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November 9, 2022

How Raccoon Stealer v2 Infects Systems

Learn about Raccoon Stealer v2's infection process and its implications for cybersecurity. Discover effective strategies to protect your systems.
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
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09
Nov 2022

Raccoon Stealer Malware

Since the release of version 2 of Raccoon Stealer in May 2022, Darktrace has observed huge volumes of Raccoon Stealer v2 infections across its client base. The info-stealer, which seeks to obtain and then exfiltrate sensitive data saved on users’ devices, displays a predictable pattern of network activity once it is executed. In this blog post, we will provide details of this pattern of activity, with the goal of helping security teams to recognize network-based signs of Raccoon Stealer v2 infection within their own networks. 

What is Raccoon Stealer?

Raccoon Stealer is a classic example of information-stealing malware, which cybercriminals typically use to gain possession of sensitive data saved in users’ browsers and cryptocurrency wallets. In the case of browsers, targeted data typically includes cookies, saved login details, and saved credit card details. In the case of cryptocurrency wallets (henceforth, ‘crypto-wallets’), targeted data typically includes public keys, private keys, and seed phrases [1]. Once sensitive browser and crypto-wallet data is in the hands of cybercriminals, it will likely be used to conduct harmful activities, such as identity theft, cryptocurrency theft, and credit card fraud.

How do you obtain Raccoon Stealer?

Like most info-stealers, Raccoon Stealer is purchasable. The operators of Raccoon Stealer sell Raccoon Stealer samples to their customers (called ‘affiliates’), who then use the info-stealer to gain possession of sensitive data saved on users’ devices. Raccoon Stealer affiliates typically distribute their samples via SEO-promoted websites providing free or cracked software. 

Is Raccoon Stealer Still Active?

On the 25th of March 2022, the operators of Raccoon Stealer announced that they would be suspending their operations because one of their core developers had been killed during the Russia-Ukraine conflict [2]. The presence of the hardcoded RC4 key ‘edinayarossiya’ (Russian for ‘United Russia’) within observed Raccoon Stealer v2 samples [3] provides potential evidence of the Raccoon Stealer operators’ allegiances.

Recent details shared by the US Department of Justice [4]/[5] indicate that it was in fact the arrest, rather than the death, of an operator which led the Raccoon Stealer team to suspend their operations [6]. As a result of the FBI, along with law enforcement partners in Italy and the Netherlands, dismantling Raccoon Stealer infrastructure in March 2022 [4], the Raccoon Stealer team was forced to build a new version of the info-stealer.  

On the 17th May 2022, the completion of v2 of the info-stealer was announced on the Raccoon Stealer Telegram channel [7].  Since its release in May 2022, Raccoon Stealer v2 has become extremely popular amongst cybercriminals. The prevalence of Raccoon Stealer v2 in the wider landscape has been reflected in Darktrace’s client base, with hundreds of infections being observed within client networks on a monthly basis.   

Since Darktrace’s SOC first saw a Raccoon Stealer v2 infection on the 22nd May 2022, the info-stealer has undergone several subtle changes. However, the info-stealer’s general pattern of network activity has remained essentially unchanged.  

How Does Raccoon Stealer v2 Infection Work?

A Raccoon Stealer v2 infection typically starts with a user attempting to download cracked or free software from an SEO-promoted website. Attempting to download software from one of these cracked/free software websites redirects the user’s browser (typically via several .xyz or .cfd endpoints) to a page providing download instructions. In May, June, and July, many of the patterns of download behavior observed by Darktrace’s SOC matched the pattern of behavior observed in a cracked software campaign reported by Avast in June [8].   

webpage whose download instructions led to a Raccoon Stealer v2
Figure 1: Above is a webpage whose download instructions led to a Raccoon Stealer v2 sample hosted on Discord CDN
example of a webpage whose download instructions led to a Raccoon Stealer v2
Figure 2: Above is an example of a webpage whose download instructions led to a Raccoon Stealer v2 sample hosted on Bitbucket
example of a webpage whose download instructions led to a Raccoon Stealer v2
Figure 3: Above is an example of a webpage whose download instructions led to a Raccoon Stealer v2 sample hosted on MediaFire

Following the instructions on the download instruction page causes the user’s device to download a password-protected RAR file from a file storage service such as ‘cdn.discordapp[.]com’, ‘mediafire[.]com’, ‘mega[.]nz’, or ‘bitbucket[.]org’. Opening the downloaded file causes the user’s device to execute Raccoon Stealer v2. 

