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July 18, 2023

Understanding Email Security & the Psychology of Trust

We explore how psychological research into the nature of trust relates to our relationship with technology - and what that means for AI solutions.
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
Hanah Darley
Director of Threat Research
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18
Jul 2023

When security teams discuss the possibility of phishing attacks targeting their organization, often the first reaction is to assume it is inevitable because of the users. Users are typically referenced in cyber security conversations as organizations’ greatest weaknesses, cited as the causes of many grave cyber-attacks because they click links, open attachments, or allow multi-factor authentication bypass without verifying the purpose.

While for many, the weakness of the user may feel like a fact rather than a theory, there is significant evidence to suggest that users are psychologically incapable of protecting themselves from exploitation by phishing attacks, with or without regular cyber awareness trainings. The psychology of trust and the nature of human reliance on technology make the preparation of users for the exploitation of that trust in technology very difficult – if not impossible.

This Darktrace long read will highlight principles of psychological and sociological research regarding the nature of trust, elements of the trust that relate to technology, and how the human brain is wired to rely on implicit trust. These principles all point to the outcome that humans cannot be relied upon to identify phishing. Email security driven by machine augmentation, such as AI anomaly detection, is the clearest solution to tackle that challenge.

What is the psychology of trust?

Psychological and sociological theories on trust largely centre around the importance of dependence and a two-party system: the trustor and the trustee. Most research has studied the impacts of trust decisions on interpersonal relationships, and the characteristics which make those relationships more or less likely to succeed. In behavioural terms, the elements most frequently referenced in trust decisions are emotional characteristics such as benevolence, integrity, competence, and predictability.1

Most of the behavioural evaluations of trust decisions survey why someone chooses to trust another person, how they made that decision, and how quickly they arrived at their choice. However, these micro-choices about trust require the context that trust is essential to human survival. Trust decisions are rooted in many of the same survival instincts which require the brain to categorize information and determine possible dangers. More broadly, successful trust relationships are essential in maintaining the fabric of human society, critical to every element of human life.

Trust can be compared to dark matter (Rotenberg, 2018), which is the extensive but often difficult to observe material that binds planets and earthly matter. In the same way, trust is an integral but often a silent component of human life, connecting people and enabling social functioning.2

Defining implicit and routine trust

As briefly mentioned earlier, dependence is an essential element of the trusting relationship. Being able to build a routine of trust, based on the maintenance rather than establishment of trust, becomes implicit within everyday life. For example, speaking to a friend about personal issues and life developments is often a subconscious reaction to the events occurring, rather than an explicit choice to trust said friend each time one has new experiences.

Active and passive levels of cognition are important to recognize in decision-making, such as trust choices. Decision-making is often an active cognitive process requiring a lot of resource from the brain. However, many decisions occur passively, especially if they are not new choices e.g. habits or routines. The brain’s focus turns to immediate tasks while relegating habitual choices to subconscious thought processes, passive cognition. Passive cognition leaves the brain open to impacts from inattentional blindness, wherein the individual may be abstractly aware of the choice but it is not the focus of their thought processes or actively acknowledged as a decision. These levels of cognition are mostly referenced as “attention” within the brain’s cognition and processing.3

This idea is essentially a concept of implicit trust, meaning trust which is occurring as background thought processes rather than active decision-making. This implicit trust extends to multiple areas of human life, including interpersonal relationships, but also habitual choice and lifestyle. When combined with the dependence on people and services, this implicit trust creates a haze of cognition where trust is implied and assumed, rather than actively chosen across a myriad of scenarios.

Trust and technology

As researchers at the University of Cambridge highlight in their research into trust and technology, ‘In a fundamental sense, all technology depends on trust.’  The same implicit trust systems which allow us to navigate social interactions by subconsciously choosing to trust, are also true of interactions with technology. The implied trust in technology and services is perhaps most easily explained by a metaphor.

Most people have a favourite brand of soda. People will routinely purchase that soda and drink it without testing it for chemicals or bacteria and without reading reviews to ensure the companies that produce it have not changed their quality standards. This is a helpful, representative example of routine trust, wherein the trust choice is implicit through habitual action and does not mean the person is actively thinking about the ramifications of continuing to use a product and trust it.

