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How AI-Powered Email Solutions Can Level Up Security Teams
The modern security team faces challenges on all fronts – it is too often overstretched dealing with an increased attack surface, enabling workforces for secure remote work, and managing multiple security tools to protect that workforce. Added to that, the surge in more sophisticated phishing campaigns – now supported by AI tools – means that it’s harder than ever to pre-empt attacks.
The needs of the security team should be a key consideration when deploying an email security solution, as it’s them who will be accountable for the success and maintenance of the product. Minimizing time spent inside the user interface – through trusted detection and response technology combined with intuitive reporting and optimized workflows – should be front of mind for vendors in order to assure teams of their value.
Taking security teams off the frontline
No team should be spending all of their time maintaining email security policies, releasing emails that shouldn’t have been held, or holding back emails that should have been – all the things that traditional email security solutions have almost forced them to become accustomed to. A day in the life of an admin shouldn’t include tens – and certainly not hundreds – of minutes spent in their email security dashboard.
At the moment, teams are logging in far too often, and when they do, they’re forced to make individual decisions about safe listing and blocking domains, or releasing emails. These can lead to the creation of blanket rules that open up future windows for attackers – unintended consequences that ultimately create more work in the future. This type of hand-to-hand combat puts security teams on the frontline, when their time could be much better spent doing the high-level strategic work humans are best at.
Understanding You: A Different Approach to Email Security
In today’s discussions about email security, there is a consensus that relying on a gateway is no longer feasible. The new era is one of ICES (Integrated cloud email security) solutions and other tools leveraging artificial intelligence and APIs. But there's no point adopting new technology with an old philosophy – and most of these solutions use AI to automate the same old approach: looking at past attacks to try and stop the next.
This is where Darktrace/Email takes a fundamentally different and unique approach. It’s not just about using AI; it’s about using it in the right capacity. Our AI understands you – learning where users log in from, who they email, their behavior throughout the day – to tailor the detection and response process according to their individual profile. There’s no point withholding an email if only a tiny element of it poses a risk – Darktrace/Email takes the least aggressive action required to neutralize a threat. Instead of a blanket allow-deny criteria, it can rewrite links or withhold attachments based on its knowledge of the user’s normal inbox activity. Stopping malicious emails while allowing legitimate emails through – with risky elements neutralized – lifts security teams out of the fire-fighting activities described earlier and frees up their time for more strategic and valuable decision-making.
This is going to get me to reduce my current email security stack… this is going to take it to that level that I need it to”
- Early Look Customer, Darktrace/Email
Account Takeover
Embedded account takeover protection is an essential component of modern email security. Security teams need visibility not just over email breaches but of what happens once an attacker has control of an inbox, particularly in the most damaging use cases like Business Email Compromise (BEC) and ransomware. This entails understanding a user’s behavior in their inbox, outbound emails and beyond into their wider account activity. Darktrace captures a user’s activity across email and their Microsoft or Google account in a single pane of glass – detecting and countering all of the markers that could signify a compromised account.
Insights from other cloud applications and network devices gleaned from Darktrace's wider visibility of the business can bring a 360° understanding of the user, further enhancing detection of account takeover and other harmful activity.
What ‘user-friendly’ actually looks like
The best user interface is one that you never have to log into. In an ideal world, teams are able to visit their tools less frequently because intelligent AI is automating work previously done by humans. This is made possible by Darktrace’s precision detection and response technology, which takes appropriate action on emails and accounts to neutralize threats without disrupting day-to-day business operations.
The second-best user interface is one where you can quickly log in and get key insights fast, whether that’s regarding an action taken or the current activity of a user – and then get out. Darktrace/Email enables teams to get key information quickly, at both a high and granular level. The dashboard offers immediate insights into users and emails, with a real-time snapshot of active user identities, targeted user and actioned emails, segmented by type of attack.
At every touchpoint, Darktrace reduces friction with optimized workflows. From being able to quickly identify VIPs to safely previewing links and attachments, security teams can get the information they need without needing to switch between windows or navigate inaccessible interfaces. Explainable AI gives users natural-language summaries of individual emails or the overall health of an email environment, and simplified action flows allow security teams to personalize security for different employees – for example, sending VIPs a unique notification, or taking extra precautions around employees who work in accounting. Taken together, this meaning that admins can spend even less time managing policies.
The ideal interface is also the one that’s the most accessible to you. The mobile app guarantees convenience for security teams, making available all the main functions of the interface for on-the-go analysis at any time or place. Teams can travel or leave the office while retaining the peace of mind that if a critical incident was to occur, they would be able to get instant visibility on the data and take action without needing to get back to their desks.
With every passing day, the security team can rest easier. Every activity is taken into account to help the AI tune and adapt over time to become even better at detecting and responding to threats.
Having email on the app is going to be game changing”
- Early Look Customer, Darktrace/Email
Getting the full picture
Most often, email is the entry point from which a threat actor moves stealthily throughout an organization collecting information and assets. Most solutions look at email in isolation, without prioritizing or connecting disparate events into a wider pattern.
In contrast, Darktrace/Email integrates seamlessly with Darktrace's Cyber AI Analyst, a technology that conducts autonomous enterprise-wide investigations around every alert produced by the wider Darktrace platform. Through this integration, malicious email activity is analyzed and displayed in the context of the full security incident to which it belongs. As a result, security teams can see why and how a wider problem might have originated in email and spread to other apps, endpoints, or the wider corporate network.
Empowering employees to take an active role in security
The role of the security team can be made more difficult if employees take a lax or disengaged approach to security – or if a user is given too much control, and has the ability to make potentially dangerous decisions. Training employees on security procedures is another to-do which can easily fall to the bottom of the agenda during busy periods, especially as point-in-time phishing simulations have proven to be not particularly effective.
To this end, Darktrace/Email uses Explainable AI to say in natural language what it thought about an email, and delivers its findings not just to the security team, but optionally to the wider workforce as well. Delivered in the form of contextual banners in emails, periodic digests, or directly in Outlook, these insights transform security education from a quarterly or yearly exercise into real-time security awareness. Our next blog will dive deeper into how employee engagement can support the security team’s efforts and harden defenses throughout the organization.
Because Darktrace is built on a fundamentally different approach, it not only stops novel and targeted sophisticated attacks but allows legitimate emails to flow through. This is what makes it a truly set-and-forget technology, with the AI taking on much of the heavy lifting previously undertaken by security teams.
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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.
