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February 13, 2025

Why Darktrace / EMAIL Excels Against APTs

APTs are sophisticated threat actors with the resources to coordinate and achieve long-term objectives. Amidst the skyrocketing numbers of BEC attacks, every organization should be worried about the ability of intruders to infiltrate and exploit. This blog will look at several recent examples of complex email attacks and how Darktrace / EMAIL successfully disarmed and prevented intrusion.
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
Carlos Gray
Senior Product Marketing Manager, Email
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13
Feb 2025

What are APTs?

An Advanced Persistent Threat (APT) describes an adversary with sophisticated levels of expertise and significant resources, with the ability to carry out targeted cyber campaigns. These campaigns may penetrate an organization and remain undetected for long periods, allowing attackers to gather intelligence or cause damage over time.

Over the last few decades, the term APT has evolved from being almost exclusively associated with nation-state actors to a broader definition that includes highly skilled, well-resourced threat groups. While still distinct from mass, opportunistic cybercrime or "spray and pray" attacks, APT now refers to the elite tier of adversaries, whether state-sponsored or not, who demonstrate advanced capabilities, persistence, and a clear strategic focus. This shift reflects the growing sophistication of cyber threats, where non-state actors can now rival nation-states in executing covert, methodical intrusions to achieve long-term objectives.

These attacks are resource-intensive for threat actors to execute, but the potential rewards—ranging from financial gain to sensitive data theft—can be significant. In 2020, Business Email Compromise (BEC) attacks netted cybercriminals over $1.8 billion.1

And recently, the advent of AI has helped to automate launching these attacks, lowering the barriers to entry and making it more efficient to orchestrate the kind of attack that might previously have taken weeks to create. Research shows that AI can do 90% of a threat actor’s work2 – reducing time-to-target by automating tasks rapidly and avoiding errors in phishing communications. Email remains the most popular vector for initiating these sophisticated attacks, making it a critical battleground for cyber defense.

What makes APTs so successful?

The success of Advanced Persistent Threats (APTs) lies in their precision, persistence, and ability to exploit human and technical vulnerabilities. These attacks are carefully tailored to specific targets, using techniques like social engineering and spear phishing to gain initial access.

Once inside, attackers move laterally through networks, often remaining undetected for months or even years, silently gathering intelligence or preparing for a decisive strike. Alternatively, they might linger inside an account within the M365 environment, which could be even more valuable in terms of gathering information – in 2023 the average time to identify a breach in 2023 was 204 days.3

The subtle and long-term outlook nature of APTs makes them highly effective, as traditional security measures often fail to identify the subtle signs of compromise.

How Darktrace’s approach is designed to catch the most advanced threats

Luckily for our customers, Darktrace’s AI approach is uniquely equipped to detect and neutralize APTs. Unlike the majority of email security solutions that rely on static rules and signatures, or that train their AI on previous known-bad attack patterns, Darktrace leverages Self-Learning AI that baselines normal patterns of behavior within an organization, to immediately detect unusual activity that may signal an APT in progress.  

But in the modern era of email threats, no email security solution can guarantee 100% effectiveness. Because attackers operate with great sophistication, carefully adapting their tactics to evade detection – whether by altering attachments, leveraging compromised accounts, or moving laterally across an organization – a siloed security approach risks missing these subtle, multi-domain threats. That’s why a robust defense-in-depth strategy is essential to mitigate APTs.

Real-world threat finds: Darktrace / EMAIL in action

Let’s take a look at some real-world scenarios where Darktrace / EMAIL stopped tactics associated with APT campaigns in their tracks – from adversary-in-the-middle attacks to suspicious lateral movement.

1: How Darktrace disrupted an adversary-in-the-middle attack by identifying abnormal login redirects and blocking credential exfiltration

In October 2024, Darktrace detected an adversary-in-the-middle (AiTM) attack targeting a Darktrace customer. The attack began with a phishing email from a seemingly legitimate Dropbox address, which contained multiple link payloads inviting the recipient to access a file. Other solutions would have struggled to catch this attack, as the initial AitM attack was launched through delivering a malicious URL through a trusted vendor or service. Once compromised, the threat actor could have laid low on the target account, gathering reconnaissance, without detection from the email security solution.  

Darktrace / EMAIL identified the abnormal login redirects and flagged the suspicious activity. Darktrace / IDENTITY then detected unusual login patterns and blocked credential exfiltration attempts, effectively disrupting the attack and preventing the adversary from gaining unauthorized access. Read more.

