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Inside the SOC

PrivateLoader: network-based indicators of compromise

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26
Jul 2022
26
Jul 2022
This blog explores the network-based IOCs for PrivateLoader, a modular downloader which is increasingly being used by pay-per-install (PPI) providers to deliver malicious payloads.

Instead of delivering their malicious payloads themselves, threat actors can pay certain cybercriminals (known as pay-per-install (PPI) providers) to deliver their payloads for them. Since January 2022, Darktrace’s SOC has observed several cases of PPI providers delivering their clients’ payloads using a modular malware downloader known as ‘PrivateLoader’.

This blog will explore how these PPI providers installed PrivateLoader onto systems and outline the steps which the infected PrivateLoader bots took to install further malicious payloads. The details provided here are intended to provide insight into the operations of PrivateLoader and to assist security teams in identifying PrivateLoader bots within their own networks.  

Threat Summary 

Between January and June 2022, Darktrace identified the following sequence of network behaviours within the environments of several Darktrace clients. Patterns of activity involving these steps are paradigmatic examples of PrivateLoader activity:

1. A victim’s device is redirected to a page which instructs them to download a password-protected archive file from a file storage service — typically Discord Content Delivery Network (CDN)

2. The device contacts a file storage service (typically Discord CDN) via SSL connections

3. The device either contacts Pastebin via SSL connections, makes an HTTP GET request with the URI string ‘/server.txt’ or ‘server_p.txt’ to 45.144.225[.]57, or makes an HTTP GET request with the URI string ‘/proxies.txt’ to 212.193.30[.]45

4. The device makes an HTTP GET request with the URI string ‘/base/api/statistics.php’ to either 212.193.30[.]21, 85.202.169[.]116, 2.56.56[.]126 or 2.56.59[.]42

5. The device contacts a file storage service (typically Discord CDN) via SSL connections

6. The device makes a HTTP POST request with the URI string ‘/base/api/getData.php’ to either 212.193.30[.]21, 85.202.169[.]116, 2.56.56[.]126 or 2.56.59[.]42

7. The device finally downloads malicious payloads from a variety of endpoints

The PPI Business 

Before exploring PrivateLoader in more detail, the pay-per-install (PPI) business should be contextualized. This consists of two parties:  

1. PPI clients - actors who want their malicious payloads to be installed onto a large number of target systems. PPI clients are typically entry-level threat actors who seek to widely distribute commodity malware [1]

2. PPI providers - actors who PPI clients can pay to install their malicious payloads 

As the smugglers of the cybercriminal world, PPI providers typically advertise their malware delivery services on underground web forums. In some cases, PPI services can even be accessed via Clearnet websites such as InstallBest and InstallShop [2] (Figure 1).  

Figure 1: A snapshot of the InstallBest PPI login page [2]


To utilize a PPI provider’s service, a PPI client must typically specify: 

(A)  the URLs of the payloads which they want to be installed

(B)  the number of systems onto which they want their payloads to be installed

(C)  their geographical targeting preferences. 

Payment of course, is also required. To fulfil their clients’ requests, PPI providers typically make use of downloaders - malware which instructs the devices on which it is running to download and execute further payloads. PPI providers seek to install their downloaders onto as many systems as possible. Follow-on payloads are usually determined by system information garnered and relayed back to the PPI providers’ command and control (C2) infrastructure. PPI providers may disseminate their downloaders themselves, or they may outsource the dissemination to third parties called ‘affiliates’ [3].  

Back in May 2021, Intel 471 researchers became aware of PPI providers using a novel downloader (dubbed ‘PrivateLoader’) to conduct their operations. Since Intel 471’s public disclosure of the downloader back in Feb 2022 [4], several other threat research teams, such as the Walmart Cyber Intel Team [5], Zscaler ThreatLabz [6], and Trend Micro Research [7] have all provided valuable insights into the downloader’s behaviour. 

