Blog
/
Network
/
February 15, 2024

Detecting & Containing Gootloader Malware

Learn how Darktrace helps detect and contain multi-functional threats like the Gootloader malware. Stay ahead of cyber threats with Darktrace AI solutions.
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
Ashiq Shafee
Cyber Security Analyst
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
15
Feb 2024

What is multi-functional malware?

While traditional malware variants were designed with one specific objective in mind, the emergence of multi-functional malware, such as loader malware, means that organizations are likely to be confronted with multiple malicious tools and strains of malware at once. These threats often have non-linear attack patterns and kill chains that can quickly adapt and progress quicker than human security teams are able to react. Therefore, it is more important than ever for organizations to adopt an anomaly approach to combat increasingly versatile and fast-moving threats.

Example of Multi-functional malware

One example of a multi-functional malware recently observed by Darktrace can be seen in Gootloader, a multi-payload loader variant that has been observed in the wild since 2020. It is known to primarily target Windows-based systems across multiple industries in the US, Canada, France, Germany, and South Korea [1].  

How does Gootloader malware work?

Once installed on a target network, Gootloader can download additional malicious payloads that allow threat actors to carry out a range of harmful activities, such as stealing sensitive information or encrypting files for ransom.

The Gootloader malware is known to infect networks via search engine optimization (SEO) poisoning, directing users searching for legitimate documents to compromised websites hosting a malicious payload masquerading as the desired file.

If the malware remains undetected, it paves the way for a second stage payload known as Gootkit, which functions as a banking trojan and information-stealer, or other malware tools including Cobalt Strike and Osiris [2].

Darktrace detection of Gootloader malware

In late 2023, Darktrace observed one instance of Gootloader affecting a customer in the US. Thanks to its anomaly-focused approach, Darktrace quickly identified the anomalous activity surrounding this emerging attack and brought it to the immediate attention of the customer’s security team. All the while, Darktrace's Autonomous Response was in place and able to autonomously intervene, containing the suspicious activity and ensuring the Gootloader compromise could not progress any further.

Autonomous Response was in place and able to autonomously intervene, containing the suspicious activity and ensuring the Gootloader compromise could not progress any further.

In September 2023, Darktrace identified an instance of the Gootloader malware attempting to propagate within the network of a customer in the US. Darktrace identified the first indications of the compromise when it detected a device beaconing to an unusual external location and performing network scanning. Following this, the device was observed making additional command-and-control (C2) connections, before finally downloading an executable (.exe) file which likely represented the download of a further malicious payload.

As this customer had subscribed to the Proactive Notification Service (PTN), the suspicious activity was escalated to the Darktrace Security Operations Center (SOC) for further investigation by Darktrace’s expert analysts. The SOC team were able to promptly triage the incident and advise urgent follow-up actions.

Gootloader Attack Overview

Figure 1: Timeline of Anomalous Activities seen on the breach device.

Initial Beaconing and Scanning Activity

On September 21, 2023, Darktrace observed the first indications of compromise on the network when a device began to make regular connections to an external endpoint that was considered extremely rare for the network, namely ‘analyzetest[.]ir’.

Although the endpoint did not overtly seem malicious in nature (it appeared to be related to laboratory testing), Darktrace recognized that it had never previously been seen on the customer’s network and therefore should be treated with caution.  This initial beaconing activity was just the beginning of the malicious C2 communications, with several additional instances of beaconing detected to numerous suspicious endpoints, including funadhoo.gov[.]mv, tdgroup[.]ru’ and ‘army.mil[.]ng.

Figure 2: Initial beaconing activity detected on the breach device.

Soon thereafter, Darktrace detected the device performing internal reconnaissance, with an unusually large number of connections to other internal locations observed. This scanning activity appeared to primarily be targeting the SMB protocol by scanning port 445.

