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May 9, 2023
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Breaking Down "ICES": An Umbrella Term With Wide Variety

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09
May 2023
Integrated Cloud Email Security (ICES) can be an effective email security solution, but Darktrace/Email's self-learning AI should be your solution of choice.

While organizing email security solutions into categories can help security teams understand the types of products available, it can also lead to generalizations that overlook important differences within those categories and can become like comparing apples to oranges.

This is true for the Integrated Cloud Email Security (ICES) category. Among the products that qualify, there are important variations in approach that can mean the difference between stopping a novel phishing attack on the first encounter and catching it as many as 13 days later.

These distinctions highlight that not all ICES products and not all AI tools are made equal, and it’s critical to look deeper than the “ICES” label when examining an email security solution. 

What is an ICES solution?

Gartner devised the term ICES in 2021 to describe an advanced email security that augments the native capabilities of email providers by using API access to analyze email content without requiring changing the MX record. 

In other words, ICES solutions integrate with an organization’s cloud email provider to filter out malicious emails.

ICES has risen in popularity as more and more organizations shift to cloud-based or hybrid email servers, and encounter new, more sophisticated threats. Organizations pair ICES with improved native capabilities of email providers. For example, in the 2023 Market Guide for Email Security, Gartner acknowledged that “Microsoft, in particular, continues to make significant investments in improving protection effectiveness and providing better configuration guidance.” 

Native capabilities can detect traditional indicators of compromise, while ICES products can detect nuanced attacks. They integrate directly with cloud-based email providers, meaning emails do not have to be rerouted for analysis, therefore reducing the time security teams would have to spend configuring and maintaining that connection or risking operational outage. 

ICES protects against sophisticated attacks

Before the rise of ICES, the mainstream email security solutions were Secure Email Gateways (SEGs), which can be characterized as tools that rely on historic data to create rules and signatures. This purely reactive approach cannot contend with the current email threat landscape, which includes attacks that abuse legitimate services, originate from compromised known senders, or are entirely novel. They also struggle to detect multi-stage attacks and insider threats

Instead, ICES products use natural language processing and natural language understanding to identify social engineering like business email compromises, spoofing, supply chain attacks, account takeovers, and more.  However, although ICES products can detect more sophisticated threats than SEGs, not all of them can stop entirely unknown attacks. 

Achieving bespoke security with AI that understands you

Even though several ICES products rely on machine learning to identify and stop malicious emails, not all AI is the same. Typically, other vendors’ AIs are trained on insights pulled from across their respective customer-bases and past attacks. However, this does not account for nuanced distinctions that arise from organizations’ sizes, industries, or even the individual employees working at each company. 

Instead, Darktrace understands you. Self-Learning AI™ focuses on the organization it is installed in, instead of generalizing across a wider pool. Darktrace even learns on a granular level, building profiles of every individual employee by analyzing behaviors like how they typically communicate, where and when they log in, the tone and sentiment of their emails, file and link sharing patterns, and hundreds of other signals. This level of specificity ensures that the email security is tailored to each specific organization. 

The ability to learn employee behavior allows Darktrace to detect what is not normal, therefore revealing sophisticated threats on the first encounter. It can detect all types of attacks, including BEC, account takeover, insider threat, compromised internal accounts, and even human error. 

But it’s the ability to stop novel attacks upon the first encounter that sets it apart. Darktrace/Email™ can detect novel email attacks an average of 13 days earlier than email security tools that are trained on knowledge of historical threats. 

Moreover, Darktrace can take precise action to respond to threats, beyond simply allowing or blocking a suspicious email. The AI makes micro-decisions to neutralize only the malicious components of emails. For example, it might flatten an attached PDF, rewrite a shared link, or file an email as junk. 

Darktrace/Email goes further than other ICES by considering the employee experience. With an employee-AI feedback loop, the AI can fine-tune security based on the employees while also providing inline security awareness training in real-time and with real-life examples. By engaging down to the employee level, Darktrace AI can even leverage personalized insights for productivity gains, sorting out graymail based on how each user prefers to interact with it. 

