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September 4, 2022

Steps of a BumbleBee Intrusion to a Cobalt Strike

Discover the steps of a Bumblebee intrusion, from initial detection to Cobalt Strike deployment. Learn how Darktrace defends against evolving threats with AI.
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
Sam Lister
Specialist Security Researcher
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04
Sep 2022

Introduction

Throughout April 2022, Darktrace observed several cases in which threat actors used the loader known as ‘BumbleBee’ to install Cobalt Strike Beacon onto victim systems. The threat actors then leveraged Cobalt Strike Beacon to conduct network reconnaissance, obtain account password data, and write malicious payloads across the network. In this article, we will provide details of the actions threat actors took during their intrusions, as well as details of the network-based behaviours which served as evidence of the actors’ activities.  

BumbleBee 

In March 2022, Google’s Threat Analysis Group (TAG) provided details of the activities of an Initial Access Broker (IAB) group dubbed ‘Exotic Lily’ [1]. Before March 2022, Google’s TAG observed Exotic Lily leveraging sophisticated impersonation techniques to trick employees of targeted organisations into downloading ISO disc image files from legitimate file storage services such as WeTransfer. These ISO files contained a Windows shortcut LNK file and a BazarLoader Dynamic Link Library (i.e, DLL). BazarLoader is a member of the Bazar family — a family of malware (including both BazarLoader and BazarBackdoor) with strong ties to the Trickbot malware, the Anchor malware family, and Conti ransomware. BazarLoader, which is typically distributed via email campaigns or via fraudulent call campaigns, has been known to drop Cobalt Strike as a precursor to Conti ransomware deployment [2]. 

In March 2022, Google’s TAG observed Exotic Lily leveraging file storage services to distribute an ISO file containing a DLL which, when executed, caused the victim machine to make HTTP requests with the user-agent string ‘bumblebee’. Google’s TAG consequently called this DLL payload ‘BumbleBee’. Since Google’s discovery of BumbleBee back in March, several threat research teams have reported BumbleBee samples dropping Cobalt Strike [1]/[3]/[4]/[5]. It has also been reported by Proofpoint [3] that other threat actors such as TA578 and TA579 transitioned to BumbleBee in March 2022.  

Interestingly, BazarLoader’s replacement with BumbleBee seems to coincide with the leaking of the Conti ransomware gang’s Jabber chat logs at the end of February 2022. On February 25th, 2022, the Conti gang published a blog post announcing their full support for the Russian state’s invasion of Ukraine [6]. 

Figure 1: The Conti gang's public declaration of their support for Russia's invasion of Ukraine

Within days of sharing their support for Russia, logs from a server hosting the group’s Jabber communications began to be leaked on Twitter by @ContiLeaks [7]. The leaked logs included records of conversations among nearly 500 threat actors between Jan 2020 and March 2022 [8]. The Jabber logs were supposedly stolen and leaked by a Ukrainian security researcher [3]/[6].

Affiliates of the Conti ransomware group were known to use BazarLoader to deliver Conti ransomware [9]. BumbleBee has now also been linked to the Conti ransomware group by several threat research teams [1]/[10]/[11]. The fact that threat actors’ transition from BazarLoader to BumbleBee coincides with the leak of Conti’s Jabber chat logs may indicate that the transition occurred as a result of the leaks [3]. Since the transition, BumbleBee has become a significant tool in the cyber-crime ecosystem, with links to several ransomware operations such as Conti, Quantum, and Mountlocker [11]. The rising use of BumbleBee by threat actors, and particularly ransomware actors, makes the early detection of BumbleBee key to identifying the preparatory stages of ransomware attacks.  

Intrusion Kill Chain 

In April 2022, Darktrace observed the following pattern of threat actor activity within the networks of several Darktrace clients: 

1.     Threat actor socially engineers user via email into running a BumbleBee payload on their device

2.     BumbleBee establishes HTTPS communication with a BumbleBee C2 server

3.     Threat actor instructs BumbleBee to download and execute Cobalt Strike Beacon

4.     Cobalt Strike Beacon establishes HTTPS communication with a Cobalt Strike C2 server

5.     Threat actor instructs Cobalt Strike Beacon to scan for open ports and to enumerate network shares

6.     Threat actor instructs Cobalt Strike Beacon to use the DCSync technique to obtain password account data from an internal domain controller

7.     Threat actor instructs Cobalt Strike Beacon to distribute malicious payloads to other internal systems 

With limited visibility over affected clients’ email environments, Darktrace was unable to determine how the threat actors interacted with users to initiate the BumbleBee infection. However, based on open-source reporting on BumbleBee [3]/[4]/[10]/[11]/[12]/[13]/[14]/[15]/[16]/[17], it is likely that the actors tricked target users into running BumbleBee by sending them emails containing either a malicious zipped ISO file or a link to a file storage service hosting the malicious zipped ISO file. These ISO files typically contain a LNK file and a BumbleBee DLL payload. The properties of these LNK files are set in such a way that opening them causes the corresponding DLL payload to run. 

