Learn how Darktrace leveraged generative AI tools to detect and combat phishing email campaigns. Discover how AI is reshaping cybersecurity strategies.
Stopping the bad while allowing the good
Since its inception, email has been regarded as one of the most important tools for businesses, revolutionizing communication and allowing global teams to become even more connected. But besides organizations heavily relying on email for their daily operations, threat actors have also recognized that the inbox is one of the easiest ways to establish an initial foothold on the network.
Today, not only are phishing campaigns and social engineering attacks becoming more prevalent, but the level of sophistication of these attacks are also increasing with the help of generative AI tools that allow for the creation of hyper-realistic emails with minimal errors, effectively lowering the barrier to entry for threat actors. These diverse and stealthy types of attacks evade traditional email security tools based on rules and signatures, because they are less likely to contain the low-sophistication markers of a typical phishing attack.
In a situation where the sky is the limit for attackers and security teams are lean, how can teams equip themselves to tackle these threats? How can they accurately detect increasingly realistic malicious emails and neutralize these threats before it is too late? And importantly, how can email security block these threats while allowing legitimate emails to flow freely?
Instead of relying on past attack data, Darktrace’s Self-Learning AI detects the slightest deviation from a user’s pattern of life and responds autonomously to contain potential threats, stopping novel attacks in their tracks before damage is caused. It doesn’t define ‘good’ and ‘bad’ like traditional email tools, rather it understands each user and what is normal for them – and what’s not.
This blog outlines how Darktrace/Email™ used its understanding of ‘normal’ to accurately detect and respond to a sustained phishing campaign targeting a real-life company.
Responding to a sustained phishing attack
Over the course of 24 hours, Darktrace detected multiple emails containing different subjects, all from different senders to different recipients in one organization. These emails were sent from different IP addresses, but all came from the same autonomous system number (ASN).
Figure 1: The sender freemail addresses and subject lines all followed a certain format. The subject lines followed the format of “<First name> <Last name>”, possibly to induce curiosity. The senders were all freemail accounts and contained first names, last names and some numbers, showing the attempts to make these email addresses appear legitimate.
The emails themselves had many suspicious indicators. All senders had no prior association with the recipient, and the emails generated a high general inducement score. This score is generated by structural and non-specific content analysis of the email – a high score indicates that the email is trying to induce the recipient into taking a particular action, which may lead to account compromise.
Additionally, each email contained a visually prominent link to a file storage service, hidden behind a shortened bit.ly link. The similarities across all these emails pointed to a sustained campaign targeting the organization by a single threat actor.
Figure 2: One of the emails is shown above. Like all the other emails, it contained a highly suspicious and shortened link.
Figure 3: In another one of the emails, the link observed had similar characteristics. But this email stands out from the rest. The sender's name seems to be randomly set – the 3 alphabets are close to each other on the keyboard.
With all these suspicious indicators, many models were breached. This drove up the anomaly score, causing Darktrace/Email to hold all suspicious emails from the recipients’ inboxes, safeguarding the recipients from potential account compromise and disallowing the threats from taking hold in the network.
Imagining a phishing attack without Darktrace/Email
So what could have happened if Darktrace had not withheld these emails, and the recipients had clicked on the links? File storage sites have a wide variety of uses that allow attackers to be creative in their attack strategy. If the user had clicked on the shortened link, the possible consequences are numerous. The link could have led to a login page for unsuspecting victims to input their credentials, or it could have hosted malware that would automatically download if the link was clicked. With the compromised credentials, threat actors could even bypass MFA, change email rules, or gain privileged access to a network. The downloaded malware might also be a keylogger, leading to cryptojacking, or could open a back door for threat actors to return to at a later time.
Figure 4: Darktrace/Email highlights suspicious link characteristics and provides an option to preview the pages.
Figure 5: At the point of writing, both links could not be reached. This could be because they were one-time unique links created specifically for the user, and can no longer be accessed once the campaign has ceased.
The limits of traditional email security tools
Secure email gateways (SEGs) and static AI security tools may have found it challenging to detect this phishing campaign as malicious. While Darktrace was able to correlate these emails to determine that a sustained phishing campaign was taking place, the pattern among these emails is far too generic for specific rules as set in traditional security tools. If we take the characteristic of the freemail account sender as an example, setting a rule to block all emails from freemail accounts may lead to more legitimate emails being withheld, since these addresses have a variety of uses.
With these factors in mind, these emails could have easily slipped through traditional security filters and led to a devastating impact on the organization.
Conclusion
As threat actors step up their attacks in sophistication, prioritizing email security is more crucial than ever to preserving a safe digital environment. In response to these challenges, Darktrace/Email offers a set-and-forget solution that continuously learns and adapts to changes in the organization.
Through an evolving understanding of every environment in which it is deployed, its threat response becomes increasingly precise in neutralizing only the bad, while allowing the good – delivering email security that doesn’t come at the expense of business growth.
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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
ABOUT ThE AUTHOR
Germaine Tan
VP of Cyber Risk Management
Germaine is the Director of Analysis, APAC at Darktrace. Based in Singapore, she works with CISOs, managers and security teams all over APAC on model optimization and operationalization of Darktrace in their digital environments. She also manages the team of 17 analysts in the APAC region that threat hunts and monitors networks from all over the world. Germaine holds a Bachelor of Science in Engineering and a Masters of Science in Technology Management from Nanyang Technological University. She is CISSP, CRISC and CEH certified.
How to Protect your Organization Against Microsoft Teams Phishing Attacks
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.
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.
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.
Don’t Take the Bait: How Darktrace Keeps Microsoft Teams Phishing Attacks at Bay
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.
Figure 1: Darktrace’s detection of unusual messages being sent by a suspicious external user via Microsoft Teams.
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.
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.
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.
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.
Conclusion
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
Appendix
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
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