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

2: How Darktrace stopped lateral movement to block NTLM hash theft

In early 2024, Darktrace detected an attack by the TA577 threat group, which aimed to steal NTLM hashes to gain unauthorized access to systems. The attack began with phishing emails containing ZIP files that connected to malicious infrastructure.  

A traditional email security solution would have likely missed this attack by focusing too heavily on analyzing the zip file payloads or relying on reputation analysis to understand whether the infrastructure was registered as bad before this activity was a recognized IoC.

Because it correlates activity across domains, Darktrace identified unusual lateral movement within the network and promptly blocked the attempts to steal NTLM hashes, effectively preventing the attackers from accessing sensitive credentials and securing the network. Read more.

Figure 2: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace / EMAIL

3: How Darktrace prevented the WarmCookie backdoor deployment embedded in phishing emails

In mid-2024, Darktrace identified a phishing campaign targeting organizations with emails impersonating recruitment firms. These emails contained malicious links that, when clicked, deployed the WarmCookie backdoor.  

These emails are difficult to detect, as they use social engineering tactics to manipulate users into engaging with emails and following the embedded malicious links – but if a security solution is not analysing content and context, these could be allowed through.

In several observed cases across customer environments, Darktrace detected and blocked the suspicious behavior associated with WarmCookie that had already managed to evade customers’ native email security. By using behavioral analysis to correlate anomalous activity across the digital estate, Darktrace was able to identify the backdoor malware strain and notify customers. Read more.

Conclusion

These threat examples highlight a key principle of the Darktrace approach – that a backwards-facing approach grounded in threat intelligence will always be one step behind.

Most threat actors operate in campaigns, carefully crafting attacks and testing them across multiple targets. Once a campaign is identified, good defenders and traditional security solutions quickly update their defenses with new threat intelligence, rules, and signatures. However, APTs have the resources to rapidly adapt – spinning up new infrastructure, modifying payloads and altering their attack footprint to evade detection.

This is where Darktrace / EMAIL excels. Only by analyzing each user, message and interaction can an email security solution hope to catch the types of highly-sophisticated attacks that have the potential to cause major reputational and financial damage. Darktrace / EMAIL ensures that even the most subtle threats are detected and blocked with autonomous response, before causing impact – helping organizations remain one step ahead of increasingly adaptive threat actors.

Download the Darktrace / EMAIL Solution Brief

Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.

  • Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
  • Experience 20-25% more threat blocking power with Darktrace / EMAIL
  • Stop the 58% of threats bypassing traditional email security

References

[1] FBI Internet Crime Report 2020

[2] https://www.optiv.com/insights/discover/blog/future-security-automation-how-ai-machine-learning-and-automation-are

[3] IBM Cost of a Data Breach Report 2023

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
Carlos Gray
Senior Product Marketing Manager, Email

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September 30, 2025

Out of Character: Detecting Vendor Compromise and Trusted Relationship Abuse with Darktrace

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What is Vendor Email Compromise?

Vendor Email Compromise (VEC) refers to an attack where actors breach a third-party provider to exploit their access, relationships, or systems for malicious purposes. The initially compromised entities are often the target’s existing partners, though this can extend to any organization or individual the target is likely to trust.

It sits at the intersection of supply chain attacks and business email compromise (BEC), blending technical exploitation with trust-based deception. Attackers often infiltrate existing conversations, leveraging AI to mimic tone and avoid common spelling and grammar pitfalls. Malicious content is typically hosted on otherwise reputable file sharing platforms, meaning any shared links initially seem harmless.

While techniques to achieve initial access may have evolved, the goals remain familiar. Threat actors harvest credentials, launch subsequent phishing campaigns, attempt to redirect invoice payments for financial gain, and exfiltrate sensitive corporate data.

Why traditional defenses fall short

These subtle and sophisticated email attacks pose unique challenges for defenders. Few busy people would treat an ongoing conversation with a trusted contact with the same level of suspicion as an email from the CEO requesting ‘URGENT ASSISTANCE!’ Unfortunately, many traditional secure email gateways (SEGs) struggle with this too. Detecting an out-of-character email, when it does not obviously appear out of character, is a complex challenge. It’s hardly surprising, then, that 83% of organizations have experienced a security incident involving third-party vendors [1].  

