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Cyber Security Threats - Email Compromise With Generative AI

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01
Apr 2023
01
Apr 2023
Discover how generative AI is impacting email attacks and what companies can do to prepare for more sophisticated and targeted attacker campaigns.

Email communications in the era of generative AI

Today’s headlines on cyber security attacks are dominated by serious breaches that cripple critical national infrastructure providers, wreak geopolitical havoc through nation state espionage, and create paralyzing financial demands through extortion and ransomware. But how do these breaches occur in the first place, and why do they keep happening?

Social engineering – specifically malicious cyber campaigns delivered via email - remain the primary source of an organization’s vulnerability to attack. A recent survey conducted by Darktrace to 6,700 global cross-industry professionals across the UK, US, Australia, France, Germany, and Netherlands, found almost a third (30%) have fallen victim to a fraudulent email. The risk, as ever, seems to be uncontrollably on the rise – 70% of respondents have noticed an increase in the frequency of malicious emails in the last six months. 

At the end of last year, I wrote about how widespread accessibility to generative AI has compounded the problem, leading to likely efficiency gains for skilled threat actors launching email attacks. Just a few weeks ago, we published research which demonstrated that while the number of email attacks across our own customer base has remained steady since ChatGPT’s release, those that rely on tricking victims into clicking malicious links have declined, while linguistic complexity, including text volume, punctuation, and sentence length among others, have increased. This indicates that cyber-criminals may be redirecting their focus to crafting more sophisticated social engineering scams that exploit user trust delivered over email. 

Our latest findings, conducted by Darktrace Research, today reveal a 135% increase in ‘novel social engineering attacks’ across thousands of active Darktrace/Email customers from January to February 2023, corresponding with the widespread adoption of ChatGPT. A novel social engineering phishing email is an email attack that shows a strong linguistic deviation – semantically and syntactically – compared to other phishing emails. The trend suggests that generative AI, such as ChatGPT, is providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale.

Organizations are already well aware of the danger novel threats pose – globally, 82% of respondents reported are concerned that hackers can use generative AI to create scam emails that are indistinguishable from genuine communication.

Navigating the trust deficit 

Employees are being exploited continuously through their primary means of communication - email. Given that humans, and our psychology, are at the heart of the problem, organizations have scrambled to develop awareness and training programs that are delivered routinely to employees in an attempt to help them defend themselves and their organization. While a defense-in-depth approach is generally a good practice to follow, the value of security awareness training, teaching employees to spot attempts at social engineering delivered in text format, is diminishing rapidly. This problem has become especially evident now that we find ourselves in a world where ‘bad’ emails look all but undistinguishable to the human eye from ‘good’ emails. 

Over emphasizing the responsibility of employees poses a business challenge as well as a security problem: a bloated trust deficit. In times of economic uncertainty, business success is predicated on employee productivity, creativity, and efficiency. All three of these are squashed when employees treat the communication they receive, both internal and external, with forensic suspicion and mistrust. 

As generative AI becomes more mainstream – across images, audio, video, and text – we anticipate that this erosion of trust in digital communication will only continue. What happens to the workplace if an employee is left questioning their own perception when communicating with their manager or a colleague, who they can see and hear over a video conference call, but who may be an entirely fictitious creation?

The way forward

The future lies in a partnership between artificial intelligence and human beings where the algorithms are responsible for determining whether communication is malicious or benign, thereby taking the burden of responsibility off the human. In turn, humans can pursue activities that drive productivity and performance. Current training and awareness programs, coupled with traditional email security technologies which assume that knowledge of past attacks will help predict campaigns, are not sustainable in this rapidly evolving landscape. 

Our research reveals that traditional email security tools that rely on knowledge of past threats, take an average of thirteen days from an attack being launched on a victim to that attack being detected. This leaves defenders vulnerable for almost two weeks if they rely solely on traditional tools. When this statistic is contextualized against the 135% increase we’ve seen in novel social engineering campaigns, the inefficiency of ‘attack centric’ email security is made perfectly evident. If we don’t know how to define entirely new and unique attacks, how can we ever hope to recognize them based on past attacks? 

