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April 19, 2023
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Flexible Deployments for Enhanced Email Security

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19
Apr 2023
Learn about the benefits of flexible deployment with Darktrace's cutting-edge technology. Explore how to stay ahead of email attacks and stay safe with AI.

With the widespread adoption of cloud email services, security vendors are collaborating with cloud providers to offer faster and more seamless ways of rolling out security solutions like API-driven one-click deployment. These new methods of deployment can install in seconds, reduce the risk of email disruption and scale without any additional configurations.  

Third-party SEGs (Secure Email Gateways) traditionally provided the foundation for email security and operations, operating via an on-premises or virtual appliance or a cloud service. SEGs process and screen all email traffic according to a set of pre-defined rules to protect against phishing attacks. In order to implement, these solutions require organizations to reroute their mail exchange (MX) record to direct emails towards the SEG.

In recent years Microsoft and Google have leveled up their security significantly, making valuable extensions to foundational email security. However, it is just that, foundational. The current email threat landscape has led to more sophisticated malware delivery techniques and social engineering tactics, creating demand for advanced email security solutions that can collaborate with native vendors and combine diverse approaches to provide in-depth defense – for example, the established partnership between Darktrace and Microsoft. Indeed, Gartner reported that the industry is moving towards a combination of native provider security and API-based vendors, allowing for full-breadth coverage of the variety of use cases.

API-driven deployment  

With cloud email services now ubiquitous for almost every business, it makes sense for email security vendors to leverage these cloud services for deployment. Because these products co-exist with, rather than replace, the in-built security of cloud email, they don’t require rerouting the domain name services mail exchanger (DNS MX) record. Instead, vendors can offer seamless delivery of their products by using APIs, which integrate fully via cloud applications without affecting the email delivery path – making installation and uninstallation straightforward while offering uninterrupted workflows.  

And communication doesn’t stop at email; in the world of hybrid work, email is just one of the tools employees use to connect and send sensitive information. APIs allow security solutions to integrate with other collaboration tools – including Microsoft Teams, Slack, Salesforce and Dropbox – to allow for full visibility of an organization beyond just the inbox.

API + Journaling  

While APIs are unmistakably the future of deployment, they can also be easily augmented. That’s where API+Journaling comes in. Where API-only analyzes emails after they have passed through initial cloud security, and has the ability to quarantine or return them to the inbox post-delivery, API with added journaling in Microsoft 365 takes the raw email data before it enters the inbox to analyze in parallel with the provider’s native security.  

As both scenarios take place at machine speed the difference is often imperceptible, but there can be instances where API-only is marginally slower – in certain cases even a second can be detrimental when dealing with such a critical communication platform as email. For these organizations, journaling reduces latency to ensure best in class detection speeds, as much as 30 times faster than API-only.

Diagram infographic depicting the workflow of a sent email after the deployment of Darktrace.
Figure 1: Darktrace deploys in parallel, without any changes to the delivery path and no risk of operational outage

Darktrace/Email: Flexible Deployment to Suit You  

In a crowded market for ICES vendors, those who can offer flexible deployment will remain ahead of the game. Organizations should be able to choose from speedy deployment using API-only, or longer deployment with journaling – with the option to deploy via cloud or on-premise.  

Darktrace/Email offers the best of both worlds – giving customers the choice of deployment via API or API+Journaling in Microsoft 365 to meet their organization’s needs. Equally, they can choose to deploy fully via cloud or fully on premise, whichever best suits their team setup. Either way, there’s no change to the email path. With 1-click deployment that installs in seconds, or 5-minute deployment with added journaling – it can scale from just a handful of inboxes to tens of thousands, without any re-routing or additional configurations aside from accepting permissions.

Diagram infographic illustrating the quick installation of Darktrace via API.
Figure 2: 1-Click deployment installs in seconds via API, with advanced API+Journaling options for reduced latency.

Added features increase the efficiency of workflows to benefit teams – such as the ability to recuperate a delivered message from a user’s inbox post-delivery, whether it is in bulk or a single email. Seamless integration within the email application creates an intuitive user experience, introducing non-invasive banners and simple AI analysis inside the inbox.  