Anatomy of a PrivateLoader Infection

The PrivateLoader downloader, which is written in C++, was originally monolithic (i.e, consisted of only one module). At some point, however, the downloader became modular (i.e, consisting of multiple modules). The modules communicate via HTTP and employ various anti-analysis methods. PrivateLoader currently consists of the following three modules [8]: 

  • The loader module: Instructs the system on which it is running to retrieve the IP address of the main C2 server and to download and execute the PrivateLoader core module
  • The core module: Instructs the system on which it is running to send system information to the main C2 server, to download and execute further malicious payloads, and to relay information regarding installed payloads back to the main C2 server
  • The service module: Instructs the system on which it is running to keep the PrivateLoader modules running

Kill Chain Deep-Dive 

The chain of activity starts with the user’s browser being redirected to a webpage which instructs them to download a password-protected archive file from a file storage service such as Discord CDN. Discord is a popular VoIP and instant messaging service, and Discord CDN is the service’s CDN infrastructure. In several cases, the webpages to which users’ browsers were redirected were hosted on ‘hero-files[.]com’ (Figure 2), ‘qd-files[.]com’, and ‘pu-file[.]com’ (Figure 3). 

Figure 2: An image of a page hosted on hero-files[.]com - an endpoint which Darktrace observed systems contacting before downloading PrivateLoader from Discord CDN
Figure 3: An image of a page hosted on pu-file[.]com- an endpoint which Darktrace observed systems contacting before downloading PrivateLoader from Discord CDN


On attempting to download cracked/pirated software, users’ browsers were typically redirected to download instruction pages. In one case however, a user’s device showed signs of being infected with the malicious Chrome extension, ChromeBack [9], immediately before it contacted a webpage providing download instructions (Figure 4). This may suggest that cracked software downloads are not the only cause of users’ browsers being redirected to these download instruction pages (Figure 5). 

Figure 4: The event log for this device (taken from the Darktrace Threat Visualiser interface) shows that the device contacted endpoints associated with ChromeBack ('freychang[.]fun') prior to visiting a page ('qd-file[.]com') which instructed the device’s user to download an archive file from Discord CDN
 Figure 5: An image of the website 'crackright[.]com'- a provider of cracked software. Systems which attempted to download software from this website were subsequently led to pages providing instructions to download a password-protected archive from Discord CDN


After users’ devices were redirected to pages instructing them to download a password-protected archive, they subsequently contacted cdn.discordapp[.]com over SSL. The archive files which users downloaded over these SSL connections likely contained the PrivateLoader loader module. Immediately after contacting the file storage endpoint, users’ devices were observed either contacting Pastebin over SSL, making an HTTP GET request with the URI string ‘/server.txt’ or ‘server_p.txt’ to 45.144.225[.]57, or making an HTTP GET request with the URI string ‘/proxies.txt’ to 212.193.30[.]45 (Figure 6).

Distinctive user-agent strings such as those containing question marks (e.g. ‘????ll’) and strings referencing outdated Chrome browser versions were consistently seen in these HTTP requests. The following chrome agent was repeatedly observed: ‘Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/74.0.3729.169 Safari/537.36’.

In some cases, devices also displayed signs of infection with other strains of malware such as the RedLine infostealer and the BeamWinHTTP malware downloader. This may suggest that the password-protected archives embedded several payloads.

Figure 6: This figure, obtained from Darktrace's Advanced Search interface, represents the post-infection behaviour displayed by a PrivateLoader bot. After visiting hero-files[.]com and downloading the PrivateLoader loader module from Discord CDN, the device can be seen making HTTP GET requests for ‘/proxies.txt’ and ‘/server.txt’ and contacting pastebin[.]com

It seems that PrivateLoader bots contact Pastebin, 45.144.225[.]57, and 212.193.30[.]45 in order to retrieve the IP address of PrivateLoader’s main C2 server - the server which provides PrivateLoader bots with payload URLs. This technique used by the operators of PrivateLoader closely mirrors the well-known espionage tactic known as ‘dead drop’.