In several cases observed by Darktrace, devices contacted a file storage service such as Microsoft OneDrive or Google Cloud Storage immediately before they displayed signs of BumbleBee infection. In these cases, it is likely that BumbleBee was executed on the users’ devices as a result of the users interacting with an ISO file which they were tricked into downloading from a file storage service. 

Figure 2: The above figure, taken from the event log for an infected device, shows that the device contacted a OneDrive endpoint immediately before making HTTPS connections to the BumbleBee C2 server, 45.140.146[.]244
Figure 3: The above figure, taken from the event log for an infected device, shows that the device contacted a Google Cloud Storage endpoint and then the malicious endpoint ‘marebust[.]com’ before making HTTPS connections to the  BumbleBee C2 servers, 108.62.118[.]61 and 23.227.198[.]217

After users ran a BumbleBee payload, their devices immediately initiated communications with BumbleBee C2 servers. The BumbleBee samples used HTTPS for their C2 communication, and all presented a common JA3 client fingerprint, ‘0c9457ab6f0d6a14fc8a3d1d149547fb’. All analysed samples excluded domain names in their ‘client hello’ messages to the C2 servers, which is unusual for legitimate HTTPS communication. External SSL connections which do not specify a destination domain name and whose JA3 client fingerprint is ‘0c9457ab6f0d6a14fc8a3d1d149547fb’ are potential indicators of BumbleBee infection. 

Figure 4:The above figure, taken from Darktrace's Advanced Search interface, depicts an infected device's spike in HTTPS connections with the JA3 client fingerprint ‘0c9457ab6f0d6a14fc8a3d1d149547fb’

Once the threat actors had established HTTPS communication with the BumbleBee-infected systems, they instructed BumbleBee to download and execute Cobalt Strike Beacon. This behaviour resulted in the infected systems making HTTPS connections to Cobalt Strike C2 servers. The Cobalt Strike Beacon samples all had the same JA3 client fingerprint ‘a0e9f5d64349fb13191bc781f81f42e1’ — a fingerprint associated with previously seen Cobalt Strike samples [18]. The domain names ‘fuvataren[.]com’ and ‘cuhirito[.]com’ were observed in the samples’ HTTPS communications. 

Figure 5:The above figure, taken from Darktrace's Advanced Search interface, depicts the Cobalt Strike C2 communications which immediately followed a device's BumbleBee C2 activity

Cobalt Strike Beacon payloads call home to C2 servers for instructions. In the cases observed, threat actors first instructed the Beacon payloads to perform reconnaissance tasks, such as SMB port scanning and SMB enumeration. It is likely that the threat actors performed these steps to inform the next stages of their operations.  The SMB enumeration activity was evidenced by the infected devices making NetrShareEnum and NetrShareGetInfo requests to the srvsvc RPC interface on internal systems.

Figure 6: The above figure, taken from Darktrace’s Advanced Search interface, depicts a spike in srvsvc requests coinciding with the infected device's Cobalt Strike C2 activity

After providing Cobalt Strike Beacon with reconnaissance tasks, the threat actors set out to obtain account password data in preparation for the lateral movement phase of their operation. To obtain account password data, the actors instructed Cobalt Strike Beacon to use the DCSync technique to replicate account password data from an internal domain controller. This activity was evidenced by the infected devices making DRSGetNCChanges requests to the drsuapi RPC interface on internal domain controllers. 

Figure 7: The above figure, taken from Darktrace’s Advanced Search interface, depicts a spike in DRSGetNCChanges requests coinciding with the infected device’s Cobalt Strike C2 activity

After leveraging the DCSync technique, the threat actors sought to broaden their presence within the targeted networks.  To achieve this, they instructed Cobalt Strike Beacon to get several specially selected internal systems to run a suspiciously named DLL (‘f.dll’). Cobalt Strike first established SMB sessions with target systems using compromised account credentials. During these sessions, Cobalt Strike uploaded the malicious DLL to a hidden network share. To execute the DLL, Cobalt Strike abused the Windows Service Control Manager (SCM) to remotely control and manipulate running services on the targeted internal hosts. Cobalt Strike first opened a binding handle to the svcctl interface on the targeted destination systems. It then went on to make an OpenSCManagerW request, a CreateServiceA request, and a StartServiceA request to the svcctl interface on the targeted hosts: 

·      Bind request – opens a binding handle to the relevant RPC interface (in this case, the svcctl interface) on the destination device

·      OpenSCManagerW request – establishes a connection to the Service Control Manager (SCM) on the destination device and opens a specified SCM database