Security teams can also get a clearer picture of how effective their current email solution is, as emails aren’t stopped by the SEG before reaching the provider – allowing for improved visibility from first deployment.  

Darktrace works with email providers to take advantage of their native security and combine it with our Self-Learning AI, offering flexibility without compromising on speed of deployment. This approach enhances detection by leveraging the same API connections to gather additional context from other SaaS applications like Microsoft Teams and SharePoint – hardening defenses across the organization.

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
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.

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November 7, 2024

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Inside the SOC

Onomastics Gymnastics: How Darktrace Detects Spoofing and Business Email Compromise in Multi-Name Users

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Note: For privacy reasons, actual surnames and email addresses observed in these incidents below have been replaced with fictitious placeholder names, using the common Spanish names “Fulano” and “Mengano”.

Naming conventions

Modeling names and their variants of members of an organization is a critical component to properly detect if those same names and variants are being spoofed by malicious actors. For many predominantly English-speaking organizations, these variants can largely be captured by variants of a person’s given name (e.g. James-Jimmy-Jim) and a consistent, singular surname or family name (e.g. Smith). Naming conventions, however, are far from universal. This piece will review how Darktrace / EMAIL manages the common naming conventions of much of the Spanish-speaking world, and can use its modeling to create high-fidelity detections of multiple types of spoofing attempts.

A brief summary of the common convention across Spain and much of Spanish-speaking America: most people are given one or two given names (e.g. Roberto, Juan, María, Natalia), and their surnames are the first surname of their father, followed by the first surname of their mother. While there are various exceptions to this norm, the below graphic Wikipedia [1][2] highlights the general rule.

Example Spanish naming convention for father “José García Torres” and mother “María Acosta Gómez” for child “Pablo García Acosta”. If shortened to one surname, the convention holds the child would be referred to as “Pablo García”
Figure 1: Example Spanish naming convention for father “José García Torres” and mother “María Acosta Gómez” for child “Pablo García Acosta”. If shortened to one surname, the convention holds the child would be referred to as “Pablo García” [1].

Detection of improper name usage

Implicit in the above comment that shortening to one surname follows the convention of using the first surname, shortening to the second surname is often a tell-tale sign of someone unfamiliar with the person or their broader culture. This can be a useful corroborating feature in detecting a spoof attempt – analogous to a spelling error.

In the case of a Spanish customer, this misuse of name shortening contributed to the detection of a spoof attempt trying to solicit a response by impersonating an internal user forwarding information about ‘Data Protection’.

Figure 2: The Cyber AI Analyst summary of the Darktrace / EMAIL detections shows the use of the Gmail sender impersonating Isabel Maria Fulano Mengano, but incorrectly uses the second surname Mengano.

While the limited communication history from the sender and the nature of the text content already marks the mail as suspicious, Darktrace / EMAIL notes the personal name used in the email is similar to a high-value user (‘whale’ to use the terminology of spearphishing). The additional context provided by the detection of the attempted spoof prompted more severe actioning of this email, leading to a ‘Hold’ action instead of a less-severe ‘Unspoof’ action via a banner on the email.

The content summary of the sender showing the ‘Personal’ field of the email being ‘Isabel Mengano’, breaking from the standard name-shortening convention. The additional metrics identify features that might be anomalous about the sender.
Figure 3: The content summary of the sender showing the ‘Personal’ field of the email being ‘Isabel Mengano’, breaking from the standard name-shortening convention. The additional metrics identify features that might be anomalous about the sender.

Malicious email properly using both surnames

Misusing the name-shortening convention is not the only way that Darktrace / EMAIL can detect spoofing attempts. In the case of another Spanish customer,  Darktrace observed a whale impersonation being sent to 230 users with solicitation content, but no links or attachments. Although the name was modeled internally in the “Surname, Given-name” format, Darktrace identified the spoofing attempt targeting a high-value user and took action, blocking the series of emails from reaching end-user inboxes to prevent unsuspecting users from responding.

Cyber AI Analyst summary of a suspicious email
Figure 4: Cyber AI Analyst summary of a suspicious email. The personal field is visible as ‘juan fulano mengano’, which is consistent with the reverse-order modelled user ‘fulano mengano, juan’. The subject line ‘Urgent Request’ sent to 230 users gives an intuitive indicator of the emails potentially being part of a malicious solicitation campaign.