The Event Log for an infected device,
Figure 4: The Event Log for an infected device, taken from Darktrace’s Threat Visualiser interface, shows a device contacting two cracked software websites (‘crackedkey[.]org’ and ‘crackedpc[.]co’) before contacting a webpage (‘premiumdownload[.]org) providing instructions to download Raccoon Stealer v2 from Bitbucket

Once Raccoon Stealer v2 is running on a device, it will make an HTTP POST request with the target URI ‘/’ and an unusual user-agent string (such as ‘record’, ‘mozzzzzzzzzzz’, or ‘TakeMyPainBack’) to a C2 server. This POST request consists of three strings: a machine GUID, a username, and a 128-bit RC4 key [9]. The posted data has the following form:

machineId=X | Y & configId=Z (where X is a machine GUID, Y is a username and Z is a 128-bit RC4 key) 

PCAP showing a device making an HTTP POST request with the User Agent header ‘record’ 
Figure 5:PCAP showing a device making an HTTP POST request with the User Agent header ‘record’ 
PCAP showing a device making an HTTP POST request with the User Agent header ‘mozzzzzzzzzzz’
Figure 6: PCAP showing a device making an HTTP POST request with the User Agent header ‘mozzzzzzzzzzz’
PCAP showing a device making an HTTP POST request with the User Agent header ‘TakeMyPainBack’
Figure 7: PCAP showing a device making an HTTP POST request with the User Agent header ‘TakeMyPainBack’

The C2 server responds to the info-stealer’s HTTP POST request with custom-formatted configuration details. These configuration details consist of fields which tell the info-stealer what files to download, what data to steal, and what target URI to use in its subsequent exfiltration POST requests. Below is a list of the fields Darktrace has observed in the configuration details retrieved by Raccoon Stealer v2 samples:

  • a ‘libs_mozglue’ field, which specifies a download address for a Firefox library named ‘mozglue.dll’
  • a ‘libs_nss3’ field, which specifies a download address for a Network System Services (NSS) library named ‘nss3.dll’ 
  • a ‘libs_freebl3’ field, which specifies a download address for a Network System Services (NSS) library named ‘freebl3.dll’
  • a ‘libs_softokn3’ field, which specifies a download address for a Network System Services (NSS) library named ‘softokn3.dll’
  • a ‘libs_nssdbm3’ field, which specifies a download address for a Network System Services (NSS) library named ‘nssdbm3.dll’
  • a ‘libs_sqlite3’ field, which specifies a download address for a SQLite command-line program named ‘sqlite3.dll’
  • a ‘libs_ msvcp140’ field, which specifies a download address for a Visual C++ runtime library named ‘msvcp140.dll’
  • a ‘libs_vcruntime140’ field, which specifies a download address for a Visual C++ runtime library named ‘vcruntime140.dll’
  • a ‘ldr_1’ field, which specifies the download address for a follow-up payload for the sample to download 
  • ‘wlts_X’ fields (where X is the name of a crypto-wallet application), which specify data for the sample to obtain from the specified crypto-wallet application
  • ‘ews_X’ fields (where X is the name of a crypto-wallet browser extension), which specify data for the sample to obtain from the specified browser extension
  • ‘xtntns_X’ fields (where X is the name of a password manager browser extension), which specify data for the sample to obtain from the specified browser extension
  • a ‘tlgrm_Telegram’ field, which specifies data for the sample to obtain from the Telegram Desktop application 
  • a ‘grbr_Desktop’ field, which specifies data within a local ‘Desktop’ folder for the sample to obtain 
  • a ‘grbr_Documents’ field, which specifies data within a local ‘Documents’ folder for the sample to obtain
  • a ‘grbr_Recent’ field, which specifies data within a local ‘Recent’ folder for the sample to obtain
  • a ‘grbr_Downloads’ field, which specifies data within a local ‘Downloads’ folder for the sample to obtain
  • a ‘sstmnfo_System Info.txt’ field, which specifies whether the sample should gather and exfiltrate a profile of the infected host 
  • a ‘scrnsht_Screenshot.jpeg’ field, which specifies whether the sample should take and exfiltrate screenshots of the infected host
  • a ‘token’ field, which specifies a 32-length string of hexadecimal digits for the sample to use as the target URI of its HTTP POST requests containing stolen data 

