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
Share
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.
Identity-based attacks: How attackers are bypassing traditional defenses
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.
From Rockstar2FA to FlowerStorm: Investigating a Blooming Phishing-as-a-Service Platform
FlowerStorm is a phishing-as-a-service platform that leverages Adversary-in-the-Middle attacks to steal Microsoft 365 credentials and bypass MFA. Darktrace detected a SaaS compromise linked to FlowerStorm, identifying suspicious logins, password resets, and privilege escalation attempts, enabling early containment through AI-driven threat detection and response.
MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services
Tycoon 2FA uses AiTM phishing and legitimate services to bypass MFA. Darktrace AI stopped it, read the blog to learn how Self-Learning AI detects sophisticated threats.
Behind the Veil: Darktrace's Detection of VPN Exploitation in SaaS Environments
A recent phishing attack compromised an internal email account, but Darktrace’s advanced AI quickly intervened. By identifying unusual activity across email and SaaS environments, Darktrace uncovered the attacker’s use of VPNs to mask their location and shut down the threat.
Modernising UK Cyber Regulation: Implications of the Cyber Security and Resilience Bill
The need for security and continued cyber resilience
The UK government has made national security a key priority, and the new Cyber Security and Resilience Bill (CSRB) is a direct reflection of that focus. In introducing the Bill, Secretary of State for Science, Innovation and Technology, Peter Kyle, recognised that the UK is “desperately exposed” to cyber threats—from criminal groups to hostile nation-states that are increasingly targeting the UK's digital systems and critical infrastructure[1].
Context and timeline for the new legislation
First announced during the King’s Speech of July 2024, and elaborated in a Department for Science, Innovation and Technology (DSIT) policy statement published in April 2025, the CSRB is expected to be introduced in Parliament during the 2025-26 legislative session.
For now, organisations in the UK remain subject to the 2018 Network and Information Systems (NIS) Regulations – an EU-derived law which was drafted before today’s increasing digitisation of critical services, rise in cloud adoption and emergence of AI-powered threats.
Why modernisation is critical
Without modernisation, the Government believes UK’s infrastructure and economy risks falling behind international peers. The EU, which revised its cybersecurity regulation under the NIS2 Directive, already imposes stricter requirements on a broader set of sectors.
The urgency of the Bill is also underscored by recent high-impact incidents, including the Synnovis attack which targeted the National Health Service (NHS) suppliers and disrupted thousands of patient appointments and procedures[2]. The Government has argued that such events highlight a systemic failure to keep pace with a rapidly evolving threat landscape[3].
What the Bill aims to achieve
This Bill represents a decisive shift. According to the Government, it will modernise and future‑proof the UK’s cyber laws, extending oversight to areas where risk has grown but regulation has not kept pace[4]. While the legislation builds on previous consultations and draws lessons from international frameworks like the EU’s NIS2 directive, it also aims to tailor solutions to the UK’s unique threat environment.
Importantly, the Government is framing cybersecurity not as a barrier to growth, but as a foundation for it. The policy statement emphasises that strong digital resilience will create the stability businesses need to thrive, innovate, and invest[5]. Therefore, the goals of the Bill will not only be to enhance security but also act as an enabler to innovation and economic growth.
Recognition that AI changes cyber threats
The CSRB policy statement recognises that AI is fundamentally reshaping the threat landscape, with adversaries now leveraging AI and commercial cyber tools to exploit vulnerabilities in critical infrastructure and supply chains. Indeed, the NCSC has recently assessed that AI will almost certainly lead to “an increase in the frequency and intensity of cyber threats”[6]. Accordingly, the policy statement insists that the UK’s regulatory framework “must keep pace and provide flexibility to respond to future threats as and when they emerge”[7].
To address the threat, the Bill signals new obligations for MSPs and data centres, timely incident reporting and dynamic guidance that can be refreshed without fresh primary legislation, making it essential for firms to follow best practices.
What might change in day-to-day practice?
New organisations in scope of regulation
Under the existing Network and Information Systems (NIS) Regulations[8], the UK already supervises operators in five critical sectors—energy, transport, drinking water, health (Operators of Essential Services, OES) and digital infrastructure (Relevant Digital Service Providers, RDSPs).
