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March 12, 2025

Darktrace's Detection of State-Linked ShadowPad Malware

In 2024, Darktrace identified a cluster of intrusions involving the state-linked malware, ShadowPad. This blog will detail ShadowPad and the associated activities detected by Darktrace.
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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12
Mar 2025


An integral part of cybersecurity is anomaly detection, which involves identifying unusual patterns or behaviors in network traffic that could indicate malicious activity, such as a cyber-based intrusion. However, attribution remains one of the ever present challenges in cybersecurity. Attribution involves the process of accurately identifying and tracing the source to a specific threat actor(s).

Given the complexity of digital networks and the sophistication of attackers who often use proxies or other methods to disguise their origin, pinpointing the exact source of a cyberattack is an arduous task. Threat actors can use proxy servers, botnets, sophisticated techniques, false flags, etc. Darktrace’s strategy is rooted in the belief that identifying behavioral anomalies is crucial for identifying both known and novel threat actor campaigns.

The ShadowPad cluster

Between July 2024 and November 2024, Darktrace observed a cluster of activity threads sharing notable similarities. The threads began with a malicious actor using compromised user credentials to log in to the target organization's Check Point Remote Access virtual private network (VPN) from an attacker-controlled, remote device named 'DESKTOP-O82ILGG'.  In one case, the IP from which the initial login was carried out was observed to be the ExpressVPN IP address, 194.5.83[.]25. After logging in, the actor gained access to service account credentials, likely via exploitation of an information disclosure vulnerability affecting Check Point Security Gateway devices. Recent reporting suggests this could represent exploitation of CVE-2024-24919 [27,28]. The actor then used these compromised service account credentials to move laterally over RDP and SMB, with files related to the modular backdoor, ShadowPad, being delivered to the  ‘C:\PerfLogs\’ directory of targeted internal systems. ShadowPad was seen communicating with its command-and-control (C2) infrastructure, 158.247.199[.]185 (dscriy.chtq[.]net), via both HTTPS traffic and DNS tunneling, with subdomains of the domain ‘cybaq.chtq[.]net’ being used in the compromised devices’ TXT DNS queries.

Darktrace’s Advanced Search data showing the VPN-connected device initiating RDP connections to a domain controller (DC). The device subsequently distributes likely ShadowPad-related payloads and makes DRSGetNCChanges requests to a second DC.
Figure 1: Darktrace’s Advanced Search data showing the VPN-connected device initiating RDP connections to a domain controller (DC). The device subsequently distributes likely ShadowPad-related payloads and makes DRSGetNCChanges requests to a second DC.
Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.
Figure 2: Event Log data showing a DC making DNS queries for subdomains of ‘cbaq.chtq[.]net’ to 158.247.199[.]185 after receiving SMB and RDP connections from the VPN-connected device, DESKTOP-O82ILGG.

Darktrace observed these ShadowPad activity threads within the networks of European-based customers in the manufacturing and financial sectors.  One of these intrusions was followed a few months later by likely state-sponsored espionage activity, as detailed in the investigation of the year in Darktrace’s Annual Threat Report 2024.

[related-resource]

Related ShadowPad activity

Additional cases of ShadowPad were observed across Darktrace’s customer base in 2024. In some cases, common C2 infrastructure with the cluster discussed above was observed, with dscriy.chtq[.]net and cybaq.chtq[.]net both involved; however, no other common features were identified. These ShadowPad infections were observed between April and November 2024, with customers across multiple regions and sectors affected.  Darktrace’s observations align with multiple other public reports that fit the timeframe of this campaign.

Darktrace has also observed other cases of ShadowPad without common infrastructure since September 2024, suggesting the use of this tool by additional threat actors.

The data theft thread

One of the Darktrace customers impacted by the ShadowPad cluster highlighted above was a European manufacturer. A distinct thread of activity occurred within this organization’s network several months after the ShadowPad intrusion, in October 2024.

The thread involved the internal distribution of highly masqueraded executable files via Sever Message Block (SMB) and WMI (Windows Management Instrumentation), the targeted collection of sensitive information from an internal server, and the exfiltration of collected information to a web of likely compromised sites. This observed thread of activity, therefore, consisted of three phrases: lateral movement, collection, and exfiltration.

The lateral movement phase began when an internal user device used an administrative credential to distribute files named ‘ProgramData\Oracle\java.log’ and 'ProgramData\Oracle\duxwfnfo' to the c$ share on another internal system.  

Darktrace model alert highlighting an SMB write of a file named ‘ProgramData\Oracle\java.log’ to the c$ share on another device.
Figure 3: Darktrace model alert highlighting an SMB write of a file named ‘ProgramData\Oracle\java.log’ to the c$ share on another device.