After retrieving its configuration data, Raccoon Stealer v2 downloads the library files specified in the ‘libs_’ fields. Unusual user-agent strings (such as ‘record’, ‘qwrqrwrqwrqwr’, and ‘TakeMyPainBack’) are used in the HTTP GET requests for these library files. In all Raccoon Stealer v2 infections seen by Darktrace, the paths of the URLs specified in the ‘libs_’ fields have the following form:

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/X (where X is the name of the targeted DLL file) 

Advanced Search logs for an infected host
Figure 8: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device making an HTTP POST request to retrieve configuration details, and then making HTTP GET requests with the User Agent header ‘record’ for DLL files
Advanced Search logs for an infected host
Figure 9: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device making an HTTP POST request to retrieve configuration details, and then making HTTP GET requests with the User Agent header ‘qwrqrwrqwrqwr’ for DLL files
Advanced Search logs for an infected host
Figure 10: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device making an HTTP POST request to retrieve configuration details, and then making HTTP GET requests with the User Agent header ‘TakeMyPainBack’ for DLL files

Raccoon Stealer v2 uses the DLLs which it downloads to gain access to sensitive data (such as cookies, credit card details, and login details) saved in browsers running on the infected host.  

Depending on the data provided in the configuration details, Raccoon Stealer v2 will typically seek to obtain, in addition to sensitive data saved in browsers, the following information:

  • Information about the Operating System and applications installed on the infected host
  • Data from specified crypto-wallet software
  • Data from specified crypto-wallet browser extensions
  • Data from specified local folders
  • Data from Telegram Desktop
  • Data from specified password manager browser extensions
  • Screenshots of the infected host 

Raccoon Stealer v2 exfiltrates the data which it obtains to its C2 server by making HTTP POST requests with unusual user-agent strings (such as ‘record’, ‘rc2.0/client’, ‘rqwrwqrqwrqw’, and ‘TakeMyPainBack’) and target URIs matching the 32-length string of hexadecimal digits specified in the ‘token’ field of the configuration details. The stolen data exfiltrated by Raccoon Stealer typically includes files named ‘System Info.txt’, ‘---Screenshot.jpeg’, ‘\cookies.txt’, and ‘\passwords.txt’. 

Advanced Search logs for an infected host
Figure 11: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device retrieving configuration details via a POST request, downloading several DLLs, and then exfiltrating files named ‘System Info.txt’ and ‘---Screenshot.jpeg’
Advanced Search logs for an infected host
Figure 12: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device retrieving configuration details via a POST request, downloading several DLLs, and then exfiltrating a file named ‘System Info.txt’ 
Advanced Search logs for an infected host
Figure 13: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device retrieving configuration details via a POST request, downloading several DLLs, and then exfiltrating files named ‘System Info.txt’, ‘\cookies.txt’ and ‘\passwords.txt’
Advanced Search logs for an infected host
Figure 14: Advanced Search logs for an infected host, found on Darktrace’s Advanced Search interface, show a device retrieving configuration details via a POST request, downloading several DLLs, and then exfiltrating a file named ‘System Info.txt’

If a ‘ldr_1’ field is present in the retrieved configuration details, then Raccoon Stealer will complete its operation by downloading the binary file specified in the ‘ldr_1’ field. In all observed cases, the paths of the URLs specified in the ‘ldr_1’ field end in a sequence of digits, followed by ‘.bin’. The follow-up payload seems to vary between infections, likely due to this additional-payload feature being customizable by Raccoon Stealer affiliates. In many cases, the info-stealer, CryptBot, was delivered as the follow-up payload. 

