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February 21, 2020

Lessons Learned from a Sodinokibi Ransomware Attack

Gain insights into a targeted Sodinokibi ransomware attack and learn how to better prepare your organization for potential cyber threats.
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
Max Heinemeyer
Global Field CISO
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21
Feb 2020

Introduction

Last week, Darktrace detected a targeted Sodinokibi ransomware attack during a 4-week trial with a mid-sized company.

This blog post will go through every stage of the attack lifecycle and detail the attacker’s techniques, tools and procedures used, and how Darktrace detected the attack.

The Sodinokibi group is an innovative threat-actor that is sometimes referred to as a ‘double-threat’, due to their ability to run targeted attacks using ransomware while simultaneously exfiltrating their victim’s data. This enables them to threaten to make the victim’s data publicly available if the ransom is not paid.

While Darktrace’s AI was able to identify the attack in real time as it was emerging, unfortunately the security team didn’t have eyes on the technology and was unable to action the alerts — nor was Antigena set in active mode, which would have slowed down and contained the threat instantaneously.

Timeline

The timeline below provides a rough overview of the major attack phases. Most of the attack took place over the course of a week, with the majority of activity distributed over the last three days.

Technical analysis

Darktrace detected two main devices being hit by the attack: an internet-facing RDP server (‘RDP server’) and a Domain Controller (‘DC’), that also acts as a SMB file server.

In previous attacks, Sodinokibi has used host-level encryption for ransomware activity where the encryption takes place on the compromised host itself — in contrast to network-level encryption where the bulk of the ransomware activity takes place over network protocols such as SMB.

Initial compromise

Over several days, the victim’s external-facing RDP server was receiving successful RDP connections from a rare external IP address located in Ukraine.

Shortly before the initial reconnaissance started, Darktrace saw another RDP connection coming into the RDP server with the same RDP account as seen before. This connection lasted for almost an hour.

It is highly likely that the RDP credential used in this attack had been compromised prior to the attack, either via common brute-force methods, credential stuffing attacks, or phishing.

Thanks to Darktrace’s Deep-Packet Inspection, we can clearly see the connection and all related information.

Suspicious RDP connection information:

Time: 2020-02-10 16:57:06 UTC
Source: 46.150.70[.]86 (Ukraine)
Destination: 192.168.X.X
Destination Port: 64347
Protocol: RDP
Cookie: [REDACTED]
Duration: 00h41m40s
Data out: 8.44 MB
Data in: 1.86 MB

Darktrace detects incoming RDP connections from IP addresses that usually do not connect to the organization.

Attack tools download

Approximately 45 minutes after the suspicious RDP connection from Ukraine, the RDP server connected to the popular file sharing platform, Megaupload, and downloaded close to 300MB from there.

Darktrace’s AI recognized that neither this server, nor its automatically detected peer group, nor, in fact, anyone else on the network commonly utilized Megaupload — and therefore instantly detected this as anomalous behavior, and flagged it as unusual.

As well as the full hostname and actual IP used for the download, Megaupload is 100% rare for this organization.

Later on, we will see over 40GB being uploaded to Megaupload. This initial download of 300MB however is likely additional tooling and C2 implants downloaded by the threat-actor into the victim’s environment.

Internal reconnaissance

Only 3 minutes after the download from Megaupload onto the RDP server, Darktrace alerted on the RDP server doing an anomalous network scan:

The RDP server scanned 9 other internal devices on the same subnet on 7 unique ports: 21, 80, 139, 445, 3389, 4899, 8080
 . Anybody with some offensive security know-how will recognize most of these ports as default ports one would scan for in a Windows environment for lateral movement. Since this RDP server does not usually conduct network scans, Darktrace again identified this activity as highly anomalous.

Later on, we see the threat-actor do more network scanning. They become bolder and use more generic scans — one of them showing that they are using Nmap with a default user agent:

Additional Command and Control traffic

While the initial Command and Control traffic was most likely using predominantly RDP, the threat-actor now wanted to establish more persistence and create more resilient channels for C2.

Shortly after concluding the initial network scans (ca. 19:17 on 10th February 2020), the RDP server starts communicating with unusual external services that are unique and unusual for the victim’s environment.

Communications to Reddcoin

Again, nobody else is using Reddcoin on the network. The combination of application protocol and external port is extremely unusual for the network as well.

The communications also went to the Reddcoin API, indicating the installation of a software agent rather than manual communications. This was detected as Reddcoin was not only rare for the network, but also ‘young’ — i.e. this particular external destination had never been seen to be contacted before on the network until 25 minutes before.

Communications to the Reddcoin API

Communications to Exceptionless[.]io

As we can see, the communications to exceptionalness[.]io were done in a beaconing manner, using a Let’s Encrypt certificate, being rare for the network and using an unusual JA3 client hash. All of this indicates the presence of new software on the device, shortly after the threat-actor downloaded their 300MB of tooling.

While most of the above network activity started directly after the threat-actor dropped their tooling on the RDP server, the exact purpose of interfacing with Reddcoin and Exceptionless is unclear. The attacker seems to favor off-the-shelf tooling (Megaupload, Nmap, …) so they might use these services for C2 or telemetry-gathering purposes.

This concluded most of the activity on February 10.

More Command and Control traffic

Why would an attacker do this? Surely using all this C2 at the same time is much noisier than just using 1 or 2 channels?

Another significant burst of activity was observed on February 12 and 13.

