May 10, 2024

Exploitation of ConnectWise ScreenConnect Vulnerabilities

Uncover the tactics used to exploit ConnectWise vulnerabilities and strategies to protect your systems.

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

Justin Torres

Cyber Analyst

May 2024

Introduction

Across an ever changing cyber landscape, it is common place for threat actors to actively identify and exploit newly discovered vulnerabilities within commonly utilized services and applications. While attackers are likely to prioritize developing exploits for the more severe and global Common Vulnerabilities and Exposures (CVEs), they typically have the most success exploiting known vulnerabilities within the first couple years of disclosure to the public.

Addressing these vulnerabilities in a timely manner reduces the effectiveness of known vulnerabilities, decreasing the pace of malicious actor operations and forcing pursuit of more costly and time-consuming methods, such as zero-day related exploits or attacking software supply chain operations. While actors also develop tools to exploit other vulnerabilities, developing exploits for critical and publicly known vulnerabilities gives actors impactful tools at a low cost they are able to use for quite some time.

Between January and March 2024, the Darktrace Threat Research team investigated one such example that involved indicators of compromise (IoCs) suggesting the exploitation of vulnerabilities in ConnectWise’s remote monitoring and management (RMM) software ScreenConnect.

What are the ConnectWise ScreenConnect vulnerabilities?

CVE-2024-1708 is an authentication bypass vulnerability in ScreenConnect 23.9.7 (and all earlier versions) that, if exploited, would enable an attacker to execute remote code or directly impact confidential information or critical systems. This exploit would pave the way for a second ScreenConnect vulnerability, CVE-2024-1709, which allows attackers to directly access confidential information or critical systems [1].

ConnectWise released a patch and automatically updated cloud versions of ScreenConnect 23.9.9, while urging security teams to update on-premise versions immediately [3].

If exploited in conjunction, these vulnerabilities could allow a malicious actor to create new administrative accounts on publicly exposed instances by evading existing security measures. This, in turn, could enable attackers to assume an administrative role and disable security tools, create backdoors, and disrupt RMM processes. Access to an organization’s environment in this manner poses serious risk, potentially leading to significant consequences such as deploying ransomware, as seen in various incidents involving the exploitation of ScreenConnect [2]

Darktrace Coverage of ConnectWise Exploitation

Darktrace’s anomaly-based detection was able to identify evidence of exploitation related to CVE-2024-1708 and CVE-2024-1709 across two distinct timelines; these detections included connectivity with endpoints that were later confirmed to be malicious by multiple open-source intelligence (OSINT) vendors. The activity observed by Darktrace suggests that threat actors were actively exploiting these vulnerabilities across multiple customer environments.

In the cases observed across the Darktrace fleet, Darktrace DETECT™ and Darktrace RESPOND™ were able to work in tandem to pre-emptively identify and contain network compromises from the onset. While Darktrace RESPOND was enabled in most customer environments affected by the ScreenConnect vulnerabilities, in the majority of cases it was configured in Human Confirmation mode. Whilst in Human Confirmation mode, RESPOND will provide recommended actions to mitigate ongoing attacks, but these actions require manual approval from human security teams.

When enabled in autonomous response mode, Darktrace RESPOND will take action automatically, shutting down suspicious activity as soon as it is detected without the need for human intervention. This is the ideal end state for RESPOND as actions can be taken at machine speed, without any delays waiting for user approval.

Looking within the patterns of activity observed by Darktrace , the typical attack timeline included:

Darktrace observed devices on affected customer networks performing activity indicative of ConnectWise ScreenConnect usage, for example connections over 80 and 8041, connections to screenconnect[.]com, and the use of the user agent “LabTech Agent”. OSINT research suggests that this user agent is an older name for ConnectWise Automate [5] which also includes ScreenConnect as standard [6].

Figure 1: Darktrace DETECT model alert highlighting the use of a remote management tool, namely “screenconnect[.]com”.

This activity was typically followed by anomalous connections to the external IP address 108.61.210[.]72 using URIs of the form “/MyUserName_DEVICEHOSTNAME”, as well as additional connections to another external, IP 185.62.58[.]132. Both of these external locations have since been reported as potentially malicious [14], with 185.62.58[.]132 in particular linked to ScreenConnect post-exploitation activity [2].

Figure 2: Darktrace DETECT model alert highlighting the unusual connection to 185.62.58[.]132 via port 8041.