Darktrace Coverage of Raccoon Stealer

Once a user’s device becomes infected with Raccoon Stealer v2, it will immediately start to communicate over HTTP with a C2 server. The HTTP requests made by the info-stealer have an empty Host header (although Host headers were used by early v2 samples) and highly unusual User Agent headers. When Raccoon Stealer v2 was first observed in May 2022, the user-agent string ‘record’ was used in its HTTP requests. Since then, it appears that the operators of Raccoon Stealer have made several changes to the user-agent strings used by the info-stealer,  likely in an attempt to evade signature-based detections. Below is a timeline of the changes to the info-stealer’s user-agent strings, as observed by Darktrace’s SOC:

  • 22nd May 2022: Samples seen using the user-agent string ‘record’
  • 2nd July 2022: Samples seen using the user-agent string ‘mozzzzzzzzzzz’
  • 29th July 2022: Samples seen using the user-agent string ‘rc2.0/client’
  • 10th August 2022: Samples seen using the user-agent strings ‘qwrqrwrqwrqwr’ and ‘rqwrwqrqwrqw’
  • 16th Sep 2022: Samples seen using the user-agent string ‘TakeMyPainBack’

The presence of these highly unusual user-agent strings within infected devices’ HTTP requests causes the following Darktrace DETECT/Network models to breach:

  • Device / New User Agent
  • Device / New User Agent and New IP
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Device / Three or More New User Agents

These DETECT models look for devices making HTTP requests with unusual user-agent strings, rather than specific user-agent strings which are known to be malicious. This method of detection enables the models to continually identify Raccoon Stealer v2 HTTP traffic, despite the changes made to the info-stealer’s user-agent strings.   

After retrieving configuration details from a C2 server, Raccoon Stealer v2 samples make HTTP GET requests for several DLL libraries. Since these GET requests are directed towards highly unusual IP addresses, the downloads of the DLLs cause the following DETECT models to breach:

  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Script from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations

Raccoon Stealer v2 samples send data to their C2 server via HTTP POST requests with an absent Host header. Since these POST requests lack a Host header and have a highly unusual destination IP, their occurrence causes the following DETECT model to breach:

  • Anomalous Connection / Posting HTTP to IP Without Hostname

Certain Raccoon Stealer v2 samples download (over HTTP) a follow-up payload once they have exfiltrated data. Since the target URIs of the HTTP GET requests made by v2 samples end in a sequence of digits followed by ‘.bin’, the samples’ downloads of follow-up payloads cause the following DETECT model to breach:

  • Anomalous File / Numeric File Download

If Darktrace RESPOND/Network is configured within a customer’s environment, then Raccoon Stealer v2 activity should cause the following inhibitive actions to be autonomously taken on infected systems: 

  • Enforce pattern of life — This action results in a device only being able to make connections which are normal for it to make
  • Enforce group pattern of life — This action results in a device only being able to make connections which are normal for it or any of its peers to make
  • Block matching connections — This action results in a device being unable to make connections to particular IP/Port pairs
  • Block all outgoing traffic — This action results in a device being unable to make any connections 
The Event Log for an infected device
Figure 15: The Event Log for an infected device, taken from Darktrace’s Threat Visualiser interface, shows Darktrace RESPOND taking inhibitive actions in response to the HTTP activities of a Raccoon Stealer v2 sample downloaded from MediaFire

Given that Raccoon Stealer v2 infections move extremely fast, with the time between initial infection and data exfiltration sometimes less than a minute, the availability of Autonomous Response technology such as Darktrace RESPOND is vital for the containment of Raccoon Stealer v2 infections.  

Timeline of Darktrace stopping raccoon stealer.
Figure 16: Figure displaying the steps of a Raccoon Stealer v2 infection, along with the corresponding Darktrace detections

Conclusion

Since the release of Raccoon Stealer v2 back in 2022, the info-stealer has relentlessly infected the devices of unsuspecting users. Once the info-stealer infects a user’s device, it retrieves and then exfiltrates sensitive information within a matter of minutes. The distinctive pattern of network behavior displayed by Raccoon Stealer v2 makes the info-stealer easy to spot. However, the changes which the Raccoon Stealer operators make to the User Agent headers of the info-stealer’s HTTP requests make anomaly-based methods key for the detection of the info-stealer’s HTTP traffic. The operators of Raccoon Stealer can easily change the superficial features of their malware’s C2 traffic, however, they cannot easily change the fact that their malware causes highly unusual network behavior. Spotting this behavior, and then autonomously responding to it, is likely the best bet which organizations have at stopping a Raccoon once it gets inside their networks.  