In Summary: A case of onomastics gymnastics

The variety in valid usage of human language can be a barrier to evaluating when a given text is benign or malicious. Despite this, Darktrace / EMAIL is designed to manage this variety, as exemplified by the detections of two spoofing attempts seen against organizations using the distinct Spanish-speaking world’s common naming convention. The scope of this design as seen in this onomastic context, extends to a wide range of detections surrounding emails and their behavioral anomalies.

Credit to Roberto Romeu (Principal Cyber Analyst), Justin Torres (Senior Cyber Analyst) and Natalia Sánchez Rocafort (Senior Analyst Consultant).

Darktrace / Email solution brief screenshot

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  • Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
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  • Stop the 58% of threats bypassing traditional email security

References

[1] https://en.wikipedia.org/wiki/Naming_customs_of_Hispanic_America

[2] https://en.wikipedia.org/wiki/Spanish_naming_customs

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About the author
Roberto Romeu
Senior SOC Analyst

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October 31, 2024

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OT

Understanding the NERC-CIP015 Internal Network Security Monitoring (INSM) Requirements

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Background: NERC CIP-015

In January of 2023 the Federal Energy Regulatory Commission (FERC) released FERC Order 887 which addresses a critical security gap in Critical Infrastructure Protection (CIP) standards, the lack of internal network security monitoring (INSM).

The current NERC CIP standards only require solutions that use traditional detection systems that identify malicious code based on known rules and signatures. The new legislation will now require electric cooperatives to implement INSMs to detect malicious activity in east-west network traffic. INSMs establish a baseline of network activity and detect anomalies that would bypass traditional detection systems, improving an organization’s ability to detect novel threats. Without INSM, organizations have limited visibility into malicious activities inside their networks, leaving them vulnerable if attackers breach initial defenses like firewalls and anti-virus software.

Implementation of NERC CIP-015

Once approved, Bulk Electronic Systems (BESs) will have 36 months to implement INSM, and medium-impact BESs with external routable connectivity (ERC) will have 60 months to do so.

While the approval of the NERC CIP-015 requirements have not been finalized, preparation on the part of electric cooperatives should start as soon as possible. Darktrace is committed to helping electric cooperatives meet the requirements for INSM and help reach compliance standards.

Why is internal network security monitoring important?

NERC CIP-015 aims to enhance the detection of anomalies or unauthorized network activity within CIP environments, underscoring the importance of monitoring East-West traffic within trust zones. This approach enables faster response and recovery times.

INSMs are essential to detecting threats that bypass traditional defenses. For example, insider threats, sophisticated new attack techniques, and threats that exploit compromised credentials—such as those obtained through phishing or other malicious activities—can easily bypass traditional firewalls and antivirus software. These threats either introduce novel methods or leverage legitimate access, making them difficult to detect.

INSMs don’t rely on rules and signatures to detect anomalous activity, they spot abnormalities in network traffic and create alerts based on this activity making them vital to detecting sophisticated threats. Additionally, INSM sits behind the firewall and provides detections utilizing the passive monitoring of east west and north south traffic within the enforcement boundary.

Buyers should be aware of the discrepancies between different INSMs. Some systems require constant tuning and updating, external connectivity forcing holes in segmentation or have intrusive deployments that put sensitive OT assets at risk.

What are the NERC CIP-015 requirements?

The goal of this directive is to ensure that cyber threats are identified early in the attack lifecycle by mandating implementation of security systems that detect and speed up mitigation of malicious activity.

The requirements are divided into three sections:

  • Network security monitoring
  • Data retention for anomalous activity
  • Data protection

NERC CIP-015 emphasizes the importance of having documented processes and evidence of implementation, with a focus on risk-based monitoring, anomaly detection, evaluation, retention of data, and protection against unauthorized access. Below is a breakdown of each requirement.

R1: Network Security Monitoring

The NERC CIP-015 requires the implementation of and a documented process for monitoring networks within Electronic Security Perimeters (ESPs) that contain high and medium impact BES Cyber Systems.

