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October 18, 2022

Kill Chain Insights: Detecting AutoIT Malware Compromise

Discover how AutoIt malware operates and learn strategies to combat this emerging threat in our latest blog post.
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
Joel Davidson
Cyber Analyst
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18
Oct 2022

Introduction 

Good defence is like an onion, it has layers. Each part of a security implementation should have checks built in so that if one wall is breached, there are further contingencies. Security aficionados call this ‘defence in depth’, a military concept introduced to the cyber-sphere in 2009 [1]. Since then, it has remained a central tenet when designing secure systems, digital or otherwise [2]. Despite this, the attacker’s advantage is ever-present with continued development of malware and zero-day exploits. No matter how many layers a security platform has, how can organisations be expected to protect against a threat they do not know or even understand? 

Take the case of one Darktrace customer, a government-contracted manufacturing company located in the Americas. This company possesses a modern OT and IT network comprised of several thousand devices. They have dozens of servers, a few of which host Microsoft Exchange. Every week, these few mail servers receive hundreds of malicious payloads which will ultimately attempt to make their way into over a thousand different inboxes while dodging different security gateways. Had the RESPOND portion of Darktrace for Email been properly enabled, this is where the story would have ended. However, in June 2022 an employee made an instinctual decision that could have potentially cost the company its time, money, and reputation as a government contractor. Their crime: opening an unknown html file attached to a compelling phishing email. 

Following this misstep, a download was initiated which resulted in compromise of the system via vulnerable Microsoft admin tools from endpoints largely unknown to conventional OSINT sources. Using these tools, further malicious connectivity was accomplished before finally petering out. Fortunately, their existing Microsoft security gateway was up to date on the command and control (C2) domains observed in this breach and refused the connections.

Darktrace detected this activity at every turn, from the initial email to the download and subsequent attempted C2. Cyber AI Analyst stitched the events together for easy understanding and detected Indicators of Compromise (IOCs) that were not yet flagged in the greater intelligence community and, critically, did this all at machine speed. 

So how did the attacker evade action for so long? The answer is product misconfiguration - they did not refine their ‘layers’.  

Attack Details

On the night of June 8th an employee received a malicious email. Darktrace detected that this email contained a html attachment which itself contained links to endpoints 100% rare to the network. This email also originated from a never-before-seen sender. Although it would usually have been withheld based on these factors, the customer’s Darktrace/Email deployment was set to Advisory Mode meaning it continued through to the inbox. Late the next day, this user opened the attachment which then routed them to the 100% rare endpoint ‘xberxkiw[.]club’, a probable landing page for malware that did not register on OSINT available at the time.

Figure 1- Popular OSINT VirusTotal showing zero hits against the rare endpoint 

Only seconds after reaching the endpoint, Darktrace detected the Microsoft BITS user agent reaching out to another 100% rare endpoint ‘yrioer[.]mikigertxyss[.]com’, which generated a DETECT/Network model breach, ‘Unusual BITS Activity’. This was immediately suspicious since BITS is a deprecated and insecure windows admin tool which has been known to facilitate the movement of malicious payloads into and around a network. Upon successfully establishing a connection, the affected device began downloading a self-professed .zip file. However, Darktrace detected this file to be an extension-swapped .exe file. A PCAP of this activity can be seen below in Figure 2.

Figure 2- PCAP highlighting BITs service connections and false .zip (.exe) download

This activity also triggered a correlating breach of the ‘Masqueraded File Transfer’ model and pushed a high-fidelity alert to the Darktrace Proactive Threat Notification (PTN) service. This ensured both Darktrace and the customer’s SOC team were alerted to the anomalous activity.

At this stage the local SOC were likely beginning their triage. However further connections were being made to extend the compromise on the employee’s device and the network. The file they downloaded was later revealed to be ‘AutoIT3.exe’, a default filename given to any AutoIt script. AutoIt scripts do have legitimate use cases but are often associated with malicious activity for their ability to interact with the Windows GUI and bypass client protections. After opening, these scripts would launch on the host device and probe for other weaknesses. In this case, the script may have attempted to hunt passwords/default credentials, scan the local directory for common sensitive files, or scout local antivirus software on the device. It would then share any information gathered via established C2 channels.  

After the successful download of this mismatched MIME type, the device began attempting to further establish C2 to the endpoint ‘dirirxhitoq[.]kialsoyert[.]tk’. Even though OSINT still did not flag this endpoint, Darktrace detected this outreach as suspicious and initiated its first Cyber AI Analyst investigation into the beaconing activity. Following the sixth connection made to this endpoint on the 10th of June, the infected device breached C2 models, such as ‘Agent Beacon (Long Period)’ and ‘HTTP Beaconing to Rare Destination’. 