Thanks to the Threat Research Team for its contributions to this blog.

References

[1] https://www.microsoft.com/security/blog/2022/05/17/in-hot-pursuit-of-cryware-defending-hot-wallets-from-attacks/

[2] https://twitter.com/3xp0rtblog/status/1507312171914461188

[3] https://www.esentire.com/blog/esentire-threat-intelligence-malware-analysis-raccoon-stealer-v2-0

[4] https://www.justice.gov/usao-wdtx/pr/newly-unsealed-indictment-charges-ukrainian-national-international-cybercrime-operation

[5] https://www.youtube.com/watch?v=Fsz6acw-ZJ

[6] https://riskybiznews.substack.com/p/raccoon-stealer-dev-didnt-die-in

[7] https://medium.com/s2wblog/raccoon-stealer-is-back-with-a-new-version-5f436e04b20d

[8] https://blog.avast.com/fakecrack-campaign

[9] https://blog.sekoia.io/raccoon-stealer-v2-part-2-in-depth-analysis/

Appendices

MITRE ATT&CK Mapping

Resource Development

• T1588.001 — Obtain Capabilities: Malware

• T1608.001 — Stage Capabilities: Upload Malware

• T1608.005 — Stage Capabilities: Link Target

• T1608.006 — Stage Capabilities: SEO Poisoning

Execution

•  T1204.002 — User Execution: Malicious File

Credential Access

• T1555.003 — Credentials from Password Stores:  Credentials from Web Browsers

• T1555.005 — Credentials from Password Stores:  Password Managers

• T1552.001 — Unsecured Credentials: Credentials  In Files

Command and Control

•  T1071.001 — Application Layer Protocol: Web Protocols

•  T1105 — Ingress Tool Transfer

IOCS

Type

IOC

Description

User-Agent String

record

String used in User Agent header of  Raccoon Stealer v2’s HTTP requests

User-Agent  String

mozzzzzzzzzzz

String used inUser Agent header of Raccoon Stealer v2’s HTTP requests

User-Agent String

rc2.0/client

String used in User Agent header of  Raccoon Stealer v2’s HTTP requests

User-Agent  String

qwrqrwrqwrqwr

String used in  User Agent header of Raccoon Stealer v2’s HTTP requests

User-Agent String

rqwrwqrqwrqw

String used in User Agent header of  Raccoon Stealer v2’s HTTP requests

User-Agent  String

TakeMyPainBack

String used in  User Agent header of Raccoon Stealer v2’s HTTP requests

Domain Name

brain-lover[.]xyz  

Raccoon Stealer v2 C2 infrastructure

Domain  Name

polar-gift[.]xyz

Raccoon Stealer  v2 C2 infrastructure

Domain Name

cool-story[.]xyz

Raccoon Stealer v2 C2 infrastructure

Domain  Name

fall2sleep[.]xyz

Raccoon Stealer  v2 C2 infrastructure

Domain Name

broke-bridge[.]xyz

Raccoon Stealer v2 C2 infrastructure

Domain  Name

use-freedom[.]xyz

Raccoon Stealer  v2 C2 infrastructure

Domain Name

just-trust[.]xyz

Raccoon Stealer v2 C2 infrastructure

Domain  Name

soft-viper[.]site

Raccoon Stealer  v2 C2 infrastructure

Domain Name

tech-lover[.]xyz

Raccoon Stealer v2 C2 infrastructure

Domain  Name

heal-brain[.]xyz

Raccoon Stealer  v2 C2 infrastructure

Domain Name

love-light[.]xyz

Raccoon Stealer v2 C2 infrastructure

IP  Address

104.21.80[.]14

Raccoon Stealer  v2 C2 infrastructure

IP Address

107.152.46[.]84

Raccoon Stealer v2 C2 infrastructure

IP  Address

135.181.147[.]255

Raccoon Stealer  v2 C2 infrastructure

IP Address

135.181.168[.]157

Raccoon Stealer v2 C2 infrastructure

IP  Address

138.197.179[.]146

Raccoon Stealer  v2 C2 infrastructure

IP Address

141.98.169[.]33

Raccoon Stealer v2 C2 infrastructure

IP  Address

146.19.170[.]100

Raccoon Stealer  v2 C2 infrastructure

IP Address

146.19.170[.]175

Raccoon Stealer v2 C2 infrastructure

IP  Address

146.19.170[.]98

Raccoon Stealer  v2 C2 infrastructure

IP Address

146.19.173[.]33

Raccoon Stealer v2 C2 infrastructure

IP  Address

146.19.173[.]72

Raccoon Stealer  v2 C2 infrastructure

IP Address

146.19.247[.]175

Raccoon Stealer v2 C2 infrastructure

IP  Address

146.19.247[.]177

Raccoon Stealer  v2 C2 infrastructure

IP Address

146.70.125[.]95

Raccoon Stealer v2 C2 infrastructure

IP  Address

152.89.196[.]234

Raccoon Stealer  v2 C2 infrastructure

IP Address

165.225.120[.]25

Raccoon Stealer v2 C2 infrastructure

IP  Address

168.100.10[.]238

Raccoon Stealer  v2 C2 infrastructure

IP Address

168.100.11[.]23

Raccoon Stealer v2 C2 infrastructure

IP  Address

168.100.9[.]234

Raccoon Stealer  v2 C2 infrastructure

IP Address

170.75.168[.]118

Raccoon Stealer v2 C2 infrastructure

IP  Address

172.67.173[.]14

Raccoon Stealer  v2 C2 infrastructure

IP Address

172.86.75[.]189

Raccoon Stealer v2 C2 infrastructure

IP  Address

172.86.75[.]33

Raccoon Stealer  v2 C2 infrastructure

IP Address

174.138.15[.]216

Raccoon Stealer v2 C2 infrastructure

IP  Address

176.124.216[.]15

Raccoon Stealer  v2 C2 infrastructure

IP Address

185.106.92[.]14

Raccoon Stealer v2 C2 infrastructure

IP  Address

185.173.34[.]161