A deep understanding of ‘you’ is needed in the face of these radical changes to the email threat landscape. Instead of trying to predict attacks, an understanding of your employees’ behavior, based from their email inbox, is needed to create patterns of life for every email user: their relationships, tone and sentiments and hundreds of other data points. By leveraging AI to combat email security threats, we not only reduce risk, but revitalize organizational trusts and contribute to business outcomes.

Ironically, generative AI may be worsening the social engineering challenge, but AI that knows you, could be the parry. 

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Darktrace Cyber-Analysten sind erstklassige Experten für Threat Intelligence, Threat Hunting und Incident Response. Sie bieten Tausenden von Darktrace Kunden auf der ganzen Welt rund um die Uhr SOC-Support. Einblicke in das SOC-Team wird ausschließlich von diesen Experten verfasst und bietet Analysen von Cyber-Vorfällen und Bedrohungstrends, die auf praktischen Erfahrungen in diesem Bereich basieren.
AUTOR
ÜBER DEN AUTOR
Max Heinemeyer
Leiter der Produktabteilung

Max is a cyber security expert with over a decade of experience in the field, specializing in a wide range of areas such as Penetration Testing, Red-Teaming, SIEM and SOC consulting and hunting Advanced Persistent Threat (APT) groups. At Darktrace, Max is closely involved with Darktrace’s strategic customers & prospects. He works with the R&D team at Darktrace, shaping research into new AI innovations and their various defensive and offensive applications. Max’s insights are regularly featured in international media outlets such as the BBC, Forbes and WIRED. Max holds an MSc from the University of Duisburg-Essen and a BSc from the Cooperative State University Stuttgart in International Business Information Systems.

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How to Protect your Organization Against Microsoft Teams Phishing Attacks

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21
May 2024

The problem: Microsoft Teams phishing attacks are on the rise

Around 83% of Fortune 500 companies rely on Microsoft Office products and services1, with Microsoft Teams and Microsoft SharePoint in particular emerging as critical platforms to the business operations of the everyday workplace. Researchers across the threat landscape have begun to observe these legitimate services being leveraged more and more by malicious actors as an initial access method.

As Teams becomes a more prominent feature of the workplace many employees rely on it for daily internal and external communication, even surpassing email usage in some organizations. As Microsoft2 states, "Teams changes your relationship with email. When your whole group is working in Teams, it means you'll all get fewer emails. And you'll spend less time in your inbox, because you'll use Teams for more of your conversations."

However, Teams can be exploited to send targeted phishing messages to individuals either internally or externally, while appearing legitimate and safe. Users might receive an external message request from a Teams account claiming to be an IT support service or otherwise affiliated with the organization. Once a user has accepted, the threat actor can launch a social engineering campaign or deliver a malicious payload. As a primarily internal tool there is naturally less training and security awareness around Teams – due to the nature of the channel it is assumed to be a trusted source, meaning that social engineering is already one step ahead.

Screenshot of a Microsoft Teams message request from a Midnight Blizzard-controlled account (courtesy of Microsoft)
Figure 1: Screenshot of a Microsoft Teams message request from a Midnight Blizzard-controlled account (courtesy of Microsoft)

Microsoft Teams Phishing Examples

Microsoft has identified several major phishing attacks using Teams within the past year.

In July 2023, Microsoft announced that the threat actor known as Midnight Blizzard – identified by the United States as a Russian state-sponsored group – had launched a series of phishing campaigns via Teams with the aim of stealing user credentials. These attacks used previously compromised Microsoft 365 accounts and set up new domain names that impersonated legitimate IT support organizations. The threat actors then used social engineering tactics to trick targeted users into sharing their credentials via Teams, enabling them to access sensitive data.  

At a similar time, threat actor Storm-0324 was observed sending phishing lures via Teams containing links to malicious SharePoint-hosted files. The group targeted organizations that allow Teams users to interact and share files externally. Storm-0324’s goal is to gain initial access to hand over to other threat actors to pursue more dangerous follow-on attacks like ransomware.