The principle of dependence is especially important in trust and technology discussions, because the modern human is entirely reliant on technology and so has no way to avoid trusting it.5   Specifically important in workplace scenarios, employees are given a mandatory set of technologies, from programs to devices and services, which they must interact with on a daily basis. Over time, the same implicit trust that would form between two people forms between the user and the technology. The key difference between interpersonal trust and technological trust is that deception is often much more difficult to identify.

The implicit trust in workplace technology

To provide a bit of workplace-specific context, organizations rely on technology providers for the operation (and often the security) of their devices. The organizations also rely on the employees (users) to use those technologies within the accepted policies and operational guidelines. The employees rely on the organization to determine which products and services are safe or unsafe.

Within this context, implicit trust is occurring at every layer of the organization and its technological holdings, but often the trust choice is only made annually by a small security team rather than continually evaluated. Systems and programs remain in place for years and are used because “that’s the way it’s always been done. Within that context, the exploitation of that trust by threat actors impersonating or compromising those technologies or services is extremely difficult to identify as a human.

For example, many organizations utilize email communications to promote software updates for employees. Typically, it would consist of email prompting employees to update versions from the vendors directly or from public marketplaces, such as App Store on Mac or Microsoft Store for Windows. If that kind of email were to be impersonated, spoofing an update and including a malicious link or attachment, there would be no reason for the employee to question that email, given the explicit trust enforced through habitual use of that service and program.

Inattentional blindness: How the brain ignores change

Users are psychologically predisposed to trust routinely used technologies and services, with most of those trust choices continuing subconsciously. Changes to these technologies would often be subject to inattentional blindness, a psychological phenomenon wherein the brain either overwrites sensory information with what the brain expects to see rather than what is actually perceived.

A great example of inattentional blindness6 is the following experiment, which asks individuals to count the number of times a ball is passed between multiple people. While that is occurring, something else is going on in the background, which, statistically, those tested will not see. The shocking part of this experiment comes after, when the researcher reveals that the event occurring in the background not seen by participants was a person in a gorilla suit moving back and forth between the group. This highlights how significant details can be overlooked by the brain and “overwritten” with other sensory information. When applied to technology, inattentional blindness and implicit trust makes spotting changes in behaviour, or indicators that a trusted technology or service has been compromised, nearly impossible for most humans to detect.

With all this in mind, how can you prepare users to correctly anticipate or identify a violation of that trust when their brains subconsciously make trust decisions and unintentionally ignore cues to suggest a change in behaviour? The short answer is, it’s difficult, if not impossible.

How threats exploit our implicit trust in technology

Most cyber threats are built around the idea of exploiting the implicit trust humans place in technology. Whether it’s techniques like “living off the land”, wherein programs normally associated with expected activities are leveraged to execute an attack, or through more overt psychological manipulation like phishing campaigns or scams, many cyber threats are predicated on the exploitation of human trust, rather than simply avoiding technological safeguards and building backdoors into programs.

In the case of phishing, it is easy to identify the attempts to leverage the trust of users in technology and services. The most common example of this would be spoofing, which is one of the most common tactics observed by Darktrace/Email. Spoofing is mimicking a trusted user or service, and can be accomplished through a variety of mechanisms, be it the creation of a fake domain meant to mirror a trusted link type, or the creation of an email account which appears to be a Human Resources, Internal Technology or Security service.

In the case of a falsified internal service, often dubbed a “Fake Support Spoof”, the user is exploited by following instructions from an accepted organizational authority figure and service provider, whose actions should normally be adhered to. These cases are often difficult to spot when studying the sender’s address or text of the email alone, but are made even more difficult to detect if an account from one of those services is compromised and the sender’s address is legitimate and expected for correspondence. Especially given the context of implicit trust, detecting deception in these cases would be extremely difficult.

How email security solutions can solve the problem of implicit trust

How can an organization prepare for this exploitation? How can it mitigate threats which are designed to exploit implicit trust? The answer is by using email security solutions that leverage behavioural analysis via anomaly detection, rather than traditional email gateways.