Figure 3: Darktrace DETECT model alert highlighting connections to 108.61.210[.]72 using a new user agent and the “/MyUserName_DEVICEHOSTNAME” URI.

Same Exploit, Different Tactics?

While the majority of instances of ConnectWise ScreenConnect exploitation observed by Darktrace followed the above pattern of activity, Darktrace was able to identify some deviations from this.

In one customer environment, Darktrace’s detection of post-exploitation activity began with the same indicators of ScreenConnect usage, including connections to screenconnect[.]com via port 8041, followed by connections to unusual domains flagged as malicious by OSINT, in this case 116.0.56[.]101 [16] [17]. However, on this deployment Darktrace also observed threat actors downloading a suspicious AnyDesk installer from the endpoint with the URI “hxxp[:]//116.0.56[.]101[:]9191/images/Distribution.exe”.

Figure 4: Darktrace DETECT model alert highlighting the download of an unusual executable file from 116.0.56[.]101.

Further investigation by Darktrace’s Threat Research team revealed that this endpoint was associated with threat actors exploiting CVE-2024-1708 and CVE-2024-1709 [1]. Darktrace was additionally able to identify that, despite the customer being based in the United Kingdom, the file downloaded came from Pakistan. Darktrace recognized that this represented a deviation from the device’s expected pattern of activity and promptly alerted for it, bringing it to the attention of the customer.

Figure 5: External Sites Summary within the Darktrace UI pinpointing the geographic locations of external endpoints, in this case highlighting a file download from Pakistan.

Darktrace’s Autonomous Response

In this instance, the customer had Darktrace enabled in autonomous response mode and the post-exploitation activity was swiftly contained, preventing the attack from escalating.

As soon as the suspicious AnyDesk download was detected, Darktrace RESPOND applied targeted measures to prevent additional malicious activity. This included blocking connections to 116.0.56[.]101 and “*.56.101”, along with blocking all outgoing traffic from the device. Furthermore, RESPOND enforced a “pattern of life” on the device, restricting its activity to its learned behavior, allowing connections that are considered normal, but blocking any unusual deviations.

Figure 6: Darktrace RESPOND enforcing a “pattern of life” on the offending device after detecting the suspicious AnyDesk download.

Figure 7: Darktrace RESPOND blocking connections to the suspicious endpoint 116.0.56[.]101 and “*.56.101” following the download of the suspicious AnyDesk installer.

The customer was later able to use RESPOND to manually quarantine the offending device, ensuring that all incoming and outgoing traffic to or from the device was prohibited, thus preventing any further malicious communication or lateral movement attempts.

Figure 8: The actions applied by Darktrace RESPOND in response to the post-exploitation activity related to the ScreenConnect vulnerabilities, including the manually applied “Quarantine device” action.

Conclusion

In the observed cases of the ConnectWise ScreenConnect vulnerabilities being exploited across the Darktrace fleet, Darktrace was able to pre-emptively identify and contain network compromises from the onset, offering vital protection against disruptive cyber-attacks.

While much of the post-exploitation activity observed by Darktrace remained the same across different customer environments, important deviations were also identified suggesting that threat actors may be adapting their tactics, techniques and procedures (TTPs) from campaign to campaign.

While new vulnerabilities will inevitably surface and threat actors will continually look for novel ways to evolve their methods, Darktrace’s Self-Learning AI and behavioral analysis offers organizations full visibility over new or unknown threats. Rather than relying on existing threat intelligence or static lists of “known bads”, Darktrace is able to detect emerging activity based on anomaly and respond to it without latency, safeguarding customer environments whilst causing minimal disruption to business operations.

Credit: Emma Foulger, Principal Cyber Analyst for their contribution to this blog.

Appendices

Darktrace Model Coverage

DETECT Models

Compromise / Agent Beacon (Medium Period)

Compromise / Agent Beacon (Long Period)

Anomalous File / EXE from Rare External Location

Device / New PowerShell User Agent

Anomalous Connection / Powershell to Rare External

Anomalous Connection / New User Agent to IP Without Hostname

User / New Admin Credentials on Client

Device / New User Agent

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Compromise / Suspicious Request Data

Compliance / Remote Management Tool On Server

Anomalous File / Anomalous Octet Stream (No User Agent)

RESPOND Models

Antigena / Network::External Threat::Antigena Suspicious File Block

Antigena / Network::External Threat::Antigena File then New Outbound Block

Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block

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

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

Antigena / Network::Insider Threat::Antigena Unusual Privileged User Activities Block

Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Pattern of Life Block

List of IoCs

IoC - Type - Description + Confidence

185.62.58[.]132 – IP- IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

108.61.210[.]72- IP - IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

116.0.56[.]101 - IP - IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

/MyUserName_ DEVICEHOSTNAME – URI - URI linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

/images/Distribution.exe – URI - URI linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

24780657328783ef50ae0964b23288e68841a421 - SHA1 Filehash - Filehash linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

a21768190f3b9feae33aaef660cb7a83 - MD5 Filehash - Filehash linked with threat actors exploiting CVE-2024-1708 and CVE-2024-1709

MITRE ATT&CK Mapping

Technique – Tactic – ID - Sub-technique of

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

Web Services - RESOURCE DEVELOPMENT - T1583.006 - T1583

Drive-by Compromise - INITIAL ACCESS - T1189 – NA

Ingress Tool Transfer - COMMAND AND CONTROL - T1105 - NA

Malware - RESOURCE DEVELOPMENT - T1588.001- T1588

Exploitation of Remote Services - LATERAL MOVEMENT - T1210 – NA

PowerShell – EXECUTION - T1059.001 - T1059

Pass the Hash - DEFENSE EVASION, LATERAL MOVEMENT - T1550.002 - T1550

Valid Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078 – NA

Man in the Browser – COLLECTION - T1185 - NA

Exploit Public-Facing Application - INITIAL ACCESS - T1190 - NA

Exfiltration Over C2 Channel – EXFILTRATION - T1041 – NA

IP Addresses – RECONNAISSANCE - T1590.005 - T1590

Remote Access Software - COMMAND AND CONTROL - T1219 – NA

Lateral Tool Transfer - LATERAL MOVEMENT - T1570 – NA

Application Layer Protocol - COMMAND AND CONTROL - T1071 – NA

References:

[1] https://unit42.paloaltonetworks.com/connectwise-threat-brief-cve-2024-1708-cve-2024-1709/

[2] https://www.huntress.com/blog/slashandgrab-screen-connect-post-exploitation-in-the-wild-cve-2024-1709-cve-2024-1708

[3] https://www.huntress.com/blog/a-catastrophe-for-control-understanding-the-screenconnect-authentication-bypass

[4] https://www.speedguide.net/port.php?port=8041

[5] https://www.connectwise.com/company/announcements/labtech-now-connectwise-automate

[6] https://www.connectwise.com/solutions/software-for-internal-it/automate

[7] https://www.securityweek.com/slashandgrab-screenconnect-vulnerability-widely-exploited-for-malware-delivery/

[8] https://arcticwolf.com/resources/blog/cve-2024-1709-cve-2024-1708-follow-up-active-exploitation-and-pocs-observed-for-critical-screenconnect-vulnerabilities/https://success.trendmicro.com/dcx/s/solution/000296805?language=en_US&sfdcIFrameOrigin=null

[9] https://www.connectwise.com/company/trust/security-bulletins/connectwise-screenconnect-23.9.8

[10] https://socradar.io/critical-vulnerabilities-in-connectwise-screenconnect-postgresql-jdbc-and-vmware-eap-cve-2024-1597-cve-2024-22245/

[11] https://www.trendmicro.com/en_us/research/24/b/threat-actor-groups-including-black-basta-are-exploiting-recent-.html

[12] https://otx.alienvault.com/indicator/ip/185.62.58.132

[13] https://www.virustotal.com/gui/ip-address/185.62.58.132/community

[14] https://www.virustotal.com/gui/ip-address/108.61.210.72/community

[15] https://otx.alienvault.com/indicator/ip/108.61.210.72

[16] https://www.virustotal.com/gui/ip-address/116.0.56[.]101/community

[17] https://otx.alienvault.com/indicator/ip/116.0.56[.]101

執筆者

Justin Torres

Cyber Analyst

Inside the SOC

Written by

Justin Torres

Cyber Analyst

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Network

June 25, 2026

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

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].

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.

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

About the author

Justin Torres

Cyber Analyst

Blog

AI

June 25, 2026

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

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.

About the author

Nabil Zoldjalali

VP, Field CISO

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

Why prompt analysis is emerging as a key AI security challenge

How prompt language differs from traditional security telemetry

Why existing security approaches only partially explain prompt risk

Prompts as behavioral signals, not just text to classify

Example: How context changes prompt risk entirely

What security teams need to analyze prompts effectively

How organizations should think about prompt analysis going forward

Why prompts become less useful when analyzed in isolation