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April 10, 2023

Employee-Conscious Email Security Solutions in the Workforce

Email threats commonly affect organizations. Read Darktrace's expert insights on how to safeguard your business by educating employees about email security.
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
Written by
Carlos Gray
Senior Product Marketing Manager, Email
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10
Apr 2023

When considering email security, IT teams have historically had to choose between excluding employees entirely, or including them but giving them too much power and implementing unenforceable, trust-based policies that try to make up for it. 

However, just because email security should not rely on employees, this does not mean they should be excluded entirely. Employees are the ones interacting with emails daily, and their experiences and behaviors can provide valuable security insights and even influence productivity. 

AI technology supports employee engagement in this non-intrusive, nuanced way to not only maintain email security, but also enhance it. 

Finding a Balance of Employee Involvement in Security Strategies

Historically, security solutions offered ‘all or nothing’ approaches to employee engagement. On one hand, when employees are involved, they are unreliable. Employees cannot all be experts in security on top of their actual job responsibilities, and mistakes are bound to happen in fast-paced environments.  

Although there have been attempts to raise security awareness, they often have shortcomings, as training emails lack context and realism, leaving employees with poor understandings that often lead to reporting emails that are actually safe. Having users constantly triaging their inboxes and reporting safe emails wastes time that takes away from their own productivity as well as the productivity of the security team.

Other historic forms of employee involvement also put security at risk. For example, users could create blanket rules through feedback, which could lead to common problems like safe-listing every email that comes from the gmail.com domain. Other times, employees could choose for themselves to release emails without context or limitations, introducing major risks to the organization. While these types of actions include employees to participate in security, they do so at the cost of security. 

Even lower stakes employee involvement can prove ineffective. For example, excessive warnings when sending emails to external contacts can lead to banner fatigue. When employees see the same warning message or alert at the top of every message, it’s human nature that they soon become accustomed and ultimately immune to it.

On the other hand, when employees are fully excluded from security, an opportunity is missed to fine-tune security according to the actual users and to gain feedback on how well the email security solution is working. 

So, both options of historically conventional email security, to include or exclude employees, prove incapable of leveraging employees effectively. The best email security practice strikes a balance between these two extremes, allowing more nuanced interactions that maintain security without interrupting daily business operations. This can be achieved with AI that tailors the interactions specifically to each employee to add to security instead of detracting from it. 

Reducing False Reports While Improving Security Awareness Training 

Humans and AI-powered email security can simultaneously level up by working together. AI can inform employees and employees can inform AI in an employee-AI feedback loop.  

By understanding ‘normal’ behavior for every email user, AI can identify unusual, risky components of an email and take precise action based on the nature of the email to neutralize them, such as rewriting links, flattening attachments, and moving emails to junk. AI can go one step further and explain in non-technical language why it has taken a specific action, which educates users. In contrast to point-in-time simulated phishing email campaigns, this means AI can share its analysis in context and in real time at the moment a user is questioning an email. 

The employee-AI feedback loop educates employees so that they can serve as additional enrichment data. It determines the appropriate levels to inform and teach users, while not relying on them for threat detection

In the other direction, the AI learns from users’ activity in the inbox and gradually factors this into its decision-making. This is not a ‘one size fits all’ mechanism – one employee marking an email as safe will never result in blanket approval across the business – but over time, patterns can be observed and autonomous decision-making enhanced.  

Figure 1: The employee-AI feedback loop increases employee understanding without putting security at risk.

The employee-AI feedback loop draws out the maximum potential benefits of employee involvement in email security. Other email security solutions only consider the security team, enhancing its workflow but never considering the employees that report suspicious emails. Employees who try to do the right thing but blindly report emails never learn or improve and end up wasting their own time. By considering employees and improving security awareness training, the employee-AI feedback loop can level up users. They learn from the AI explanations how to identify malicious components, and so then report fewer emails but with greater accuracy. 

While AI programs have classically acted like black boxes, Darktrace trains its AI on the best data, the organization’s actual employees, and invites both the security team and employees to see the reasoning behind its conclusions. Over time, employees will trust themselves more as they better learn how to discern unsafe emails. 

Leveraging AI to Generate Productivity Gains

Uniquely, AI-powered email security can have effects outside of security-related areas. It can save time by managing non-productive email. As the AI constantly learns employee behavior in the inbox, it becomes extremely effective at detecting spam and graymail – emails that aren't necessarily malicious, but clutter inboxes and hamper productivity. It does this on a per-user basis, specific to how each employee treats spam, graymail, and newsletters. The AI learns to detect this clutter and eventually learns which to pull from the inbox, saving time for the employees. This highlights how security solutions can go even further than merely protecting the email environment with a light touch, to the point where AI can promote productivity gains by automating tasks like inbox sorting.

Preventing Email Mishaps: How to Deal with Human Error

Improved user understanding and decision making cannot stop natural human error. Employees are bound to make mistakes and can easily send emails to the wrong people, especially when Outlook auto-fills the wrong recipient. This can have effects ranging anywhere from embarrassing to critical, with major implications on compliance, customer trust, confidential intellectual property, and data loss. 

However, AI can help reduce instances of accidentally sending emails to the wrong people. When a user goes to send an email in Outlook, the AI will analyze the recipients. It considers the contextual relationship between the sender and recipients, the relationships the recipients have with each other, how similar each recipient’s name and history is to other known contacts, and the names of attached files.  

If the AI determines that the email is outside of a user’s typical behavior, it may alert the user. Security teams can customize what the AI does next: it can block the email, block the email but allow the user to override it, or do nothing but invite the user to think twice. Since the AI analyzes each email, these alerts are more effective than consistent, blanket alerts warning about external recipients, which often go ignored. With this targeted approach, the AI prevents data leakage and reduces cyber risk. 

Since the AI is always on and continuously learning, it can adapt autonomously to employee changes. If the role of an employee evolves, the AI will learn the new normal, including common behaviors, recipients, attached file names, and more. This allows the AI to continue effectively flagging potential instances of human error, without needing manual rule changes or disrupting the employee’s workflow. 

Email Security Informed by Employee Experience

As the practical users of email, employees should be considered when designing email security. This employee-conscious lens to security can strengthen defenses, improve productivity, and prevent data loss.  

In these ways, email security can benefit both employees and security teams. Employees can become another layer of defense with improved security awareness training that cuts down on false reports of safe emails. This insight into employee email behavior can also enhance employee productivity by learning and sorting graymail. Finally, viewing security in relation to employees can help security teams deploy tools that reduce data loss by flagging misdirected emails. With these capabilities, Darktrace/Email™ enables security teams to optimize the balance of employee involvement in email security.

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
Written by
Carlos Gray
Senior Product Marketing Manager, Email

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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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