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January 9, 2025

Detecting and Mitigating Adversary-in-the-Middle Phishing Attacks with Darktrace Services

Threat actors often use advanced phishing toolkits and Adversary-in-the-Middle (AitM) attacks in Business Email Compromise (BEC) campaigns, Discover how Darktrace detected and mitigated a sophisticated attack leveraging Dropbox, highlighting the importance of robust cybersecurity measures.
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
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09
Jan 2025

What is an Adversary-in-the-Middle Attack?

Threat actors are increasingly utilizing advanced phishing toolkits and techniques to carry out Adversary-in-the-Middle (AitM) attacks. These attacks involve the use of a proxy to a legitimate service, where the attacker’s webpage mimics the expected site. While the victim believes they are visiting the legitimate site, they are actually interacting with the attacker’s device, allowing the malicious actor to monitor all interactions and control the authenticated session, ultimately gaining access to the user’s account [1][2].

This blog will explore how Darktrace detected AitM techniques being leveraged in a Business Email Compromise (BEC) attack that used the widely used and trusted cloud storage service, Dropbox, for delivery. Dropbox’s popularity has made it a prime target for attackers to exploit in recent years. Threat actors can exploit the service for various malicious activities, including distributing malware and exposing sensitive information.

Attack Overview

In these types of AitM BEC attacks, recipients are often targeted with Dropbox-related emails, featuring subject headings like ‘FirstLast shared "Filename" with you,’ which suggest an individual is sharing an invoice-related attachment. These email subjects are common in such attacks, as threat actors attempt to encourage victims to access Dropbox links by masquerading them as legitimate files.

While higher priority users are, of course, targeted, the scope of these attacks remains broad. For instance, if a lower priority user is targeted by a phishing attack or their token is stolen, an attacker can still attempt BEC for further malicious intent and financial gain.

In October 2024, a Darktrace customer received a phishing email from a seemingly legitimate Dropbox address. This email originated from the IP, 54.240.39[.]219 and contained multiple link payloads to Dropbox-related hostnames were observed, inviting the user to access a file. Based on anomaly indicators and detection by Darktrace / EMAIL, Darktrace recognized that one of the payloads was attempting to abuse a legitimate cloud platform to share files or other unwanted material with the recipient.

Overview of the malicious email in the Darktrace / EMAIL console, highlighting Dropbox associated content/link payloads.
Figure 1: Overview of the malicious email in the Darktrace / EMAIL console, highlighting Dropbox associated content/link payloads.

Following the recipient’s engagement with this email, Darktrace / IDENTITY identified a series of suspicious activities within the customer’s environment.

AitM attacks allow threat actors to bypass multi-factor authentication (MFA). Initially, when a user is phished, the malicious infrastructure captures both the user’s credentials and the token. This includes replaying a token issued to user that has already completed the MFA requirement, allowing the threat actor to satisfy the validity of the requirement and gain access to sensitive organizational resources. Darktrace is able to analyze user activity and authentication patterns to determine whether MFA requirements were met. This capability helps verify and indicate token theft via AitM.

Darktrace observed the associated user account making requests over Microsoft 365 from the IP 41.90.175[.]46. Given the unusual nature and rare geolocation based in Kenya, Africa, this activity did not appear indicative of legitimate business operations.

Geographical location of the SaaS user
Figure 2: Geographical location of the SaaS user in relation to the source IP 41.90.175[.]46.

Further analysis using open-source intelligence (OSINT) revealed that the endpoint was likely associated with a call-back proxy network [3]. This suggested the presence of a network device capable of re-routing traffic and harvesting information.

Darktrace also detected that the same SaaS user was logging in from two different locations around the same time. One login was from a common, expected location, while the other was from an unusual location. Additionally, the user was observed registering security information using the Microsoft Authenticator app, indicating an attempt by an attacker to maintain access to the account by establishing a new method of MFA. This new MFA method could be used to bypass future MFA requirements, allowing the attacker to access sensitive material or carry out further malicious activities.

