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February 24, 2025

Detecting and Containing Account Takeover with Darktrace

Account takeovers are rising with SaaS adoption. Learn how Darktrace detects deviations in user behavior and autonomously stops threats before they escalate.
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
Min Kim
Cyber Security Analyst
women on laptop in officeDefault blog image
24
Feb 2025

Thanks to its accessibility from anywhere with an internet connection and a web browser, Software-as-a-Service (SaaS) platforms have become nearly universal across organizations worldwide. However, with this growing popularity comes greater responsibility. Increased attention attracts a larger audience, including those who may seek to exploit these widely used services. One crucial factor to be vigilant about in the SaaS landscape is safeguarding internal credentials. Minimal protection on accounts can lead to SaaS hijacking, which could allow further escalations within the network.

How does SaaS account takeover work?

SaaS hijacking occurs when a malicious actor takes control of a user’s active session with a SaaS application. Attackers can achieve this through various methods, including employees using company credentials on compromised or spoofed external websites, brute-force attacks, social engineering, and exploiting outdated software or applications.

After the hijack, attackers may escalate their actions by changing email rules and using internal addresses for additional social engineering attacks. The larger goal of these actions is often to steal internal data, damage reputations, and disrupt operations.

Account takeover protection

It has become essential to have security tools capable of outsmarting potential malicious actors. Traditional tools that rely on rules and signatures may not be able to identify new events, such as logins or activities from a rare endpoint, unless they come from a known malicious source.

Darktrace relies on analysis of user and network behavior, tailored to each customer, allowing it to identify anomalous events that the user typically does not engage in. In this way, unusual SaaS activities can be detected, and unwanted actions can be halted to allow time for remediation before further escalations.

The following cases, drawn from the global customer base, illustrate how Darktrace detects potential SaaS hijack attempts and further escalations, and applies appropriate actions when necessary.

Case 1: Unusual login after a phishing email

A customer in the US received a suspicious email that seemed to be from the legitimate file storage service, Dropbox. However, Darktrace identified that the reply-to email address, hremployeepyaroll@mail[.]com, was masquerading as one associated with the customer’s Human Resources (HR) department.

Further inspection of this sender address revealed that the attacker had intentionally misspelled ‘payroll’ to trick recipients into believing it was legitimate

Furthermore, the subject of the email indicated that the attackers were attempting a social engineering attack by sharing a file related to pay raises and benefits to capture the recipients' attention and increase the likelihood of their targets engaging with the email and its attachment.

Figure 1: Subject of the phishing email.
Figure 1: Subject of the phishing email.

Unknowingly, the recipient, who believed the email to be a legitimate HR communication, acted on it, allowing malicious attackers to gain access to the account. Following this, the recipient’s account was observed logging in from a rare location using multi-factor authentication (MFA) while also being active from another more commonly observed location, indicating that the SaaS account had been compromised.

Darktrace’s Autonomous Response action triggered by an anomalous email received by an internal user, followed by a failed login attempt from a rare external source.
Figure 2: Darktrace’s Autonomous Response action triggered by an anomalous email received by an internal user, followed by a failed login attempt from a rare external source.

Darktrace subsequently observed the SaaS actor creating new inbox rules on the account. These rules were intended to mark as read and move any emails mentioning the file storage company, whether in the subject or body, to the ‘Conversation History’ folder. This was likely an attempt by the threat actor to hide any outgoing phishing emails or related correspondence from the legitimate account user, as the ‘Conversation History’ folder typically goes unread by most users.

Typically, Darktrace / EMAIL would have instantly placed the phishing email in the junk folder before they reached user’s inbox, while also locking the links identified in the suspicious email, preventing them from being accessed. Due to specific configurations within the customer’s deployment, this did not happen, and the email remained accessible to the user.

Case 2: Login using unusual credentials followed by password change

In the latter half of 2024, Darktrace detected an unusual use of credentials when a SaaS actor attempted to sign into a customer’s Microsoft 365 application from an unfamiliar IP address in the US. Darktrace recognized that since the customer was located within the Europe, Middle East, and Africa (EMEA) region, a login from the US was unexpected and suspicious. Around the same time, the legitimate account owner logged into the customer’s SaaS environment from another location – this time from a South African IP, which was commonly seen within the environment and used by other internal SaaS accounts.

Darktrace understood that this activity was highly suspicious and unlikely to be legitimate, given one of the IPs was known and expected, while the other had never been seen before in the environment, and the simultaneous logins from two distant locations were geographically impossible.

