and exfiltration risk. All of these perspectives matter, but individually can’t fully explain the problem.

The challenge with securing AI is not just that a new application category has emerged. It is that language has become a new operating layer in the enterprise.

Employees now use prompts to summarize documents, generate code, analyze spreadsheets, query internal knowledge, and trigger multi-step actions through agents. In each case, prompt language acts as the interface between human intent and machine execution. That makes prompts incredibly valuable from a security perspective as they can hint at misuse, policy violations, data exposure, or attempts to circumvent controls. However, they can also be deeply ambiguous when viewed in isolation. That ambiguity is the heart of the issue.

Prompts as behavioral signals, not just text to classify

A prompt by itself tells you what was asked. It does not necessarily tell you whether the request is expected, risky, accidental, or entirely legitimate in context. Two nearly identical prompts can carry very different meanings depending on the role and function of who issued them, what systems they can access, and what actions followed. In other words, prompts are not just text to classify. They are behavioral signals to interpret.

Example: How context changes prompt risk entirely

Consider a common enterprise scenario. An employee is pulled into a new project with an aggressive deadline. Almost overnight, their use of AI tools spikes. They begin prompting more frequently, working across unfamiliar documents, querying new data sources, and interacting with more systems than usual to accelerate delivery. Viewed narrowly, this may look suspicious. Prompt volume increases, file access patterns change, API and SaaS activity rise. From some vantage points, it may resemble insider risk or unmanaged AI usage.

But now add context. Imagine that, earlier that day, the employee received instructions from a senior leader asking them to support a time-sensitive initiative. Their communication history shows that this leader is a legitimate reporting-line superior. Their recent collaboration patterns align with the new project team. Their subsequent activity, while unusual for that individual’s baseline, is consistent with the business task they were assigned.

What initially looked like a risk event may actually be a normal response to business pressure. Without the surrounding context of communication, organizational relationships, and broader behavioral patterns, prompt activity alone could generate more noise than insight.

The reverse is also true. A prompt may appear benign on the surface while the context around it suggests elevated risk. A request that seems routine could originate from a compromised user, a newly connected external agent, a shadow AI workflow, or a user acting outside their normal role. The language itself may not contain anything obviously malicious, but the surrounding conditions may tell a very different story.

What security teams need to analyze prompts effectively

The future of prompt analysis is not just about understanding language. It is about understanding language in context.

To do that well, security teams need more than prompt inspection. They need to understand:

  • Who is issuing the prompt, whether human or agent
  • How that identity normally behaves across the enterprise
  • What systems, data, and workflows are connected to the interaction
  • Which relationships and communications explain the surrounding activity
  • Whether the downstream actions align with expected business behavior

When those layers are absent, prompt analysis can become another isolated control surface: useful in theory, but limited in practice. Security teams may detect unusual wording but miss the operational function behind it, overreact to benign changes in behavior, or miss subtle misuse because the prompt itself did not appear dangerous.

How organizations should think about prompt analysis going forward

Security teams have seen this pattern before. In the cloud, posture without runtime context left important gaps. In identity, access control without behavioral understanding missed misuse that looked legitimate on paper. In data security, content inspection without business context often created friction without resolving risk. AI is exposing the same lesson again: controls are strongest when they are coordinated, not isolated. As organizations work to secure AI and identify gaps across their security operations, prompt analysis will become an increasingly important source of insight, but only as part of a broader strategy.

Prompt analysis will undoubtedly become more common, as prompts are one of the clearest windows into how people and agents are using AI systems. However, what matters most is not simply collecting prompts or filtering dangerous phrases, but being able to place that language inside a wider behavioral and operational picture.

Organizations that already have a broader understanding of how work gets done across the enterprise will be better positioned to make sense of prompt language as this category matures. They will be better able to distinguish urgency from abuse, experimentation from exfiltration, and productive AI adoption from hidden risk.

Figure 1: Darktrace / SECURE AI reconstructs the full sequence of events, showing every user and agent interaction in context, with risky prompts highlighted and categorized, including PII, sensitive data, and other policy violations.

At Darktrace, this is the key lesson emerging from the market: prompt language does matter, but it does not stand alone. It is most valuable when treated as a new behavioral input that can enrich understanding across the enterprise, not as a self-contained source of truth.

Why prompts become less useful when analyzed in isolation

The curious case of prompt language analysis, then, is this: the more important prompts become, the less useful they are in a vacuum.

The real opportunity is not just to see what was asked. It is to understand why it was asked, what it meant in that moment, and what happened next.

For a deeper look at how organizations are approaching this challenge from the strengths of prompt analysis to its limitations in isolation see Prompt Security in Enterprise AI: Strengths, Weaknesses, and Common Approaches, which expands on the role prompt-level controls play within a broader, context-driven security strategy.

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About the author
Nabil Zoldjalali
VP, Field CISO
Your data. Our AI.
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