For a more in depth look at how Darktrace stops Microsoft Teams phishing read our blog: Don’t Take the Bait: How Darktrace Keeps Microsoft Teams Phishing Attacks at Bay

The market: Existing Microsoft Teams security solutions are insufficient

Microsoft’s native Teams security focuses on payloads, namely links and attachments, as the principal malicious component of any phishing. These payloads are relatively straightforward to detect with their experience in anti-virus, sandboxing, and IOCs. However, this approach is unable to intervene before the stage at which payloads are delivered, before the user even gets the chance to accept or deny an external message request. At the same time, it risks missing more subtle threats that don’t include attachments or links – like early stage phishing, which is pure social engineering – or completely new payloads.

Equally, the market offering for Teams security is limited. Security solutions available on the market are always payload-focused, rather than taking into account the content and context in which a link or attachment is sent. Answering questions like:

  • Does it make sense for these two accounts to speak to each other?
  • Are there any linguistic indicators of inducement?

Furthermore, they do not correlate with email to track threats across multiple communication environments which could signal a wider campaign. Effectively, other market solutions aren’t adding extra value – they are protecting against the same types of threats that Microsoft is already covering by default.

The other aspect of Teams security that native and market solutions fail to address is the account itself. As well as focusing on Teams threats, it’s important to analyze messages to understand the normal mode of communication for a user, and spot when a user’s Teams activity might signal account takeover.

The solution: How Darktrace protects Microsoft Teams against sophisticated threats

With its biggest update to Darktrace/Email ever, Darktrace now offers support for Microsoft Teams. With that, we are bringing the same AI philosophy that protects your email and accounts to your messaging environment.  

Our Self-Learning AI looks at content and context for every communication, whether that’s sent in an email or Teams message. It looks at actual user behavior, including language patterns, relationship history of sender and recipient, tone and payloads, to understand if a message poses a threat. This approach allows Darktrace to detect threats such as social engineering and payloadless attacks using visibility and forensic capabilities that Microsoft security doesn’t currently offer, as well as early symptoms of account compromise.  

Unlike market solutions, Darktrace doesn’t offer a siloed approach to Teams security. Data and signals from Teams are shared across email to inform detection, and also with the wider Darktrace ActiveAI security platform. By correlating information from email and Teams with network and apps security, Darktrace is able to better identify suspicious Teams activity and vice versa.  

Interested in the other ways Darktrace/Email augments threat detection? Read our latest blog on how improving the quality of end-user reporting can decrease the burden on the SOC. To find our more about Darktrace's enduring partnership with Microsoft, click here.

References

[1] Essential Microsoft Office Statistics in 2024

[2] Microsoft blog, Microsoft Teams and email, living in harmony, 2024

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Carlos Gray
Product Manager

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Don’t Take the Bait: How Darktrace Keeps Microsoft Teams Phishing Attacks at Bay

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20
May 2024

Social Engineering in Phishing Attacks

Faced with increasingly cyber-aware endpoint users and vigilant security teams, more and more threat actors are forced to think psychologically about the individuals they are targeting with their phishing attacks. Social engineering methods like taking advantage of the human emotions of their would-be victims, pressuring them to open emails or follow links or face financial or legal repercussions, and impersonating known and trusted brands or services, have become common place in phishing campaigns in recent years.

Phishing with Microsoft Teams

The malicious use of the popular communications platform Microsoft Teams has become widely observed and discussed across the threat landscape, with many organizations adopting it as their primary means of business communication, and many threat actors using it as an attack vector. As Teams allows users to communicate with people outside of their organization by default [1], it becomes an easy entry point for potential attackers to use as a social engineering vector.

In early 2024, Darktrace/Apps™ identified two separate instances of malicious actors using Microsoft Teams to launch a phishing attack against Darktrace customers in the Europe, the Middle East and Africa (EMEA) region. Interestingly, in this case the attackers not only used a well-known legitimate service to carry out their phishing campaign, but they were also attempting to impersonate an international hotel chain.

Despite these attempts to evade endpoint users and traditional security measures, Darktrace’s anomaly detection enabled it to identify the suspicious phishing messages and bring them to the customer’s attention. Additionally, Darktrace’s autonomous response capability, was able to follow-up these detections with targeted actions to contain the suspicious activity in the first instance.