Model alert in Darktrace / IDENTITY: Detecting a login from a different source while the user is already active from another source.
Figure 3: Model alert in Darktrace / IDENTITY: Detecting a login from a different source while the user is already active from another source.

Darktrace detected several unusual login attempts, including a successful login from an uncommon US source. Subsequently, Darktrace / NETWORK identified the device associated with this user making external connections to rare endpoints, some of which were only two weeks old. As this customer had integrated Darktrace with Microsoft Defender, the Darktrace detection was enriched by Defender, adding the additional context that the user had likely been compromised in an Adversary-in-the-Middle (AiTM) phishing attack. AiTM phishing attacks occur when a malicious attacker intercepts communications between a user and a legitimate authentication service, potentially leading to account hijacking. These attacks are harder to identify as they can bypass security measures like MFA.

Following this, Darktrace observed the attacker using the now compromised credentials to access password management and change the account's password. Such behavior is common in account takeover incidents, as attackers seek to maintain persistence within the SaaS environment.

While Darktrace’s Autonomous Response was not fully configured on the customer’s SaaS environment, they were subscribed to the Managed Threat Detection service offered by Darktrace’s Security Operations Center (SOC). This 24/7 service ensures that Darktrace’s analysts monitor and investigate emerging suspicious activity, informing customers in real-time. As such, the customer received notification of the compromise and were able to quickly take action to prevent further escalation.

Case 3: Unusual logins, new email rules and outbound spam

Recently, Darktrace has observed a trend in SaaS compromises involving unusual logins, followed by the creation of new email rules, and then outbound spam or phishing campaigns being launched from these accounts.

In October, Darktrace identified a SaaS user receiving an email with the subject line "Re: COMPANY NAME Request for Documents" from an unknown sender using a freemail  account. As freemail addresses require very little personal information to create, threat actors can easily create multiple accounts for malicious purposes while retaining their anonymity.

Within the identified email, Darktrace found file storage links that were likely intended to divert recipients to fraudulent or malicious websites upon interaction. A few minutes after the email was received, the recipient was seen logging in from three different sources located in the US, UK, and the Philippines, all around a similar time. As the customer was based in the Philippines, a login from there was expected and not unusual. However, Darktrace understood that the logins from the UK and US were highly unusual, and no other SaaS accounts had connected from these locations within the same week.

After successfully logging in from the UK, the actor was observed updating a mailbox rule, renaming it to ‘.’ and changing its parameters to move any inbound emails to the deleted items folder and mark them as read.

Figure 4: The updated email rule intended to move any inbound emails to the deleted items folder.

Malicious actors often use ambiguous names like punctuation marks, repetitive letters, and unreadable words to name resources, disguising their rules to avoid detection by legitimate users or administrators. Similarly, attackers have been known to adjust existing rule parameters rather than creating new rules to keep their footprints untracked. In this case, the rule was updated to override an existing email rule and delete all incoming emails. This ensured that any inbound emails, including responses to potential phishing emails sent by the account, would be deleted, allowing the attacker to remain undetected.

Over the next two days, additional login attempts, both successful and failed, were observed from locations in the UK and the Philippines. Darktrace noted multiple logins from the Philippines where the legitimate user was attempting to access their account using a password that had recently expired or been changed, indicating that the attacker had altered the user’s original password as well.

Following this chain of events, over 500 emails titled “Reminder For Document Signed Agreement.10/28/2024” were sent from the SaaS actor’s account to external recipients, all belonging to a different organization within the Philippines.

These emails contained rare attachments with a ‘.htm’ extension, which included programming language that could initiate harmful processes on devices. While inherently not malicious, if used inappropriately, these files could perform unwanted actions such as code execution, malware downloads, redirects to malicious webpages, or phishing upon opening.

Outbound spam seen from the hijacked SaaS account containing a ‘.htm’ attachment.
Figure 5: Outbound spam seen from the hijacked SaaS account containing a ‘.htm’ attachment.

As this customer did not have Autonomous Response enabled for Darktrace / IDENTITY, the unusual activity went unattended, and the compromise was able to escalate to the point of a spam email campaign being launched from the account.

In a similar example on a customer network in EMEA, Darktrace detected unusual logins and the creation of new email rules from a foreign location through a SaaS account. However, in this instance, Autonomous Response was enabled and automatically disabled the compromised account, preventing further malicious activity and giving the customer valuable time to implement their own remediation measures.