External sites summary for the SaaS account in relation to the source IP 13.74.161[.]104, observed with Registering Security Information.
Figure 3: External sites summary for the SaaS account in relation to the source IP 13.74.161[.]104, observed with Registering Security Information.

Ultimately, this anomalous behavior was escalated to the Darktrace Security Operations Centre (SOC) via the Managed Detection & Response service for prompt triage and investigation by Darktrace’s SOC Analysts who notified the customer of strong evidence of compromise.

Fortunately, since this customer had Darktrace enabled in Autonomous Response mode, the compromised SaaS account had already been disabled, containing the attack. Darktrace’s SOC elected to extend this action to ensure the malicious activity remained halted until the customer could take further remedial action.

Attack timeline of observed activity, in chronological order; This highlighted anomalous SaaS events such as, MailItemsAccessed’, ‘Use of Unusual Credentials’, ‘User Registered Security Info’ events, and a ‘Disable User’ Autonomous Response action.
Figure 4: Attack timeline of observed activity, in chronological order; This highlighted anomalous SaaS events such as, MailItemsAccessed’, ‘Use of Unusual Credentials’, ‘User Registered Security Info’ events, and a ‘Disable User’ Autonomous Response action.

Conclusion

AitM attacks can play a crucial role in BEC campaigns. These attacks are often part of multi-staged operations, where an initial AitM attack is leveraged to launch a BEC by delivering a malicious URL through a trusted vendor or service. Attackers often attempt to lay low on their target network, sometimes persisting for extended periods, as they monitor user accounts or network segments to intercept sensitive communications.

In this instance, Darktrace successfully identified and acted against AitM techniques being leveraged in a BEC attack that used Dropbox for delivery. While Dropbox is widely used for legitimate purposes, its popularity has also made it a target for exploitation by threat actors, who have used it for a variety of malicious purposes, including delivering malware and revealing sensitive information.

Darktrace’s Security Operations Support service, combined with its Autonomous Response technology, provided timely and effective mitigation. Dedicated Security Operations Support analysts triaged the incident and implemented preventative measures, ensuring the customer was promptly notified. Meanwhile, Darktrace swiftly disabled the compromised SaaS account, allowing the customer to take further necessary actions, such as resetting the user’s password.

This case highlights the capabilities of Darktrace’s solutions, enabling the customer to resume normal business operations despite the malicious activity.

Credit to Justin Torres (Senior Cyber Analyst), Stefan Rowe (Technical Director, SOC) and Ryan Traill (Analyst Content Lead)

Appendices

References

1.    https://www.proofpoint.com/us/threat-reference/man-in-the-middle-attack-mitm

2.    https://thehackernews.com/2024/08/how-to-stop-aitm-phishing-attack.html

3.    https://spur.us/context/41.90.175.46

Darktrace Model Detections

Darktrace / NETWORK Model Alert(s):

SaaS / Compromise::SaaS Anomaly Following Anomalous Login

SaaS / Unusual Activity::Multiple Unusual SaaS Activities

SaaS / Compromise::Unusual Login and Account Update

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

SaaS / Access::Unusual External Source for SaaS Credential Use

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

SaaS / Access::MailItemsAccessed from Rare Endpoint

Darktrace/Autonomous Response Model Alert(s):

Antigena / SaaS::Antigena Suspicious SaaS Activity Block

List of Indicators of Compromise (IoCs)

(IoC - Type - Description)

41.90.175[.]46 – Source IP Observed with Suspicious Login Behavior

MITRE ATT&CK Mapping

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

Cloud Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078.004 - T1078

Email Accounts - RESOURCE DEVELOPMENT - T1586.002 - T1586

Cloud Service Dashboard - DISCOVERY - T1538

Compromise Accounts - RESOURCE DEVELOPMENT - T1586

Steal Web Session Cookie - CREDENTIAL ACCESS - T1539

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

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May 16, 2025

Catching a RAT: How Darktrace neutralized AsyncRAT

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What is a RAT?