Darktrace Coverage of Microsoft Teams Phishing

Chats Sent by External User and Following Actions by Darktrace

On February 29, 2024, Darktrace detected the presence of a new external user on the Software-as-a-Service (SaaS) environment of an EMEA customer for the first time. The user, “REDACTED@InternationalHotelChain[.]onmicrosoft[.]com” was only observed on this date and no further activities were detected from this user after February 29.

Later the same day, the unusual external user created its first chat on Microsoft Teams named “New Employee Loyalty Program”. Over the course of around 5 minutes, the user sent 63 messages across 21 different chats to unique internal users on the customer’s SaaS platform. All these chats included the ‘foreign tenant user’ and one of the customer’s internal users, likely in an attempt to remain undetected. Foreign tenant user, in this case, refers to users without access to typical internal software and privileges, indicating the presence of an external user.

Darktrace’s detection of unusual messages being sent by a suspicious external user via Microsoft Teams.
Figure 1: Darktrace’s detection of unusual messages being sent by a suspicious external user via Microsoft Teams.
Advanced Search results showing the presence of a foreign tenant user on the customer’s SaaS environment.
Figure 2: Advanced Search results showing the presence of a foreign tenant user on the customer’s SaaS environment.

Darktrace identified that the external user had connected from an unusual IP address located in Poland, 195.242.125[.]186. Darktrace understood that this was unexpected behavior for this user who had only previously been observed connecting from the United Kingdom; it further recognized that no other users within the customer’s environment had connected from this external source, thereby deeming it suspicious. Further investigation by Darktrace’s analyst team revealed that the endpoint had been flagged as malicious by several open-source intelligence (OSINT) vendors.

External Summary highlighting the rarity of the rare external source from which the Teams messages were sent.
Figure 3: External Summary highlighting the rarity of the rare external source from which the Teams messages were sent.

Following Darktrace’s initial detection of these suspicious Microsoft Teams messages, Darktrace's autonomous response was able to further support the customer by providing suggested mitigative actions that could be applied to stop the external user from sending any additional phishing messages.

Unfortunately, at the time of this attack Darktrace's autonomous response capability was configured in human confirmation mode, meaning any autonomous response actions had to be manually actioned by the customer. Had it been enabled in autonomous response mode, it would have been able promptly disrupt the attack, disabling the external user to prevent them from continuing their phishing attempts and securing precious time for the customer’s security team to begin their own remediation procedures.

Darktrace autonomous response actions that were suggested following the ’Large Volume of Messages Sent from New External User’ detection model alert.
Figure 4: Darktrace autonomous response actions that were suggested following the ’Large Volume of Messages Sent from New External User’ detection model alert.

External URL Sent within Teams Chats

Within the 21 Teams chats created by the threat actor, Darktrace identified 21 different external URLs being sent, all of which included the domain "cloud-sharcpoint[.]com”. Many of these URLs had been recently established and had been flagged as malicious by OSINT providers [3]. This was likely an attempt to impersonate “cloud-sharepoint[.]com”, the legitimate domain of Microsoft SharePoint, with the threat actor attempting to ‘typo-squat’ the URL to convince endpoint users to trust the legitimacy of the link. Typo-squatted domains are commonly misspelled URLs registered by opportunistic attackers in the hope of gaining the trust of unsuspecting targets. They are often used for nefarious purposes like dropping malicious files on devices or harvesting credentials.

Upon clicking this malicious link, users were directed to a similarly typo-squatted domain, “InternatlonalHotelChain[.]sharcpoInte-docs[.]com”. This domain was likely made to appear like the SharePoint URL used by the international hotel chain being impersonated.

Redirected link to a fake SharePoint page attempting to impersonate an international hotel chain.
Figure 5: Redirected link to a fake SharePoint page attempting to impersonate an international hotel chain.

This fake SharePoint page used the branding of the international hotel chain and contained a document named “New Employee Loyalty Program”; the same name given to the phishing messages sent by the attacker on Microsoft Teams. Upon accessing this file, users would be directed to a credential harvester, masquerading as a Microsoft login page, and prompted to enter their credentials. If successful, this would allow the attacker to gain unauthorized access to a user’s SaaS account, thereby compromising the account and enabling further escalation in the customer’s environment.

Figure 6: A fake Microsoft login page that popped-up when attempting to open the ’New Employee Loyalty Program’ document.

This is a clear example of an attacker attempting to leverage social engineering tactics to gain the trust of their targets and convince them to inadvertently compromise their account. Many corporate organizations partner with other companies and well-known brands to offer their employees loyalty programs as part of their employment benefits and perks. As such, it would not necessarily be unexpected for employees to receive such an offer from an international hotel chain. By impersonating an international hotel chain, threat actors would increase the probability of convincing their targets to trust and click their malicious messages and links, and unintentionally compromising their accounts.

In spite of the attacker’s attempts to impersonate reputable brands, platforms, Darktrace/Apps was able to successfully recognize the malicious intent behind this phishing campaign and suggest steps to contain the attack. Darktrace recognized that the user in question had deviated from its ‘learned’ pattern of behavior by connecting to the customer’s SaaS environment from an unusual external location, before proceeding to send an unusually large volume of messages via Teams, indicating that the SaaS account had been compromised.

A Wider Campaign?

Around a month later, in March 2024, Darktrace observed a similar incident of a malicious actor impersonating the same international hotel chain in a phishing attacking using Microsoft Teams, suggesting that this was part of a wider phishing campaign. Like the previous example, this customer was also based in the EMEA region.  

The attack tactics identified in this instance were very similar to the previously example, with a new external user identified within the network proceeding to create a series of Teams messages named “New Employee Loyalty Program” containing a typo-squatted external links.

There were a few differences with this second incident, however, with the attacker using the domain “@InternationalHotelChainExpeditions[.]onmicrosoft[.]com” to send their malicious Teams messages and using differently typo-squatted URLs to imitate Microsoft SharePoint.

As both customers targeted by this phishing campaign were subscribed to Darktrace’s Proactive Threat Notification (PTN) service, this suspicious SaaS activity was promptly escalated to the Darktrace Security Operations Center (SOC) for immediate triage and investigation. Following their investigation, the SOC team sent an alert to the customers informing them of the compromise and advising urgent follow-up.

Schlussfolgerung

While there are clear similarities between these Microsoft Teams-based phishing attacks, the attackers here have seemingly sought ways to refine their tactics, techniques, and procedures (TTPs), leveraging new connection locations and creating new malicious URLs in an effort to outmaneuver human security teams and conventional security tools.

As cyber threats grow increasingly sophisticated and evasive, it is crucial for organizations to employ intelligent security solutions that can see through social engineering techniques and pinpoint suspicious activity early.

Darktrace’s Self-Learning AI understands customer environments and is able to recognize the subtle deviations in a device’s behavioral pattern, enabling it to effectively identify suspicious activity even when attackers adapt their strategies. In this instance, this allowed Darktrace to detect the phishing messages, and the malicious links contained within them, despite the seemingly trustworthy source and use of a reputable platform like Microsoft Teams.

Credit to Min Kim, Cyber Security Analyst, Raymond Norbert, Cyber Security Analyst and Ryan Traill, Threat Content Lead

Anhang

Darktrace Model Detections

SaaS Model

Large Volume of Messages Sent from New External User

SaaS / Unusual Activity / Large Volume of Messages Sent from New External User

Indicators of Compromise (IoCs)

IoC – Type - Description

https://cloud-sharcpoint[.]com/[a-zA-Z0-9]{15} - Example hostname - Malicious phishing redirection link

InternatlonalHotelChain[.]sharcpolnte-docs[.]com – Hostname – Redirected Link

195.242.125[.]186 - External Source IP Address – Malicious Endpoint

MITRE Tactics

Tactic – Technique

Phishing – Initial Access (T1566)

References

[1] https://learn.microsoft.com/en-us/microsoftteams/trusted-organizations-external-meetings-chat?tabs=organization-settings

[2] https://www.virustotal.com/gui/ip-address/195.242.125.186/detection

[3] https://www.virustotal.com/gui/domain/cloud-sharcpoint.com

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About the author
Min Kim
Cyber Security Analyst
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