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March 29, 2023

Email Security & Future Innovations: Educating Employees

As online attackers change to targeted and sophisticated attacks, Darktrace stresses the importance of protection and utilizing steady verification codes.
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
Dan Fein
VP, Product
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29
Mar 2023

In an escalating threat landscape with email as the primary target, IT teams need to move far beyond traditional methods of email security that haven’t evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. By design, they are permanently playing catch up to continually innovating attackers, taking an average of 13 days to recognize new attacks[1]

Phishing attacks are getting more targeted and sophisticated as attackers innovate in two key areas: delivery tactics, and social engineering. On the malware delivery side, attackers are increasingly ‘piggybacking’ off the legitimate infrastructure and reputations of services like SharePoint and OneDrive, as well as legitimate email accounts, to evade security tools. 

To evade the human on the other end of the email, attackers are tapping into new social engineering tactics, exploiting fear, uncertainty, and doubt (FUD) and evoking a sense of urgency as ever, but now have tools at their disposal to enable tailored and personalized social engineering at scale. 

With the help of tools such as ChatGPT, threat actors can leverage AI technologies to impersonate trusted organizations and contacts – including damaging business email compromises, realistic spear phishing, spoofing, and social engineering. In fact, Darktrace found that the average linguistic complexity of phishing emails has jumped by 17% since the release of ChatGPT.  

This is just one example of accelerating attack sophistication – lowering the barrier to entry and improving outcomes for attackers. It forms part of a wider trend of the attack landscape moving from low-sophistication, low-impact, and generic phishing tactics - a 'spray and pray' approach - to more targeted, sophisticated, and higher impact attacks that fall outside of the typical detection remit for any tool relying on rules and signatures. Generative AI and other technologies in the attackers' toolkit will soon enable the launch of these attacks at scale, and only being able to catch known threats that have been seen before will no longer be enough.

Figure 1: The progression of attacks and relative coverage of email security tools

In an escalating threat landscape with email as the primary target, the vast majority of email security tools haven't evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. They look to the past to try and predict the next attack, and are designed to catch today’s attacks tomorrow.

Organizations are increasingly moving towards AI systems, but not all AI is the same, and the application of that AI is crucial. IT and security teams need to move towards email security that is context-aware and leverages AI for deep behavioral analysis. And it’s a proven approach, successfully catching attacks that slip by other tools across thousands of organizations. And email security today needs to be more about just protecting the inbox. It needs to address not just malicious emails, but the full 360-degree view of a user across their email messages and accounts, as well as extended coverage where email bleeds into collaboration tools/SaaS. For many organizations, the question is not if they should upgrade their email security, but when – how much longer can they risk relying on email security that’s stuck looking to the past?  

The Email Security Industry: Playing Catch-Up

Gateways and ICES (Integrated Cloud Email Security) providers have something in common: they look to past attacks in order to try to predict the future. They often rely on previous threat intelligence and on assembling ‘deny-lists’ of known bad elements of emails already identified as malicious – these tools fail to meet the reality of the contemporary threat landscape. Some of these tools attempt to use AI to improve this flawed approach, looking not only for direct matches, but using "data augmentation" to try and find similar-looking emails. But this approach is still inherently blind to novel threats. 

These tools tend to be resource-intensive, requiring constant policy maintenance combined with the hand-to-hand combat of releasing held-but-legitimate emails and holding back malicious phishing emails. This burden of manually releasing individual emails typically falls on security teams, teams that are frequently small with multiple areas of responsibility. The solution is to deploy technology that autonomously stops the bad while allowing the good through, and adapts to changes in the organization – technology that actually fits the definition of ‘set and forget’.  

Becoming behavioral and context-aware  

There is a seismic shift underway in the industry, from “secure” email gateways to intelligent AI-driven thinking. The right approach is to understand the behaviors of end users – how each person uses their inbox and what constitutes ‘normal’ for each user – in order to detect what’s not normal. It makes use of context – how and when people communicate, and with who – to spot the unusual and to flag to the user when something doesn’t look quite right – and why. Basically, a system that understands you. Not past attacks.  