This article explores how Darktrace detected four different vendor compromise campaigns for a single customer, within a two-week period in 2025.  Darktrace / EMAIL successfully identified the subtle indicators that these seemingly benign emails from trusted senders were, in fact, malicious. Due to the configuration of Darktrace / EMAIL in this customer’s environment, it was unable to take action against the malicious emails. However, if fully enabled to take Autonomous Response, it would have held all offending emails identified.

How does Darktrace detect vendor compromise?

The answer lies at the core of how Darktrace operates: anomaly detection. Rather than relying on known malicious rules or signatures, Darktrace learns what ‘normal’ looks like for an environment, then looks for anomalies across a wide range of metrics. Despite the resourcefulness of the threat actors involved in this case, Darktrace identified many anomalies across these campaigns.

Different campaigns, common traits

A wide variety of approaches was observed. Individuals, shared mailboxes and external contractors were all targeted. Two emails originated from compromised current vendors, while two came from unknown compromised organizations - one in an associated industry. The sender organizations were either familiar or, at the very least, professional in appearance, with no unusual alphanumeric strings or suspicious top-level domains (TLDs). Subject line, such as “New Approved Statement From [REDACTED]” and “[REDACTED] - Proposal Document” appeared unremarkable and were not designed to provoke heightened emotions like typical social engineering or BEC attempts.

All emails had been given a Microsoft Spam Confidence Level of 1, indicating Microsoft did not consider them to be spam or malicious [2]. They also passed authentication checks (including SPF, and in some cases DKIM and DMARC), meaning they appeared to originate from an authentic source for the sender domain and had not been tampered with in transit.  

All observed phishing emails contained a link hosted on a legitimate and commonly used file-sharing site. These sites were often convincingly themed, frequently featuring the name of a trusted vendor either on the page or within the URL, to appear authentic and avoid raising suspicion. However, these links served only as the initial step in a more complex, multi-stage phishing process.

A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Figure 1: A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.
Figure 2: Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.

If followed, the recipient would be redirected, sometimes via CAPTCHA, to fake Microsoft login pages designed to capturing credentials, namely http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html and https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html#.

The latter made use of homoglyphs to deceive the user, with a link referencing ‘s3cure0line’, rather than ‘secureonline’. Post-incident investigation using open-source intelligence (OSINT) confirmed that the domains were linked to malicious phishing endpoints [3] [4].

Fake Microsoft login page designed to harvest credentials.
Figure 3: Fake Microsoft login page designed to harvest credentials.
Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.
Figure 4: Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.

Darktrace Anomaly Detection

Some senders were unknown to the network, with no previous outbound or inbound emails. Some had sent the email to multiple undisclosed recipients using BCC, an unusual behavior for a new sender.  

Where the sender organization was an existing vendor, Darktrace recognized out-of-character behavior, in this case it was the first time a link to a particular file-sharing site had been shared. Often the links themselves exhibited anomalies, either being unusually prominent or hidden altogether - masked by text or a clickable image.

Crucially, Darktrace / EMAIL is able to identify malicious links at the time of processing the emails, without needing to visit the URLs or analyze the destination endpoints, meaning even the most convincing phishing pages cannot evade detection – meaning even the most convincing phishing emails cannot evade detection. This sets it apart from many competitors who rely on crawling the endpoints present in emails. This, among other things, risks disruption to user experience, such as unsubscribing them from emails, for instance.

Darktrace was also able to determine that the malicious emails originated from a compromised mailbox, using a series of behavioral and contextual metrics to make the identification. Upon analysis of the emails, Darktrace autonomously assigned several contextual tags to highlight their concerning elements, indicating that the messages contained phishing links, were likely sent from a compromised account, and originated from a known correspondent exhibiting out-of-character behavior.

A summary of the anomalous email, confirming that it contained a highly suspicious link.
Figure 5: Tags assigned to offending emails by Darktrace / EMAIL.

Figure 6: A summary of the anomalous email, confirming that it contained a highly suspicious link.

Out-of-character behavior caught in real-time

In another customer environment around the same time Darktrace / EMAIL detected multiple emails with carefully crafted, contextually appropriate subject lines sent from an established correspondent being sent to 30 different recipients. In many cases, the attacker hijacked existing threads and inserted their malicious emails into an ongoing conversation in an effort to blend in and avoid detection. As in the previous, the attacker leveraged a well-known service, this time ClickFunnels, to host a document containing another malicious link. Once again, they were assigned a Microsoft Spam Confidence Level of 1, indicating that they were not considered malicious.