The dead drop is a method of espionage tradecraft in which an individual leaves a physical object such as papers, cash, or weapons in an agreed hiding spot so that the intended recipient can retrieve the object later on without having to come in to contact with the source. When threat actors host information about core C2 infrastructure on intermediary endpoints, the hosted information is analogously called a ‘Dead Drop Resolver’ or ‘DDR’. Example URLs of DDRs used by PrivateLoader:

  • https://pastebin[.]com/...
  • http://212.193.30[.]45/proxies.txt
  • http://45.144.225[.]57/server.txt
  • http://45.144.255[.]57/server_p.txt

The ‘proxies.txt’ DDR hosted on 212.193.40[.]45 contains a list of 132 IP address / port pairs. The 119th line of this list includes a scrambled version of the IP address of PrivateLoader’s main C2 server (Figures 7 & 8). Prior to June, it seems that the main C2 IP address was ‘212.193.30[.]21’, however, the IP address appears to have recently changed to ‘85.202.169[.]116’. In a limited set of cases, Darktrace also observed PrivateLoader bots retrieving payload URLs from 2.56.56[.]126 and 2.56.59[.]42 (rather than from 212.193.30[.]21 or 85.202.169[.]116). These IP addresses may be hardcoded secondary C2 address which PrivateLoader bots use in cases where they are unable to retrieve the primary C2 address from Pastebin, 212.193.30[.]45 or 45.144.255[.]57 [10]. 

Figure 7: Before June, the 119th entry of the ‘proxies.txt’ file lists '30.212.21.193' -  a scrambling of the ‘212.193.30[.]21’ main C2 IP address
Figure 8: Since June, the 119th entry of the ‘proxies.txt’ file lists '169.85.116.202' - a scrambling of the '85.202.169[.]116' main C2 IP address

Once PrivateLoader bots had retrieved C2 information from either Pastebin, 45.144.225[.]57, or 212.193.30[.]45, they went on to make HTTP GET requests for ‘/base/api/statistics.php’ to either 212.193.30[.]21, 85.202.169[.]116, 2.56.56[.]126, or 2.56.59[.]42 (Figure 9). The server responded to these requests with an XOR encrypted string. The strings were encrypted using a 1-byte key [11], such as 0001101 (Figure 10). Decrypting the string revealed a URL for a BMP file hosted on Discord CDN, such as ‘hxxps://cdn.discordapp[.]com/attachments/978284851323088960/986671030670078012/PL_Client.bmp’. These encrypted URLs appear to be file download paths for the PrivateLoader core module. 

Figure 9: HTTP response from server to an HTTP GET request for '/base/api/statistics.php'
Figure 10: XOR decrypting the string with the one-byte key, 00011101, outputs a URL in CyberChef

After PrivateLoader bots retrieved the 'cdn.discordapp[.]com’ URL from 212.193.30[.]21, 85.202.169[.]116, 2.56.56[.]126, or 2.56.59[.]42, they immediately contacted Discord CDN via SSL connections in order to obtain the PrivateLoader core module. Execution of this module resulted in the bots making HTTP POST requests (with the URI string ‘/base/api/getData.php’) to the main C2 address (Figures 11 & 12). Both the data which the PrivateLoader bots sent over these HTTP POST requests and the data returned via the C2 server’s HTTP responses were heavily encrypted using a combination of password-based key derivation, base64 encoding, AES encryption, and HMAC validation [12]. 

Figure 11: The above image, taken from Darktrace's Advanced Search interface, shows a PrivateLoader bot carrying out the following steps: contact ‘hero-files[.]com’ --> contact ‘cdn.discordapp[.]com’ --> retrieve ‘/proxies.txt’ from 212.193.30[.]45 --> retrieve ‘/base/api/statistics.php’ from 212.193.30[.]21 --> contact ‘cdn.discordapp[.]com --> make HTTP POST request with the URI ‘base/api/getData.php’ to 212.193.30[.]21
Figure 12: A PCAP of the data sent via the HTTP POST (in red), and the data returned by the C2 endpoint (in blue)

These ‘/base/api/getData.php’ POST requests contain a command, a campaign name and a JSON object. The response may either contain a simple status message (such as “success”) or a JSON object containing URLs of payloads. After making these HTTP connections, PrivateLoader bots were observed downloading and executing large volumes of payloads (Figure 13), ranging from crypto-miners to infostealers (such as Mars stealer), and even to other malware downloaders (such as SmokeLoader). In some cases, bots were also seen downloading files with ‘.bmp’ extensions, such as ‘Service.bmp’, ‘Cube_WW14.bmp’, and ‘NiceProcessX64.bmp’, from 45.144.225[.]57 - the same DDR endpoint from which PrivateLoader bots retrieved main C2 information. These ‘.bmp’ payloads are likely related to the PrivateLoader service module [13]. Certain bots made follow-up HTTP POST requests (with the URI string ‘/service/communication.php’) to either 212.193.30[.]21 or 85.202.169[.]116, indicating the presence of the PrivateLoader service module, which has the purpose of establishing persistence on the device (Figure 14). 

