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Integrating Email Security to Build a Posture Greater Than the Sum of Its Parts
While 94% of all cyber-attacks come through the inbox, their destination is almost never email. Attacks often traverse to other areas, like cloud apps and infrastructure, endpoints, or networks. As a result, although security teams must establish a strong cornerstone of email security, they should also consider how those solutions fit into the wider security posture.
On its own, Darktrace/Email™ stops attacks before they reach an employee’s inbox and considers both security teams and the employees themselves. But its value extends beyond email security, increased by its ability to integrate with the wider security ecosystem, including both Darktrace products and external tools.
Darktrace’s understanding of you and your organization can be applied anywhere your company has data. This unifying approach to cyber security lays the foundation for the Cyber AI Loop™, in which all Darktrace products feed AI outputs into each other to harden the entire security posture autonomously and continuously. The AI also enriches other security solutions an organization has in place by both ingesting and sharing data. This degree of integration transforms a security stack so that it is greater than the sum of its parts.
Integrating Beyond Email to Enhance Detection and Response
Integrating email security with other areas of the digital estate bolsters defenses, while reducing required resources. With more data, security teams gain a better understanding of the security stack and how attacks move through the system.
Traditional security solutions do this by either manually aggregating inputs from various tools or using a SIEM without native integrations to collate data. In contrast, Darktrace’s integration provides real-time intelligence communications between products to inform security teams.
For example, context of network activity can provide more holistic email security. There’s a strong correlation between the websites users visit and the people that they email, which means information like web traffic provides insight into email threats, and vice versa.
If an organization receives an email from a strange new sender, that happens to be have been sent from a domain nobody has ever visited, that added context could influence the aggression levels of actions taken. Integrations with endpoint security extends this type of informed decision-making to remote environments. These examples highlight the patented power of Darktrace/Network™ and Darktrace/Endpoint™ when paired with email coverage.
Email activity is tied to cloud/SaaS application account activity in an even more direct way. In the case of an account takeover, a suspicious Microsoft 365 login becomes even more suspicious if it is followed by highly unusual email activity, like new inbox rules being created. Too many email security solutions focus on the inbox alone, but viewing these areas in a single scope is critical for security teams wanting to understand the full timeline of an incident.
To this end, Darktrace creates a 360-degree view of each user and their behavior. This comprehensive view goes beyond native security monitoring tools, allowing security teams to identify instances of data exfiltration, human error, misdirected emails, inappropriate link sharing, unusual log activity, and more.
In one real-life example, the security team saw an attack from both an email and a SaaS perspective to quickly understand the whole picture, thanks to Darktrace/Email and Darktrace/Apps™.
Darktrace customers are getting significant value from this integrated security stack. “The whole suite of products has given us 100% visibility across our whole ecosystem, which is fantastic. A lot of times we need to use many products to do that, and with the Darktrace products, I have that all in one,” commented a vice president of enterprise security and fraud management at a major credit union.
Siloed solutions are a massive pain point in the cyber industry. Most companies have several, layered tools in their security stacks. When there is little to no communication between them, the security team must contend with an inflated workload and misses out on value. They must learn how to navigate several different dashboards, translate between languages and terms, and manually correlate data, in addition to monitoring all the solutions daily. This process makes maintaining security more difficult for the team, especially in a threat landscape with increasingly complex and fast-paced attacks.
By sending and collecting information to and from other tools that the security team already uses, whether they are a part of Darktrace’s product stack or not, Darktrace/Email optimizes workflows so security teams can reallocate resources to larger, more strategic projects.
Collaborating Across Email Security and Cyber Risk Management Tools
Syncing email protections with cyber risk management tools even further reduces risk and hardens security.
When emails are received from domain names associated with the brand of the client, an attack surface management tool can automatically analyze if those domains should be included as part of the attack surface scope or trigger malicious domain responses.
In the other direction, when the attack surface management tool identifies malicious assets, like suspicious domains, spoofing sites, and typo squatters, it can inform email security decisions. With integrations between tools, these malicious assets automatically become watched domains with heightened sensitivity for inbound email.