As the proliferation of new and more advanced cyber threats continues, the Remote Access Trojan (RAT) remains a classic tool in a threat actor's arsenal. RATs, whether standardized or custom-built, enable attackers to remotely control compromised devices, facilitating a range of malicious activities.

What is AsyncRAT?

Since its first appearance in 2019, AsyncRAT has become increasingly popular among a wide range of threat actors, including cybercriminals and advanced persistent threat (APT) groups.

Originally available on GitHub as a legitimate tool, its open-source nature has led to widespread exploitation. AsyncRAT has been used in numerous campaigns, including prolonged attacks on essential US infrastructure, and has even reportedly penetrated the Chinese cybercriminal underground market [1] [2].

How does AsyncRAT work?

Original source code analysis of AsyncRAT demonstrates that once installed, it establishes persistence via techniques such as creating scheduled tasks or registry keys and uses SeDebugPrivilege to gain elevated privileges [3].

Its key features include:

  • Keylogging
  • File search
  • Remote audio and camera access
  • Exfiltration techniques
  • Staging for final payload delivery

These are generally typical functions found in traditional RATs. However, it also boasts interesting anti-detection capabilities. Due to the popularity of Virtual Machines (VM) and sandboxes for dynamic analysis, this RAT checks for the manufacturer via the WMI query 'Select * from Win32_ComputerSystem' and looks for strings containing 'VMware' and 'VirtualBox' [4].

Darktrace’s coverage of AsyncRAT

In late 2024 and early 2025, Darktrace observed a spike in AsyncRAT activity across various customer environments. Multiple indicators of post-compromise were detected, including devices attempting or successfully connecting to endpoints associated with AsyncRAT.

On several occasions, Darktrace identified a clear association with AsyncRAT through the digital certificates of the highlighted SSL endpoints. Darktrace’s Real-time Detection effectively identified and alerted on suspicious activities related to AsyncRAT. In one notable incident, Darktrace’s Autonomous Response promptly took action to contain the emerging threat posed by AsyncRAT.

AsyncRAT attack overview

On December 20, 2024, Darktrace first identified the use of AsyncRAT, noting a device successfully establishing SSL connections to the uncommon external IP 185.49.126[.]50 (AS199654 Oxide Group Limited) via port 6606. The IP address appears to be associated with AsyncRAT as flagged by open-source intelligence (OSINT) sources [5]. This activity triggered the device to alert the ‘Anomalous Connection / Rare External SSL Self-Signed' model.

Model alert in Darktrace / NETWORK showing the repeated SSL connections to a rare external Self-Signed endpoint, 185.49.126[.]50.
Figure 1: Model alert in Darktrace / NETWORK showing the repeated SSL connections to a rare external Self-Signed endpoint, 185.49.126[.]50.

Following these initial connections, the device was observed making a significantly higher number of connections to the same endpoint 185.49.126[.]50 via port 6606 over an extended period. This pattern suggested beaconing activity and triggered the 'Compromise/Beaconing Activity to External Rare' model alert.

Further analysis of the original source code, available publicly, outlines the default ports used by AsyncRAT clients for command-and-control (C2) communications [6]. It reveals that port 6606 is the default port for creating a new AsyncRAT client. Darktrace identified both the Certificate Issuer and the Certificate Subject as "CN=AsyncRAT Server". This SSL certificate encrypts the packets between the compromised system and the server. These indicators of compromise (IoCs) detected by Darktrace further suggest that the device was successfully connecting to a server associated with AsyncRAT.

Model alert in Darktrace / NETWORK displaying the Digital Certificate attributes, IP address and port number associated with AsyncRAT.
Figure 2: Model alert in Darktrace / NETWORK displaying the Digital Certificate attributes, IP address and port number associated with AsyncRAT.
Darktrace’s detection of repeated connections to the suspicious IP address 185.49.126[.]50 over port 6606, indicative of beaconing behavior.
Figure 3: Darktrace’s detection of repeated connections to the suspicious IP address 185.49.126[.]50 over port 6606, indicative of beaconing behavior.
Darktrace's Autonomous Response actions blocking the suspicious IP address,185.49.126[.]50.
Figure 4: Darktrace's Autonomous Response actions blocking the suspicious IP address,185.49.126[.]50.

