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August 9, 2022

Cyber Tactics in the Russo-Ukrainian Conflict

The conflict between Russia and Ukraine has led to fears of a full-scale cyberwar. Learn the cyber attack tactics used, hacking groups involved, and more!
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
Rosa Jong
OSINT Analyst
Written by
Taisiia Garkava
Security Analyst
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09
Aug 2022

Introduction

Since the beginning of the Russian invasion of Ukraine in February 2022, cyber communities around the world have been witnessing what can be called a ‘renaissance of cyberwarfare' [1]. Rather than being financially motivated, threat actors are being guided by political convictions to defend allies or attack their enemies. This blog reviews some of the main threat actors involved in this conflict and their ongoing tactics, and advises on how organizations can best protect themselves. Darktrace’s preliminary assessments predicted that attacks would be observed globally with a focus on pro-Ukrainian nations such as North Atlantic Treaty Organization (NATO) members and that identified Advanced Persistent Threat (APT) groups would develop new and complex malware deployed through increasingly sophisticated attack vectors. This blog will show that many of these assessments had unexpected outcomes.

Context for Conflict 

Cyber confrontation between Russia and Ukraine dates back to 2013, when Viktor Yanukovych, (former President of Ukraine) rejected an EU trade pact in favour of an agreement with Russia. This sparked mass protests leading to his overthrow, and shortly after, Russian troops annexed Crimea and initiated the beginning of Russian-Ukrainian ground and cyber warfare. Since then, Russian threat actors have been periodically targeting Ukrainian infrastructure. One of the most notable examples of this, an attack against their national power grid in December 2015, resulted in power outages for approximately 255,000 people in Ukraine and was later attributed to the Russian hacking group Sandworm [2 & 3]. 

Another well-known attack in June 2017 overwhelmed the websites of hundreds of Ukrainian organizations using the infamous NotPetya malware. This attack is still considered the most damaging cyberattack in history, with more than €10 billion euros in financial damage [4]. In February 2022, countries witnessed the next stage of cyberwar against Ukraine with both new and familiar actors deploying various techniques to target their rival’s critical infrastructure. 

Tactic 1: Ransomware

Although some sources suggest US ransomware incidents and expectations of ransom may have declined during the conflict, ransomware still remained a significant tactic deployed globally across this period [5] [6] [7]. A Ukrainian hacking group, Network Battalion 65 (NB65), used ransomware to attack the Russian state-owned television and radio broadcasting network VGTRK. NB65 managed to steal 900,000 emails and 4000 files, and later demanded a ransom which they promised to donate to the Ukrainian army. This attack was unique because the group used the previously leaked source code of Conti, another infamous hacker group that had pledged its support to the Russian government earlier in the conflict. NB65 modified the leaked code to make unique ransomware for each of its targets [5]. 

Against expectations, Darktrace’s customer base appeared to deviate from these ransom trends. Analysts have seen relatively unsophisticated ransomware attacks during the conflict period, with limited evidence to suggest they were connected to any APT activity. Between November 2021 and June 2022, there were 51 confirmed ransomware compromises across the Darktrace customer base. This represents an increase of 43.16% compared to the same period the year before, accounting for relative customer growth. Whilst this suggests an overall growth in ransom cases, many of these confirmed incidents were unattributed and did not appear to be targeting any particular verticals or regions. While there was an increase in the energy sector, this could not be explicitly linked to the conflict. 

The Darktrace DETECT family has a variety of models related to ransomware visibility:

Darktrace Detections for T1486 (Data Encrypted for Impact):

- Compromise / Ransomware / Ransom or Offensive Words Written to SMB

- Compromise / Ransomware / Suspicious SMB Activity

- Anomalous Connection / Sustained MIME Type Conversion

- Unusual Activity / Sustained Anomalous SMB Activity

- Compromise / Ransomware / Suspicious SMB File Extension

- Unusual Activity / Anomalous SMB Read & Write

- Unusual Activity / Anomalous SMB Read & Write from New Device

- SaaS / Resource / SaaS Resources with Additional Extensions

- Compromise / Ransomware / Possible Ransom Note Read

- [If RESPOND is enabled] Antigena / Network / External Threat / Antigena Ransomware Block

Tactic 2: Wipers

One of the largest groups of executables seen during the conflict were wipers. On the eve of the invasion, Ukrainian organizations were targeted by a new wiper malware given the name “HermeticWiper”. Hermetic refers to the name of the Cyprian company “Hermetica Digital Ltd.” which was used by attackers to request a code signing certificate [6]. Such a digital certificate is used to verify the ownership of the code and that it has not been altered. The 24-year-old owner of Hermetica Digital says he had no idea that his company was abused to retrieve a code signing certificate [7]. 

HermeticWiper consists of three components: a worm, decoy ransomware and the wiper malware. The custom worm designed for HermeticWiper was used to spread the malware across the network of its infected machines. ESET researchers discovered that the decoy ransomware and the wiper were released at the same time [8]. The decoy ransomware was used to make it look like the machine was hit by ransomware, when in reality the wiper was already permanently wiping data from the machines. In the attack’s initial stage, it bypasses Windows security features designed to prevent overwriting boot records by installing a separate driver. After wiping data from the machine, HermeticWiper prevents that data from being re-fragmented and overwrites the files to fragment it further. This is done to make it more challenging to reconstruct data for post-compromise forensics [9]. Overall, the function and purpose of HermeticWiper seems similar to that of NotPetya ransomware. 

HermeticWiper is not the only conflict-associated wiper malware which has been observed. In January 2022, Microsoft warned Ukrainian customers that they detected wiper intrusion activity against several European organizations. One example of this was the MBR (Master Boot Record) wiper. This type of wiper overwrites the MBR, the disk sector that instructs a computer on how to load its operating system, with a ransomware note. In reality, the note is a misdirection and the malware destroys the MBR and targeted files [10].  

One of the most notable groups that used wiper malware was Sandworm. Sandworm is an APT attributed to Russia’s foreign military intelligence agency, GRU. The group has been active since 2009 and has used a variety of TTPs within their attacks. They have a history of targeting Ukraine including attacks in 2015 on Ukraine’s energy distribution companies and in 2017 when they used the aforementioned NotPetya malware against several Ukrainian organizations [11]. Another Russian (or pro-Russian) group using wiper malware to target Ukraine is DEV-0586. This group targeted various Ukrainian organizations in January 2022 with Whispergate wiper malware. This type of wiper malware presents itself as ransomware by displaying a file instructing the victim to pay Bitcoin to have their files decrypted [12].  

Darktrace did not observe any confirmed cases of HermeticWiper nor other conflict-associated wipers (e.g IsaacWiper and CaddyWiper) within the customer base over this period. Despite this, Darktrace DETECT has a variety of models related to wipers and data destruction:

Darktrace Detections for T1485 (Data Destruction)- this is the main technique exploited during wiper attacks

- Unusual Activity / Anomalous SMB Delete Volume

- IaaS / Unusual Activity / Anomalous AWS Resources Deleted

- IaaS / Storage / S3 Bucket Delete

- SaaS / Resource / Mass Email Deletes from Rare Location

- SaaS / Resource / Anomalous SaaS Resources Deleted

- SaaS / Resource / Resource Permanent Delete

- [If RESPOND is enabled] Antigena / Network / Manual / Enforce Pattern of Life

- [If RESPOND is enabled] Antigena / SaaS / Antigena Unusual Activity Block

Tactic 3: Spear-Phishing

Another strategy that some threat actors employ is spear-phishing. Targeting can be done using email, social media, messaging, or other platforms.

The hacking group Armageddon (also known as Gamaredon) has been responsible for several spear-phishing attacks during the crisis, primarily targeting individuals involved in the Ukrainian Government [13]. Since the beginning of the war, the group has been sending out a large volume of emails containing an HTML file which, if opened, downloads and launches a RAR payload. Those who click the attached link download an HTA with a PowerShell script which obtains the final Armageddon payload. Using the same strategy, the group is also targeting governmental agencies in the European Union [14]. With high-value targets, the need to improve teaching around phishing identification to minimize the chance of being caught in an attacker's net is higher than ever. 

In comparison to the wider trends, Darktrace analysts again saw little-to-no evidence of conflict-associated phishing campaigns affecting customers. Those phishing attempts which did target customers were largely not conflict-related. In some cases, the conflict was used opportunistically, such as when one customer was targeted with a phishing email referencing Russian bank exclusions from the SWIFT payment system (Figures 1 and 2). The email was identified by Darktrace/Email as a probable attempt at financial extortion and inducement - in this case the company received a spoofed email from a major bank’s remittance department.  

Figure 1- Screencap of targeted phishing email sent to Darktrace customer
Figure 2- Attached file contains soliciting reference to SWIFT, a money payment system which select Russian banks were removed from because of the conflict [15]

 Although the conflict was used as a reference in some examples, in most of Darktrace’s observed phishing cases during the conflict period there was little-to-no evidence to suggest that the company being targeted nor the threat actor behind the phishing attempt was associated with or attributable to the Russia-Ukraine conflict.

However, Darktrace/Email has several model categories which pick up phishing related threats:

Sample of Darktrace for Email Detections for T1566 (Phishing)- this is the overarching technique exploited during spear-phishing events

Model Categories:

- Inducement

- Internal / External User Spoofing

- Internal / External Domain Spoofing

- Fake Support

- Link to Rare Domains

- Link to File Storage

- Redirect Links

- Anomalous / Malicious Attachments

- Compromised Known Sender

Specific models can be located on the Email Console

 

Tactic 4: Distributed-Denial-of-Service (DDoS)

Another tactic employed by both pro-Russian and pro-Ukrainian threat actors was DDoS (Distributed Denial of Service) attacks. Both pro-Russia and pro-Ukraine actors were seen targeting critical infrastructure, information resources, and governmental platforms with mass DDoS attacks. The Ukrainian Minister of Digital Transformation, Mykhailo Fedorov, called on an IT Army of underground Ukrainian hackers and volunteers to protect Ukraine's critical infrastructure and conduct DDoS attacks against Russia [16]. As of 1 August 2022, more than two hundred thousand people are subscribed to the group's official Telegram channel, where potential DDoS targets are announced [17].

Darktrace observed similar pro-Ukraine DDoS behaviors within a variety of customer environments. These DDoS campaigns appeared to involve low-volume individual support combined with crowd-sourced DDoS activity. They were hosted on a range of public-sourced DDoS sites and seemed to share sentiments of groups such as the IT Army of Ukraine (Figure 3).

Figure 3- Example DDoS outsource domain with unusual TLD 

From the Russian side, one of the prominent newly emerged groups, Killnet, is striking back, launching several massive DDoS attacks against the critical infrastructure of countries that provide weaponry to Ukraine [18 & 19]. Today, the number of supporters of Killnet has grown to eighty-four thousand on their Telegram channel. The group has already launched a number of mass attacks on several NATO states, including Germany, Poland, Italy, Lithuania and Norway. This shows the conflict has attracted new and fast-growing groups with large backing and the capacity to undertake widespread attacks. 

DETECT has several models to identify anomalous DoS/DDoS activity:

Darktrace Detection for T1498 (Network Denial of Service)- this is the main technique exploited during DDoS attacks

- Device / Anomaly Indicators / Denial of Service Activity Indicator

- Anomalous Server Activity / Possible Denial of Service Activity

- [If RESPOND is enabled] Antigena / Network / External Threat / Antigena Suspicious Activity Block

What did Darktrace observe?

Darktrace’s cross-fleet detections were largely contrary to expectations. Analysts did not see large-scale complex conflict-linked attacks utilizing either conflict-associated ransomware, malware, or other TTPs. Instead, cyber incidents observed were largely opportunistic, using malware that could be purchased through Malware-as-a-Service models and other widely available toolkits, (rather than APT or conflict-attributable attacks). Overall, this is not to say there have been no repercussions from the conflict or that opportunistic attacks will cease, but evidence suggests that there were fewer wider cyber consequences beyond the initial APT-based attacks seen in the public forum. 

Another trend expected since the beginning of the conflict was targeted responses to sanction announcements focusing on NATO businesses and governments. Analysts, however, saw the limited reactive actions, with little-to-no direct impact from sanction announcements. Although cyber-attacks on some NATO organizations did take place, they were not as widespread or impactful as expected. Lastly, it was thought that exposure to new and sophisticated exploits would increase and be used to weaken NATO nations - especially corporations in critical industries. However, analysts observed relatively common exploits deployed indiscriminately and opportunistically. Overall, with the wider industry expecting chaos, Darktrace analysts did not see the crisis taken advantage of to target wider businesses outside of Ukraine. Based on this comparison between expectations and reality, the conflict has demonstrated the danger of  falling prey to confirmation bias and the need to remain vigilant and expect the unexpected. It may be possible to say that cyberwar is ‘cold’ right now, however the element of surprise is always present, and it is better to be prepared to protect yourself and your organization.    

What to Expect from the Future

As cyberattacks continue to become less monetarily and physically costly, it is to be expected that they will increase in frequency. Even after a political ceasefire is established, hacking groups can harbour resentment and continue their attacks, though possibly on a smaller scale.  

Additionally, the longer this conflict continues, the more sophisticated hacking groups’s attacks may become. In one of their publications, Killnet shared with subscribers that they had created ‘network weaponry’ powerful enough to simultaneously take down five European countries (Figure 4) [20]. Whether or not this claim is true, it is vital to be prepared. The European Union and the United States have supported Ukraine since the start of the invasion, and the EU has also stated that it is considering providing further assistance to help Ukraine in cyberspace [21].

Figure 4- Snapshot of Killnet Telegram announcement

How to Protect Against these Attacks

In the face of wider conflict and cybersecurity tensions, it is crucial that organizations evaluate their security stack and practise the following: 

·       Know what your critical assets are and what software is running on them. 

·       Keep your software up to date. Prioritize patching critical and high vulnerabilities that allow remote code execution. 

·       Enforce Multifactor Authentication (MFA) to the greatest extent possible. 

·       Require the use of a password manager to generate strong and unique passwords for each separate account. 

·       Backup all the essential files on the cloud and external drives and regularly maintain them. 

·       Train your employees to recognize phishing emails, suspicious websites, infected links or other abnormalities to prevent successful compromise of email accounts. 

In order to prevent an organization from suffering damage due to one of the attacks mentioned above, a full-circle approach is needed. This defence starts with a thorough understanding of the attack surface to provide timely mitigation. This can be supported by Darktrace products: 

·       As shown throughout this blog, Darktrace DETECT and Darktrace/Email have several models relating to conflict-associated TTPs and attacks. These help to quickly alert security teams and provide visibility of anomalous behaviors.

·       Darktrace PREVENT/ASM helps to identify vulnerable external-facing assets. By patching and securing these devices, the risk of exploit is drastically reduced.

·       Darktrace RESPOND and RESPOND/Email can make targeted actions to a range of threats such as blocking incoming DDoS connections or locking malicious email links.

Thanks to the Darktrace Threat Intelligence Unit for their contributions to this blog.

Appendices 

Reference List

[1] https://www.atlanticcouncil.org/blogs/ukrainealert/vladimir-putins-ukraine-invasion-is-the-worlds-first-full-scale-cyberwar/ 

[2] https://www.reuters.com/article/us-ukraine-cybersecurity-idUSKCN0VY30K

[3] https://www.reuters.com/article/us-ukraine-cybersecurity-sandworm-idUSKBN0UM00N20160108

[4 & 11] https://www.wired.com/story/notpetya-cyberattack-ukraine-russia-code-crashed-the-world/ 

[5] https://www.scmagazine.com/analysis/ransomware/despite-hopes-for-decline-ransomware-attacks-increased-during-russia-ukraine-conflict

[6] https://ransomware.org/blog/has-the-ukraine-conflict-disrupted-ransomware-attacks/

[7] https://www.cfr.org/blog/financial-incentives-may-explain-perceived-lack-ransomware-russias-latest-assault-ukraine

[8] https://www.bleepingcomputer.com/news/security/hackers-use-contis-leaked-ransomware-to-attack-russian-companies/ 

[9] https://voi.id/en/technology/138937/hermetica-owner-from-cyprus-didnt-know-his-server-was-used-in-malicious-malware-attack-in-ukraine 

[10] https://www.reuters.com/article/ukraine-crisis-cyber-cyprus-idCAKBN2KT2QI 

[11] https://www.eset.com/int/about/newsroom/press-releases/research/eset-research-ukraine-hit-by-destructive-attacks-before-and-during-the-russian-invasion-with-hermet/ 

[12] https://blog.malwarebytes.com/threat-intelligence/2022/03/hermeticwiper-a-detailed-analysis-of-the-destructive-malware-that-targeted-ukraine/ 

[13] https://www.microsoft.com/security/blog/2022/01/15/destructive-malware-targeting-ukrainian-organizations/ 

[15] https://www.cisa.gov/uscert/ncas/alerts/aa22-057a 

[16] https://attack.mitre.org/groups/G0047/ 

[17] https://cyware.com/news/ukraine-cert-warns-of-increasing-attacks-by-armageddon-group-850081f8 

[18] https://www.bbc.co.uk/news/business-60521822

[19] https://foreignpolicy.com/2022/04/11/russia-cyberwarfare-us-ukraine-volunteer-hackers-it-army/

[20] https://t.me/itarmyofukraine2022

[21] https://www.csoonline.com/article/3664859/russian-ddos-attack-on-lithuania-was-planned-on-telegram-flashpoint-says.html

[19 & 20] https://flashpoint.io/blog/killnet-kaliningrad-and-lithuanias-transport-standoff-with-russia/ 

[21] https://presidence-francaise.consilium.europa.eu/en/news/member-states-united-in-supporting-ukraine-and-strengthening-the-eu-s-telecommunications-and-cybersecurity-resilience/ 

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
Rosa Jong
OSINT Analyst
Written by
Taisiia Garkava
Security Analyst

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December 18, 2025

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

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Why outbound email DLP needs reinventing

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

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

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

How data loss actually happens

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

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

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

What traditional DLP approaches offer (and where gaps remain)

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

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

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

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

1) Label-free (vs. data classification)

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

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

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

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

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

3) Proprietary DSLM (vs. generic LLM)

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

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

The Darktrace approach to DLP

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

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

A buyer’s checklist for DLP solutions

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

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

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

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

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

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

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

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

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

What does an AiTM attack look like?

Inbound phishing email

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

Proxy-based credential theft and session hijacking

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

Follow-on attacks

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

Darktrace’s detection of an AiTM attack

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

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

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

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

Internal and external phishing

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

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

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

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

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

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

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

Darktrace’s Response

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

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

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

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

Conclusion

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

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

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

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

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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