Darktrace has developed a fundamentally different approach to AI, one that doesn’t learn what’s dangerous from historical data but from a deep continuous understanding of each organization and their users. Only a complex understanding of the normal day-to-day behavior of each employee can accurately determine whether or not an email actually belongs in that recipient’s inbox. 

Whether it’s phishing, ransomware, invoice fraud, executive impersonation, or a novel technique, leveraging AI for behavioral analysis allows for faster decision-making – it doesn’t need to wait for a Patient Zero to contain a new attack because it can stop malicious threats on first encounter. This increased confidence in detection allows for more a precise response – targeted action to remove only the riskiest parts of an email, rather than taking a broad blanket response out of caution – in order to reduce risk with minimal disruption to the business. 

Returning to our attack spectrum, as the attack landscape moves increasingly towards highly sophisticated attacks that use novel or seemingly legitimate infrastructure to deliver malware and induce victims, it has never been more important to detect and issue an appropriate response to these high-impact and targeted attacks. 

Fig 2: How Darktrace combined with native email security to cover the full spectrum of attacks

Understanding you and a 360° view of the end user  

We know that modern email security isn’t limited to the inbox alone – it has to encompass a full understanding of a user’s normal behavior across email and beyond. Traditional email tools are focused solely on inbound email as the point of breach, which fails to protect against the potentially catastrophic damage caused by a successful email attack once an account has been compromised.    

Fig 3: A 360° understanding of a user reveals their digital touchpoints beyond Microsoft

In order to have complete context around what is normal for a user, it’s crucial to understand their activity within Microsoft 365, Google Workspace, Salesforce, Dropbox, and even their device on the network. Monitoring devices (as well as inboxes) for symptoms of infection is crucial to determining whether or not an email has been malicious, and if similar emails need to be withheld in the future. Combining with data from cloud apps enables a more holistic view of identity-based attacks. 

Understanding a user in the context of the whole organization – which also means network, cloud, and endpoint data – brings additional context to light to improve decision making, and connecting email security with external data on the attack surface can help proactively find malicious domains, so that defenses can be hardened before an attack is even launched.

Educating and Engaging Your Employees

Ultimately, it’s employees who interact with any given email. If organizations can successfully empower this user base, they will end up with a smarter workforce, fewer successful attacks, and a security team with more time on their hands for better, strategic work. 

The tools that succeed best will be those that can leverage AI to help employees become more security-conscious. While some emails are evidently malicious and should never enter an employee’s inbox, there is a significant grey area of emails that have potentially risky elements. The majority of security tools will either withhold these emails completely – even though they might be business critical – or let them through scot-free. But what if these grey-area emails could in fact be used as training opportunities?    

As opposed to phishing simulation vendors, behavioral AI can improve security awareness holistically throughout organizations by training users with a light touch via their own inboxes – bringing the end user into the loop to harden defenses.  

The new frontier of email security fights AI with AI, and organizations who lag behind might end up learning the hard way. Read on for our blog series about how these technologies can transform the employee experience, dynamize deployment, augment security teams and form part of an integrated defensive loop.    

[1] 13 days is the mean average of phishing payloads active in the wild between the response of Darktrace/Email compared to the earliest of 16 independent feeds submitted by other email security technologies.

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
Dan Fein
VP, Product

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August 19, 2026

When AI Becomes the Lure: A Fake Gemini Installer Delivers Vidar

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Key takeaways

  • Darktrace observed a customer download a fake Google Gemini installer hosted on Google Colab, resulting in the execution of the Vidar information stealer.
  • Darktrace identified the compromise through behavioral indicators, including suspicious process activity, anomalous network communications, and indicators of credential theft, before autonomously containing the threat.
  • The incident highlights how threat actors are increasingly exploiting trusted platforms and a growing interest in AI tools to distribute malware through seemingly legitimate software acquisition workflows.