·      CreateServiceA request – creates a service object and adds it to the specified SCM database 

·      StartServiceA request – starts a specified service

Figure 8: The above figure, taken from Darktrace’s Advanced Search interface, outlines an infected system’s lateral movement activities. After writing a file named ‘f.dll’ to the C$ share on an internal server, the infected device made several RPC requests to the svcctl interface on the targeted server

It is likely that the DLL file which the threat actors distributed was a Cobalt Strike payload. In one case, however, the threat actor was also seen distributing and executing a payload named ‘procdump64.exe’. This may suggest that the threat actor was seeking to use ProcDump to obtain authentication material stored in the process memory of the Local Security Authority Subsystem Service (LSASS). Given that ProcDump is a legitimate Windows Sysinternals tool primarily used for diagnostics and troubleshooting, it is likely that threat actors leveraged it in order to evade detection. 

In all the cases which Darktrace observed, threat actors’ attempts to conduct follow-up activities after moving laterally were thwarted with the help of Darktrace’s SOC team. It is likely that the threat actors responsible for the reported activities were seeking to deploy ransomware within the targeted networks. The steps which the threat actors took to make progress towards achieving this objective resulted in highly unusual patterns of network traffic. Darktrace’s detection of these unusual network activities allowed security teams to prevent these threat actors from achieving their disruptive objectives. 

Darktrace Coverage

Once threat actors succeeded in tricking users into running BumbleBee on their devices, Darktrace’s Self-Learning AI immediately detected the command-and-control (C2) activity generated by the loader. BumbleBee’s C2 activity caused the following Darktrace models to breach:

·      Anomalous Connection / Anomalous SSL without SNI to New External

·      Anomalous Connection / Suspicious Self-Signed SSL

·      Anomalous Connection / Rare External SSL Self-Signed

·      Compromise / Suspicious TLS Beaconing To Rare External

·      Compromise / Beacon to Young Endpoint

·      Compromise / Beaconing Activity To External Rare

·      Compromise / Sustained SSL or HTTP Increase

·      Compromise / Suspicious TLS Beaconing To Rare External

·      Compromise / SSL Beaconing to Rare Destination

·      Compromise / Large Number of Suspicious Successful Connections

·      Device / Multiple C2 Model Breaches 

BumbleBee’s delivery of Cobalt Strike Beacon onto target systems resulted in those systems communicating with Cobalt Strike C2 servers. Cobalt Strike Beacon’s C2 communications resulted in breaches of the following models: 

·      Compromise / Beaconing Activity To External Rare

·      Compromise / High Volume of Connections with Beacon Score

·      Compromise / Large Number of Suspicious Successful Connections

·      Compromise / Sustained SSL or HTTP Increase

·      Compromise / SSL or HTTP Beacon

·      Compromise / Slow Beaconing Activity To External Rare

·      Compromise / SSL Beaconing to Rare Destination 

The threat actors’ subsequent port scanning and SMB enumeration activities caused the following models to breach:

·      Device / Network Scan

·      Anomalous Connection / SMB Enumeration

·      Device / Possible SMB/NTLM Reconnaissance

·      Device / Suspicious Network Scan Activity  

The threat actors’ attempts to obtain account password data from domain controllers using the DCSync technique resulted in breaches of the following models: 

·      Compromise / Unusual SMB Session and DRS

·      Anomalous Connection / Anomalous DRSGetNCChanges Operation

Finally, the threat actors’ attempts to internally distribute and execute payloads resulted in breaches of the following models:

·      Compliance / SMB Drive Write

·      Device / Lateral Movement and C2 Activity

·      Device / SMB Lateral Movement

·      Device / Multiple Lateral Movement Model Breaches

·      Anomalous File / Internal / Unusual SMB Script Write

·      Anomalous File / Internal / Unusual Internal EXE File Transfer

·      Anomalous Connection / High Volume of New or Uncommon Service Control

If Darktrace/Network had been configured in the targeted environments, then it would have blocked BumbleBee’s C2 communications, which would have likely prevented the threat actors from delivering Cobalt Strike Beacon into the target networks. 

Figure 9: Attack timeline

Conclusion

Threat actors use loaders to smuggle more harmful payloads into target networks. Prior to March 2022, it was common to see threat actors using the BazarLoader loader to transfer their payloads into target environments. However, since the public disclosure of the Conti gang’s Jabber chat logs at the end of February, the cybersecurity world has witnessed a shift in tradecraft. Threat actors have seemingly transitioned from using BazarLoader to using a novel loader known as ‘BumbleBee’. Since BumbleBee first made an appearance in March 2022, a growing number of threat actors, in particular ransomware actors, have been observed using it.