Over the next few days, Darktrace detected several other internal systems using administrative credentials to upload files with the following names to the c$ share on internal systems:

ProgramData\Adobe\ARM\webservices.dll

ProgramData\Adobe\ARM\wksprt.exe

ProgramData\Oracle\Java\wksprt.exe

ProgramData\Oracle\Java\webservices.dll

ProgramData\Microsoft\DRM\wksprt.exe

ProgramData\Microsoft\DRM\webservices.dll

ProgramData\Abletech\Client\webservices.dll

ProgramData\Abletech\Client\client.exe

ProgramData\Adobe\ARM\rzrmxrwfvp

ProgramData\3Dconnexion\3DxWare\3DxWare.exe

ProgramData\3Dconnexion\3DxWare\webservices.dll

ProgramData\IDMComp\UltraCompare\updater.exe

ProgramData\IDMComp\UltraCompare\webservices.dll

ProgramData\IDMComp\UltraCompare\imtrqjsaqmm

Cyber AI Analyst highlighting an SMB write of a file named ‘ProgramData\Adobe\ARM\webservices.dll’ to the c$ share on an internal system.
Figure 4: Cyber AI Analyst highlighting an SMB write of a file named ‘ProgramData\Adobe\ARM\webservices.dll’ to the c$ share on an internal system.

The threat actor appears to have abused the Microsoft RPC (MS-RPC) service, WMI, to execute distributed payloads, as evidenced by the ExecMethod requests to the IWbemServices RPC interface which immediately followed devices’ SMB uploads.  

Cyber AI Analyst data highlighting a thread of activity starting with an SMB data upload followed by ExecMethod requests.
Figure 5: Cyber AI Analyst data highlighting a thread of activity starting with an SMB data upload followed by ExecMethod requests.

Several of the devices involved in these lateral movement activities, both on the source and destination side, were subsequently seen using administrative credentials to download tens of GBs of sensitive data over SMB from a specially selected server.  The data gathering stage of the threat sequence indicates that the threat actor had a comprehensive understanding of the organization’s system architecture and had precise objectives for the information they sought to extract.

Immediately after collecting data from the targeted server, devices went on to exfiltrate stolen data to multiple sites. Several other likely compromised sites appear to have been used as general C2 infrastructure for this intrusion activity. The sites used by the threat actor for C2 and data exfiltration purport to be sites for companies offering a variety of service, ranging from consultancy to web design.

Screenshot of one of the likely compromised sites used in the intrusion. 
Figure 6: Screenshot of one of the likely compromised sites used in the intrusion.

At least 16 sites were identified as being likely data exfiltration or C2 sites used by this threat actor in their operation against this organization. The fact that the actor had such a wide web of compromised sites at their disposal suggests that they were well-resourced and highly prepared.  

Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.
Figure 7: Darktrace model alert highlighting an internal device slowly exfiltrating data to the external endpoint, yasuconsulting[.]com.
Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com    
Figure 8: Darktrace model alert highlighting an internal device downloading nearly 1 GB of data from an internal system just before uploading a similar volume of data to another suspicious endpoint, www.tunemmuhendislik[.]com  

Cyber AI Analyst spotlight

Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.
Figure 9: Cyber AI Analyst identifying and piecing together the various steps of a ShadowPad intrusion.  
Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.
Figure 10: Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.

As shown in the above figures, Cyber AI Analyst’s ability to thread together the different steps of these attack chains are worth highlighting.

In the ShadowPad attack chains, Cyber AI Analyst was able to identify SMB writes from the VPN subnet to the DC, and the C2 connections from the DC. It was also able to weave together this activity into a single thread representing the attacker’s progression.

Similarly, in the data exfiltration attack chain, Cyber AI Analyst identified and connected multiple types of lateral movement over SMB and WMI and external C2 communication to various external endpoints, linking them in a single, connected incident.

These Cyber AI Analyst actions enabled a quicker understanding of the threat actor sequence of events and, in some cases, faster containment.

Attribution puzzle

Publicly shared research into ShadowPad indicates that it is predominantly used as a backdoor in People’s Republic of China (PRC)-sponsored espionage operations [5][6][7][8][9][10]. Most publicly reported intrusions involving ShadowPad  are attributed to the China-based threat actor, APT41 [11][12]. Furthermore, Google Threat Intelligence Group (GTIG) recently shared their assessment that ShadowPad usage is restricted to clusters associated with APT41 [13]. Interestingly, however, there have also been public reports of ShadowPad usage in unattributed intrusions [5].

