Employee-Conscious Email Security Solutions in the Workforce
10
Apr 2023
Email threats commonly affect organizations. Read Darktrace's expert insights on how to safeguard your business by educating employees about email security.
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.
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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.
Author
Dan Fein
VP, Product
Based in New York, Dan joined Darktrace’s technical team in 2015, helping customers quickly achieve a complete and granular understanding of Darktrace’s product suite. Dan has a particular focus on Darktrace/Email, ensuring that it is effectively deployed in complex digital environments, and works closely with the development, marketing, sales, and technical teams. Dan holds a Bachelor’s degree in Computer Science from New York University.
Carlos Gray
Product Manager
Carlos Gonzalez Gray is a Product Marketing Manager at Darktrace, based in the Madrid Office. As an email security Subject Matter Expert he collaborates with the global product team to align each product with the company’s ethos and ensures Darktrace are continuously pushing the boundaries of innovation. His prior role at Darktrace was in Sales Engineering, leading the Iberian team and specializing in both the email and OT sectors. Additionally, his prior experience as a consultant to IBEX 35 companies in Spain has made him well-versed in compliance, auditing, and data privacy. Carlos holds an Honors BA in Political Science and a Masters in Cybersecurity from IE University.
Darktrace's Detection of State-Linked ShadowPad Malware
An integral part of cybersecurity is anomaly detection, which involves identifying unusual patterns or behaviors in network traffic that could indicate malicious activity, such as a cyber-based intrusion. However, attribution remains one of the ever present challenges in cybersecurity. Attribution involves the process of accurately identifying and tracing the source to a specific threat actor(s).
Given the complexity of digital networks and the sophistication of attackers who often use proxies or other methods to disguise their origin, pinpointing the exact source of a cyberattack is an arduous task. Threat actors can use proxy servers, botnets, sophisticated techniques, false flags, etc. Darktrace’s strategy is rooted in the belief that identifying behavioral anomalies is crucial for identifying both known and novel threat actor campaigns.
The ShadowPad cluster
Between July 2024 and November 2024, Darktrace observed a cluster of activity threads sharing notable similarities. The threads began with a malicious actor using compromised user credentials to log in to the target organization's Check Point Remote Access virtual private network (VPN) from an attacker-controlled, remote device named 'DESKTOP-O82ILGG'. In one case, the IP from which the initial login was carried out was observed to be the ExpressVPN IP address, 194.5.83[.]25. After logging in, the actor gained access to service account credentials, likely via exploitation of an information disclosure vulnerability affecting Check Point Security Gateway devices. Recent reporting suggests this could represent exploitation of CVE-2024-24919 [27,28]. The actor then used these compromised service account credentials to move laterally over RDP and SMB, with files related to the modular backdoor, ShadowPad, being delivered to the ‘C:\PerfLogs\’ directory of targeted internal systems. ShadowPad was seen communicating with its command-and-control (C2) infrastructure, 158.247.199[.]185 (dscriy.chtq[.]net), via both HTTPS traffic and DNS tunneling, with subdomains of the domain ‘cybaq.chtq[.]net’ being used in the compromised devices’ TXT DNS queries.
Figure 1: Darktrace’s Advanced Search data showing the VPN-connected device initiating RDP connections to a domain controller (DC). The device subsequently distributes likely ShadowPad-related payloads and makes DRSGetNCChanges requests to a second DC.
Figure 2: Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.
Additional cases of ShadowPad were observed across Darktrace’s customer base in 2024. In some cases, common C2 infrastructure with the cluster discussed above was observed, with dscriy.chtq[.]net and cybaq.chtq[.]net both involved; however, no other common features were identified. These ShadowPad infections were observed between April and November 2024, with customers across multiple regions and sectors affected. Darktrace’s observations align with multiple other public reports that fit the timeframe of this campaign.
Darktrace has also observed other cases of ShadowPad without common infrastructure since September 2024, suggesting the use of this tool by additional threat actors.
The data theft thread
One of the Darktrace customers impacted by the ShadowPad cluster highlighted above was a European manufacturer. A distinct thread of activity occurred within this organization’s network several months after the ShadowPad intrusion, in October 2024.