Figure 13: The above image, taken from Darktrace's Advanced Search interface, outlines the plethora of malware payloads downloaded by a PrivateLoader bot after it made an HTTP POST request to the ‘/base/api/getData.php’ endpoint. The PrivateLoader service module is highlighted in red
Figure 14: The event log for a PrivateLoader bot, obtained from the Threat Visualiser interface, shows a device making HTTP POST requests to ‘/service/communication.php’ and connecting to the NanoPool mining pool, indicating successful execution of downloaded payloads

In several observed cases, PrivateLoader bots downloaded another malware downloader called ‘SmokeLoader’ (payloads named ‘toolspab2.exe’ and ‘toolspab3.exe’) from “Privacy Tools” endpoints [14], such as ‘privacy-tools-for-you-802[.]com’ and ‘privacy-tools-for-you-783[.]com’. These “Privacy Tools” domains are likely impersonation attempts of the legitimate ‘privacytools[.]io’ website - a website run by volunteers who advocate for data privacy [15]. 

After downloading and executing malicious payloads, PrivateLoader bots were typically seen contacting crypto-mining pools, such as NanoPool, and making HTTP POST requests to external hosts associated with SmokeLoader, such as hosts named ‘host-data-coin-11[.]com’ and ‘file-coin-host-12[.]com’ [16]. In one case, a PrivateLoader bot went on to exfiltrate data over HTTP to an external host named ‘cheapf[.]link’, which was registered on the 14th March 2022 [17]. The name of the file which the PrivateLoader bot used to exfiltrate data was ‘NOP8QIMGV3W47Y.zip’, indicating information stealing activities by Mars Stealer (Figure 15) [18]. By saving the HTTP stream as raw data and utilizing a hex editor to remove the HTTP header portions, the hex data of the ZIP file was obtained. Saving the hex data using a ‘.zip’ extension and extracting the contents, a file directory consisting of system information and Chrome and Edge browsers’ Autofill data in cleartext .txt file format could be seen (Figure 16).

Figure 15: A PCAP of a PrivateLoader bot’s HTTP POST request to cheapf[.]link, with data sent by the bot appearing to include Chrome and Edge autofill data, as well as system information
Figure 16: File directory structure and files of the ZIP archive 

When left unattended, PrivateLoader bots continued to contact C2 infrastructure in order to relay details of executed payloads and to retrieve URLs of further payloads. 

Figure 17: Timeline of the attack

Darktrace Coverage 

Most of the incidents surveyed for this article belonged to prospective customers who were trialling Darktrace with RESPOND in passive mode, and thus without the ability for autonomous intervention. However in all observed cases, Darktrace DETECT was able to provide visibility into the actions taken by PrivateLoader bots. In one case, despite the infected bot being disconnected from the client’s network, Darktrace was still able to provide visibility into the device’s network behaviour due to the client’s usage of Darktrace/Endpoint. 

If a system within an organization’s network becomes infected with PrivateLoader, it will display a range of anomalous network behaviours before it downloads and executes malicious payloads. For example, it will contact Pastebin or make HTTP requests with new and unusual user-agent strings to rare external endpoints. These network behaviours will generate some of the following alerts on the Darktrace UI:

  • Compliance / Pastebin 
  • Device / New User Agent and New IP
  • Device / New User Agent
  • Device / Three or More New User Agents
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Connection / POST to PHP on New External Host
  • Anomalous Connection / Posting HTTP to IP Without Hostname

Once the infected host obtains URLs for malware payloads from a C2 endpoint, it will likely start to download and execute large volumes of malicious files. These file downloads will usually cause Darktrace to generate some of the following alerts:

  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Numeric Exe Download
  • Anomalous File / Masqueraded File Transfer
  • Anomalous File / Multiple EXE from Rare External Locations
  • Device / Initial Breach Chain Compromise