The data theft activity that later occurred in the same Darktrace customer network as one of these ShadowPad compromises appeared to be the targeted collection and exfiltration of sensitive data. Such an objective indicates the activity may have been part of a state-sponsored operation. The tactics, techniques, and procedures (TTPs), artifacts, and C2 infrastructure observed in the data theft thread appear to resemble activity seen in previous Democratic People’s Republic of Korea (DPRK)-linked intrusion activities [15] [16] [17] [18] [19].

The distribution of payloads to the following directory locations appears to be a relatively common behavior in DPRK-sponsored intrusions.

Observed examples:

C:\ProgramData\Oracle\Java\  

C:\ProgramData\Adobe\ARM\  

C:\ProgramData\Microsoft\DRM\  

C:\ProgramData\Abletech\Client\  

C:\ProgramData\IDMComp\UltraCompare\  

C:\ProgramData\3Dconnexion\3DxWare\

Additionally, the likely compromised websites observed in the data theft thread, along with some of the target URI patterns seen in the C2 communications to these sites, resemble those seen in previously reported DPRK-linked intrusion activities.

No clear evidence was found to link the ShadowPad compromise to the subsequent data theft activity that was observed on the network of the manufacturing customer. It should be noted, however, that no clear signs of initial access were found for the data theft thread – this could suggest the ShadowPad intrusion itself represents the initial point of entry that ultimately led to data exfiltration.

Motivation-wise, it seems plausible for the data theft thread to have been part of a DPRK-sponsored operation. DPRK is known to pursue targets that could potentially fulfil its national security goals and had been publicly reported as being active in months prior to this intrusion [21]. Furthermore, the timing of the data theft aligns with the ratification of the mutual defense treaty between DPRK and Russia and the subsequent accused activities [20].

Darktrace assesses with medium confidence that a nation-state, likely DPRK, was responsible, based on our investigation, the threat actor applied resources, patience, obfuscation, and evasiveness combined with external reporting, collaboration with the cyber community, assessing the attacker’s motivation and world geopolitical timeline, and undisclosed intelligence.


Conclusion

When state-linked cyber activity occurs within an organization’s environment, previously unseen C2 infrastructure and advanced evasion techniques will likely be used. State-linked cyber actors, through their resources and patience, are able to bypass most detection methods, leaving anomaly-based methods as a last line of defense.

Two threads of activity were observed within Darktrace’s customer base over the last year: The first operation involved the abuse of Check Point VPN credentials to log in remotely to organizations’ networks, followed by the distribution of ShadowPad to an internal domain controller. The second operation involved highly targeted data exfiltration from the network of one of the customers impacted by the previously mentioned ShadowPad activity.

Despite definitive attribution remaining unresolved, both the ShadowPad and data exfiltration activities were detected by Darktrace’s Self-Learning AI, with Cyber AI Analyst playing a significant role in identifying and piecing together the various steps of the intrusion activities.  

Credit to Sam Lister (R&D Detection Analyst), Emma Foulger (Principal Cyber Analyst), Nathaniel Jones (VP), and the Darktrace Threat Research team.

Appendices

Darktrace / NETWORK model alerts

User / New Admin Credentials on Client

Anomalous Connection / Unusual Admin SMB Session

Compliance / SMB Drive Write  

Device / Anomalous SMB Followed By Multiple Model Breaches

Anomalous File / Internal / Unusual SMB Script Write

User / New Admin Credentials on Client  

Anomalous Connection / Unusual Admin SMB Session

Compliance / SMB Drive Write

Device / Anomalous SMB Followed By Multiple Model Breaches

Anomalous File / Internal / Unusual SMB Script Write

Device / New or Uncommon WMI Activity

Unusual Activity / Internal Data Transfer

Anomalous Connection / Download and Upload

Anomalous Server Activity / Rare External from Server

Compromise / Beacon to Young Endpoint

Compromise / Agent Beacon (Short Period)

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Connection / POST to PHP on New External Host

Compromise / Sustained SSL or HTTP Increase

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Device / Multiple C2 Model Alerts

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Download and Upload

Unusual Activity / Unusual External Data Transfer

Anomalous Connection / Low and Slow Exfiltration

Anomalous Connection / Uncommon 1 GiB Outbound  

MITRE ATT&CK mapping

(Technique name – Tactic ID)

ShadowPad malware threads

Initial Access - Valid Accounts: Domain Accounts (T1078.002)

Initial Access - External Remote Services (T1133)

Privilege Escalation - Exploitation for Privilege Escalation (T1068)