Expecting humans to identify the exploitation of their own trust is a high-risk low-reward endeavour, especially when it takes different forms, affects different users or portions of the organization differently, and doesn’t always have obvious red flags to identify it as suspicious. Cue email security using anomaly detection as the key answer to this evolving problem.

Anomaly detection enabled by machine learning and artificial intelligence (AI) removes the inattentional blindness that plagues human users and security teams and enables the identification of departures from the norm, even those designed to mimic expected activity. Using anomaly detection mitigates multiple human cognitive biases which might prevent teams from identifying evolving threats, and also guarantees that all malicious behaviour will be detected. Of course, anomaly detection means that security teams may be alerted to benign anomalous activity, but still guarantees that no threat, no matter how novel or cleverly packaged, won’t be identified and raised to the human security team.

Utilizing machine learning, especially unsupervised machine learning, mimics the benefits of human decision making and enables the identification of patterns and categorization of information without the framing and biases which allow trust to be leveraged and exploited.

For example, say a cleverly written email is sent from an address which appears to be a Microsoft affiliate, suggesting to the user that they need to patch their software due to the discovery of a new vulnerability. The sender’s address appears legitimate and there are news stories circulating on major media providers that a new Microsoft vulnerability is causing organizations a lot of problems. The link, if clicked, forwards the user to a login page to verify their Microsoft credentials before downloading the new version of the software. After logging in, the program is available for download, and only requires a few minutes to install. Whether this email was created by a service like ChatGPT (generative AI) or written by a person, if acted upon it would give the threat actor(s) access to the user’s credential and password as well as activate malware on the device and possibly broader network if the software is downloaded.

If we are relying on users to identify this as unusual, there are a lot of evidence points that enforce their implicit trust in Microsoft services that make them want to comply with the email rather than question it. Comparatively, anomaly detection-driven email security would flag the unusualness of the source, as it would likely not be coming from a Microsoft-owned IP address and the sender would be unusual for the organization, which does not normally receive mail from the sender. The language might indicate solicitation, an attempt to entice the user to act, and the link could be flagged as it contains a hidden redirect or tailored information which the user cannot see, whether it is hidden beneath text like “Click Here” or due to link shortening. All of this information is present and discoverable in the phishing email, but often invisible to human users due to the trust decisions made months or even years ago for known products and services.

AI-driven Email Security: The Way Forward

Email security solutions employing anomaly detection are critical weapons for security teams in the fight to stay ahead of evolving threats and varied kill chains, which are growing more complex year on year. The intertwining nature of technology, coupled with massive social reliance on technology, guarantees that implicit trust will be exploited more and more, giving threat actors a variety of avenues to penetrate an organization. The changing nature of phishing and social engineering made possible by generative AI is just a drop in the ocean of the possible threats organizations face, and most will involve a trusted product or service being leveraged as an access point or attack vector. Anomaly detection and AI-driven email security are the most practical solution for security teams aiming to prevent, detect, and mitigate user and technology targeting using the exploitation of trust.

References

1https://www.kellogg.northwestern.edu/trust-project/videos/waytz-ep-1.aspx

2Rotenberg, K.J. (2018). The Psychology of Trust. Routledge.

3https://www.cognifit.com/gb/attention

4https://www.trusttech.cam.ac.uk/perspectives/technology-humanity-society-democracy/what-trust-technology-conceptual-bases-common

5Tyler, T.R. and Kramer, R.M. (2001). Trust in organizations : frontiers of theory and research. Thousand Oaks U.A.: Sage Publ, pp.39–49.

6https://link.springer.com/article/10.1007/s00426-006-0072-4

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
Hanah Darley
Director of Threat Research

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June 26, 2025

Patch and Persist: Darktrace’s Detection of Blind Eagle (APT-C-36)

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What is Blind Eagle?

Since 2018, APT-C-36, also known as Blind Eagle, has been observed performing cyber-attacks targeting various sectors across multiple countries in Latin America, with a particular focus on Colombian organizations.

Blind Eagle characteristically targets government institutions, financial organizations, and critical infrastructure [1][2].