A few days later, the same device was detected making numerous connections to a different IP address, 195.26.255[.]81 (AS40021 NL-811-40021), via various ports including 2106, 6606, 7707, and 8808. Notably, ports 7707 and 8808 are also default ports specified in the original AsyncRAT source code [6].

Darktrace’s detection of connections to the suspicious endpoint 195.26.255[.]81, where the default ports (6606, 7707, and 8808) for AsyncRAT were observed.
Figure 5: Darktrace’s detection of connections to the suspicious endpoint 195.26.255[.]81, where the default ports (6606, 7707, and 8808) for AsyncRAT were observed.

Similar to the activity observed with the first endpoint, 185.49.126[.]50, the Certificate Issuer for the connections to 195.26.255[.]81 was identified as "CN=AsyncRAT Server". Further OSINT investigation confirmed associations between the IP address 195.26.255[.]81 and AsyncRAT [7].

Darktrace's detection of a connection to the suspicious IP address 195.26.255[.]81 and the domain name identified under the common name (CN) of a certificate as AsyncRAT Server
Figure 6: Darktrace's detection of a connection to the suspicious IP address 195.26.255[.]81 and the domain name identified under the common name (CN) of a certificate as AsyncRAT Server.

Once again, Darktrace's Autonomous Response acted swiftly, blocking the connections to 195.26.255[.]81 throughout the observed AsyncRAT activity.

Figure 7: Darktrace's Autonomous Response actions were applied against the suspicious IP address 195.26.255[.]81.

A day later, Darktrace again alerted to further suspicious activity from the device. This time, connections to the suspicious endpoint 'kashuub[.]com' and IP address 191.96.207[.]246 via port 8041 were observed. Further analysis of port 8041 suggests it is commonly associated with ScreenConnect or Xcorpeon ASIC Carrier Ethernet Transport [8]. ScreenConnect has been observed in recent campaign’s where AsyncRAT has been utilized [9]. Additionally, one of the ASN’s observed, namely ‘ASN Oxide Group Limited’, was seen in both connections to kashuub[.]com and 185.49.126[.]50.

This could suggest a parallel between the two endpoints, indicating they might be hosting AsyncRAT C2 servers, as inferred from our previous analysis of the endpoint 185.49.126[.]50 and its association with AsyncRAT [5]. OSINT reporting suggests that the “kashuub[.]com” endpoint may be associated with ScreenConnect scam domains, further supporting the assumption that the endpoint could be a C2 server.

Darktrace’s Autonomous Response technology was once again able to support the customer here, blocking connections to “kashuub[.]com”. Ultimately, this intervention halted the compromise and prevented the attack from escalating or any sensitive data from being exfiltrated from the customer’s network into the hands of the threat actors.

Darktrace’s Autonomous Response applied a total of nine actions against the IP address 191.96.207[.]246 and the domain 'kashuub[.]com', successfully blocking the connections.
Figure 8: Darktrace’s Autonomous Response applied a total of nine actions against the IP address 191.96.207[.]246 and the domain 'kashuub[.]com', successfully blocking the connections.

Due to the popularity of this RAT, it is difficult to determine the motive behind the attack; however, from existing knowledge of what the RAT does, we can assume accessing and exfiltrating sensitive customer data may have been a factor.

Conclusion

While some cybercriminals seek stability and simplicity, openly available RATs like AsyncRAT provide the infrastructure and open the door for even the most amateur threat actors to compromise sensitive networks. As the cyber landscape continually shifts, RATs are now being used in all types of attacks.

Darktrace’s suite of AI-driven tools provides organizations with the infrastructure to achieve complete visibility and control over emerging threats within their network environment. Although AsyncRAT’s lack of concealment allowed Darktrace to quickly detect the developing threat and alert on unusual behaviors, it was ultimately Darktrace Autonomous Response's consistent blocking of suspicious connections that prevented a more disruptive attack.