Putting the “I” in “ICES”

Many ICES vendors emphasize the “integrated” part of the acronym, however Darktrace excels at this. Since Darktrace can be installed anywhere a company has data, it can natively interact across the digital estate, saving the security team time and resources otherwise spent learning various dashboards and languages, correlating data across different areas, and manually monitoring daily activity. Darktrace/Email can also integrate with external tools, including SIEMs and SOARs, to further enhance workflows

Moreover, since combining ICES solutions with native security email capabilities creates a hardened security posture, Darktrace/Email benefits from its strong, established integration with Microsoft

Introducing flexibility to ICES deployments

Finally, the security and integration capabilities of Darktrace/Email deploy easily. In the 2023 Market Guide for Email Security, Gartner predicted that “by 2025, 20% of anti-phishing solutions will be delivered via API integration with the email platform, up from less than 5% today.” Darktrace/Email can be rolled out via API or API + Journaling in Microsoft 365, whichever better fits the organization’s needs.

While all ICES products are API-based, that does not mean they are AI-first, or are using the best AI approach. Even some SEGs can deploy via API. That means that the ability to deploy via API does not guarantee a level of security that can stop the most sophisticated threats. Security teams should look beyond deployment method and select the ICES and AI solutions that provide tailored, effective security. 

Finding nuance as an ICES solution

Email security continues to advance in tandem with the threat landscape and organizations’ digital infrastructures. ICES solutions are supplanting SEGs as the mainstream email security solutions, however that broad category includes a range of tools with varying applications of AI. These differences make it critical to not put all ICES products in the same basket. 

Darktrace/Email is the only ICES solution that uses Self-Learning AI to detect all types of email threats, including novel attacks, within seconds.

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.

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November 28, 2024

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Cloud

Cloud security: addressing common CISO challenges with advanced solutions

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Cloud adoption is a cornerstone of modern business with its unmatched potential for scalability, cost efficiency, flexibility, and net-zero targets around sustainability. However, as organizations migrate more workloads, applications, and sensitive data to the cloud it introduces more complex challenges for CISO’s. Let’s dive into the most pressing issues keeping them up at night—and how Darktrace / CLOUD provides a solution for each.

1. Misconfigurations: The Silent Saboteur

Misconfigurations remain the leading cause of cloud-based data breaches. In 2023 alone over 80%  of data breaches involved data stored in the cloud.1  Think open storage buckets or overly permissive permissions; seemingly minor errors that are easily missed and can snowball into major disasters. The fallout of breaches can be costly—both financially and reputationally.

How Darktrace / CLOUD Helps:

Darktrace / CLOUD continuously monitors your cloud asset configurations, learning your environment and using these insights to flag potential misconfigurations. New scans are triggered when changes take place, then grouped and prioritised intelligently, giving you an evolving and prioritised view of vulnerabilities, best practice and mitigation strategies.

2. Hybrid Environments: The Migration Maze

Many organizations are migrating to the cloud, but hybrid setups (where workloads span both on-premises and cloud environments) create unique challenges and visibility gaps which significantly increase complexity. More traditional and most cloud native security tooling struggles to provide adequate monitoring for these setups.

How Darktrace / CLOUD Helps:

Provides the ability to monitor runtime activity for both on-premises and cloud workloads within the same user interface. By leveraging the right AI solution across this diverse data set, we understand the behaviour of your on-premises workloads and how they interact with cloud systems, spotting unusual connectivity or data flow activity during and after the migration process.

This unified visibility enables proactive detection of anomalies, ensures seamless monitoring across hybrid environments, and provides actionable insights to mitigate risks during and after the migration process.

3. Securing Productivity Suites: The Last Mile

Cloud productivity suites like Microsoft 365 (M365) are essential for modern businesses and are often the first step for an organization on a journey to Infrastructure as a Service (IaaS) or Platform as a Service (PaaS) use cases. They also represent a prime target for attackers. Consider a scenario where an attacker gains access to an M365 account, and proceeds to; access sensitive emails, downloading files from SharePoint, and impersonating the user to send phishing emails to internal employees and external partners. Without a system to detect these behaviours, the attack may go unnoticed until significant damage is done.

How Darktrace helps:

Darktrace’s Active AI platform integrates with M365 and establishes an understanding of normal business activity, enabling the detection of abnormalities across its suite including Email, SharePoint and Teams. By identifying subtle deviations in behaviour, such as:

   •    Unusual file accesses

   •    Anomalous login attempts from unexpected locations or devices.

   •    Suspicious email forwarding rules created by compromised accounts.

Darktrace’s Autonomous Response can act precisely to block malicious actions, by disabling compromised accounts and containing threats before they escalate. Precise actions also ensure that critical business operations are maintained even when a response is triggered.  

4. Agent Fatigue: The Visibility Struggle

To secure cloud environments, visibility is critical. If you don’t know what’s there, how can you secure it? Many solutions require agents to be deployed on every server, workload, and endpoint. But managing and deploying agents across sprawling hybrid environments can be both complex and time-consuming when following change controls, and especially as cloud resources scale dynamically.

How Darktrace / CLOUD Helps:

Darktrace reduces or eliminates the need for widespread agent deployment. Its agentless by default, integrating directly with cloud environments and providing instant visibility without the operational headache. Darktrace ensures coverage with minimal friction. By intelligently graphing the relationships between assets and logically grouping your deployed Cloud resources, you are equipped with real-time visibility to quickly understand and protect your environment.

So why Darktrace / CLOUD?

Darktrace’s Self-Learning AI redefines cloud security by adapting to your unique environment, detecting threats as they emerge, and responding in real-time. From spotting misconfigurations to protecting productivity suites and securing hybrid environments. Darktrace / CLOUD simplifies cloud security challenges without adding operational burdens.

From Chaos to Clarity

Cloud security doesn’t have to be a game of endless whack-a-mole. With Darktrace / CLOUD, CISOs can achieve the visibility, control, and proactive protection they need to navigate today’s complex cloud ecosystems confidently.

[1] https://hbr.org/2024/02/why-data-breaches-spiked-in-2023

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About the author
Adam Stevens
Director of Product, Cloud Security

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November 27, 2024

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Inside the SOC

Behind the veil: Darktrace's detection of VPN exploitation in SaaS environments

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Introduction

In today’s digital landscape, Software-as-a-Service (SaaS) platforms have become indispensable for businesses, offering unparalleled flexibly, scalability, and accessibly across locations. However, this convenience comes with a significant caveat - an expanded attack surface that cyber criminals are increasingly exploiting. In 2023, 96.7% of organizations reported security incidents involving at least one SaaS application [1].

Virtual private networks (VPNs) play a crucial role in SaaS security, acting as gateways for secure remote access and safeguarding sensitive data and systems when properly configured. However, vulnerabilities in VPNs can create openings for attacks to exploit, allowing them to infiltrate SaaS environments, compromise data, and disrupt business operations. Notably, in early 2024, the Darktrace Threat Research team investigated the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPNs, which would allow threat actors to gain access to sensitive systems and execute remote code.

More recently, in August, Darktrace identified a SaaS compromise where a threat actor logged into a customer’s VPN from an unusual IP address, following an initial email compromise. The attacker then used a separate VPN to create a new email rule designed to obfuscate the phishing campaign they would later launch.

Attack Overview

The initial attack vector in this case appeared to be through the customer’s email environment. A trusted external contact received a malicious email from another mutual contact who had been compromised and forwarded it to several of the organization’s employees, believing it to be legitimate. Attackers often send malicious emails from compromised accounts to their past contacts, leveraging the trust associated with familiar email addresses. In this case, that trust caused an external victim to unknowingly propagate the attack further. Unfortunately, an internal user then interacted with a malicious payload included in the reply section of the forwarded email.

Later the same day, Darktrace / IDENTITY detected unusual login attempts from the IP 5.62.57[.]7, which had never been accessed by other SaaS users before. There were two failed attempts prior to the successful logins, with the error messages “Authentication failed due to flow token expired” and “This occurred due to 'Keep me signed in' interrupt when the user was signing in.” These failed attempts indicate that the threat actor may have been attempting to gain unauthorized access using stolen credentials or exploiting session management vulnerabilities. Furthermore, there was no attempt to use multi-factor authentication (MFA) during the successful login, suggesting that the threat actor had compromised the account’s credentials.

Following this, Darktrace detected the now compromised account creating a new email rule named “.” – a telltale sign of a malicious actor attempting to hide behind an ambiguous or generic rule name.

The email rule itself was designed to archive incoming emails and mark them as read, effectively hiding them from the user’s immediate view. By moving emails to the “Archive” folder, which is not frequently checked by end users, the attacker can conceal malicious communications and avoid detection. The settings also prevent any automatic deletion of the rules or forced overrides, indicating a cautious approach to maintaining control over the mailbox without raising suspicion. This technique allows the attacker to manipulate email visibility while maintaining a façade of normality in the compromised account.

Email Rule:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: .
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace further identified that this email rule had been created from another IP address, 95.142.124[.]42, this time located in Canada. Open-source intelligence (OSINT) sources indicated this endpoint may have been malicious [2].