The legitimate ClickFunnels page used to host a malicious phishing link.
Figure 7: The legitimate ClickFunnels page used to host a malicious phishing link.

This time, however, the customer had Darktrace / EMAIL fully enabled to take Autonomous Response against suspicious emails. As a result, when Darktrace detected the out-of-character behavior, specifically, the sharing of a link to a previously unused file-sharing domain, and identified the likely malicious intent of the message, it held the email, preventing it from reaching recipients’ inboxes and effectively shutting down the attack.

Figure 8: Darktrace / EMAIL’s detection of malicious emails inserted into an existing thread.*

*To preserve anonymity, all real customer names, email addresses, and other identifying details have been redacted and replaced with fictitious placeholders.

Legitimate messages in the conversation were assigned an Anomaly Score of 0, while the newly inserted malicious emails identified and were flagged with the maximum score of 100.

Key takeaways for defenders

Phishing remains big business, and as the landscape evolves, today’s campaigns often look very different from earlier versions. As with network-based attacks, threat actors are increasingly leveraging legitimate tools and exploiting trusted relationships to carry out their malicious goals, often staying under the radar of security teams and traditional email defenses.

As attackers continue to exploit trusted relationships between organizations and their third-party associates, security teams must remain vigilant to unexpected or suspicious email activity. Protecting the digital estate requires an email solution capable of identifying malicious characteristics, even when they originate from otherwise trusted senders.

Credit to Jennifer Beckett (Cyber Analyst), Patrick Anjos (Senior Cyber Analyst), Ryan Traill (Analyst Content Lead), Kiri Addison (Director of Product)

Appendices

IoC - Type - Description + Confidence  

- http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html#p – fake Microsoft login page

- https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html# - link to domain used in homoglyph attack

MITRE ATT&CK Mapping  

Tactic – Technique – Sub-Technique  

Initial Access - Phishing – (T1566)  

References

1.     https://gitnux.org/third-party-risk-statistics/

2.     https://learn.microsoft.com/en-us/defender-office-365/anti-spam-spam-confidence-level-scl-about

3.     https://www.virustotal.com/gui/url/5df9aae8f78445a590f674d7b64c69630c1473c294ce5337d73732c03ab7fca2/detection

4.     https://www.virustotal.com/gui/url/695d0d173d1bd4755eb79952704e3f2f2b87d1a08e2ec660b98a4cc65f6b2577/details

The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.

Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.

Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.

The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content

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October 1, 2025

Announcing Unified OT Security with Dedicated OT Workflows, Segmentation-Aware Risk Insights, and Next-Gen Endpoint Visibility for Industrial Teams

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The challenge of convergence without clarity

Convergence is no longer a roadmap idea, it is the daily reality for industrial security teams. As Information Technology (IT) and Operational Technology (OT) environments merge, the line between a cyber incident and an operational disruption grows increasingly hard to define. A misconfigured firewall rule can lead to downtime. A protocol misuse might look like a glitch. And when a pump stalls but nothing appears in the Security Operations Center (SOC) dashboard, teams are left asking: is this operational or is this a threat?

The lack of shared context slows down response, creates friction between SOC analysts and plant engineers, and leaves organizations vulnerable at exactly the points where IT and OT converge. Defenders need more than alerts, they need clarity that both sides can trust.

The breakthrough with Darktrace / OT

This latest Darktrace / OT release was built to deliver exactly that. It introduces shared context between Security, IT, and OT operations, helping reduce friction and close the security gaps at the intersection of these domains.

With a dedicated dashboard built for operations teams, extended visibility into endpoints for new forms of detection and CVE collection, expanded protocol coverage, and smarter risk modeling aligned to segmentation policies, teams can now operate from a shared source of truth. These enhancements are not just incremental upgrades, they are foundational improvements designed to bring clarity, efficiency, and trust to converged environments.

A dashboard built for OT engineers

The new Operational Overview provides OT engineers with a workspace designed for them, not for SOC analysts. It brings asset management, risk insights and operational alerts into one place. Engineers can now see activity like firmware changes, controller reprograms or the sudden appearance of a new workstation on the network, providing a tailored view for critical insights and productivity gains without navigating IT-centric workflows. Each device view is now enriched with cross-linked intelligence, make, model, firmware version and the roles inferred by Self-Learning AI, making it easier to understand how each asset behaves, what function it serves, and where it fits within the broader industrial process. By suppressing IT-centric noise, the dashboard highlights only the anomalies that matter to operations, accelerating triage, enabling smoother IT/OT collaboration, and reducing time to root cause without jumping between tools.