The Cyber Security and Resilience Bill retains this foundation and adds Managed Service Providers (MSPs) and data centres to the scope of regulation to “better recognise the increasing reliance on digital services and the vulnerabilities posed by supply chains”[9]. It also grants the Secretary of State for Science, Innovation and Technology the power to add new sectors or sub‑sectors via secondary legislation, following consultation with Parliament and industry.
Managed service providers (MSPs)
MSPs occupy a central position within the UK’s enterprise information‑technology infrastructure. Because they remotely run or monitor clients’ systems, networks and data, they hold privileged, often continuous access to multiple environments. This foothold makes them an attractive target for malicious actors.
The Bill aims to bring MSPs in scope of regulation by making them subject to the same duties as those placed on firms that provide digital services under the 2018 NIS Regulations. By doing so, the Bill seeks to raise baseline security across thousands of customer environments and to provide regulators with better visibility of supply‑chain risk.
The proposed definition for MSPs is a service which:
Is provided to another organisation
Relies on the use of network and information systems to deliver the service
Relates to ongoing management support, active administration and/or monitoring of AI systems, IT infrastructure, applications, and/or IT networks, including for the purpose of activities relating to cyber security.
Involves a network connection and/or access to the customer’s network and information systems.
Data centres
Building on the September 2024 designation of data centres as critical national infrastructure, the CSRB will fold data infrastructure into the NIS-style regime by naming it an “relevant sector" and data centres as “essential service”[10].
About 182 colocation facilities run by 64 operators will therefore come under statutory duties to notify the regulator, maintain proportionate CAF-aligned controls and report significant incidents, regardless of who owns them or what workloads they host.
New requirements for regulated organisations
Incident reporting processes
There could be stricter timelines or broader definitions of what counts as a reportable incident. This might nudge organisations to formalise detection, triage, and escalation procedures.
The Government is proposing to introduce a new two-stage incident reporting process. This would include an initial notification which would be submitted within 24 hours of becoming aware of a significant incident, followed by a full incident report which should be submitted within 72 hours of the same.
Supply chain assurance requirements
Supply chains for the UK's most critical services are becoming increasingly complex and present new and serious vulnerabilities for cyber-attacks. The recent Synnovis ransomware attacks on the NHS[11] exemplify the danger posed by attacks against the supply chains of important services and organisations. This is concerning when reflecting on the latest Cyber Security Breaches survey conducted by DSIT, which highlights that fewer than 25% of large businesses review their supply chain risks[12].
Despite these risks, the UK’s legacy cybersecurity regulatory regime does not explicitly cover supply chain risk management. The UK instead relies on supporting and non-statutory guidance to close this gap, such as the NCSC’s Cyber Assessment Framework (CAF)[13].
The CSRB policy statement acts on this regulatory shortcoming and recognises that “a single supplier’s disruption can have far-reaching impacts on the delivery of essential or digital services”[14].
To address this, the Bill would make in-scope organisations (OES and RDPS) directly accountable for the cybersecurity of their supply chains. Secondary legislation would spell out these duties in detail, ensuring that OES and RDSPs systematically assess and mitigate third-party cyber risks.
Updated and strengthened security requirements
By placing the CAF into a firmer footing and backing it with a statutory Code of Practice, the Government is setting clearer expectations about government expectations on technical standards and methods organisations will need to follow to prove their resilience.
How Darktrace can help support affected organizations
Demonstrate resilience
Darktrace’s Self-Learning AITM continuously monitors your digital estate across cloud, network, OT, email, and endpoint to detect, investigate, and autonomously respond to emerging threats in real time. This persistent visibility and defense posture helps organizations demonstrate cyber resilience to regulators with confidence.
Streamline incident reporting and compliance
Darktrace surfaces clear alerts and automated investigation reports, complete with timeline views and root cause analysis. These insights reduce the time and complexity of regulatory incident reporting and support internal compliance workflows with auditable, AI-generated evidence.
Improve supply chain visibility
With full visibility across connected systems and third-party activity, Darktrace detects early indicators of lateral movement, account compromise, and unusual behavior stemming from vendor or partner access, reducing the risk of supply chain-originated cyber-attacks.