Key parts:

Part 1.1: Use a risk-based rationale to implement network data feeds that monitor connections, devices, and communications.

Part 1.2: Detect anomalous network activity using the data feeds.

Part 1.3: Evaluate the anomalous activity to determine necessary actions.

M1: Evidence for R1 Implementation: Documentation of processes, including risk-based rationale for data collection, detection events, configuration settings, and network baselines.

Incorporating automated solutions for network baselining is essential for effective internal monitoring, especially in diverse environments like substations and control centers. Each environment requires unique baselines—what’s typical for a substation may differ significantly from a control center, making manual monitoring impractical.

A continuous internal monitoring solution powered by artificial intelligence (AI) simplifies this challenge by instantly detecting all connected assets, dynamically learning the environment’s baseline behavior, and identifying anomalies in real-time. Unlike traditional methods, Darktrace’s AI-driven approach requires no external connectivity or repeated tuning, offering a seamless, adaptive solution for maintaining secure operations across all environments.

R2: Data Retention for Anomalous Activity

Documented processes must be in place to retain network security data related to detected anomalies until the required actions are completed.

Note: Data that does not relate to detected anomalies (Part 1.2) is not required to be retained.

M2: Evidence for Data Retention (R2): Documentation of data retention processes, system configurations, or reports showing compliance with R2.

R3: Data Protection: Implement documented processes to protect the collected security monitoring data from unauthorized deletion or modification.

M3: Evidence for Data Protection (R3): Documentation demonstrating how network security monitoring data is protected from unauthorized access or changes.

How to choose the right INSM for your organization?

Several vendors will offer INSM, but how do you choose the right solution for your organization?

Here are seven questions to help you get started evaluating potential INSM vendors:

  1. How does the solution help with ongoing compliance and reporting including CIP-015? Or any other regulations we comply with?
  2. Does the solution provide real-time monitoring of east-west traffic across critical systems? And what kind of threats has it proven capable of finding?
  3. How deep is the traffic visibility—does it offer Layer 7 (application) insights, or is it limited to Layers 3-4?
  4. Is the solution compatible with our existing infrastructure (firewalls, IDS/IPS, SIEM, OT networks)?
  5. Is this solution inline, passive, or hybrid? What impact will it have on network latency?
  6. Does the vendor have experience with electric utilities or critical infrastructure environments?
  7. Where and how are logs and monitoring data stored?

How Darktrace helps electric utilities with INSM requirements

Darktrace's ActiveAI Security Platform is uniquely designed to continuously monitor network activity and detect anomalous activity across both IT and OT environments successfully detecting insider threats and novel ransomware, while accelerating time to detection and incident reporting.

Most INSM solutions require repeated baselining, which creates more work and increases the likelihood of false positives, as even minor deviations trigger alerts. Since networks are constantly changing, baselines need to adjust in real time. Unlike these solutions, Darktrace does not depend on external connectivity or cloud access over the public internet. Our passive network analysis requires no agents or intrusive scanning, minimizing disruptions and reducing risks to OT systems.

Darktrace's AI-driven threat detection, asset management, and incident response capabilities can help organizations comply with the requirements of NERC CIP-015 for internal network security monitoring and data protection. Built specifically to deploy in OT environments, Darktrace / OT comprehensively manages, detects, evaluates, and protects network activity and anomalous events across IT and OT environments, facilitating adherence to regulatory requirements like data retention and anomaly management.

See how INSM with Darktrace can enhance your security operations, schedule a personalized demo today.

Disclaimer

The information provided in this blog is intended for informational purposes only and reflects Darktrace’s understanding of the NERC CIP-015 INSM requirements as of the publication date. While every effort has been made to ensure the accuracy and reliability of the content, Darktrace makes no warranties or representations regarding its accuracy, completeness, or applicability to specific situations. This blog does not constitute legal or compliance advice and readers are encouraged to consult with qualified professionals for guidance specific to their circumstances. Darktrace disclaims any liability for actions taken or not taken based on the information contained herein.

References

1.     https://www.nerc.com/pa/Stand/Reliability%20Standards/CIP-015-1.pdf

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About the author
Daniel Simonds
Director of Operational Technology
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