Within seconds of Darktrace's detection of this suspicious SMB scanning activity, Darktrace's Autonomous Response moved to contain the compromise by blocking the device from connecting to port 445 and enforcing its ‘pattern of life’. Darktrace’s Self-Learning AI enables it to learn a device’s normal behavior and recognize if it deviates from this; by enforcing a pattern of life on an affected device, malicious activity is inhibited but the device is allowed to continue its expected activity, minimizing disruption to business operations.

Figure 3: The breach device Model Breach Event Log showing Darktrace identifying suspicious SMB scanning activity and the corresponding respose actions.

Following the initial detection of this anomalous activity, Darktrace’s Cyber AI Analyst launched an autonomous investigation into the beaconing and scanning activity and was able to connect these seemingly separate events into one incident. AI Analyst analyzes thousands of connections to hundreds of different endpoints at machine speed and then summarizes its findings in a single pane of glass, giving customers the necessary information to assess the threat and begin remediation if necessary. This significantly lessens the burden for human security teams, saving them previous time and resources, while ensuring they maintain full visibility over any suspicious activity on their network.

Figure 4: Cyber AI Analyst incident log summarizing the technical details of the device’s beaconing and scanning behavior.

Beaconing Continues

Darktrace continued to observe the device carrying out beaconing activity over the next few days, likely representing threat actors attempting to establish communication with their malicious infrastructure and setting up a foothold within the customer’s environment. In one such example, the device was seen connecting to the suspicious endpoint ‘fysiotherapie-panken[.]nl’. Multiple open-source intelligence (OSINT) vendors reported this endpoint to be a known malware delivery host [3].

Once again, Darktrace Autonomous Response was in place to quickly intervene in response to these suspicious external connection attempts. Over the course of several days, Darktrace blocked the offending device from connecting to suspicious endpoints via port 443 and enforced its pattern of life. These autonomous actions by Darktrace effectively mitigated and contained the attack, preventing it from escalating further along the kill chain and providing the customer’s security team crucial time to take act and employ their own remediation.

Figure 5: A sample of the Autonomous Response actions that was applied on the affected device.

Possible Payload Retrieval

A few days later, on September 26, 2023, Darktrace observed the affected device attempting to download a Windows Portable Executable via file transfer protocol (FTP) from the external location ‘ftp2[.]sim-networks[.]com’, which had never previously been seen on the network. This download likely represented the next step in the Gootloader infection, wherein additional malicious tooling is downloaded to further cement the malicious actors’ control over the device. In response, Darktrace immediately blocked the device from making any external connections, ensuring it could not download any suspicious files that may have rapidly escalated the attackers’ efforts.

Figure 6: DETECT’s identification of the offending device downloading a suspicious executable file via FTP.

The observed combination of beaconing activity and a suspicious file download triggered an Enhanced Monitoring breach, a high-fidelity DETECT model designed to detect activities that are more likely to be indicative of compromise. These models are monitored by the Darktrace SOC round the clock and investigated by Darktrace’s expert team of analysts as soon as suspicious activity emerges.

In this case, Darktrace’s SOC triaged the emerging activity and sent an additional notice directly to the customer’s security team, informing them of the compromise and advising on next steps. As this customer had subscribed to Darktrace’s Ask the Expert (ATE) service, they also had a team of expert analysts available to them at any time to aid their investigations.

Figure 7: Enhanced Monitoring Model investigated by the Darktrace SOC.

Conclusion

Loader malware variants such as Gootloader often lay the groundwork for further, potentially more severe threats to be deployed within compromised networks. As such, it is crucial for organizations and their security teams to identify these threats as soon as they emerge and ensure they are effectively contained before additional payloads, like information-stealing malware or ransomware, can be downloaded.

In this instance, Darktrace demonstrated its value when faced with a multi-payload threat by detecting Gootloader at the earliest stage and responding to it with swift targeted actions, halting any suspicious connections and preventing the download of any additional malicious tooling.