Privilege Escalation - Valid Accounts: Default Accounts (T1078.001)

Defense Evasion - Masquerading: Match Legitimate Name or Location (T1036.005)

Lateral Movement - Remote Services: Remote Desktop Protocol (T1021.001)

Lateral Movement - Remote Services: SMB/Windows Admin Shares (T1021.002)

Command and Control - Proxy: Internal Proxy (T1090.001)

Command and Control - Application Layer Protocol: Web Protocols (T1071.001)

Command and Control - Encrypted Channel: Asymmetric Cryptography (T1573.002)

Command and Control - Application Layer Protocol: DNS (T1071.004)

Data theft thread

Resource Development - Compromise Infrastructure: Domains (T1584.001)

Privilege Escalation - Valid Accounts: Default Accounts (T1078.001)

Privilege Escalation - Valid Accounts: Domain Accounts (T1078.002)

Execution - Windows Management Instrumentation (T1047)

Defense Evasion - Masquerading: Match Legitimate Name or Location (T1036.005)

Defense Evasion - Obfuscated Files or Information (T1027)

Lateral Movement - Remote Services: SMB/Windows Admin Shares (T1021.002)

Collection - Data from Network Shared Drive (T1039)

Command and Control - Application Layer Protocol: Web Protocols (T1071.001)

Command and Control - Encrypted Channel: Asymmetric Cryptography (T1573.002)

Command and Control - Proxy: External Proxy (T1090.002)

Exfiltration - Exfiltration Over C2 Channel (T1041)

Exfiltration - Data Transfer Size Limits (T1030)

List of indicators of compromise (IoCs)

IP addresses and/or domain names (Mid-high confidence):

ShadowPad thread

- dscriy.chtq[.]net • 158.247.199[.]185 (endpoint of C2 comms)

- cybaq.chtq[.]net (domain name used for DNS tunneling)  

Data theft thread

- yasuconsulting[.]com (45.158.12[.]7)

- hobivan[.]net (94.73.151[.]72)

- mediostresbarbas.com[.]ar (75.102.23[.]3)

- mnmathleague[.]org (185.148.129[.]24)

- goldenborek[.]com (94.138.200[.]40)

- tunemmuhendislik[.]com (94.199.206[.]45)

- anvil.org[.]ph (67.209.121[.]137)

- partnerls[.]pl (5.187.53[.]50)

- angoramedikal[.]com (89.19.29[.]128)

- awork-designs[.]dk (78.46.20[.]225)

- digitweco[.]com (38.54.95[.]190)

- duepunti-studio[.]it (89.46.106[.]61)

- scgestor.com[.]br (108.181.92[.]71)

- lacapannadelsilenzio[.]it (86.107.36[.]15)

- lovetamagotchith[.]com (203.170.190[.]137)

- lieta[.]it (78.46.146[.]147)

File names (Mid-high confidence):

ShadowPad thread:

- perflogs\1.txt

- perflogs\AppLaunch.exe

- perflogs\F4A3E8BE.tmp

- perflogs\mscoree.dll

Data theft thread

- ProgramData\Oracle\java.log

- ProgramData\Oracle\duxwfnfo

- ProgramData\Adobe\ARM\webservices.dll

- ProgramData\Adobe\ARM\wksprt.exe

- ProgramData\Oracle\Java\wksprt.exe

- ProgramData\Oracle\Java\webservices.dll

- ProgramData\Microsoft\DRM\wksprt.exe

- ProgramData\Microsoft\DRM\webservices.dll

- ProgramData\Abletech\Client\webservices.dll

- ProgramData\Abletech\Client\client.exe

- ProgramData\Adobe\ARM\rzrmxrwfvp

- ProgramData\3Dconnexion\3DxWare\3DxWare.exe

- ProgramData\3Dconnexion\3DxWare\webservices.dll

- ProgramData\IDMComp\UltraCompare\updater.exe

- ProgramData\IDMComp\UltraCompare\webservices.dll

- ProgramData\IDMComp\UltraCompare\imtrqjsaqmm

- temp\HousecallLauncher64.exe

Attacker-controlled device hostname (Mid-high confidence)

- DESKTOP-O82ILGG

References  

[1] https://www.kaspersky.com/about/press-releases/shadowpad-how-attackers-hide-backdoor-in-software-used-by-hundreds-of-large-companies-around-the-world  

[2] https://media.kasperskycontenthub.com/wp-content/uploads/sites/43/2017/08/07172148/ShadowPad_technical_description_PDF.pdf

[3] https://blog.avast.com/new-investigations-in-ccleaner-incident-point-to-a-possible-third-stage-that-had-keylogger-capacities

[4] https://securelist.com/operation-shadowhammer-a-high-profile-supply-chain-attack/90380/

[5] https://assets.sentinelone.com/c/Shadowpad?x=P42eqA

[6] https://www.cyfirma.com/research/the-origins-of-apt-41-and-shadowpad-lineage/

[7] https://www.csoonline.com/article/572061/shadowpad-has-become-the-rat-of-choice-for-several-state-sponsored-chinese-apts.html

[8] https://global.ptsecurity.com/analytics/pt-esc-threat-intelligence/shadowpad-new-activity-from-the-winnti-group

[9] https://cymulate.com/threats/shadowpad-privately-sold-malware-espionage-tool/

[10] https://www.secureworks.com/research/shadowpad-malware-analysis

[11] https://blog.talosintelligence.com/chinese-hacking-group-apt41-compromised-taiwanese-government-affiliated-research-institute-with-shadowpad-and-cobaltstrike-2/

[12] https://hackerseye.net/all-blog-items/tails-from-the-shadow-apt-41-injecting-shadowpad-with-sideloading/

[13] https://cloud.google.com/blog/topics/threat-intelligence/scatterbrain-unmasking-poisonplug-obfuscator

[14] https://www.domaintools.com/wp-content/uploads/conceptualizing-a-continuum-of-cyber-threat-attribution.pdf

[15] https://www.nccgroup.com/es/research-blog/north-korea-s-lazarus-their-initial-access-trade-craft-using-social-media-and-social-engineering/  

[16] https://www.microsoft.com/en-us/security/blog/2021/01/28/zinc-attacks-against-security-researchers/

[17] https://www.microsoft.com/en-us/security/blog/2022/09/29/zinc-weaponizing-open-source-software/  

[18] https://www.welivesecurity.com/en/eset-research/lazarus-luring-employees-trojanized-coding-challenges-case-spanish-aerospace-company/  

[19] https://blogs.jpcert.or.jp/en/2021/01/Lazarus_malware2.html  

[20] https://usun.usmission.gov/joint-statement-on-the-unlawful-arms-transfer-by-the-democratic-peoples-republic-of-korea-to-russia/

[21] https://media.defense.gov/2024/Jul/25/2003510137/-1/-1/1/Joint-CSA-North-Korea-Cyber-Espionage-Advance-Military-Nuclear-Programs.PDF  

[22] https://kyivindependent.com/first-north-korean-troops-deployed-to-front-line-in-kursk-oblast-ukraines-military-intelligence-says/

[23] https://www.microsoft.com/en-us/security/blog/2024/12/04/frequent-freeloader-part-i-secret-blizzard-compromising-storm-0156-infrastructure-for-espionage/  

[24] https://www.microsoft.com/en-us/security/blog/2024/12/11/frequent-freeloader-part-ii-russian-actor-secret-blizzard-using-tools-of-other-groups-to-attack-ukraine/  

[25] https://www.sentinelone.com/labs/chamelgang-attacking-critical-infrastructure-with-ransomware/    

[26] https://thehackernews.com/2022/06/state-backed-hackers-using-ransomware.html/  

[27] https://blog.checkpoint.com/security/check-point-research-explains-shadow-pad-nailaolocker-and-its-protection/

[28] https://www.orangecyberdefense.com/global/blog/cert-news/meet-nailaolocker-a-ransomware-distributed-in-europe-by-shadowpad-and-plugx-backdoors

[related-resource]

AI Cybersecurity: Insights for 2025

We surveyed 1,500+ cybersecurity professionals globally to explore their views, knowledge, and priorities on AI cybersecurity in 2025.

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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December 18, 2025

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

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Why outbound email DLP needs reinventing

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

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

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

How data loss actually happens

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

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

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

What traditional DLP approaches offer (and where gaps remain)

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

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

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

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

1) Label-free (vs. data classification)

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

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

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

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

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

3) Proprietary DSLM (vs. generic LLM)

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

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

The Darktrace approach to DLP

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

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

A buyer’s checklist for DLP solutions

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

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

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

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

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

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

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with DarktraceDefault blog imageDefault blog image

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

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

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

What does an AiTM attack look like?

Inbound phishing email

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

Proxy-based credential theft and session hijacking

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

Follow-on attacks

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

Darktrace’s detection of an AiTM attack

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

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

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

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

Internal and external phishing

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

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

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

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

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

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

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

Darktrace’s Response

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

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

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

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

Conclusion

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

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

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

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

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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About the author
David Ison
Cyber Analyst
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