This is usability with purpose, a view that matches OT workflows and accelerates response.

Figure 1: The Operational Overview provides an intuitive dashboard summarizing all OT Assets, Alerts, and Risk.

Full-spectrum coverage across endpoints, sensors and protocols

The release also extends visibility into areas that have traditionally been blind spots. Engineering workstations, Human-Machine Interfaces (HMIs), contractor laptops and field devices are often the entry points for attackers, yet the hardest to monitor.

Darktrace introduces Network Endpoint eXtended Telemetry (NEXT) for OT, a lightweight collector built for segmented and resource-constrained environments. NEXT for OT uses Endpoint sensors to capture localized network, and now process-level telemetry, placing it in context alongside other network and asset data to:

  1. Identify vulnerabilities and OS data, which is leveraged by OT Risk Management for risk scoring and patching prioritization, removing the need for third-party CVE collection.
  1. Surface novel threats using Self-Learning AI that standalone Endpoint Detection and Response (EDR) would miss.
  1. Extend Cyber AI Analyst investigations through to the endpoint root cause.

NEXT is part of our existing cSensor endpoint agent, can be deployed standalone or alongside existing EDR tools, and allows capabilities to be enabled or disabled depending on factors such as security or OT team objectives and resource utilization.

Figure 2: Darktrace / OT delivers CVE patch priority insights by combining threat intelligence with extended network and endpoint telemetry

The family of Darktrace Endpoint sensors also receive a boost in deployment flexibility, with on-prem server-based setups, as well as a Windows driver tailored for zero-trust and high-security environments.

Protocol coverage has been extended where it matters most. Darktrace now performs protocol analysis of a wider range of GE and Mitsubishi protocols, giving operators real-time visibility into commands and state changes on Programmable Logic Controllers (PLCs), robots and controllers. Backed by Self-Learning AI, this inspection does more than parse traffic, it understands what normal looks like and flags deviations that signal risk.

Integrated risk and governance workflows

Security data is only valuable when it drives action. Darktrace / OT delivers risk insights that go beyond patching, helping teams take meaningful steps even when remediation isn't possible. Risk is assessed not just by CVE presence, but by how network segmentation, firewall policies, and attack path logic neutralize or contain real-world exposure. This approach empowers defenders to deprioritize low-impact vulnerabilities and focus effort where risk truly exists. Building on the foundation introduced in release 6.3, such as KEV enrichment, endpoint OS data, and exploit mapping, this release introduces new integrations that bring Darktrace / OT intelligence directly into governance workflows.

Fortinet FortiGate firewall ingestion feeds segmentation rules into attack path modeling, revealing real exposure when policies fail and closing feeds into patching prioritization based on a policy to CVE exposure assessment.

  • ServiceNow Configuration Management Database (CMDB) sync ensures asset intelligence stays current across governance platforms, eliminating manual inventory work.

Risk modeling has also been made more operationally relevant. Scores are now contextualized by exploitability, asset criticality, firewall policy, and segmentation posture. Patch recommendations are modeled in terms of safety, uptime and compliance rather than just Common Vulnerability Scoring System (CVSS) numbers. And importantly, risk is prioritized across the Purdue Model, giving defenders visibility into whether vulnerabilities remain isolated to IT or extend into OT-critical layers.

Figure 3: Attack Path Modeling based on NetFlow and network topology reveals high risk points of IT/OT convergence.

The real-world impact for defenders

In today’s environments, attackers move fluidly between IT and OT. Without unified visibility and shared context, incidents cascade faster than teams can respond.

With this release, Darktrace / OT changes that reality. The Operational Overview gives Engineers a dashboard they can use daily, tailored to their workflows. SOC analysts can seamlessly investigate telemetry across endpoints, sensors and protocols that were once blind spots. Operators gain transparency into PLCs and controllers. Governance teams benefit from automated integrations with platforms like Fortinet and ServiceNow. And all stakeholders work from risk models that reflect what truly matters: safety, uptime and compliance.

This release is not about creating more alerts. It is about providing more clarity. By unifying context across IT and OT, Darktrace / OT enables defenders to see more, understand more and act faster.

Because in environments where safety and uptime are non-negotiable, clarity is what matters most.

Join us for our live event where we will discuss these product innovations in greater detail

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