Bytesize Security: Insider Threats in Google Workspace
Insider threats pose significant risks due to access to internal systems. Darktrace detected a former employee attempting to steal data from the customer’s Google Workspace platform. Learn about this threat here.
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
Vivek Rajan
Cyber Analyst
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28
Jan 2025
What is an insider threat?
An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.
Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.
For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.
Attack overview: Insider threat
In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.
While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.
In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.
Conclusion
Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.
Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.
Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)
Get the latest insights on emerging cyber threats
Attackers are adapting, are you ready? This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.
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Zero-day exploitation: The rise of previously unknown vulnerabilities
AI-driven threats: How adversaries are leveraging AI to outmaneuver security controls
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.
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Patch and Persist: Darktrace’s Detection of Blind Eagle (APT-C-36)
What is Blind Eagle?
Since 2018, APT-C-36, also known as Blind Eagle, has been observed performing cyber-attacks targeting various sectors across multiple countries in Latin America, with a particular focus on Colombian organizations.
Blind Eagle characteristically targets government institutions, financial organizations, and critical infrastructure [1][2].
Attacks carried out by Blind Eagle actors typically start with a phishing email and the group have been observed utilizing various Remote Access Trojans (RAT) variants, which often have in-built methods for hiding command-and-control (C2) traffic from detection [3].
What we know about Blind Eagle from a recent campaign
Since November 2024, Blind Eagle actors have been conducting an ongoing campaign targeting Colombian organizations [1].
In this campaign, threat actors have been observed using phishing emails to deliver malicious URL links to targeted recipients, similar to the way threat actors have previously been observed exploiting CVE-2024-43451, a vulnerability in Microsoft Windows that allows the disclosure of a user’s NTLMv2 password hash upon minimal interaction with a malicious file [4].
Despite Microsoft patching this vulnerability in November 2024 [1][4], Blind Eagle actors have continued to exploit the minimal interaction mechanism, though no longer with the intent of harvesting NTLMv2 password hashes. Instead, phishing emails are sent to targets containing a malicious URL which, when clicked, initiates the download of a malicious file. This file is then triggered by minimal user interaction.
Clicking on the file triggers a WebDAV request, with a connection being made over HTTP port 80 using the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19044’. WebDAV is a transmission protocol which allows files or complete directories to be made available through the internet, and to be transmitted to devices [5]. The next stage payload is then downloaded via another WebDAV request and malware is executed on the target device.
Attackers are notified when a recipient downloads the malicious files they send, providing an insight into potential targets [1].
Darktrace’s coverage of Blind Eagle
In late February 2025, Darktrace observed activity assessed with medium confidence to be associated with Blind Eagle on the network of a customer in Colombia.
Within a period of just five hours, Darktrace / NETWORK detected a device being redirected through a rare external location, downloading multiple executable files, and ultimately exfiltrating data from the customer’s environment.
Since the customer did not have Darktrace’s Autonomous Response capability enabled on their network, no actions were taken to contain the compromise, allowing it to escalate until the customer’s security team responded to the alerts provided by Darktrace.
Darktrace observed a device on the customer’s network being directed over HTTP to a rare external IP, namely 62[.]60[.]226[.]112, which had never previously been seen in this customer’s environment and was geolocated in Germany. Multiple open-source intelligence (OSINT) providers have since linked this endpoint with phishing and malware campaigns [9].
The device then proceeded to download the executable file hxxp://62[.]60[.]226[.]112/file/3601_2042.exe.
Figure 1: Darktrace’s detection of the affected device connecting to an unusual location based in Germany.
Figure 2: Darktrace’s detection of the affected device downloading an executable file from the suspicious endpoint.
The device was then observed making unusual connections to the rare endpoint 21ene.ip-ddns[.]com and performing unusual external data activity.
This dynamic DNS endpoint allows a device to access an endpoint using a domain name in place of a changing IP address. Dynamic DNS services ensure the DNS record of a domain name is automatically updated when the IP address changes. As such, malicious actors can use these services and endpoints to dynamically establish connections to C2 infrastructure [6].
