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July 26, 2022

Identifying PrivateLoader Network Threats

Learn how Darktrace identifies network-based indicators of compromise for the PrivateLoader malware. Gain insights into advanced threat detection.
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.
Written by
Sam Lister
Specialist Security Researcher
Written by
Shuh Chin Goh
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26
Jul 2022

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.
Written by
Sam Lister
Specialist Security Researcher
Written by
Shuh Chin Goh

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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About the author
David Ison
Cyber Analyst
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