The thread involved the internal distribution of highly masqueraded executable files via Sever Message Block (SMB) and WMI (Windows Management Instrumentation), the targeted collection of sensitive information from an internal server, and the exfiltration of collected information to a web of likely compromised sites. This observed thread of activity, therefore, consisted of three phrases: lateral movement, collection, and exfiltration.
The lateral movement phase began when an internal user device used an administrative credential to distribute files named ‘ProgramData\Oracle\java.log’ and 'ProgramData\Oracle\duxwfnfo' to the c$ share on another internal system.
Figure 3: Darktrace model alert highlighting an SMB write of a file named ‘ProgramData\Oracle\java.log’ to the c$ share on another device.
Over the next few days, Darktrace detected several other internal systems using administrative credentials to upload files with the following names to the c$ share on internal systems:
ProgramData\Adobe\ARM\webservices.dll
ProgramData\Adobe\ARM\wksprt.exe
ProgramData\Oracle\Java\wksprt.exe
ProgramData\Oracle\Java\webservices.dll
ProgramData\Microsoft\DRM\wksprt.exe
ProgramData\Microsoft\DRM\webservices.dll
ProgramData\Abletech\Client\webservices.dll
ProgramData\Abletech\Client\client.exe
ProgramData\Adobe\ARM\rzrmxrwfvp
ProgramData\3Dconnexion\3DxWare\3DxWare.exe
ProgramData\3Dconnexion\3DxWare\webservices.dll
ProgramData\IDMComp\UltraCompare\updater.exe
ProgramData\IDMComp\UltraCompare\webservices.dll
ProgramData\IDMComp\UltraCompare\imtrqjsaqmm
Figure 4: Cyber AI Analyst highlighting an SMB write of a file named ‘ProgramData\Adobe\ARM\webservices.dll’ to the c$ share on an internal system.
The threat actor appears to have abused the Microsoft RPC (MS-RPC) service, WMI, to execute distributed payloads, as evidenced by the ExecMethod requests to the IWbemServices RPC interface which immediately followed devices’ SMB uploads.
Figure 5: Cyber AI Analyst data highlighting a thread of activity starting with an SMB data upload followed by ExecMethod requests.
Several of the devices involved in these lateral movement activities, both on the source and destination side, were subsequently seen using administrative credentials to download tens of GBs of sensitive data over SMB from a specially selected server. The data gathering stage of the threat sequence indicates that the threat actor had a comprehensive understanding of the organization’s system architecture and had precise objectives for the information they sought to extract.
Immediately after collecting data from the targeted server, devices went on to exfiltrate stolen data to multiple sites. Several other likely compromised sites appear to have been used as general C2 infrastructure for this intrusion activity. The sites used by the threat actor for C2 and data exfiltration purport to be sites for companies offering a variety of service, ranging from consultancy to web design.
Figure 6: Screenshotof one of the likely compromised sites used in the intrusion.
At least 16 sites were identified as being likely data exfiltration or C2 sites used by this threat actor in their operation against this organization. The fact that the actor had such a wide web of compromised sites at their disposal suggests that they were well-resourced and highly prepared.
Figure 7: Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.
Figure 8: Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com
Cyber AI Analyst spotlight
Figure 9: Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.
Figure 10: Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.
As shown in the above figures, Cyber AI Analyst’s ability to thread together the different steps of these attack chains are worth highlighting.
In the ShadowPad attack chains, Cyber AI Analyst was able to identify SMB writes from the VPN subnet to the DC, and the C2 connections from the DC. It was also able to weave together this activity into a single thread representing the attacker’s progression.
Similarly, in the data exfiltration attack chain, Cyber AI Analyst identified and connected multiple types of lateral movement over SMB and WMI and external C2 communication to various external endpoints, linking them in a single, connected incident.
These Cyber AI Analyst actions enabled a quicker understanding of the threat actor sequence of events and, in some cases, faster containment.
