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July 27, 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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27
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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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

microsoft darktrace integrationDefault blog imageDefault blog image

AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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