This integrated risk reduction can occur internally as well. When security teams look at cyber risk from an internal perspective, they may identify attack paths and high value targets within the company’s digital estate. By leveraging this understanding, Darktrace can determine which employees are critical components of potential attack paths. Once determined, the AI can test them by creating phishing simulations using details like real-life communication patterns and calendar data. These tests generate insights that feed back into Darktrace/Email to harden the environment, for example by heightening sensitivity.
This demonstrates the benefits of combining Darktrace/Email and Darktrace PREVENT™. As part of the Cyber AI Loop, these connections between email security and cyber risk management are made easy for the security team to understand and act on. One customer noted how this integration had improved its security team’s workflow.
“The more you use of Darktrace, the better it can correlate on your behalf,” said a Chief Information Officer at a construction company. “That’s why we’re all in with Darktrace now. We now have a holistic Darktrace footprint, which benefits us because we have more of the modules working on our behalf and not having to do the correlations separately or in isolation.”
Supporting Compatibility with External Security Solutions
Darktrace/Email also works together with external tools. In addition to its mature integration with email providers like Microsoft 365 and Google Workspaces, Darktrace/Email has an open architecture that makes it immensely flexible. It is both API-driven and compatible with syslog, so it can integrate with any security tool and feed into any SIEM or SOAR.
This unlimited capacity for integration allows Darktrace to detect and respond to threats more precisely with access to more data, as well as reduce the security team’s time-to-meaning by putting all relevant information in a single pane of glass.
Darktrace/Email is also part of the Darktrace Mobile App, so security teams can view notifications, reports, and remediation actions at any time, even on the go. In this way, Darktrace not only fits into the greater security posture, but also with employees’ day-to-day workflow.
Finally, Darktrace/Email supports data exports. These translate and share the data it collects within the email environment, allowing the security team to communicate key takeaways generated by Darktrace/Email to anyone within the organization. It can export directly to Microsoft Excel, or any other data analytics tool. This is especially useful for security teams as they work with other departments like IT, compliance, finance, and more.
Integrations Add Value to the Darktrace Partnership
While Darktrace/Email is a powerful tool on its own, a major source of its value comes from its compatibility with the rest of Darktrace, other tools, people, and processes.
Deploying multiple Darktrace products builds a robust security ecosystem that enhances detection while breaking down silos and improving workflows, therefore enabling the security team to take on higher-level and more strategic work. By integrating with external tools, Darktrace not only increases its own value but also maximizes the return on investment of other security solutions a team already has.
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Inside the SOC
How Abuse of ‘PerfectData Software’ May Create a Perfect Storm: An Emerging Trend in Account Takeovers
Amidst the ever-changing threat landscape, new tactics, techniques, and procedures (TTPs) seem to emerge daily, creating extreme challenges for security teams. The broad range of attack methods utilized by attackers seems to present an insurmountable problem: how do you defend against a playbook that does not yet exist?
Faced with the growing number of novel and uncommon attack methods, it is essential for organizations to adopt a security solution able to detect threats based on their anomalies, rather than relying on threat intelligence alone.
In March 2023, Darktrace observed an emerging trend in the use of an application known as ‘PerfectData Software’ for probable malicious purposes in several Microsoft 365 account takeovers.
Using its anomaly-based detection, Darktrace DETECT™ was able to identify the activity chain surrounding the use of this application, potentially uncovering a novel piece of threat actor tradecraft in the process.
Microsoft 365 Intrusions
In recent years, Microsoft’s Software-as-a-Service (SaaS) suite, Microsoft 365, along with its built-in identity and access management (IAM) service, Azure Active Directory (Azure AD), have been heavily targeted by threat actors due to their near-ubiquitous usage across industries. Four out of every five Fortune 500 companies, for example, use Microsoft 365 services [1].
Malicious actors typically gain entry to organizations’ Microsoft 365 environments by abusing either stolen account credentials or stolen session cookies [2]. Once inside, actors can access sensitive data within mailboxes or SharePoint repositories, and send out emails or Teams messages. This activity can often result in serious financial harm, especially in cases where the malicious actor’s end-goal is to elicit fraudulent transactions.