Attacks carried out by Blind Eagle actors typically start with a phishing email and the group have been observed utilizing various Remote Access Trojans (RAT) variants, which often have in-built methods for hiding command-and-control (C2) traffic from detection [3].

What we know about Blind Eagle from a recent campaign

Since November 2024, Blind Eagle actors have been conducting an ongoing campaign targeting Colombian organizations [1].

In this campaign, threat actors have been observed using phishing emails to deliver malicious URL links to targeted recipients, similar to the way threat actors have previously been observed exploiting CVE-2024-43451, a vulnerability in Microsoft Windows that allows the disclosure of a user’s NTLMv2 password hash upon minimal interaction with a malicious file [4].

Despite Microsoft patching this vulnerability in November 2024 [1][4], Blind Eagle actors have continued to exploit the minimal interaction mechanism, though no longer with the intent of harvesting NTLMv2 password hashes. Instead, phishing emails are sent to targets containing a malicious URL which, when clicked, initiates the download of a malicious file. This file is then triggered by minimal user interaction.

Clicking on the file triggers a WebDAV request, with a connection being made over HTTP port 80 using the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19044’. WebDAV is a transmission protocol which allows files or complete directories to be made available through the internet, and to be transmitted to devices [5]. The next stage payload is then downloaded via another WebDAV request and malware is executed on the target device.

Attackers are notified when a recipient downloads the malicious files they send, providing an insight into potential targets [1].

Darktrace’s coverage of Blind Eagle

In late February 2025, Darktrace observed activity assessed with medium confidence to be  associated with Blind Eagle on the network of a customer in Colombia.

Within a period of just five hours, Darktrace / NETWORK detected a device being redirected through a rare external location, downloading multiple executable files, and ultimately exfiltrating data from the customer’s environment.

Since the customer did not have Darktrace’s Autonomous Response capability enabled on their network, no actions were taken to contain the compromise, allowing it to escalate until the customer’s security team responded to the alerts provided by Darktrace.

Darktrace observed a device on the customer’s network being directed over HTTP to a rare external IP, namely 62[.]60[.]226[.]112, which had never previously been seen in this customer’s environment and was geolocated in Germany. Multiple open-source intelligence (OSINT) providers have since linked this endpoint with phishing and malware campaigns [9].

The device then proceeded to download the executable file hxxp://62[.]60[.]226[.]112/file/3601_2042.exe.

Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
Figure 1: Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
Darktrace’s detection of the affected device downloading an executable file from the suspicious endpoint.
Figure 2: Darktrace’s detection of the affected device downloading an executable file from the suspicious endpoint.

The device was then observed making unusual connections to the rare endpoint 21ene.ip-ddns[.]com and performing unusual external data activity.

This dynamic DNS endpoint allows a device to access an endpoint using a domain name in place of a changing IP address. Dynamic DNS services ensure the DNS record of a domain name is automatically updated when the IP address changes. As such, malicious actors can use these services and endpoints to dynamically establish connections to C2 infrastructure [6].

Further investigation into this dynamic endpoint using OSINT revealed multiple associations with previous likely Blind Eagle compromises, as well as Remcos malware, a RAT commonly deployed via phishing campaigns [7][8][10].

Darktrace’s detection of the affected device connecting to the suspicious dynamic DNS endpoint, 21ene.ip-ddns[.]com.
Figure 3: Darktrace’s detection of the affected device connecting to the suspicious dynamic DNS endpoint, 21ene.ip-ddns[.]com.

Shortly after this, Darktrace observed the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19045’, indicating usage of the aforementioned transmission protocol WebDAV. The device was subsequently observed connected to an endpoint associated with Github and downloading data, suggesting that the device was retrieving a malicious tool or payload. The device then began to communicate to the malicious endpoint diciembrenotasenclub[.]longmusic[.]com over the new TCP port 1512 [11].

Around this time, the device was also observed uploading data to the endpoints 21ene.ip-ddns[.]com and diciembrenotasenclub[.]longmusic[.]com, with transfers of 60 MiB and 5.6 MiB observed respectively.

Figure 4: UI graph showing external data transfer activity.