Ensure MSPs can meet new standards
For managed service providers, Darktrace offers native multi-tenant support and autonomous threat response that can be embedded directly into customer environments. This ensures consistent, scalable security standards across clients—helping MSPs address increasing regulatory obligations.
Unpacking ClickFix: Darktrace’s detection of a prolific social engineering tactic
What is ClickFix and how does it work?
Amid heightened security awareness, threat actors continue to seek stealthy methods to infiltrate target networks, often finding the human end user to be the most vulnerable and easily exploited entry point.
ClickFix baiting is an exploitation of the end user, making use of social engineering techniques masquerading as error messages or routine verification processes, that can result in malicious code execution.
Since March 2024, the simplicity of this technique has drawn attention from a range of threat actors, from individual cybercriminals to Advanced Persistent Threat (APT) groups such as APT28 and MuddyWater, linked to Russia and Iran respectively, introducing security threats on a broader scale [1]. ClickFix campaigns have been observed affecting organizations in across multiple industries, including healthcare, hospitality, automotive and government [2][3].
Actors carrying out these targeted attacks typically utilize similar techniques, tools and procedures (TTPs) to gain initial access. These include spear phishing attacks, drive-by compromises, or exploiting trust in familiar online platforms, such as GitHub, to deliver malicious payloads [2][3]. Often, a hidden link within an email or malvertisements on compromised legitimate websites redirect the end user to a malicious URL [4]. These take the form of ‘Fix It’ or fake CAPTCHA prompts [4].
From there, users are misled into believing they are completing a human verification step, registering a device, or fixing a non-existent issue such as a webpage display error. As a result, they are guided through a three-step process that ultimately enables the execution of malicious PowerShell commands:
Open a Windows Run dialog box [press Windows Key + R]
Automatically or manually copy and paste a malicious PowerShell command into the terminal [press CTRL+V]
And run the prompt [press ‘Enter’] [2]
Once the malicious PowerShell command is executed, threat actors then establish command and control (C2) communication within the targeted environment before moving laterally through the network with the intent of obtaining and stealing sensitive data [4]. Malicious payloads associated with various malware families, such as XWorm, Lumma, and AsyncRAT, are often deployed [2][3].
Based on investigations conducted by Darktrace’s Threat Research team in early 2025, this blog highlights Darktrace’s capability to detect ClickFix baiting activity following initial access.
Darktrace’s coverage of a ClickFix attack chain
Darktrace identified multiple ClickFix attacks across customer environments in both Europe, the Middle East, and Africa (EMEA) and the United States. The following incident details a specific attack on a customer network that occurred on April 9, 2025.
Although the initial access phase of this specific attack occurred outside Darktrace’s visibility, other affected networks showed compromise beginning with phishing emails or fake CAPTCHA prompts that led users to execute malicious PowerShell commands.
Darktrace’s visibility into the compromise began when the threat actor initiated external communication with their C2 infrastructure, with Darktrace / NETWORK detecting the use of a new PowerShell user agent, indicating an attempt at remote code execution.
Figure 1: Darktrace / NETWORK's detection of a device making an HTTP connection with new PowerShell user agent, indicating PowerShell abuse for C2 communications.
Download of Malicious Files for Lateral Movement
A few minutes later, the compromised device was observed downloading a numerically named file. Numeric files like this are often intentionally nondescript and associated with malware. In this case, the file name adhered to a specific pattern, matching the regular expression: /174(\d){7}/. Further investigation into the file revealed that it contained additional malicious code designed to further exploit remote services and gather device information.
Figure 2: Darktrace / NETWORK's detection of a numeric file, one minute after the new PowerShell User Agent alert.
The file contained a script that sent system information to a specified IP address using an HTTP POST request, which also processed the response. This process was verified through packet capture (PCAP) analysis conducted by the Darktrace Threat Research team.
By analyzing the body content of the HTTP GET request, it was observed that the command converts the current time to Unix epoch time format (i.e., 9 April 2025 13:26:40 GMT), resulting in an additional numeric file observed in the URI: /1744205200.
Figure 3: PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.