Darktrace regularly observes malicious actors behaving in predictable ways once they gain access to customer Microsoft 365 environment. One typical example is the creation of new inbox rules and sending deceitful emails intended to convince recipients to carry out subsequent actions, such as following a malicious link or providing sensitive information. It is also common for actors to register new applications in Azure AD so that they can be used to conduct follow-up activities, like mass-mailing or data theft. The registration of applications in Azure AD therefore seems to be a relatively predictable threat actor behavior [3][4]. Darktrace DETECT understands that unusual application registrations in Azure AD may constitute a deviation in expected behavior, and therefore a possible indicator of account compromise.
These registrations of applications in Azure AD are evidenced by creations of, as well as assignments of permissions to, Service Principals in Azure AD. Darktrace has detected a growing trend in actors creating and assigning permissions to a Service Principal named ‘PerfectData Software’. Further investigation of this Azure AD activity revealed it to be part of an ongoing account takeover.
‘PerfectData Software’ Activity
Darktrace observed variations of the following pattern of activity relating to an application named ‘PerfectData Software’ within its customer base:
- Actor signs in to a Microsoft 365 account from an endpoint associated with a Virtual Private Server (VPS) or Virtual Private Network (VPN) service
- Actor registers an application called 'PerfectData Software' with Azure AD, and then grants permissions to the application
- Actor accesses mailbox data and creates inbox rule
In two separate incidents, malicious actors were observed conducting their activities from endpoints associated with VPN services (HideMyAss (HMA) VPN and Surfshark VPN, respectively) and from endpoints within the Autonomous System AS396073 MAJESTIC-HOSTING-01.
In March 2023, Darktrace observed a malicious actor signing in to a Microsoft 365 account from a Kuwait-based IP address within the Autonomous System, AS198605 AVAST Software s.r.o. This IP address is associated with the VPN service, HMA VPN. Over the next couple of days, an actor (likely the same malicious actor) signed in to the account several more times from two different Nigeria-based endpoints, as well as a VPS-related endpoint and a HMA VPN endpoint.
During their login sessions, the actor performed a variety of actions. First, they created and assigned permissions to a Service Principal named ‘PerfectData Software’. This Service Principal creation represents the registration of an application called ‘PerfectData Software’ in Azure AD. Although the reason for registering this application is unclear, within a few days the actor registered and granted permission to another application, ‘Newsletter Software Supermailer’, and created a new inbox rule names ‘s’ on the mailbox of the hijacked account. This inbox rule moved emails meeting certain conditions to a folder named ‘RSS Subscription. The ‘Newsletter Software Supermailer’ application was likely registered by the actor to facilitate mass-mailing activity.
Immediately after these actions, Darktrace detected the actor sending out thousands of malicious emails from the account. The emails included an attachment named ‘Credit Transfer Copy.html’, which contained a suspicious link. Further investigation revealed that the customer’s network had received several fake invoice emails prior to this initial intrusion activity. Additionally, there was an unusually high volume of failed logins to the compromised account around the time of the initial access.
In a separate case also observed by Darktrace in March 2023, a malicious actor was observed signing in to a Microsoft 365 account from an endpoint within the Autonomous System, AS397086 LAYER-HOST-HOUSTON. The endpoint appears to be related to the VPN service, Surfshark VPN. This login was followed by several failed and successful logins from a VPS-related within the Autonomous System, AS396073 MAJESTIC-HOSTING-01. The actor was then seen registering and assigning permissions to an application called ‘PerfectData Software’. As with the previous example, the motives for this registration are unclear. The actor proceeded to log in several more times from a Surfshark VPN endpoint, however, they were not observed carrying out any further suspicious activity.
It was not clear in either of these examples, nor in fact any of cases observed by Darktrace, why actors had registered and assigned permissions to an application called ‘PerfectData Software’, and there do not appear to be any open-source intelligence (OSINT) resources or online literature related to the malicious usage of an application by that name. That said, there are several websites which appear to provide email migration and data recovery/backup tools under the moniker ‘PerfectData Software’.
It is unclear whether the use of ‘PerfectData Software’ by malicious actors observed on the networks of Darktrace customers was one of these tools. However, given the nature of the tools, it is possible that the actors intended to use them to facilitate the exfiltration of email data from compromises mailboxes.