The Growing Abuse of Generative AI

As organizations are increasingly adopting generative AI tools into their daily workflows, attackers are adapting their distribution methods accordingly too. As part of their day-to-day work, users are now searching for AI assistants, programming tools, browser extensions, desktop applications, and productivity integrations.

Recent reports have highlighted campaigns that use fake AI software and AI-related installers to distribute malware and steal credentials [1]. Researchers have documented campaigns that exploit fake AI-themed websites and services to distribute information stealers and backdoors [2]. Security researchers have also observed attackers disguising malware as legitimate installers for AI software to increase the likelihood of victim interaction and execution [3].

In July 2026, Darktrace observed one such case within a customer environment in the Europe, Middle East and Africa (EMEA) region, where attackers used a fake generative AI installer to deliver the prolific information stealer Vidar. This incident highlights how threat actors are exploiting interest in AI services to distribute established malware using increasingly convincing social engineering techniques.

How a Fake Gemini Installer Delivered Vidar

Initial Access: From Search Result to Malware Download

Unlike many malware campaigns that begin with a phishing email, this activity appears to have originated from a user searching for and downloading software.

Darktrace first observed unusual activity on the customer network after a suspicious executable file was launched from a user’s Download folder. Further investigation revealed that the file purported to be a Google Gemini installer and was named “Download_Google_Gemini_For_Windows.exe”.

During the initial analysis, it was noted that the top search result for the suspicious filename associated pointed to a file hosted on Google Colab, a cloud-based Jupyter notebook platform, commonly used by developers, researchers, and data scientists to run code and machine learning workloads through a web browser. By leveraging another trusted Google platform, the attacker increased the likelihood that users would perceive the download as legitimate, making the lure more convincing to those searching for Gemini-related software.

Figure 1: The Google Colab page containing a download prompt for the fake Google Gemini installer.

Further investigation of the Google Colab page revealed that the download prompt redirected users to a secondary site, hxxps://micronsoftwares[.]com, which posed as a "Windows Software Hub" download page and offered the fake Gemini installer for download.

Figure 2: The secondary website posing as a "Windows Software Hub" download page, which likely hosted the fake Gemini installer.

While the investigation did not uncover any HTTP or file-download telemetry data that conclusively identified the download source, SSL communication sessions with Google Colab were detected immediately before the suspicious file was executed. The timing of these connections suggests that the user interacted with the Colab resource before being redirected to the secondary site from which the executable was downloaded.

The user was not simply tricked into opening an email attachment; instead, the attacker embedded malicious content into a process many users would consider entirely legitimate: searching for and downloading software associated with a trusted platform.

Weaponizing Trusted Platforms

At the time of review (July 15, 2026), Darktrace's Threat Research team confirmed that the Google Colab page was still active and prompting users to download a ZIP archive containing the binary file.

The archive also appeared to contain a README file instructing users to run the binary file with administrator privileges and add it to their antivirus software’s exception lists. These instructions suggest that the campaign relied heavily on social engineering, convincing users to take actions that would facilitate malware execution and potentially bypass security checks.

The use of a legitimate platform also complicates the user’s decision-making. Downloads associated with a trusted service are often perceived as less suspicious than those hosted on unfamiliar domains. When combined with the branding of a widely used AI tool, the lure becomes even more convincing.

Malware Analysis

Darktrace’s Threat Research team identified the executable file as the information-stealing malware Vidar. Analysis revealed that the binary file was a newer Go-compiled variant that communicated with Telegram-based infrastructure. Darktrace’s researchers also identified dtm[.]kijangturbo88[.]top as a command-and-control (C2) endpoint associated with the activity. While the malware itself was not novel, the lure and delivery mechanism was.

For a deeper look at the information stealer, see Darktrace’s 2023 analysis of Vidar.