Conclusion

Whether it is an unexpected login or an unusual sequence of events – such as a login followed by a phishing email being sent – unauthorized or unexpected activities can pose a significant risk to an organization’s SaaS environment. The threat becomes even greater when these activities escalate to account hijacking, with the compromised account potentially providing attackers access to sensitive corporate data. Organizations, therefore, must have robust SaaS security measures in place to prevent data theft, ensure compliance and maintain continuity and trust.

The Darktrace suite of products is well placed to detect and contain SaaS hijack attempts at multiple stages of an attack. Darktrace / EMAIL identifies initial phishing emails that attackers use to gain access to customer SaaS environments, while Darktrace / IDENTITY detects anomalous SaaS behavior on user accounts which could indicate they have been taken over by a malicious actor.

By identifying these threats in a timely manner and taking proactive mitigative measures, such as logging or disabling compromised accounts, Darktrace prevents escalation and ensures customers have sufficient time to response effectively.

Credit to Min Kim (Cyber Analyst) and Ryan Traill (Analyst Content Lead)

[related-resource]

Appendices

Darktrace Model Detections Case 1

SaaS / Compromise / SaaS Anomaly Following Anomalous Login

SaaS / Compromise / Unusual Login and New Email Rule

SaaS / Compliance / Anomalous New Email Rule

SaaS / Unusual Activity / Multiple Unusual SaaS Activities

SaaS / Access / Unusual External Source for SaaS Credential Us

SaaS / Compromise / Login From Rare Endpoint While User is Active

SaaS / Email Nexus / Unusual Login Location Following Link to File Storage

Antigena / SaaS / Antigena Email Rule Block (Autonomous Response)

Antigena / SaaS / Antigena Suspicious SaaS Activity Block (Autonomous Response)

Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block (Autonomous Response)

List of Indicators of Compromise (IoCs)

176.105.224[.]132 – IP address – Unusual SaaS Activity Source

hremployeepyaroll@mail[.]com – Email address – Reply-to email address

MITRE ATT&CK Mapping

Cloud Accounts – DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS – T1078

Outlook Rules – PERSISTENCE – T1137

Cloud Service Dashboard – DISCOVERY – T1538

Compromise Accounts – RESOURCE DEVELOPMENT – T1586

Steal Web Session Cookie – CREDENTIAL ACCESS – T1539

Darktrace Model Detections Case 2

SaaS / Compromise / SaaS Anomaly Following Anomalous Login

SaaS / Compromise / Unusual Login and Account Update

Security Integration / High Severity Integration Detection

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Compromise / Login From Rare Endpoint While User Is Active

SaaS / Compromise / Login from Rare High Risk Endpoint

SaaS / Access / M365 High Risk Level Login

Antigena / SaaS / Antigena Suspicious SaaS Activity Block (Autonomous Response)

Antigena / SaaS / Antigena Enhanced Monitoring from SaaS user Block (Autonomous Response)

List of IoCs

74.207.252[.]129 – IP Address – Suspicious SaaS Activity Source

MITRE ATT&CK Mapping

Cloud Accounts – DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS – T1078

Cloud Service Dashboard – DISCOVERY – T1538

Compromise Accounts – RESOURCE DEVELOPMENT – T1586

Steal Web Session Cookie – CREDENTIAL ACCESS – T1539

Darktrace Model Detections Case 3

SaaS / Compromise / Unusual Login and Outbound Email Spam

SaaS / Compromise / New Email Rule and Unusual Email Activity

SaaS / Compromise / Unusual Login and New Email Rule

SaaS / Email Nexus / Unusual Login Location Following Sender Spoof

SaaS / Email Nexus / Unusual Login Location Following Link to File Storage

SaaS / Email Nexus / Possible Outbound Email Spam

SaaS / Unusual Activity / Multiple Unusual SaaS Activities

SaaS / Email Nexus / Suspicious Internal Exchange Activity

SaaS / Compliance / Anomalous New Email Rule

List of IoCs

95.142.116[.]1 – IP Address – Suspicious SaaS Activity Source

154.12.242[.]58 – IP Address – Unusual Source

MITRE ATT&CK Mapping

Cloud Accounts – DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS – T1078

Compromise Accounts – RESOURCE DEVELOPMENT – T1586

Email Accounts – RESOURCE DEVELOPMENT – T1585

Phishing – INITIAL ACCESS – T1566

Outlook Rules – PERSISTENCE – T1137

Internal Spear phishing – LATERAL MOVEMENT - T1534

Get the latest insights on emerging cyber threats

This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.

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
Min Kim
Cyber Security 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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About the author
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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