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July 26, 2022

Self-Learning AI for Zero-Day and N-Day Attack Defense

Explore the differences between zero-day and n-day attacks on different customer servers to learn how Darktrace detects and prevents cyber threats effectively.
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
Lewis Morgan
Cyber Analyst
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26
Jul 2022

Key Terms:

Zero-day | A recently discovered security vulnerability in computer software that has no currently available fix or patch. Its name come from the reality that vendors have “zero days” to act and respond.

N-day | A vulnerability that emerges in computer software in which a vendor is aware and may have already issued (or are currently working on) a patch or fix. Active exploits often already exist and await abuse by nefarious actors.

Traditional security solutions often apply signature-based-detection when identifying cyber threats, helping to defend against legacy attacks but consequently missing novel ones. Therefore, security teams often lend a lot of focus to ensuring that the risk of zero-day vulnerabilities is reduced [1]. As explored in this blog, however, organizations can face just as much of a risk from n-day attacks, since they invite the most attention from malicious actors [2]. This is due in part to the reduced complexity, cost and time invested in researching and finding new exploits compared with that found when attackers exploit zero-days. 

This blog will examine both a zero-day and n-day attack that two different Darktrace customers faced in the fall of 2021. This will include the activity Darktrace detected, along with the steps taken by Darktrace/Network to intervene. It will then compare the incidents, discuss the possible dangers of third-party integrations, and assess the deprecation of legacy security tools.

Revisiting zero-day attacks 

Zero-days are among the greatest concerns security teams face in the era of modern technology and networking. Defending critical systems from zero-day compromises is a task most legacy security solutions are often unable to handle. Due to the complexity of uncovering new security flaws and developing elaborate code that can exploit them, these attacks are often carried out by funded or experienced groups such as nation-state actors and APTs. One of history’s most prolific zero-days, ‘Stuxnet’, sent security teams worldwide into a global panic in 2010. This involved a widespread attack on Iranian nuclear infrastructure and was widely accepted to be a result of nation-state actors [3]. The Stuxnet worm took advantage of four zero-day exploits, compromising over 200,000 devices and physically damaging around 10% of the 9,000 critical centrifuges at the Natanz nuclear site. 

More recently, 2021 saw the emergence of several critical zero-day vulnerabilities within SonicWall’s product suite [4]. SonicWall is a security hardware manufacturer that provides hardware firewall devices, unified threat management, VPN gateways and network security solutions. Some of these vulnerabilities lie within their Secure Mobile Access (SMA) 100 series (for example, CVE-2019-7481, CVE-2021-20016 and CVE-2021-20038 to name a few). These directly affected VPN devices and often allowed attackers easy remote access to company devices. CVE-2021-20016 in particular incorporates an SQL-Injection vulnerability within SonicWall’s SSL VPN SMA 100 product line [5]. If exploited, this defect would allow an unauthenticated remote attacker to perform their own malicious SQL query in order to access usernames, passwords and other session related information. 

The N-day underdog

The shadow cast by zero-day attacks often shrouds that of n-day attacks. N-days, however, often pose an equal - if not greater - risk to the majority of organizations, particularly those in industrial sectors. Since these vulnerabilities have fixes available, all of the hard work around research is already done; malicious actors only need to view proof of concepts (POCs) or, if proficient in coding, reverse-engineer software to reveal code-changes (binary diffing) in order to exploit these security flaws in the wild. These vulnerabilities are typically attributed to opportunistic hackers and script-kiddies, where little research or heavy lifting is required.  

August 2021 gave rise to a critical vulnerability in Atlassian Confluence servers, namely CVE-2021-26084 [6]. Confluence is a widely used collaboration wiki tool and knowledge-sharing platform. As introduced and discussed a few months ago in a previous Darktrace blog (Explore Internet-Facing System Vulnerabilities), this vulnerability allows attackers to remotely execute code on internet-facing servers after exploiting injection vulnerabilities in Object-Graph Navigation Language (OGNL). Whilst Confluence had patches and fixes available to users, attackers still jumped on this opportunity and began scanning the internet for signs of critical devices serving this outdated software [7]. Once identified, they would  exploit the vulnerability, often installing crypto mining software onto the device. More recently, Darktrace explored a new vulnerability (CVE-2022-26134), disclosed midway through 2022, that affected Confluence servers and data centers using similar techniques to that found in CVE-2021-26084 [8]. 

SonicWall in the wild – 1. Zero-day attack

At the beginning of August 2021, Darktrace prevented an attack from taking place within a European automotive customer’s environment (Figure 1). The attack targeted a vulnerable internet-facing SonicWall VPN server, and while the attacker’s motive remains unclear, similar historic events suggest that they intended to perform ransomware encryption or data exfiltration. 