Across Darktrace’s investigations into other customers' affected by ClickFix campaigns, both internal information discovery events and further execution of malicious code were observed.
Data Exfiltration
By following the HTTP stream in the same PCAP, the Darktrace Threat Research Team assessed the activity as indicative of data exfiltration involving system and device information to the same command-and-control (C2) endpoint, , 193.36.38[.]237. This endpoint was flagged as malicious by multiple open-source intelligence (OSINT) vendors [5].
Figure 4: PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.
Further analysis of Darktrace’s Advanced Search logs showed that the attacker’s malicious code scanned for internal system information, which was then sent to a C2 server via an HTTP POST request, indicating data exfiltration
Figure 5: Advanced Search further highlights Darktrace's observation of the HTTP POST request, with the second numeric file representing data exfiltration.
Actions on objectives
Around ten minutes after the initial C2 communications, the compromised device was observed connecting to an additional rare endpoint, 188.34.195[.]44. Further analysis of this endpoint confirmed its association with ClickFix campaigns, with several OSINT vendors linking it to previously reported attacks [6].
In the final HTTP POST request made by the device, Darktrace detected a file at the URI /init1234 in the connection logs to the malicious endpoint 188.34.195[.]44, likely depicting the successful completion of the attack’s objective, automated data egress to a ClickFix C2 server.
Darktrace / NETWORK grouped together the observed indicators of compromise (IoCs) on the compromised device and triggered an Enhanced Monitoring model alert, a high-priority detection model designed to identify activity indicative of the early stages of an attack. These models are monitored and triaged 24/7 by Darktrace’s Security Operations Center (SOC) as part of the Managed Threat Detection service, ensuring customers are promptly notified of malicious activity as soon as it emerges.
Figure 6: Darktrace correlated the separate malicious connections that pertained to a single campaign.
Darktrace Autonomous Response
In the incident outlined above, Darktrace was not configured in Autonomous Response mode. As a result, while actions to block specific connections were suggested, they had to be manually implemented by the customer’s security team. Due to the speed of the attack, this need for manual intervention allowed the threat to escalate without interruption.
However, in a different example, Autonomous Response was fully enabled, allowing Darktrace to immediately block connections to the malicious endpoint (138.199.156[.]22) just one second after the initial connection in which a numerically named file was downloaded [7].
Figure 7: Darktrace Autonomous Response blocked connections to a suspicious endpoint following the observation of the numeric file download.
This customer was also subscribed to our Managed Detection and Response service, Darktrace’s SOC extended a ‘Quarantine Device’ action that had already been autonomously applied in order to buy their security team additional time for remediation.
Figure 8: Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.
Conclusion
ClickFix baiting is a widely used tactic in which threat actors exploit human error to bypass security defenses. By tricking end point users into performing seemingly harmless, everyday actions, attackers gain initial access to systems where they can access and exfiltrate sensitive data.
Darktrace’s anomaly-based approach to threat detection identifies early indicators of targeted attacks without relying on prior knowledge or IoCs. By continuously learning each device’s unique pattern of life, Darktrace detects subtle deviations that may signal a compromise. In this case, Darktrace's Autonomous Response, when operating in a fully autonomous mode, was able to swiftly contain the threat before it could progress further along the attack lifecycle.
Credit to Keanna Grelicha (Cyber Analyst) and Jennifer Beckett (Cyber Analyst)
Appendices
NETWORK Models
Device / New PowerShell User Agent
Anomalous Connection / New User Agent to IP Without Hostname
Anomalous Connection / Posting HTTP to IP Without Hostname
Anomalous Connection / Powershell to Rare External
Device / Suspicious Domain
Device / New User Agent and New IP
Anomalous File / New User Agent Followed By Numeric File Download (Enhanced Monitoring Model)
.jpg)
![PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/684068fac1b4368f672c17cc_Screenshot%202025-06-04%20at%208.40.32%E2%80%AFAM.png)
![PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6840694509d92b6220ccf5f1_Screenshot%202025-06-04%20at%208.41.48%E2%80%AFAM.png)
![Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/68406a1f723c9d6fda9c5268_Screenshot%202025-06-04%20at%208.45.23%E2%80%AFAM.png)