Further investigation into this dynamic endpoint using OSINT revealed multiple associations with previous likely Blind Eagle compromises, as well as Remcos malware, a RAT commonly deployed via phishing campaigns [7][8][10].
Figure 3: Darktrace’s detection of the affected device connecting to the suspicious dynamic DNS endpoint, 21ene.ip-ddns[.]com.
Shortly after this, Darktrace observed the user agent ‘Microsoft-WebDAV-MiniRedir/10.0.19045’, indicating usage of the aforementioned transmission protocol WebDAV. The device was subsequently observed connected to an endpoint associated with Github and downloading data, suggesting that the device was retrieving a malicious tool or payload. The device then began to communicate to the malicious endpoint diciembrenotasenclub[.]longmusic[.]com over the new TCP port 1512 [11].
Around this time, the device was also observed uploading data to the endpoints 21ene.ip-ddns[.]com and diciembrenotasenclub[.]longmusic[.]com, with transfers of 60 MiB and 5.6 MiB observed respectively.
Figure 4: UI graph showing external data transfer activity.
This chain of activity triggered an Enhanced Monitoring model alert in Darktrace / NETWORK. These high-priority model alerts are designed to trigger in response to higher fidelity indicators of compromise (IoCs), suggesting that a device is performing activity consistent with a compromise.
Figure 5: Darktrace’s detection of initial attack chain activity.
A second Enhanced Monitoring model was also triggered by this device following the download of the aforementioned executable file (hxxp://62[.]60[.]226[.]112/file/3601_2042.exe) and the observed increase in C2 activity.
Following this activity, Darktrace continued to observe the device beaconing to the 21ene.ip-ddns[.]com endpoint.
Darktrace’s Cyber AI Analyst was able to correlate each of the individual detections involved in this compromise, identifying them as part of a broader incident that encompassed C2 connectivity, suspicious downloads, and external data transfers.
Figure 6: Cyber AI Analyst’s investigation into the activity observed on the affected device.
Figure 7: Cyber AI Analyst’s detection of the affected device’s broader connectivity throughout the course of the attack.
As the affected customer did not have Darktrace’s Autonomous Response configured at the time, the attack was able to progress unabated. Had Darktrace been properly enabled, it would have been able to take a number of actions to halt the escalation of the attack.
For example, the unusual beaconing connections and the download of an unexpected file from an uncommon location would have been shut down by blocking the device from making external connections to the relevant destinations.
Conclusion
The persistence of Blind Eagle and ability to adapt its tactics, even after patches were released, and the speed at which the group were able to continue using pre-established TTPs highlights that timely vulnerability management and patch application, while essential, is not a standalone defense.
Organizations must adopt security solutions that use anomaly-based detection to identify emerging and adapting threats by recognizing deviations in user or device behavior that may indicate malicious activity. Complementing this with an autonomous decision maker that can identify, connect, and contain compromise-like activity is crucial for safeguarding organizational networks against constantly evolving and sophisticated threat actors.