If the legitimate software ‘PerfectData’ is the application in question in these incidents, it is likely being purchased and misused by attackers for malicious purposes. It is also possible the application referenced in the incidents is a spoof of the legitimate ‘PerfectData’ software designed to masquerade a malicious application as legitimate.
Darktrace Coverage
Cases of ‘PerfectData Software’ activity chains detected by Darktrace typically began with an actor signing into an internal user’s Microsoft 365 account from a VPN or VPS-related endpoint. These login events, along with the suspicious email and/or brute-force activity which preceded them, caused the following DETECT models to breach:
- SaaS / Access / Unusual External Source for SaaS Credential Use
- SaaS / Access / Suspicious Login Attempt
- SaaS / Compromise / Login From Rare Following Suspicious Login Attempt(s)
- SaaS / Email Nexus / Unusual Location for SaaS and Email Activity
Subsequent activities, including inbox rule creations, registration of applications in Azure AD, and mass-mailing activity, resulted in breaches of the following DETECT models.
- SaaS / Admin / OAuth Permission Grant
- SaaS / Compromise / Unusual Logic Following OAuth Grant
- SaaS / Admin / New Application Service Principal
- IaaS / Admin / Azure Application Administration Activities
- SaaS / Compliance / New Email Rule
- SaaS / Compromise / Unusual Login and New Email Rule
- SaaS / Email Nexus / Suspicious Internal Exchange Activity
- SaaS / Email Nexus / Possible Outbound Email Spam
- SaaS / Compromise / Unusual Login and Outbound Email Spam
- SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
In cases where Darktrace RESPOND™ was enabled in autonomous response mode, ‘PerfectData Software’ activity chains resulted in breaches of the following RESPOND models:
• Antigena / SaaS / Antigena Suspicious SaaS Activity Block
• Antigena / SaaS / Antigena Significant Compliance Activity Block
In response to these model breaches, Darktrace RESPOND took immediate action, performing aggressive, inhibitive actions, such as forcing the actor to log out of the SaaS platform, and disabling the user entirely. When applied autonomously, these RESPOND actions would seriously impede an attacker’s progress and minimize network disruption.
In addition, Darktrace Cyber AI Analyst was able to autonomously investigate registrations of the ‘PerfectData Software’ application and summarized its findings into digestible reports.
Conclusion
Due to the widespread adoption of Microsoft 365 services in the workplace and continued emphasis on a remote workforce, account hijackings now pose a more serious threat to organizations around the world than ever before. The cases discussed here illustrate the tendency of malicious actors to conduct their activities from endpoints associated with VPN services, while also registering new applications, like PerfectData Software, with malicious intent.
While it was unclear exactly why the malicious actors were using ‘PerfectData Software’ as part of their account hijacking, it is clear that either the legitimate or spoofed version of the application is becoming an very likely emergent piece of threat actor tradecraft.
Darktrace DETECT’s anomaly-based approach to threat detection allowed it to recognize that the use of ‘PerfectData Software’ represented a deviation in the SaaS user’s expected behavior. While Darktrace RESPOND, when enabled in autonomous response mode, was able to quickly take preventative action against threat actors, blocking the potential use of the application for data exfiltration or other nefarious purposes.
Appendices
MITRE ATT&CK Mapping
Reconnaissance:
• T1598 – Phishing for Information
Credential Access:
• T1110 – Brute Force
Initial Access:
• T1078.004 – Valid Accounts: Cloud Accounts
Command and Control:
• T1105 – Ingress Tool Transfer
Persistence:
• T1098.003 – Account Manipulation: Additional Cloud Roles
Collection:
• T1114 – Email Collection
Defense Evasion:
• T1564.008 – Hide Artifacts: Email Hiding Rules
Lateral Movement:
• T1534 – Internal Spearphishing
Unusual Source IPs
• 5.62.60[.]202 (AS198605 AVAST Software s.r.o.)
• 160.152.10[.]215 (AS37637 Smile-Nigeria-AS)
• 197.244.250[.]155 (AS37705 TOPNET)
• 169.159.92[.]36 (AS37122 SMILE)
• 45.62.170[.]237 (AS396073 MAJESTIC-HOSTING-01)
• 92.38.180[.]49 (AS202422 G-Core Labs S.A)
• 129.56.36[.]26 (AS327952 AS-NATCOM)
• 92.38.180[.]47 (AS202422 G-Core Labs S.A.)