Figure 1: Timeline of the SonicWall attack 

Darktrace was unable to confirm the definite tactics, techniques and procedures (TTPs) used by the attacker to compromise the customer’s environment, as the device was compromised before Darktrace installation and coverage. However, from looking at recently disclosed SonicWall VPN vulnerabilities and patterns of behaviour, it is likely CVE-2021-20016 played a part. At some point after this initial infection, it is also believed the device was able to move laterally to a domain controller (DC) using administrative credentials; it was this server that then initiated the anomalous activity that Darktrace detected and alerted on. 

On August 5th 2021 , Darktrace observed this compromised domain controller engaging in unusual ICMP scanning - a protocol used to discover active devices within an environment and create a map of an organization’s network topology. Shortly after, the infected server began scanning devices for open RDP ports and enumerating SMB shares using unorthodox methods. SMB delete and HTTP requests (over port 445 and 80 respectively) were made for files named delete.me in the root directory of numerous network shares using the user agent Microsoft WebDAV. However, no such files appeared to exist within the environment. This may have been the result of an attacker probing devices in the network in an effort to see their responses and gather information on properties and vulnerabilities they could later exploit. 

Soon the infected DC began establishing RDP tunnels back to the VPN server and making requests to an internal DNS server for multiple endpoints relating to exploit kits, likely in an effort to strengthen the attacker’s foothold within the environment. Some of the endpoints requested relate to:

-       EternalBlue vulnerability 

-       Petit Potam NTLM hash attack tool

-       Unusual GitHub repositories

-       Unusual Python repositories  

The DC made outgoing NTLM requests to other internal devices, implying the successful installation of Petit Potam exploitation tools. The server then began performing NTLM reconnaissance, making over 1,000 successful logins under ‘Administrator’ to several other internal devices. Around the same time, the device was also seen making anonymous SMBv1 logins to numerous internal devices, (possibly symptomatic of the attacker probing machines for EternalBlue vulnerabilities). 

Interestingly, the device also made numerous failed authentication attempts using a spoofed credential for one of the organization’s security managers. This was likely in an attempt to hide themselves using ‘Living off the Land’ (LotL) techniques. However, whilst the attacker clearly did their research on the company, they failed to acknowledge the typical naming convention used for credentials within the environment. This ultimately backfired and made the compromise more obvious and unusual. 

In the morning of the following day, the initially compromised VPN server began conducting further reconnaissance, engaging in similar activity to that observed by the domain controller. Until now, the customer had set Darktrace RESPOND to run in human confirmation mode, meaning interventions were not made autonomously but required confirmation by a member of the internal security team. However, thanks to Proactive Threat Notifications (PTNs) delivered by Darktrace’s dedicated SOC team, the customer was made immediately aware of this unusual behaviour, allowing them to apply manual Darktrace RESPOND blocks to all outgoing connections (Figure 2). This gave the security team enough time to respond and remediate before serious damage could be done.

Figure 2: Darktrace RESPOND model breach showing the manually applied “Quarantine Device” action taken against the compromised VPN server. This screenshot displays the UI from Darktrace version 5.1

Confluence in the wild – 2. N-day attack

Towards the end of 2021, Darktrace saw a European broadcasting customer leave an Atlassian Confluence internet-facing server unpatched and vulnerable to crypto-mining malware using CVE-2021-26084. Thanks to Darktrace, this attack was entirely immobilized within only a few hours of the initial infection, protecting the organization from damage (Figure 3). 

Figure 3: Timeline of the Confluence attack

On midday on September 1st 2021, an unpatched Confluence server was seen receiving SSL connections over port 443 from a suspicious new endpoint, 178.238.226[.]127.  The connections were encrypted, meaning Darktrace was unable to view the contents and ascertain what requests were being made. However, with the disclosure of CVE-2021-26084 just 7 days prior to this activity, it is likely that the TTPs used involved injecting OGNL expressions to Confluence server memory; allowing the attacker to remotely execute code on the vulnerable server.

Immediately after successful exploitation of the Confluence server, the infected device was observed making outgoing HTTP GET requests to several external endpoints using a new user agent (curl/7.61.1). Curl was used to silently download and configure multiple suspicious files relating to XMRig cryptocurrency miner, including ld.sh, XMRig and config.json. Subsequent outgoing connections were then made to europe.randomx-hub.miningpoolhub[.]com · 172.105.210[.]117 using the JSON-RPC protocol, seen alongside the mining credential maillocal.confluence (Figure 4). Only 3 seconds after initial compromise, the infected device began attempting to mine cryptocurrency using the Minergate protocol but was instantly and autonomously blocked by Darktrace RESPOND. This prevented the server from abusing system resources and generating profits for the attacker.