This chain of activity triggered an Enhanced Monitoring model alert in Darktrace / NETWORK. These high-priority model alerts are designed to trigger in response to higher fidelity indicators of compromise (IoCs), suggesting that a device is performing activity consistent with a compromise.

 Darktrace’s detection of initial attack chain activity.
Figure 5: Darktrace’s detection of initial attack chain activity.

A second Enhanced Monitoring model was also triggered by this device following the download of the aforementioned executable file (hxxp://62[.]60[.]226[.]112/file/3601_2042.exe) and the observed increase in C2 activity.

Following this activity, Darktrace continued to observe the device beaconing to the 21ene.ip-ddns[.]com endpoint.

Darktrace’s Cyber AI Analyst was able to correlate each of the individual detections involved in this compromise, identifying them as part of a broader incident that encompassed C2 connectivity, suspicious downloads, and external data transfers.

Cyber AI Analyst’s investigation into the activity observed on the affected device.
Figure 6: Cyber AI Analyst’s investigation into the activity observed on the affected device.
Figure 7: Cyber AI Analyst’s detection of the affected device’s broader connectivity throughout the course of the attack.

As the affected customer did not have Darktrace’s Autonomous Response configured at the time, the attack was able to progress unabated. Had Darktrace been properly enabled, it would have been able to take a number of actions to halt the escalation of the attack.

For example, the unusual beaconing connections and the download of an unexpected file from an uncommon location would have been shut down by blocking the device from making external connections to the relevant destinations.

Conclusion

The persistence of Blind Eagle and ability to adapt its tactics, even after patches were released, and the speed at which the group were able to continue using pre-established TTPs highlights that timely vulnerability management and patch application, while essential, is not a standalone defense.

Organizations must adopt security solutions that use anomaly-based detection to identify emerging and adapting threats by recognizing deviations in user or device behavior that may indicate malicious activity. Complementing this with an autonomous decision maker that can identify, connect, and contain compromise-like activity is crucial for safeguarding organizational networks against constantly evolving and sophisticated threat actors.

Credit to Charlotte Thompson (Senior Cyber Analyst), Eugene Chua (Principal Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Appendices

IoCs

IoC – Type - Confidence
Microsoft-WebDAV-MiniRedir/10.0.19045 – User Agent

62[.]60[.]226[.]112 – IP – Medium Confidence

hxxp://62[.]60[.]226[.]112/file/3601_2042.exe – Payload Download – Medium Confidence

21ene.ip-ddns[.]com – Dynamic DNS Endpoint – Medium Confidence

diciembrenotasenclub[.]longmusic[.]com  - Hostname – Medium Confidence

Darktrace’s model alert coverage

Anomalous File / Suspicious HTTP Redirect
Anomalous File / EXE from Rare External Location
Anomalous File / Multiple EXE from Rare External Location
Anomalous Server Activity / Outgoing from Server
Unusual Activity / Unusual External Data to New Endpoint
Device / Anomalous Github Download
Anomalous Connection / Multiple Connections to New External TCP Port
Device / Initial Attack Chain Activity
Anomalous Server Activity / Rare External from Server
Compromise / Suspicious File and C2
Compromise / Fast Beaconing to DGA
Compromise / Large Number of Suspicious Failed Connections
Device / Large Number of Model Alert

Mitre Attack Mapping:

Tactic – Technique – Technique Name

Initial Access - T1189 – Drive-by Compromise
Initial Access - T1190 – Exploit Public-Facing Application
Initial Access ICS - T0862 – Supply Chain Compromise
Initial Access ICS - T0865 – Spearphishing Attachment
Initial Access ICS - T0817 - Drive-by Compromise
Resource Development - T1588.001 – Malware
Lateral Movement ICS - T0843 – Program Download
Command and Control - T1105 - Ingress Tool Transfer
Command and Control - T1095 – Non-Application Layer Protocol
Command and Control - T1571 – Non-Standard Port
Command and Control - T1568.002 – Domain Generation Algorithms
Command and Control ICS - T0869 – Standard Application Layer Protocol
Evasion ICS - T0849 – Masquerading
Exfiltration - T1041 – Exfiltration Over C2 Channel
Exfiltration - T1567.002 – Exfiltration to Cloud Storage