• 107.179.20[.]214 (AS397086 LAYER-HOST-HOUSTON)
• 45.62.170[.]31 (AS396073 MAJESTIC-HOSTING-01)
References
[1] https://www.investing.com/academy/statistics/microsoft-facts/
[2] https://intel471.com/blog/countering-the-problem-of-credential-theft
[3] https://darktrace.com/blog/business-email-compromise-to-mass-phishing-campaign-attack-analysis
[4] https://darktrace.com/blog/breakdown-of-a-multi-account-compromise-within-office-365
Blog
Cloud
Darktrace Integrates Self-Learning AI with Amazon Security Lake to Support Security Investigations
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Darktrace has deepened its relationship with AWS by integrating its detection and response capabilities with Amazon Security Lake.
This development will allow mutual customers to seamlessly combine Darktrace AI’s bespoke understanding of their organization with the Threat Intelligence offered by other security tools, and investigate all of their alerts in one central location.
This integration will improve the value security teams get from both products, streamlining analyst workflows and improving their ability to detect and respond to the full spectrum of known and unknown cyber-threats.
How Darktrace and Amazon Security Lake augment security teams
Amazon Security Lake is a newly-released service that automatically centralizes an organization’s security data from cloud, on-premises, and custom sources into a customer owned purpose-built data lake. Both Darktrace and Amazon Security Lake support the Open Cybersecurity Schema Framework (OCSF), an open standard to simplify, combine, and analyze security logs.
Customers can store security logs, events, alerts, and other relevant data generated by various AWS services and security tools. By consolidating security data in a central lake, organizations can gain a holistic view of their security posture, perform advanced analytics, detect anomalies and open investigations to improve their security practices.
With Darktrace DETECT and RESPOND AI engines covering all assets across IT, OT, network, endpoint, IoT, email and cloud, organizations can augment the value of their security data lakes by feeding Darktrace’s rich and context-aware datapoints to Amazon Security Lake.
Amazon Security Lake empowers security teams to improve the protection of your digital estate:
- Quick and painless data normalization
- Fast-tracks ability to investigate, triage and respond to security events
- Broader visibility aids more effective decision-making
- Surfaces and prioritizes anomalies for further investigation
- Single interface for seamless data management
How will Darktrace customers benefit?
Across the Cyber AI Loop, all Darktrace solutions have been architected with AWS best practices in mind. With this integration, Darktrace is bringing together its understanding of ‘self’ for every organization with the centralized data visibility of the Amazon Security Lake. Darktrace’s unique approach to cyber security, powered by groundbreaking AI research, delivers a superior dataset based on a deep and interconnected understanding of the enterprise.
Where other cyber security solutions are trained to identify threats based on historical attack data and techniques, Darktrace DETECT gains a bespoke understanding of every digital environment, continuously analyzing users, assets, devices and the complex relationships between them. Our AI analyzes thousands of metrics to reveal subtle deviations that may signal an evolving issue – even unknown techniques and novel malware. It distinguishes between malicious and benign behavior, identifying harmful activity that typically goes unnoticed. This rich dataset is fed into RESPOND, which takes precise action to neutralize threats against any and every asset, no matter where data resides.
Both DETECT and RESPOND are supported by Darktrace Self-Learning AI, which provides full, real-time visibility into an organization’s systems and data. This always-on threat analysis already makes humans better at cyber security, improving decisions and outcomes based on total visibility of the digital ecosystem, supporting human performance with AI coverage and empowering security teams to proactively protect critical assets.
Converting Darktrace alerts to the Amazon Security Lake Open Cybersecurity Schema Framework (OCSF) supplies the Security Operations Center (SOC) and incident response team with contextualized data, empowering them to accelerate their investigation, triage and response to potential cyber threats.
Darktrace is available for purchase on the AWS Marketplace.
Learn more about how Darktrace provides full-coverage, AI-powered cloud security for AWS, or see how our customers use Darktrace in their AWS cloud environments.