Credit to Isabel Evans (Cyber Analyst), Priya Thapa (Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Appendices

  • Real-time Detection Models
       
    • Compromise / Suspicious SSL Activity
    •  
    • Compromise / Beaconing Activity To      External Rare
    •  
    • Compromise / High Volume of      Connections with Beacon Score
    •  
    • Anomalous Connection / Suspicious      Self-Signed SSL
    •  
    • Compromise / Sustained SSL or HTTP      Increase
    •  
    • Compromise / SSL Beaconing to Rare      Destination
    •  
    • Compromise / Suspicious Beaconing      Behaviour
    •  
    • Compromise / Large Number of      Suspicious Failed Connections
  •  
  • Autonomous     Response Models
       
    • Antigena / Network / Significant      Anomaly / Antigena Controlled and Model Alert
    •  
    • Antigena / Network / Significant      Anomaly / Antigena Enhanced Monitoring from Client Block

List of IoCs

·     185.49.126[.]50 - IP – AsyncRAT C2 Endpoint

·     195.26.255[.]81 – IP - AsyncRAT C2 Endpoint

·      191.96.207[.]246 – IP – Likely AsyncRAT C2 Endpoint

·     CN=AsyncRAT Server - SSL certificate - AsyncRATC2 Infrastructure

·      Kashuub[.]com– Hostname – Likely AsyncRAT C2 Endpoint

MITRE ATT&CK Mapping:

Tactic –Technique – Sub-Technique  

 

Execution– T1053 - Scheduled Task/Job: Scheduled Task

DefenceEvasion – T1497 - Virtualization/Sandbox Evasion: System Checks

Discovery– T1057 – Process Discovery

Discovery– T1082 – System Information Discovery

LateralMovement - T1021.001 - Remote Services: Remote Desktop Protocol

Collection/ Credential Access – T1056 – Input Capture: Keylogging

Collection– T1125 – Video Capture

Commandand Control – T1105 - Ingress Tool Transfer

Commandand Control – T1219 - Remote Access Software

Exfiltration– T1041 - Exfiltration Over C2 Channel

 

References

[1]  https://blog.talosintelligence.com/operation-layover-how-we-tracked-attack/

[2] https://intel471.com/blog/china-cybercrime-undergrond-deepmix-tea-horse-road-great-firewall

[3] https://www.attackiq.com/2024/08/01/emulate-asyncrat/

[4] https://www.fortinet.com/blog/threat-research/spear-phishing-campaign-with-new-techniques-aimed-at-aviation-companies

[5] https://www.virustotal.com/gui/ip-address/185.49.126[.]50/community

[6] https://dfir.ch/posts/asyncrat_quasarrat/

[7] https://www.virustotal.com/gui/ip-address/195.26.255[.]81

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

[9] https://www.esentire.com/blog/exploring-the-infection-chain-screenconnects-link-to-asyncrat-deployment

[10] https://scammer.info/t/taking-out-connectwise-sites/153479/518?page=26

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About the author
Isabel Evans
Cyber Analyst

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May 13, 2025

Revolutionizing OT Risk Prioritization with Darktrace 6.3

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Powering smarter protection for industrial systems

In industrial environments, security challenges are deeply operational. Whether you’re running a manufacturing line, a power grid, or a semiconductor fabrication facility (fab), you need to know: What risks can truly disrupt my operations, and what should I focus on first?

Teams need the right tools to shift from reactive defense, constantly putting out fires, to proactively thinking about their security posture. However, most OT teams are stuck using IT-centric tools that don’t speak the language of industrial systems, are consistently overwhelmed with static CVE lists, and offer no understanding of OT-specific protocols. The result? Compliance gaps, siloed insights, and risk models that don’t reflect real-world exposure, making risk prioritization seem like a luxury.

Darktrace / OT 6.3 was built in direct response to these challenges. Developed in close collaboration with OT operators and engineers, this release introduces powerful upgrades that deliver the context, visibility, and automation security teams need, without adding complexity. It’s everything OT defenders need to protect critical operations in one platform that understands the language of industrial systems.

additions to darktrace / ot 6/3

Contextual risk modeling with smarter Risk Scoring

Darktrace / OT 6.3 introduces major upgrades to OT Risk Management, helping teams move beyond generic CVE lists with AI-driven risk scoring and attack path modeling.