Darktrace DETECT recognized that the beaconing and scanning activity performed by the affected device represented a deviation from its expected behavior and was indicative of a potential network compromise. Meanwhile, Darktrace ensured that any suspicious activity was promptly shut down, buying crucial time for the customer’s security team to work with Darktrace’s SOC to investigate the threat and quarantine the compromised device.

Credit to: Ashiq Shafee, Cyber Security Analyst, Qing Hong Kwa, Senior Cyber Analyst and Deputy Analyst Team Lead, Singapore

Appendices

Darktrace DETECT Model Detections

Anomalous Connection / Rare External SSL Self-Signed

Device / Suspicious SMB Scanning Activity

Anomalous Connection / Young or Invalid Certificate SSL Connections to Rare

Compromise / High Volume of Connections with Beacon Score

Compromise / Beacon to Young Endpoint

Compromise / Beaconing Activity To External Rare

Compromise / Slow Beaconing Activity To External Rare

Compromise / Beacon for 4 Days

Anomalous Connection / Suspicious Expired SSL

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Compromise / Sustained SSL or HTTP Increase

Compromise / Large Number of Suspicious Successful Connections

Compromise / Large Number of Suspicious Failed Connections

Device / Large Number of Model Breaches

Anomalous File / FTP Executable from Rare External Location

Device / Initial Breach Chain Compromise

RESPOND Models

Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

Antigena / Network/Insider Threat/Antigena Network Scan Block

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / External Threat / Antigena Suspicious File Block

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

Antigena / Network / External Threat / Antigena Suspicious Activity Block

List of Indicators of Compromise (IoCs)

Type

Hostname

IoCs + Description

explorer[.]ee - C2 Endpoint

fysiotherapie-panken[.]nl- C2 Endpoint

devcxp2019.theclearingexperience[.]com- C2 Endpoint

campsite.bplaced[.]net- C2 Endpoint

coup2pompes[.]fr- C2 Endpoint

analyzetest[.]ir- Possible C2 Endpoint

tdgroup[.]ru- C2 Endpoint

ciedespuys[.]com- C2 Endpoint

fi.sexydate[.]world- C2 Endpoint

funadhoo.gov[.]mv- C2 Endpoint

geying.qiwufeng[.]com- C2 Endpoint

goodcomix[.]fun- C2 Endpoint

ftp2[.]sim-networks[.]com- Possible Payload Download Host

MITRE ATT&CK Mapping

Tactic – Technique

Reconnaissance - Scanning IP blocks (T1595.001, T1595)

Command and Control - Web Protocols , Application Layer Protocol, One-Way Communication, External Proxy, Non-Application Layer Protocol, Non-Standard Port (T1071.001/T1071, T1071, T1102.003/T1102, T1090.002/T1090, T1095, T1571)

Collection – Man in the Browser (T1185)

Resource Development - Web Services, Malware (T1583.006/T1583, T1588.001/T1588)

Persistence - Browser Extensions (T1176)

References

1.     https://www.blackberry.com/us/en/solutions/endpoint-security/ransomware-protection/gootloader

2.     https://redcanary.com/threat-detection-report/threats/gootloader/

3.     https://www.virustotal.com/gui/domain/fysiotherapie-panken.nl

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
Ashiq Shafee
Cyber Security Analyst

More in this series

No items found.

Blog

/

Email

/

December 18, 2025

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

Man at laptopDefault blog imageDefault blog image

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]

Continue reading
About the author
Carlos Gray
Senior Product Marketing Manager, Email

Blog

/

Email

/

December 17, 2025

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

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

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

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

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

What does an AiTM attack look like?

Inbound phishing email

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

Proxy-based credential theft and session hijacking

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

Follow-on attacks

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

Darktrace’s detection of an AiTM attack

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

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

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

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

Internal and external phishing

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

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

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

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

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

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

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

Darktrace’s Response

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

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

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

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

Conclusion

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

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

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

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

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI