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April 29, 2020

How Email Attackers Are Buying Domain Names to Get Inboxes

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29
Apr 2020
Explore how mass domain purchasing allows cyber-criminals to stay ahead of legacy email tools — and how cyber AI stops the threats that slip through.

It is by now common knowledge that the vast majority of cyber-threats start with an email. In the current working conditions, this is more true than ever – with a recent study reporting a 30,000% increase in phishing, websites, and malware targeting remote users.

Many email security tools struggle to detect threats they encounter for the first time. Attackers know this and are leveraging many techniques to take advantage of this fundamental flaw. This includes automation to mutate common threat variants, resulting in a massive increase in unknown threats. Another technique, which will be the focus of this blog post, is the rapid and widespread creation of new domains in order to evade reputation checks and signature-based detection.

The recent surge in domain creation

While traditional tools have to rely on identifying campaigns and patterns across multiple emails to establish whether or not an email is malicious, Cyber AI technology doesn’t require classifying emails into buckets in order to know they don’t belong. There is no need, therefore, to actively track campaigns. But as security researchers, it’s hard to miss some trends.

Since the coronavirus outbreak, we have seen the number of domains registered related to COVID-19 increase by 130,000. In this time, 60% of all spear phishing threats neutralized by Antigena Email were related to COVID-19 or remote work. Another recent study determined that 10,000 coronavirus-related domains are created every day, with roughly nine out of ten of these either malicious or attempting to generate sales of fake products.

With attackers also taking advantage of changing online behaviors arising from the pandemic, another trend we’ve seen is the proliferation of the keyword ‘Zoom’ in some of the unpopular domains that bypassed traditional tools, as attackers leverage the video conferencing platform’s recent rise in usage.

“I believe that hackers identified coronavirus as something users are desperate to find information on. Panic leads to irrational thinking and people forget the basics of cyber security.”

— COO, Atlas VPN

I recently wrote a blog post on the idea of ‘fearware’ and why it’s so successful. Right now, people are desperate for information, and attackers know this. Cyber-criminals play into fear, uncertainty, and doubt (FUD) through a number of mechanisms, and we have since seen a variety of imaginative attempts to engage recipients. These emails range from fake ‘virus trackers’, to sending emails purporting to be from Amazon, claiming an unmanageable rise in newly registered accounts, and demanding “re-registration” of the recipient’s credit card details should they wish to keep their account.

Domain name purchasing: A vicious cycle

Purchasing thousands of new domains and sending malicious emails en masse is a tried and tested technique that cyber-criminals have been leveraging for decades. Now with automation, they’re doing it faster than ever before.

Here’s why it works.

Traditional security tools work by analyzing emails in isolation, measuring them against static blacklists of ‘known bads’. By way of analogy, the gateway tool here is acting like a security guard standing at the perimeter of an organization’s physical premises, asking every individual who enters: “are you malicious?”

The binary answer to this sole question is extracted by looking at some metadata around the email, including the sender’s IP, their email address domain, and any embedded links or attachments. They analyze this data in a vacuum, and at face value, with no consideration towards the relationship between that data, the recipient, and the rest of the business. They run reputation checks, asking “have I seen this IP or domain before?” Crucially, if the answer is no, they let them straight through.

To spell that out, if the domain is brand new, it won’t have a reputation, and as these traditional tools have a limited ability to identify potential harmful elements via any other means, they have no choice but to let them in by default.

These methods barely scratch the surface of a much wider range of characteristics that a malicious email might contain. And as email threats get ever more sophisticated, the ‘innocent until proven guilty approach’ is not enough. For a comprehensive check, we would want to ask: does the domain have any previous relationship with the recipient? The organization as a whole? Does it look suspiciously visually similar to other domains? Is this the first time we’ve seen an inbound email from this user? Has anybody in the organization ever shared a link with this domain? Has any user ever visited this link?

Legacy tools are blatantly asking the wrong questions, to which attackers know the answers. And usually, they can skirt by these inattentive security guards by paying just a few pennies for new domains.

How to buy your way in

Let’s look at the situation from an attacker’s perspective. They just need one email to land and it could be keys to the kingdom, so an upfront purchase of a few thousand new domains will almost inevitably pay off. And they’d pay the price as long as it’s working and they’re profiting.

This is exactly what attackers are doing. Newly-registered domains consistently get through gateways until these traditional tools are armed with enough information to determine that the domains are bad, by which point thousands or even millions of emails could have been successfully delivered. As soon as the attack infrastructure is worn out, the attackers will abandon it, and very easily just purchase and deploy a new set of domains.

And so, the vicious cycle continues. Like a game of ‘whack-a-mole’, these legacy ‘solutions’ will continue to hammer down on recognized ‘bad’ emails – all the while more malicious domains are being created in the thousands in preparation for the next campaign. This is the ‘Domain Game’, and it’s a hard game for defenders to win.

Asking the right questions

Thankfully, the solution to this problem is as simple as the problem itself. It requires a movement away from the legacy approach and towards deploying technology that is up to par with the speed and scale of today’s attackers.

In the last two years, new technologies have emerged that leverage AI, seeking to understand the human behind the email address. Rather than inspecting incoming traffic at the surface-level and asking binary questions, this paradigm shift away from this insufficient legacy approach asks the right questions: not simply “are you malicious?”, but crucially: “do you belong?”

Informed by a nuanced understanding of the recipient, their peers, and the organization at large, every inbound, outbound, and internal email is analyzed in context, and is then re-analyzed over and over again in light of evolving evidence. Asking the right questions and understanding the human invariably sets a far higher standard for acceptable catch rates with unknown threats on first encounter. This approach far outpaces traditional email defenses which have proven to fail and leave companies and their employees vulnerable to malicious emails sitting in their inboxes.

Rather than desperately bashing away at blacklisted domains and IP addresses in an ill-fated attempt to beat the attackers, we can change the game altogether, tilting the scales in favor of the defenders – securing our inboxes and our organizations at large.

Learn more about Antigena Email.

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
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