As the beaconing continued, it was clear that internal reconnaissance from AutoIt was not widely achieved, although similar IOCs could be detected on at least two other internal devices. This may represent other users opening the same malicious email, or successful lateral movement and infection propagation from the initial user/device. However comparatively, these devices did not experience the same level of infection as the first employee’s machine and never downloaded any malicious executables. AutoIt has a history of being used to deliver information stealers, which suggests a possible motivation had wider network compromise been successful [3].

Thankfully, after the 10th of June no further exploitation was observed. This was likely due to the combined awareness and action brought by the PTN alerting, static security gateways and action from the local security team. The company were protected thanks to defence in depth.  

Darktrace Coverage

Despite this, the role of Darktrace itself cannot be understated. Darktrace/Email was integral to the early detection process and provided insight into the vector and delivery methods used by this attacker. Post-compromise, Darktrace/Network also observed the full range of suspicious activity brought about by this incursion. In particular, the AI analyst feature played a major role in reducing the time for the SOC team to triage by detecting and flagging key information regarding some of the earliest IOCs.

Figure 3- Sample information pulled by AI analyst about one of the involved endpoints

Alongside the early detection, there were several instances where RESPOND/Network would have intervened however autonomous actions were limited to a small test group and not enabled widely throughout the customer’s deployment. As such, this activity continued unimpeded- a weak layer. Figure 4 highlights the first Darktrace RESPOND action which would have been taken.

Figure 4- Upon detecting the download of a mismatched mime from a rare endpoint, Darktrace RESPOND would have blocked all connections to the rare endpoint on the relevant port in a targeted manner

This Darktrace RESPOND action provides a precise and limited response by blocking the anomalous file download. However, after continued anomalous activity, RESPOND would have strengthened its posture and enforced stronger curbs across the wider anomalous activity. This stronger enforcement is a measure designed to relegate a device to its established norm. The breach which would generate this response can be seen below:

Figure 5- After a prolonged period of anomalous activity, Darktrace RESPOND would have stepped in to enforce the typical pattern of life observed on this device

Although Darktrace RESPOND was not fully enabled, this company had an extra layer of security in the PTN service, which alerted them just minutes after the initial file download was detected, alongside details relevant to the investigation. This ensured both Darktrace analysts and their own could review the activity and begin to isolate and remediate the threat. 

Concluding Insights

Thankfully, with multiple layers in their security, the customer managed to escape this incident largely unscathed. Quick and comprehensive email and network detection, customer alerting and local gateway blocking C2 connections ensured that the infection did not have leeway to propagate laterally throughout the network. However, even though this infection did not lead to catastrophe, the fact that it happened in the first place should be a learning point. 

Had RESPOND/Email been properly configured, this threat would have been stopped before reaching its intended recipients, removing the need to rely on end-users as a security measure. Furthermore, had RESPOND/Network been utilized beyond a limited test group, this activity would have been blocked at every other step of the network-level kill chain. From the anomalous MIME download to the establishment of C2, Darktrace RESPOND would have been able to effectively isolate and quarantine this activity to the host device, without any reliance on slow-to-update OSINT sources. RESPOND allows for the automation of time-sensitive security decisions and adds a powerful layer of defence that conventional security solutions cannot provide. Although it can be difficult to relinquish human ownership of these decisions, doing so is necessary to prevent unknown attackers from infiltrating using unknown vectors to achieve unknown ends.  

In conclusion, this incident demonstrates an effective case study around detecting a threat with novel IOCs. However, it is also a reminder that a company’s security makeup can always be improved. Overall, when building security layers in a company’s ‘onion’, it is great to have the best tools, but it is even greater to use them in the best way. Only with continued refining can organisations guarantee defence in depth. 

Thanks to Connor Mooney and Stefan Rowe for their contributions.

Appendices

Darktrace Model Detections

·      Anomalous File / EXE from Rare External Location 

·      Compromise / Agent Beacon (Long Period) 

·      Compromise / HTTP Beaconing to Rare Destination 

·      Device / Large Number of Model Breaches 

·      Device / Suspicious Domain 

·      Device / Unusual BITS Activity 

·      Enhanced Monitoring: Anomalous File / Masqueraded File Transfer 

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
Joel Davidson
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.

[related-resource]

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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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