Credit to Charlotte Thompson (Senior Cyber Analyst), Eugene Chua (Principal Cyber Analyst) and Ryan Traill (Analyst Content Lead)
Appendices
IoCs
IoC – Type - Confidence Microsoft-WebDAV-MiniRedir/10.0.19045 – User Agent
62[.]60[.]226[.]112 – IP – Medium Confidence
hxxp://62[.]60[.]226[.]112/file/3601_2042.exe – Payload Download – Medium Confidence
21ene.ip-ddns[.]com – Dynamic DNS Endpoint – Medium Confidence
diciembrenotasenclub[.]longmusic[.]com - Hostname – Medium Confidence
Darktrace’s model alert coverage
Anomalous File / Suspicious HTTP Redirect Anomalous File / EXE from Rare External Location Anomalous File / Multiple EXE from Rare External Location Anomalous Server Activity / Outgoing from Server Unusual Activity / Unusual External Data to New Endpoint Device / Anomalous Github Download Anomalous Connection / Multiple Connections to New External TCP Port Device / Initial Attack Chain Activity Anomalous Server Activity / Rare External from Server Compromise / Suspicious File and C2 Compromise / Fast Beaconing to DGA Compromise / Large Number of Suspicious Failed Connections Device / Large Number of Model Alert
Mitre Attack Mapping:
Tactic – Technique – Technique Name
Initial Access - T1189 – Drive-by Compromise Initial Access - T1190 – Exploit Public-Facing Application Initial Access ICS - T0862 – Supply Chain Compromise Initial Access ICS - T0865 – Spearphishing Attachment Initial Access ICS - T0817 - Drive-by Compromise Resource Development - T1588.001 – Malware Lateral Movement ICS - T0843 – Program Download Command and Control - T1105 - Ingress Tool Transfer Command and Control - T1095 – Non-Application Layer Protocol Command and Control - T1571 – Non-Standard Port Command and Control - T1568.002 – Domain Generation Algorithms Command and Control ICS - T0869 – Standard Application Layer Protocol Evasion ICS - T0849 – Masquerading Exfiltration - T1041 – Exfiltration Over C2 Channel Exfiltration - T1567.002 – Exfiltration to Cloud Storage
Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision
In today’s threat landscape, email remains the most targeted vector for cyberattacks. Organizations require not only multi-layered defenses but also advanced, integrated systems that work collaboratively to proactively mitigate threats before they cause damage
That’s why we’re proud to announce a new integration between Darktrace / EMAIL and Microsoft Defender for Office 365, delivering a Unified Quarantine experience that empowers security teams with seamless visibility, control, and response across both platforms.
This announcement builds on a strong and growing collaboration. In 2024, Darktrace was honored as Microsoft UK Partner of the Year and recognized as a Security Trailblazer at the annual Microsoft Security 20/20 Awards, a testament to our shared commitment to innovation and customer-centric security.
A Shared Mission: Stopping Threats at Machine Speed
This integration is more than a technical milestone,as it’s a reflection of a shared mission: to protect organizations from both known and unknown threats, with efficiency, accuracy, and transparency.
Microsoft Defender for Office 365 delivers a comprehensive security framework that safeguards Microsoft 365 email and collaboration workloads leveraging advanced AI, global threat intelligence and information on known attack infrastructure.
Darktrace / EMAIL complements this with Self-Learning AI that understands the unique communication patterns within each organization, detecting subtle anomalies that evade traditional detection methods.
Together, we’re delivering multi-layered, adaptive protection that’s greater than the sum of its parts.
“Our integration with Microsoft gives security teams the tools they need to act faster and more precisely to detect and respond to threats,” said Jill Popelka, CEO of Darktrace. “Together, we’re strengthening defenses where it matters most to our customers: at the inbox.”
Unified Quarantine: One View, Total Clarity
The new Unified Quarantine experience gives customers a single pane of glass to view and manage email threatsregardless of which product took action. This means:
Faster investigations with consolidated visibility
Clear attribution of actions and outcomes across both platforms
Streamlined workflows for security teams managing complex environments
“This integration is a testament to the power of combining Microsoft’s global threat intelligence with Darktrace’s unique ability to understand the ‘self’ of an organization,” said Jack Stockdale, CTO of Darktrace. “Together, we’re delivering a new standard in proactive, adaptive email security.”
A New Era of Collaborative Cyber Defense
This collaboration represents a broader shift in cybersecurity: from siloed tools to integrated ecosystems. As attackers become more sophisticated, defenders must move faster, smarter, and in unison.
Through this integration, Darktrace and Microsoft establish a new standard for collaboration between native and third-party security solutions, enhancing not only threat detection but also comprehensive understanding and proactive measures against threats.
We’re excited to bring this innovation to our customers and continue building a future where AI and human expertise collaborate to secure the enterprise.
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