Figure 4: A graph showing the frequency of external connections using the JSON-RPC protocol made by the breach device over a 48-hour window. The orange-red dots represent models that breached as a result of this activity, demonstrating the “waterfall” effect commonly seen when a device suffers a compromise. This screenshot displays the UI from Darktrace version 5.1

In the afternoon, the malware persisted with its infection. The compromised server began making successive HTTP GET requests to a new rare endpoint 195.19.192[.]28 using the same curl user agent (Figures 5 & 6). These requests were for executable and dynamic library files associated with Kinsing malware (but fortunately were also blocked by Darktrace RESPOND). Kinsing is a malware strain found in numerous attack campaigns which is often associated with crypto-jacking, and has appeared in previous Darktrace blogs [9].

Figure 5: Cyber AI Analyst summarising the unusual download of Kinsing software using the new curl user agent. This screenshot displays the UI from Darktrace version 5.1

The attacker then began making HTTP POST requests to an IP 185.154.53[.]140, using the same curl user agent; likely a method for the attacker to maintain persistence within the network and establish a foothold using its C2 infrastructure. The Confluence server was then again seen attempting to mine cryptocurrency using the Minergate protocol. It made outgoing JSON-RPC connections to a different new endpoint, 45.129.2[.]107, using the following mining credential: ‘42J8CF9sQoP9pMbvtcLgTxdA2KN4ZMUVWJk6HJDWzixDLmU2Ar47PUNS5XHv4Kmfdh8aA9fbZmKHwfmFo8Wup8YtS5Kdqh2’. This was once again blocked by Darktrace RESPOND (Figure 7). 

Figure 6: VirusTotal showing the unusualness of one of these external IPs [10]
Figure 7: Log data showing the action taken by Darktrace RESPOND in response to the device breaching the “Crypto Currency Mining Activity” model. This screenshot displays the UI from Darktrace version 5.1

The final activity seen from this device involved the download of additional shell scripts over HTTP associated with Kinsing, namely spre.sh and unk.sh, from 194.38.20[.]199 and 195.3.146[.]118 respectively (Figure 8). A new user agent (Wget/1.19.5 (linux-gnu)) was used when connecting to the latter endpoint, which also began concurrently initiating repeated connections indicative of C2 beaconing. These scripts help to spread the Kinsing malware laterally within the environment and may have been the attacker's last ditch efforts at furthering their compromise before Darktrace RESPOND blocked all connections from the infected Confluence server [11]. With Darktrace RESPOND's successful actions, the customer’s security team were then able to perform their own response and remediation. 

Figure 8: Cyber AI Analyst revealing the last ditch efforts made by the threat actor to download further malicious software. This screenshot displays the UI from Darktrace version 5.1

Darktrace Coverage: N- vs Zero-days

In the SonicWall case the attacker was unable to achieve their actions on objectives (thanks to Darktrace's intervention). However, this incident displayed tactics of a more stealthy and sophisticated attacker - they had an exploited machine but waited for the right moment to execute their malicious code and initiate a full compromise. Due to the lack of visibility over attacker motive, it is difficult to deduce what type of actor led to this intrusion. However, with the disclosure of a zero-day vulnerability (CVE-2021-20016) not long before this attack, along with a seemingly dormant initially compromised device, it is highly possible that it was carried out by a sophisticated cyber criminal or gang. 

On the other hand, the Confluence case engaged in a slightly more noisy approach; it dropped crypto mining malware on vulnerable devices in the hope that the target’s security team did not maintain visibility over their network or would merely turn a blind eye. The files downloaded and credentials observed alongside the mining activity heavily imply the use of Kinsing malware [11]. Since this vulnerability (CVE-2021-26084) emerged as an n-day attack with likely easily accessible POCs, as well as there being a lack of LotL techniques and the motive being long term monetary gain, it is possible this attack was conducted by a less sophisticated or amateur actor (script-kiddie); one that opportunistically exploits known vulnerabilities in internet-facing devices in order to make a quick profit [12].

Whilst Darktrace RESPOND was enabled in human confirmation mode only during the start of the SonicWall attack, Darktrace’s Cyber AI Analyst still offered invaluable insight into the unusual activity associated with the infected machines during both the Confluence and SonicWall compromises. SOC analysts were able to see these uncharacteristic behaviours and escalate the incident through Darktrace’s PTN and ATE services. Analysts then worked through these tickets with the customers, providing support and guidance and, in the SonicWall case, quickly helping to configure Darktrace RESPOND. In both scenarios, Darktrace RESPOND was able to block abnormal connections and enforce a device’s pattern of life, affording the security team enough time to isolate the infected machines and prevent further threats such as ransomware detonation or data exfiltration. 

Concluding thoughts and dangers of third-party integrations 

Organizations with internet-facing devices will inevitably suffer opportunistic zero-day and n-day attacks. While little can be done to remove the risk of zero-days entirely, ensuring that organizations keep their systems up to date will at the very least help prevent opportunistic and script-kiddies from exploiting n-day vulnerabilities.  