If RESPOND is deployed in active mode, Darktrace will be able to autonomously block the download of additional malware payloads onto the target machine and the subsequent beaconing or crypto-mining activities through network inhibitors such as ‘Block matching connections’, ‘Enforce pattern of life’ and ‘Block all outgoing traffic’. The ‘Enforce pattern of life’ action results in a device only being able to make connections and data transfers which Darktrace considers normal for that device. The ‘Block all outgoing traffic’ action will cause all traffic originating from the device to be blocked. If the customer has Darktrace’s Proactive Threat Notification (PTN) service, then a breach of an Enhanced Monitoring model such as ‘Device / Initial Breach Chain Compromise’ will result in a Darktrace SOC analyst proactively notifying the customer of the suspicious activity. Below is a list of Darktrace RESPOND (Antigena) models which would be expected to breach due to PrivateLoader activity. Such models can seriously hamper attempts made by PrivateLoader bots to download malicious payloads. 

  • Antigena / Network / External Threat / Antigena Suspicious File Block
  • Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach
  • Antigena / Network / External Threat / Antigena File then New Outbound Block
  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block 
  • Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

In one observed case, the infected bot began to download malicious payloads within one minute of becoming infected with PrivateLoader. Since RESPOND was correctly configured, it was able to immediately intervene by autonomously enforcing the device’s pattern of life for 2 hours and blocking all of the device’s outgoing traffic for 10 minutes (Figure 17). When malware moves at such a fast pace, the availability of autonomous response technology, which can respond immediately to detected threats, is key for the prevention of further damage.  

Figure 18: The event log for a Darktrace RESPOND (Antigena) model breach shows Darktrace RESPOND performing inhibitive actions once the PrivateLoader bot begins to download payloads

Conclusion

By investigating PrivateLoader infections over the past couple of months, Darktrace has observed PrivateLoader operators making changes to the downloader’s main C2 IP address and to the user-agent strings which the downloader uses in its C2 communications. It is relatively easy for the operators of PrivateLoader to change these superficial network-based features of the malware in order to evade detection [19]. However, once a system becomes infected with PrivateLoader, it will inevitably start to display anomalous patterns of network behaviour characteristic of the Tactics, Techniques and Procedures (TTPs) discussed in this blog.

Throughout 2022, Darktrace observed overlapping patterns of network activity within the environments of several customers, which reveal the archetypal steps of a PrivateLoader infection. Despite the changes made to PrivateLoader’s network-based features, Darktrace’s Self-Learning AI was able to continually identify infected bots, detecting every stage of an infection without relying on known indicators of compromise. When configured, RESPOND was able to immediately respond to such infections, preventing further advancement in the cyber kill chain and ultimately preventing the delivery of floods of payloads onto infected devices.

IoCs

MITRE ATT&CK Techniques Observed

References

[1], [8],[13] https://www.youtube.com/watch?v=Ldp7eESQotM  

[2] https://news.sophos.com/en-us/2021/09/01/fake-pirated-software-sites-serve-up-malware-droppers-as-a-service/

[3] https://www.researchgate.net/publication/228873118_Measuring_Pay-per Install_The_Commoditization_of_Malware_Distribution 

[4], [15] https://intel471.com/blog/privateloader-malware

[5] https://medium.com/walmartglobaltech/privateloader-to-anubis-loader-55d066a2653e 

[6], [10],[11], [12] https://www.zscaler.com/blogs/security-research/peeking-privateloader 

[7] https://www.trendmicro.com/en_us/research/22/e/netdooka-framework-distributed-via-privateloader-ppi.html

[9] https://www.gosecure.net/blog/2022/02/10/malicious-chrome-browser-extension-exposed-chromeback-leverages-silent-extension-loading/

[14] https://www.proofpoint.com/us/blog/threat-insight/malware-masquerades-privacy-tool 

[16] https://asec.ahnlab.com/en/30513/ 

[17]https://twitter.com/0xrb/status/1515956690642161669

[18] https://isc.sans.edu/forums/diary/Arkei+Variants+From+Vidar+to+Mars+Stealer/28468

[19] http://detect-respond.blogspot.com/2013/03/the-pyramid-of-pain.html

INSIDE THE SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
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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
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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.

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

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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