References

1)    https://research.checkpoint.com/2025/blind-eagle-and-justice-for-all/

2)    https://assets.kpmg.com/content/dam/kpmgsites/in/pdf/2025/04/kpmg-ctip-blind-eagle-01-apr-2025.pdf.coredownload.inline.pdf

3)    https://www.checkpoint.com/cyber-hub/threat-prevention/what-is-remote-access-trojan/#:~:text=They%20might%20be%20attached%20to,remote%20access%20or%20system%20administration

4)    https://msrc.microsoft.com/update-guide/vulnerability/CVE-2024-43451

5)    https://www.ionos.co.uk/digitalguide/server/know-how/webdav/

6)    https://vercara.digicert.com/resources/dynamic-dns-resolution-as-an-obfuscation-technique

7)    https://threatfox.abuse.ch/ioc/1437795

8)    https://www.checkpoint.com/cyber-hub/threat-prevention/what-is-malware/remcos-malware/

9)    https://www.virustotal.com/gui/url/b3189db6ddc578005cb6986f86e9680e7f71fe69f87f9498fa77ed7b1285e268

10) https://www.virustotal.com/gui/domain/21ene.ip-ddns.com

11) https://www.virustotal.com/gui/domain/diciembrenotasenclub.longmusic.com/community

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Charlotte Thompson
Cyber Analyst

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June 18, 2025

Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision

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In today’s threat landscape, email remains the most targeted vector for cyberattacks. Organizations require not only multi-layered defenses but also advanced, integrated systems that work collaboratively to proactively mitigate threats before they cause damage

That’s why we’re proud to announce a new integration between Darktrace / EMAIL and Microsoft Defender for Office 365, delivering a Unified Quarantine experience that empowers security teams with seamless visibility, control, and response across both platforms.

This announcement builds on a strong and growing collaboration. In 2024, Darktrace was honored as Microsoft UK Partner of the Year and recognized as a Security Trailblazer at the annual Microsoft Security 20/20 Awards, a testament to our shared commitment to innovation and customer-centric security.

A Shared Mission: Stopping Threats at Machine Speed

This integration is more than a technical milestone,as it’s a reflection of a shared mission: to protect organizations from both known and unknown threats, with efficiency, accuracy, and transparency.

  • Microsoft Defender for Office 365 delivers a comprehensive security framework that safeguards Microsoft 365 email and collaboration workloads leveraging advanced AI, global threat intelligence and information on known attack infrastructure.
  • Darktrace / EMAIL complements this with Self-Learning AI that understands the unique communication patterns within each organization, detecting subtle anomalies that evade traditional detection methods.

Together, we’re delivering multi-layered, adaptive protection that’s greater than the sum of its parts.

“Our integration with Microsoft gives security teams the tools they need to act faster and more precisely to detect and respond to threats,” said Jill Popelka, CEO of Darktrace. “Together, we’re strengthening defenses where it matters most to our customers: at the inbox.”

Unified Quarantine: One View, Total Clarity

The new Unified Quarantine experience gives customers a single pane of glass to view and manage email threatsregardless of which product took action. This means:

  • Faster investigations with consolidated visibility
  • Clear attribution of actions and outcomes across both platforms
  • Streamlined workflows for security teams managing complex environments

“This integration is a testament to the power of combining Microsoft’s global threat intelligence with Darktrace’s unique ability to understand the ‘self’ of an organization,” said Jack Stockdale, CTO of Darktrace. “Together, we’re delivering a new standard in proactive, adaptive email security.”

A New Era of Collaborative Cyber Defense

This collaboration represents a broader shift in cybersecurity: from siloed tools to integrated ecosystems. As attackers become more sophisticated, defenders must move faster, smarter, and in unison.

Through this integration, Darktrace and Microsoft establish a new standard for collaboration between native and third-party security solutions, enhancing not only threat detection but also comprehensive understanding and proactive measures against threats.

We’re excited to bring this innovation to our customers and continue building a future where AI and human expertise collaborate to secure the enterprise.

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Carlos Gray
Senior Product Marketing Manager, Email
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