However, it is often not always possible for organizations to keep their systems up to date, especially for those who require continuous availability. This may also pose issues for organizations that rely on, and put their trust in, third party integrations such as those explored in this blog (Confluence and SonicWall), as enforcing secure software is almost entirely out of their hands. Moreover, with the rising prevalence of remote working, it is essential now more than ever that organizations ensure their VPN devices are shielded from external threats, guidance on which has been released by the NSA/CISA [13].

These two case studies have shown that whilst organizations can configure their networks and firewalls to help identify known indicators of compromise (IoC), this ‘rearview mirror’ approach will not account for, or protect against, any new and undisclosed IoCs. With the aid of Self-Learning AI and anomaly detection, Darktrace can detect the slightest deviation from a device’s normal pattern of life and respond autonomously without the need for rules and signatures. This allows for the disruption and prevention of known and novel attacks before irreparable damage is caused- reassuring security teams that their digital estates are secure. 

Thanks to Paul Jennings for his contributions to this blog.

Appendices: SonicWall (Zero-day)

Darktrace model detections

·      AIA / Suspicious Chain of Administrative Credentials

·      Anomalous Connection / Active Remote Desktop Tunnel

·      Anomalous Connection / SMB Enumeration

·      Anomalous Connection / Unusual Internal Remote Desktop

·      Compliance / High Priority Compliance Model Breach

·      Compliance / Outgoing NTLM Request from DC

·      Device / Anomalous RDP Followed By Multiple Model Breaches

·      Device / Anomalous SMB Followed By Multiple Model Breaches

·      Device / ICMP Address Scan

·      Device / Large Number of Model Breaches

·      Device / Large Number of Model Breaches from Critical Network Device

·      Device / Multiple Lateral Movement Model Breaches (PTN/Enhanced Monitoring model)

·      Device / Network Scan

·      Device / Possible SMB/NTLM Reconnaissance

·      Device / RDP Scan

·      Device / Reverse DNS Sweep

·      Device / SMB Session Bruteforce

·      Device / Suspicious Network Scan Activity (PTN/Enhanced Monitoring model)

·      Unusual Activity / Possible RPC Recon Activity

Darktrace RESPOND (Antigena) actions (as displayed in example)

·      Antigena / Network / Manual / Quarantine Device

MITRE ATT&CK Techniques Observed
IoCs

Appendices: Confluence (N-day)

Darktrace model detections

·      Anomalous Connection / New User Agent to IP Without Hostname

·      Anomalous Connection / Posting HTTP to IP Without Hostname

·      Anomalous File / EXE from Rare External Location

·      Anomalous File / Script from Rare Location

·      Compliance / Crypto Currency Mining Activity

·      Compromise / High Priority Crypto Currency Mining (PTN/Enhanced Monitoring model)

·      Device / Initial Breach Chain Compromise (PTN/Enhanced Monitoring model)

·      Device / Internet Facing Device with High Priority Alert

·      Device / New User Agent

Darktrace RESPOND (Antigena) actions (displayed in example)

·      Antigena / Network / Compliance / Antigena Crypto Currency Mining Block

·      Antigena / Network / External Threat / Antigena File then New Outbound Block

·      Antigena / Network / External Threat / Antigena Suspicious Activity Block

·      Antigena / Network / External Threat / Antigena Suspicious File Block

·      Antigena / Network / Significant Anomaly / Antigena Block Enhanced Monitoring

MITRE ATT&CK Techniques Observed
IOCs

References:

[1] https://securitybrief.asia/story/why-preventing-zero-day-attacks-is-crucial-for-businesses

[2] https://electricenergyonline.com/energy/magazine/1150/article/Security-Sessions-More-Dangerous-Than-Zero-Days-The-N-Day-Threat.htm

[3] https://www.wired.com/2014/11/countdown-to-zero-day-stuxnet/

[4] https://cve.mitre.org/cgi-bin/cvekey.cgi?keyword=SonicWall+2021 

[5] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-20016

[6] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-26084

[7] https://www.zdnet.com/article/us-cybercom-says-mass-exploitation-of-atlassian-confluence-vulnerability-ongoing-and-expected-to-accelerate/

[8] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2022-26134

[9] https://attack.mitre.org/software/S0599/

[10] https://www.virustotal.com/gui/ip-address/195.19.192.28/detection 

[11] https://sysdig.com/blog/zoom-into-kinsing-kdevtmpfsi/

[12] https://github.com/alt3kx/CVE-2021-26084_PoC

[13] https://www.nsa.gov/Press-Room/Press-Releases-Statements/Press-Release-View/Article/2791320/nsa-cisa-release-guidance-on-selecting-and-hardening-remote-access-vpns/

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
Lewis Morgan
Cyber 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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