Raccoon Stealer  v2 C2 infrastructure

IP Address

185.173.34[.]161  

Raccoon Stealer v2 C2 infrastructure

IP  Address

185.225.17[.]198

Raccoon Stealer  v2 C2 infrastructure

IP Address

185.225.19[.]190

Raccoon Stealer v2 C2 infrastructure

IP  Address

185.225.19[.]229

Raccoon Stealer  v2 C2 infrastructure

IP Address

185.53.46[.]103

Raccoon Stealer v2 C2 infrastructure

IP  Address

185.53.46[.]76

Raccoon Stealer  v2 C2 infrastructure

IP Address

185.53.46[.]77

Raccoon Stealer v2 C2 infrastructure

IP  Address

188.119.112[.]230

Raccoon Stealer  v2 C2 infrastructure

IP Address

190.117.75[.]91

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.106.191[.]182

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.149.129[.]135

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.149.129[.]144

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.149.180[.]210

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.149.185[.]192

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.233.193[.]50

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.43.146[.]138

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.43.146[.]17

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.43.146[.]192

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.43.146[.]213

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.43.146[.]214

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.43.146[.]215

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.43.146[.]26

Raccoon Stealer  v2 C2 infrastructure

IP Address

193.43.146[.]45

Raccoon Stealer v2 C2 infrastructure

IP  Address

193.56.146[.]177

Raccoon Stealer  v2 C2 infrastructure

IP Address

194.180.174[.]180

Raccoon Stealer v2 C2 infrastructure

IP  Address

195.201.148[.]250

Raccoon Stealer  v2 C2 infrastructure

IP Address

206.166.251[.]156

Raccoon Stealer v2 C2 infrastructure

IP  Address

206.188.196[.]200

Raccoon Stealer  v2 C2 infrastructure

IP Address

206.53.53[.]18

Raccoon Stealer v2 C2 infrastructure

IP  Address

207.154.195[.]173

Raccoon Stealer  v2 C2 infrastructure

IP Address

213.252.244[.]2

Raccoon Stealer v2 C2 infrastructure

IP  Address

38.135.122[.]210

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.10.20[.]248

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.11.19[.]99

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.133.216[.]110

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.133.216[.]145

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.133.216[.]148

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.133.216[.]249

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.133.216[.]71

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.140.146[.]169

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.140.147[.]245

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.142.212[.]100

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.142.213[.]24

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.142.215[.]91

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.142.215[.]91  

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.142.215[.]92

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.144.29[.]18

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.144.29[.]243

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.15.156[.]11

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.15.156[.]2

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.15.156[.]31

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.15.156[.]31

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.150.67[.]156

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.153.230[.]183

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.153.230[.]228

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.159.251[.]163

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.159.251[.]164

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.61.136[.]67

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.61.138[.]162

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.67.228[.]8

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.67.231[.]202

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.67.34[.]152

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.67.34[.]234

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.8.144[.]187

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.8.144[.]54

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.8.144[.]55

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.8.145[.]174

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.8.145[.]83

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.8.147[.]39

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.8.147[.]79

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.84.0.152

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.86.86[.]78

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.89.54[.]110

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.89.54[.]110

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.89.54[.]95

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.89.55[.]115

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.89.55[.]117

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.89.55[.]193

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.89.55[.]198

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.89.55[.]20

Raccoon Stealer  v2 C2 infrastructure

IP Address

45.89.55[.]84

Raccoon Stealer v2 C2 infrastructure

IP  Address

45.92.156[.]150

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.182.36[.]154

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.182.36[.]230

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.182.36[.]231

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.182.36[.]232

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.182.36[.]233

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.182.39[.]34

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.182.39[.]74

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.182.39[.]75

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.182.39[.]77

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.118[.]33

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.176[.]62

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.177[.]217

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.177[.]234

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.177[.]43

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.177[.]47

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.177[.]92

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.177[.]98

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.22[.]142

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.23[.]100

Raccoon Stealer v2 C2 infrastructure

IP  Address

5.252.23[.]25

Raccoon Stealer  v2 C2 infrastructure

IP Address

5.252.23[.]76

Raccoon Stealer v2 C2 infrastructure

IP  Address

51.195.166[.]175

Raccoon Stealer  v2 C2 infrastructure

IP Address

51.195.166[.]176

Raccoon Stealer v2 C2 infrastructure

IP  Address

51.195.166[.]194

Raccoon Stealer  v2 C2 infrastructure

IP Address

51.81.143[.]169

Raccoon Stealer v2 C2 infrastructure

IP  Address

62.113.255[.]110

Raccoon Stealer  v2 C2 infrastructure

IP Address

65.109.3[.]107

Raccoon Stealer v2 C2 infrastructure

IP  Address

74.119.192[.]56

Raccoon Stealer  v2 C2 infrastructure

IP Address

74.119.192[.]73

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.232.39[.]101

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.73.133[.]0

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.73.133[.]4

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.73.134[.]45

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.75.230[.]25

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.75.230[.]39

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.75.230[.]70

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.75.230[.]93

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.100[.]101

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.91.102[.]12

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.102[.]230

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.91.102[.]44

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.102[.]57

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.91.102[.]84

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.103[.]31

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.91.73[.]154

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.73[.]213

Raccoon Stealer  v2 C2 infrastructure

IP Address

77.91.73[.]32

Raccoon Stealer v2 C2 infrastructure

IP  Address

77.91.74[.]67

Raccoon Stealer  v2 C2 infrastructure

IP Address

78.159.103[.]195

Raccoon Stealer v2 C2 infrastructure

IP  Address

78.159.103[.]196

Raccoon Stealer  v2 C2 infrastructure

IP Address

80.66.87[.]23

Raccoon Stealer v2 C2 infrastructure

IP  Address

80.66.87[.]28

Raccoon Stealer  v2 C2 infrastructure

IP Address

80.71.157[.]112

Raccoon Stealer v2 C2 infrastructure

IP  Address

80.71.157[.]138

Raccoon Stealer  v2 C2 infrastructure

IP Address

80.92.204[.]202

Raccoon Stealer v2 C2 infrastructure

IP  Address

87.121.52[.]10

Raccoon Stealer  v2 C2 infrastructure

IP Address

88.119.175[.]187

Raccoon Stealer v2 C2 infrastructure

IP  Address

89.185.85[.]53

Raccoon Stealer  v2 C2 infrastructure

IP Address

89.208.107[.]42

Raccoon Stealer v2 C2 infrastructure

IP  Address

89.39.106[.]78

Raccoon Stealer  v2 C2 infrastructure

IP Address

91.234.254[.]126

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.104[.]16

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.104[.]17

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.104[.]18

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.106[.]116

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.106[.]224

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.107[.]132

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.107[.]138

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.96[.]109

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.97[.]129

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.97[.]53

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.97[.]56

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.131.97[.]57

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.131.98[.]5

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.158.244[.]114

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.158.244[.]119

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.158.244[.]21

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.158.247[.]24

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.158.247[.]26

Raccoon Stealer v2 C2 infrastructure

IP  Address

94.158.247[.]30

Raccoon Stealer  v2 C2 infrastructure

IP Address

94.158.247[.]44

Raccoon Stealer v2 C2 infrastructure

IP  Address

95.216.109[.]16

Raccoon Stealer  v2 C2 infrastructure

IP Address

95.217.124[.]179

Raccoon Stealer v2 C2 infrastructure

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/mozglue.dll

URI used in  download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/nss3.dll

URI used in download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/freebl3.dll

URI used in  download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/softokn3.dll

URI used in download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/nssdbm3.dll

URI used in  download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/sqlite3.dll

URI used in download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/msvcp140.dll

URI used in  download of library file

URI

/aN7jD0qO6kT5bK5bQ4eR8fE1xP7hL2vK/vcruntime140.dll

URI used in download of library file

URI

/C9S2G1K6I3G8T3X7/56296373798691245143.bin

URI used in  download of follow-up payload

URI

/O6K3E4G6N9S8S1/91787438215733789009.bin

URI used in download of follow-up  payload

URI

/Z2J8J3N2S2Z6X2V3S0B5/45637662345462341.bin

URI used in  download of follow-up payload

URI

/rgd4rgrtrje62iuty/19658963328526236.bin

URI used in download of follow-up  payload

URI

/sd325dt25ddgd523/81852849956384.bin

URI used in  download of follow-up payload

URI

/B0L1N2H4R1N5I5S6/40055385413647326168.bin

URI used in download of follow-up  payload

URI

/F5Q8W3O3O8I2A4A4B8S8/31427748106757922101.bin

URI used in  download of follow-up payload

URI

/36141266339446703039.bin

URI used in download of follow-up  payload

URI

/wH0nP0qH9eJ6aA9zH1mN/1.bin

URI used in  download of follow-up payload

URI

/K2X2R1K4C6Z3G8L0R1H0/68515718711529966786.bin

URI used in download of follow-up  payload

URI

/C3J7N6F6X3P8I0I0M/17819203282122080878.bin

URI used in  download of follow-up payload

URI

/W9H1B8P3F2J2H2K7U1Y7G5N4C0Z4B/18027641.bin

URI used in download of follow-up  payload

URI

/P2T9T1Q6P7Y5J3D2T0N0O8V/73239348388512240560937.bin

URI used in  download of follow-up payload

URI

/W5H6O5P0E4Y6P8O1B9D9G0P9Y9G4/671837571800893555497.bin

URI used in download of follow-up  payload

URI

/U8P2N0T5R0F7G2J0/898040207002934180145349.bin

URI used in  download of follow-up payload

URI

/AXEXNKPSBCKSLMPNOMNRLUEPR/3145102300913020.bin

URI used in download of follow-up  payload

URI

/wK6nO2iM9lE7pN7e/7788926473349244.bin

URI used in  download of follow-up payload

URI

/U4N9B5X5F5K2A0L4L4T5/84897964387342609301.bin

URI used in download of follow-up  payload

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

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August 7, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

Default blog imageDefault blog image

The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

Continue reading
About the author
Adam Stevens
Senior Director of Product | Darktrace

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AI

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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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About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
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