Attribution puzzle
Publicly shared research into ShadowPad indicates that it is predominantly used as a backdoor in People’s Republic of China (PRC)-sponsored espionage operations [5][6][7][8][9][10]. Most publicly reported intrusions involving ShadowPad are attributed to the China-based threat actor, APT41 [11][12]. Furthermore, Google Threat Intelligence Group (GTIG) recently shared their assessment that ShadowPad usage is restricted to clusters associated with APT41 [13]. Interestingly, however, there have also been public reports of ShadowPad usage in unattributed intrusions [5].
The data theft activity that later occurred in the same Darktrace customer network as one of these ShadowPad compromises appeared to be the targeted collection and exfiltration of sensitive data. Such an objective indicates the activity may have been part of a state-sponsored operation. The tactics, techniques, and procedures (TTPs), artifacts, and C2 infrastructure observed in the data theft thread appear to resemble activity seen in previous Democratic People’s Republic of Korea (DPRK)-linked intrusion activities [15] [16] [17] [18] [19].
The distribution of payloads to the following directory locations appears to be a relatively common behavior in DPRK-sponsored intrusions.
Observed examples:
C:\ProgramData\Oracle\Java\
C:\ProgramData\Adobe\ARM\
C:\ProgramData\Microsoft\DRM\
C:\ProgramData\Abletech\Client\
C:\ProgramData\IDMComp\UltraCompare\
C:\ProgramData\3Dconnexion\3DxWare\
Additionally, the likely compromised websites observed in the data theft thread, along with some of the target URI patterns seen in the C2 communications to these sites, resemble those seen in previously reported DPRK-linked intrusion activities.
No clear evidence was found to link the ShadowPad compromise to the subsequent data theft activity that was observed on the network of the manufacturing customer. It should be noted, however, that no clear signs of initial access were found for the data theft thread – this could suggest the ShadowPad intrusion itself represents the initial point of entry that ultimately led to data exfiltration.
Motivation-wise, it seems plausible for the data theft thread to have been part of a DPRK-sponsored operation. DPRK is known to pursue targets that could potentially fulfil its national security goals and had been publicly reported as being active in months prior to this intrusion [21]. Furthermore, the timing of the data theft aligns with the ratification of the mutual defense treaty between DPRK and Russia and the subsequent accused activities [20].
Darktrace assesses with medium confidence that a nation-state, likely DPRK, was responsible, based on our investigation, the threat actor applied resources, patience, obfuscation, and evasiveness combined with external reporting, collaboration with the cyber community, assessing the attacker’s motivation and world geopolitical timeline, and undisclosed intelligence.
Conclusion
When state-linked cyber activity occurs within an organization’s environment, previously unseen C2 infrastructure and advanced evasion techniques will likely be used. State-linked cyber actors, through their resources and patience, are able to bypass most detection methods, leaving anomaly-based methods as a last line of defense.
Two threads of activity were observed within Darktrace’s customer base over the last year: The first operation involved the abuse of Check Point VPN credentials to log in remotely to organizations’ networks, followed by the distribution of ShadowPad to an internal domain controller. The second operation involved highly targeted data exfiltration from the network of one of the customers impacted by the previously mentioned ShadowPad activity.
Despite definitive attribution remaining unresolved, both the ShadowPad and data exfiltration activities were detected by Darktrace’s Self-Learning AI, with Cyber AI Analyst playing a significant role in identifying and piecing together the various steps of the intrusion activities.
Credit to Sam Lister (R&D Detection Analyst), Emma Foulger (Principal Cyber Analyst), Nathaniel Jones (VP), and the Darktrace Threat Research team.
Appendices
Darktrace / NETWORK model alerts
User / New Admin Credentials on Client
Anomalous Connection / Unusual Admin SMB Session
Compliance / SMB Drive Write
Device / Anomalous SMB Followed By Multiple Model Breaches
Survey findings: AI Cyber Threats are a Reality, the People are Acting Now
Artificial intelligence is changing the cybersecurity field as fast as any other, both on the offensive and defensive side. We surveyed over 1,500 cybersecurity professionals from around the world to uncover their attitudes, understanding, and priorities when it comes to AI cybersecurity in 2025. Our full report, unearthing some telling trends, is out now.