By factoring in real-world exploitability, asset criticality, and operational context, this release delivers a more accurate view of what truly puts critical systems at risk.

The platform now integrates:

  • CISA’s Known Exploited Vulnerabilities (KEV) database
  • End-of-life status for legacy OT devices
  • Firewall misconfiguration analysis
  • Incident response plan alignment

Most OT environments are flooded with vulnerability data that lacks context. CVE scores often misrepresent risk by ignoring how threats move through the environment or whether assets are even reachable. Firewalls are frequently misconfigured or undocumented, and EOL (End of Life) devices, some of the most vulnerable, often go untracked.

Legacy tools treat these inputs in isolation. Darktrace unifies them, showing teams exactly which attack paths adversaries could exploit, mapped to the MITRE ATT&CK framework, with visibility into where legacy tech increases exposure.

The result: teams can finally focus on the risks that matter most to uptime, safety, and resilience without wasting resources on noise.

Automating compliance with dynamic IEC-62443 reporting

Darktrace / OT now includes a purpose-built IEC-62443-3-3 compliance module, giving industrial teams real-time visibility into their alignment with regulatory standards. No spreadsheets required!

Industrial environments are among the most heavily regulated. However, for many OT teams, staying compliant is still a manual, time-consuming process.

Darktrace / OT introduces a dedicated IEC-62443-3-3 module designed specifically for industrial environments. Security and operations teams can now map their security posture to IEC standards in real time, directly within the platform. The module automatically gathers evidence across all four security levels, flags non-compliance, and generates structured reports to support audit preparation, all in just a few clicks.Most organizations rely on spreadsheets or static tools to track compliance, without clear visibility into which controls meet standards like IEC-62443. The result is hidden gaps, resource-heavy audits, and slow remediation cycles.

Even dedicated compliance tools are often built for IT, require complex setup, and overlook the unique devices found in OT environments. This leaves teams stuck with fragmented reporting and limited assurance that their controls are actually aligned with regulatory expectations.

By automating compliance tracking, surfacing what matters most, and being purpose built for industrial environments, Darktrace / OT empowers organizations to reduce audit fatigue, eliminate blind spots, and focus resources where they’re needed most.

Expanding protocol visibility with deep insights for specialized OT operations

Darktrace has expanded its Deep Packet Inspection (DPI) capabilities to support five industry-specific protocols, across healthcare, semiconductor manufacturing, and ABB control systems.

The new protocols build on existing capabilities across all OT industry verticals and protocol types to ensure the Darktrace Self-Learning AI TM can learn intelligently about even more assets in complex industrial environments. By enabling native, AI-driven inspection of these protocols, Darktrace can identify both security threats and operational issues without relying on additional appliances or complex integrations.

Most security platforms lack native support for industry-specific protocols, creating critical visibility gaps in customer environments like healthcare, semiconductor manufacturing, and ABB-heavy industrial automation. Without deep protocol awareness, organizations struggle to accurately identify specialized OT and IoT assets, detect malicious activity concealed within proprietary protocol traffic, and generate reliable device risk profiles due to insufficient telemetry.

These blind spots result in incomplete asset inventories, and ultimately, flawed risk posture assessments which over-index for CVE patching and legacy equipment.

By combining protocol-aware detection with full-stack visibility across IT, OT, and IoT, Darktrace’s AI can correlate anomalies across domains. For example, connecting an anomaly from a Medical IoT (MIoT) device with suspicious behavior in IT systems, providing actionable, contextual insights other solutions often miss.

Conclusion

Together, these capabilities take OT security beyond alert noise and basic CVE matching, delivering continuous compliance, protocol-aware visibility, and actionable, prioritized risk insights, all inside a single, unified platform built for the realities of industrial environments.

[related-resource]

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About the author
Pallavi Singh
Product Marketing Manager, OT Security & Compliance
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