Given that this new email rule was created just three minutes after the initial login from a different IP in a different country, Darktrace recognized a geographic inconsistency. By analyzing the timing and rarity of the involved IP addresses, Darktrace identified the likelihood of malicious activity rather than legitimate user behavior, prompting further investigation.

Figure 1: The compromised SaaS account making anomalous login attempts from an unusual IP address in the US, followed by the creation of a new email rule from another VPN IP in Canada.

Just one minute later, Darktrace observed the attacker sending a large number of phishing emails to both internal and external recipients.

Figure 2: The compromised SaaS user account sending a high volume of outbound emails to new recipients or containing suspicious content.

Darktrace / EMAIL detected a significant spike in inbound emails for the compromised account, likely indicating replies to phishing emails.

Figure 3: The figure demonstrates the spike in inbound emails detected for the compromised account, including phishing-related replies.

Furthermore, Darktrace identified that these phishing emails contained a malicious DocSend link. While docsend[.]com is generally recognized as a legitimate file-sharing service belonging to Dropbox, it can be vulnerable to exploitation for hosting malicious content. In this instance, the DocSend domain in question, ‘hxxps://docsend[.]com/view/h9t85su8njxtugmq’, was flagged as malicious by various OSINT vendors [3][4].

Figure 4: Phishing emails detected containing a malicious DocSend link.

In this case, Darktrace Autonomous Response was not in active mode in the customer’s environment, which allowed the compromise to escalate until their security team intervened based on Darktrace’s alerts. Had Autonomous Response been enabled during the incident, it could have quickly mitigated the threat by disabling users and inbox rules, as suggested by Darktrace as actions that could be manually applied, exhibiting unusual behavior within the customer’s SaaS environment.

Figure 5: Suggested Autonomous Response actions for this incident that required human confirmation.

Despite this, Darktrace’s Managed Threat Detection service promptly alerted the Security Operations Center (SOC) team about the compromise, allowing them to conduct a thorough investigation and inform the customer before any further damage could take place.

Conclusion

This incident highlights the role of Darktrace in enhancing cyber security through its advanced AI capabilities. By detecting the initial phishing email and tracking the threat actor's actions across the SaaS environment, Darktrace effectively identified the threat and brought it to the attention of the customer’s security team.

Darktrace’s proactive monitoring was crucial in recognizing the unusual behavior of the compromised account. Darktrace / IDENTITY detected unauthorized access attempts from rare IP addresses, revealing the attacker’s use of a VPN to hide their location.

Correlating these anomalies allowed Darktrace to prompt immediate investigation, showcasing its ability to identify malicious activities that traditional security tools might miss. By leveraging AI-driven insights, organizations can strengthen their defense posture and prevent further exploitation of compromised accounts.

Credit to Priya Thapa (Cyber Analyst), Ben Atkins (Senior Model Developer) and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Models

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compromise / High Priority New Email Rule
  • SaaS / Compromise / New Email Rule and Unusual Email Activity
  • SaaS / Compromise / Unusual Login and Outbound Email Spam
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
  • SaaS / Email Nexus / Possible Outbound Email Spam

Autonomous Response Models

  • Antigena / SaaS / Antigena Email Rule Block
  • Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Technique Name Tactic ID Sub-Technique of

  • Cloud Accounts. DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS T1078.004 T1078
  • Compromise Accounts RESOURCE DEVELOPMENT T1586
  • Email Accounts RESOURCE DEVELOPMENT T1586.002 T1586
  • Internal Spearphishing LATERAL MOVEMENT T1534 -
  • Outlook Rules PERSISTENCE T1137.005 T1137
  • Phishing INITIAL ACCESS T1566 -

Indicators of Compromise (IoCs)

IoC – Type – Description

5.62.57[.]7 – Unusual Login Source

95.142.124[.]42– IP – Unusual Source for Email Rule

hxxps://docsend[.]com/view/h9t85su8njxtugmq - Domain - Phishing Link

References

[1] https://wing.security/wp-content/uploads/2024/02/2024-State-of-SaaS-Report-Wing-Security.pdf

[2] https://www.virustotal.com/gui/ip-address/95.142.124.42

[3] https://urlscan.io/result/0caf3eee-9275-4cda-a28f-6d3c6c3c1039/

[4] https://www.virustotal.com/gui/url/8631f8004ee000b3f74461e5060e6972759c8d38ea8c359d85da9014101daddb

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About the author
Priya Thapa
Cyber Analyst
Your data. Our AI.
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