Nearly 74% of participants say AI-powered threats are a major challenge for their organization and 90% expect these threats to have a significant impact over the next one to two years, a slight increase from last year. These statistics highlight that AI is not just an emerging risk but a present and evolving one.
As attackers harness AI to automate and scale their operations, security teams must adapt just as quickly. Organizations that fail to prioritize AI-specific security measures risk falling behind, making proactive defense strategies more critical than ever.
Some of the most pressing AI-driven cyber threats include:
AI-powered social engineering: Attackers are leveraging AI to craft highly personalized and convincing phishing emails, making them harder to detect and more likely to bypass traditional defenses.
More advanced attacks at speed and scale: AI lowers the barrier for less skilled threat actors, allowing them to launch sophisticated attacks with minimal effort.
Attacks targeting AI systems: Cybercriminals are increasingly going after AI itself, compromising machine learning models, tampering with training data, and exploiting vulnerabilities in AI-driven applications and APIs.
Safe and secure use of AI
AI is having an effect on the cyber-threat landscape, but it also is starting to impact every aspect of a business – from marketing to HR to operations. The accessibility of AI tools for employees improves workflows, but also poses risks like data privacy violations, shadow AI, and violation of industry regulations.
How are security practitioners accommodating for this uptick in AI use across business?
Among survey participants 45% of security practitioners say they had already established a policy on the safe and secure use of AI and around 50% are in discussions to do so.
While almost all participants acknowledge that this is a topic that needs to be addressed, the gap between discussion and execution could underscore a need for greater insight, stronger leadership commitment, and adaptable security frameworks to keep pace with AI advancements in the workplace. The most popular actions taken are:
Implemented security controls to prevent unwanted exposure of corporate data when using AI technology (67%)
Implemented security controls to protect against other threats/risks associated with using AI technology (62%)
This year specifically, we see further action being taken with the implementation of security controls, training, and oversight.
For a more detailed breakdown that includes results based on industry and organizational size, download the full report here.
AI threats are rising, but security teams still face major challenges
78% of CISOs say AI-powered cyber-threats are already having a significant impact on their organization, a 5% increase from last year.
While cyber professionals feel more prepared for AI powered threats than they did 12 months ago, 45% still say their organization is not adequately prepared—down from 60% last year.
Despite this optimism, key challenges remain, including:
A shortage of personnel to manage tools and alerts
Gaps in knowledge and skills related to AI-driven countermeasures
Confidence in traditional security tools vs. new AI based tools
This year, 73% of survey participants expressed confidence in their security team’s proficiency in using AI within their tool stack, marking an increase from the previous year.
However, only 50% of participants have confidence in traditional cybersecurity tools to detect and block AI-powered threats. In contrast, 75% of participants are confident in AI-powered security solutions for detecting and blocking such threats and attacks.
As leading organizations continue to implement and optimize their use of AI, they are incorporating it into an increasing number of workflows. This growing familiarity with AI is likely to boost the confidence levels of practitioners even further.
The data indicates a clear trend towards greater reliance on AI-powered security solutions over traditional tools. As organizations become more adept at integrating AI into their operations, their confidence in these advanced technologies grows.
This shift underscores the importance of staying current with AI advancements and ensuring that security teams are well-trained in utilizing these tools effectively. The increasing confidence in AI-driven solutions reflects their potential to enhance cybersecurity measures and better protect against sophisticated threats.
The full report for Darktrace’s State of AI Cybersecurity is out now. Download the paper to dig deeper into these trends, and see how results differ by industry, region, organization size, and job title.
![Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dbda2020b168dc1d83c2_Screenshot%202025-03-12%20at%2012.07.41%E2%80%AFPM.png)
![Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dd09fe9cf54a67c48f13_Screenshot%202025-03-12%20at%2012.14.04%E2%80%AFPM.png)
![Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/67d1dd45f3743ebe06d81d89_Screenshot%202025-03-12%20at%2012.14.46%E2%80%AFPM.png)