Figure 3: Darktrace’s detection of the unusual outbound connection associated with the fake Gemini installer.

Shortly after execution, the process established communications with the external IP address 91.98.98[.]86 via port 443, directly linking the executable to suspicious network activity observed on the device. Subsequent open-source intelligence (OSINT) analysis of the revealed multiple malicious associations [5].

Additional Darktrace detections included unusual SSL activity from the affected device. Analysis of related SSL telemetry identified 91.98.111[.]49 as additional infrastructure associated  with the activity [6].

Subsequent alerts from the customer's Microsoft Defender for Endpoint integration later confirmed activity consistent with the theft of browser credentials and other sensitive data from the affected endpoint.

Taken together, these detections provided a clear picture of the attack, from the execution of a suspicious file and unusual network connections to indicators of C2 activity and credential theft.

Figure 4: Darktrace’s detection of anomalous activity following the execution of the fake Gemini installer, seen in the Model Alert Event Log.

Darktrace's Autonomous Response

Following the detection, Darktrace’s Autonomous Response took immediate containment action, including blocking communication with suspicious external infrastructure, including 91.98.98[.]86, and quarantining the compromised device.

Despite the apparent legitimacy of the activity, with the installer hosted on a trusted platform and resembling a routine software download, Darktrace was able to detect and contain the attack because the device's behavior deviated from its normal pattern.

Figure 5: Automated containment actions implemented by Darktrace's Autonomous Response following the detection of activity associated with the fake Gemini installer.

Conclusion

This investigation highlights how threat actors continue to adapt established malware delivery techniques to emerging technology trends. While the malware itself was not new, the distribution method was. By disguising Vidar as a Google Gemini installer and hosting the malicious content on a trusted platform, the attack aligned its lure with a growing behavioral trend: users actively searching for AI tools and services as part of their day-to-day work.

Although fake installers are not a new phenomenon, the rapid rise of generative AI has created new opportunities for threat actors. Rather than relying solely on traditional delivery methods, attackers can now target users who are actively searching for AI applications. As AI adoption continues to accelerate across enterprise environments, organizations should remain alert to campaigns that exploit this interest through fake applications, malicious websites, manipulated search results, the misuse of trusted platforms, and AI-themed social engineering.

Credit to Rushanth Ramanathan (Cyber Analyst) Joanna Ng (Detection Engineer)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

  • Security Integration / C2 Activity and Integration Detection
  • Endpoint / New Suspicious Executable Launched
  • Endpoint / Process Connection / Unusual Connection from New Process
  • Anomalous Connection / Rare External SSL Self-Signed
  • Security Integration / High Severity Integration Detection
  • Antigena / Network / Significant Anomaly /  Antigena Significant Security Integration and Network Activity Block

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

List of Indicators of Compromise (IoCs)

IoC Type Description
Download_Google_Gemini_For_Windows.exe File Fake Gemini-themed installer observed during the investigation.
GoogleAppInstaller.exe File Related executable identified through endpoint telemetry.
91.98.98[.]86 IP Address External destination contacted by the malicious executable.
91.98.111[.]49 IP Address Related infrastructure identified through SSL certificate pivoting.
dtm[.]kijangturbo88[.]top Domain Command-and-control endpoint identified during malware analysis.
1e13c2c9eac72daf63fd00a9946878949e159ae6ec51b54ec64f942d79d61913 SHA256 Malware sample associated with the fake Gemini installer.

MITRE ATT@CK Mapping


MITRE ATT&CK Mapping Tactic Technique
Initial Access T1204 User Execution
Execution T1204.002 User Execution: Malicious File
Defence Evasion T1036 Masquerading
Credential Access T1555 Credentials from Password Stores
Credential Access T1555.003 Credentials from Web Browsers
Command and Control T1071 Application Layer Protocol
Exfiltration T1041 Exfiltration Over C2 Channel
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About the author
Rajendra Rushanth
Cyber Analyst

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August 11, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product
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