The RDP server started making a lot of highly anomalous and rare connections to external destinations. It is inconclusive if all of the below services, IPs, and domains were used for C2 purposes only, but they are linked with high-confidence to the attacker’s activities:

  • HTTP beaconing to vkmuz[.]net
  • Significant amount of Tor usage
  • RDP connections to 198-0-244-153-static.hfc.comcastbusiness[.]net over non-standard RDP port 29348
  • RDP connections to 92.119.160[.]60 using an administrative account (geo-located in Russia)
  • Continued connections to Megaupload
  • Continued SSL beaconing to Exceptionless[.]io
  • Continued connections to api.reddcoin[.]com
  • SSL beaconing to freevpn[.]zone
  • HTTP beaconing to 31.41.116[.]201 to /index.php using a new User Agent
  • Unusual SSL connections to aj1713[.]online
  • Connections to Pastebin
  • SSL beaconing to www.itjx3no[.]com using an unusual JA3 client hash
  • SSL beaconing to safe-proxy[.]com
  • SSL connection to westchange[.]top without prior DNS hostname lookups (likely machine-driven)

What is significant here is the diversity in (potential) C2 channels: Tor, RDP going to dynamic ISP addresses, VPN solutions and possibly custom / customized off-the-shelf implants (the DGA-looking domains and HTTP to IP addresses to /index.php).

Why would an attacker do this? Surely using all this C2 at the same time is much noisier than just using 1 or 2 channels?

One answer might be that the attacker cared much more about short-term resilience than about stealth. As the overall attack in the network took less than 7 days, with a majority of the activity taking place over 2.5 days, this makes sense. Another possibility might be that various individuals were involved in parallel during this attack — maybe one attacker prefers the comfort of RDP sessions for hacking while another is more skilled and uses a particular post-exploitation framework.

The overall modus operandi in this financially-motivated attack is much more smash-and-grab than in the stealthy, espionage-related incidents observed in Advanced Persistent Threat campaigns (APT).

Data exfiltration

The DC uploaded around 40GB of data to Megaupload over the course of 24 hours.

While all of the above activity was seen on the RDP server (acting as the initial beach-head), the following data exfiltration activity was observed on a Domain Controller (DC) on the same subnet as the RDP server.

The DC uploaded around 40GB of data to Megaupload over the course of 24 hours.

Darktrace detected this data exfiltration while it was in progress — never did the DC (or any similar devices) upload similar amounts of data to the internet. Neither did any client nor server in the victim’s environment use Megaupload:

Ransom notes

Finally, Darktrace observed unusual files being accessed on internal SMB shares on February 13. These files appear to be ransom notes — they follow a similar, randomly-generated naming convention as other victims of the Sodinokibi group have reported:

413x0h8l-readme.txt
4omxa93-readme.txt

Conclusion and observations

The threat-actor seems to be using mostly off-the-shelf tooling which makes attribution harder — while also making detection more difficult.

This attack is representative of many of the current ransomware attacks: financially motivated, fast-acting, and targeted.

The threat-actor seems to be using mostly off-the-shelf tooling (RDP, Nmap, Mega, VPN solutions) which makes attribution harder — while also making detection more difficult. Using this kind of tooling often allows to blend in with regular admin activity — only once anomaly detection is used can this kind of activity be detected.

How can you spot the one anomalous outbound RDP connection amongst the thousands of regular RDP connections leaving your environment? How do you know when the use of Megaupload is malicious — compared to your users’ normal use of it? This is where the power of Darktrace’s self-learning AI comes into play.

Darktrace detected every stage of the visible attack lifecycle without using any threat intelligence or any static signatures.

The graphics below show an overview of detections on both compromised devices. The compromised devices were the highest-scoring assets for the network — even a level 1 analyst with limited previous exposure to Darktrace could detect such an in-progress attack in real time.

RDP Server

Some of the detections on the RDP server include:

  • Compliance / File Storage / Mega — using Megaupload in an unusual way
  • Device / Network Scan — detecting unusual network scans
  • Anomalous Connection / Application Protocol on Uncommon Port — detecting the use of protocols on unusual ports
  • Device / New Failed External Connections — detecting unusual failing C2
  • Compromise / Unusual Connections to Let’s Encrypt — detecting potential C2 over SSL using Let’s Encrypt
  • Compromise / Beacon to Young Endpoint — detecting C2 to new external endpoints for the network
  • Device / Attack and Recon Tools — detecting known offensive security tools like Nmap
  • Compromise / Tor Usage — detecting unusual Tor usage
  • Compromise / SSL Beaconing to Rare Destination — detecting generic SSL C2
  • Compromise / HTTP Beaconing to Rare Destination — detecting generic HTTP C2
  • Device / Long Agent Connection to New Endpoint — detecting unusual services on a device
  • Anomalous Connection / Outbound RDP to Unusual Port — detecting unusual RDP C2

DC

Some of the detections on the DC include:

  • Anomalous Activity / Anomalous External Activity from Critical Device — detecting unusual behaviour on dcs
  • Compliance / File storage / Mega — using Megaupload in an unusual way
  • Anomalous Connection / Data Sent to New External Device — data exfiltration to unusual locations
  • Anomalous Connection / Uncommon 1GB Outbound — large amounts of data leaving to unusual destinations
  • Anomalous Server Activity / Outgoing from Server — likely C2 to unusual endpoint on the internet


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
Max Heinemeyer
Global Field CISO

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

microsoft darktrace integrationDefault blog imageDefault blog image

AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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