It is likely that this trend will continue, which makes the detection of BumbleBee activity vital for the prevention of ransomware deployment within organisations’ networks. During April, Darktrace’s SOC team observed a particular pattern of threat actor activity involving the BumbleBee loader. After tricking users into running BumbleBee on their devices, threat actors were seen instructing BumbleBee to drop Cobalt Strike Beacon. Threat actors then leveraged Cobalt Strike Beacon to conduct network reconnaissance, obtain account password data from internal domain controllers, and distribute malicious payloads internally.  Darktrace’s detection of these activities prevented the threat actors from achieving their likely harmful objectives.  

Thanks to Ross Ellis for his contributions to this blog.

Appendices 

References 

[1] https://blog.google/threat-analysis-group/exposing-initial-access-broker-ties-conti/ 

[2] https://securityintelligence.com/posts/trickbot-gang-doubles-down-enterprise-infection/ 

[3] https://www.proofpoint.com/us/blog/threat-insight/bumblebee-is-still-transforming

[4] https://www.cynet.com/orion-threat-alert-flight-of-the-bumblebee/ 

[5] https://research.nccgroup.com/2022/04/29/adventures-in-the-land-of-bumblebee-a-new-malicious-loader/ 

[6] https://www.bleepingcomputer.com/news/security/conti-ransomwares-internal-chats-leaked-after-siding-with-russia/ 

[7] https://therecord.media/conti-leaks-the-panama-papers-of-ransomware/ 

[8] https://www.secureworks.com/blog/gold-ulrick-leaks-reveal-organizational-structure-and-relationships 

[9] https://www.prodaft.com/m/reports/Conti_TLPWHITE_v1.6_WVcSEtc.pdf 

[10] https://www.kroll.com/en/insights/publications/cyber/bumblebee-loader-linked-conti-used-in-quantum-locker-attacks 

[11] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/bumblebee-loader-cybercrime 

[12] https://isc.sans.edu/diary/TA578+using+thread-hijacked+emails+to+push+ISO+files+for+Bumblebee+malware/28636 

[13] https://isc.sans.edu/diary/rss/28664 

[14] https://www.logpoint.com/wp-content/uploads/2022/05/buzz-of-the-bumblebee-a-new-malicious-loader-threat-report-no-3.pdf 

[15] https://ghoulsec.medium.com/mal-series-23-malware-loader-bumblebee-6ab3cf69d601 

[16]  https://blog.cyble.com/2022/06/07/bumblebee-loader-on-the-rise/  

[17]  https://asec.ahnlab.com/en/35460/ 

[18] https://thedfirreport.com/2021/07/19/icedid-and-cobalt-strike-vs-antivirus/

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
Sam Lister
Specialist Security Researcher

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June 26, 2026

How Darktrace Transformed Cybersecurity at Our Health Center: A CIO’s Perspective

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How Darktrace Transformed Cybersecurity at Our Health Center: A CIO’s Perspective

In my role as CIO, I bring years of experience leading IT for healthcare organizations. I’ve seen firsthand the unique cybersecurity challenges that nonprofit health centers face: limited budgets, small IT teams, and the constant pressure to prioritize patient care over technology investments. Yet, the threat landscape for health is relentless, and the stakes for protecting patient data and ensuring operational continuity have never been higher. It’s a balancing act.

The search for a better solution

Like many nonprofits, organizations I work at start with Microsoft’s security stack. The discounted pricing for nonprofits makes it an obvious choice, and Microsoft Defender provided a solid foundation for endpoint and email security. However, I quickly realized that relying on a single vendor, even one as robust as Microsoft, left gaps in our defenses. Cybersecurity is never one-size-fits-all, which is why my preference was to layer an additional solution on top of our native security to improve our security posture.

Teams needed a solution that could layer seamlessly on top of Microsoft, without adding complexity or draining limited resources. That’s when I found Darktrace. I had heard of their reputation after seeing how other organizations used Darktrace to secure their infrastructure and was impressed by their AI-native, agentless approach and agreed to a proof of value (POV).

Our goal was to elavate Microsoft with an additional layer of intelligence- one that could seamlessly integrate, operate autonomously, and support a small team without increasing overhead. We turned to Darktrace because its AI-native, agentless approach offered a fundamentally different way to detect and respond to threats, learning our environment in real time and filling gaps that traditional tools can miss. With a quick POV, we were able to validate how effectively Darktrace works alongside Microsoft to deliver a more complete and resilient security architecture.

Why Darktrace stood out

From the start, Darktrace differentiated itself in several critical ways:

  • Deep visibility: Unlike other solutions that rely simply on host-based monitoring with endpoint agents, Darktrace operates passively at the network layer and integrates via APIs for email and identity security. This gave full visibility into network traffic that we previously didn’t have, going beyond our existing endpoint-based tools without adding additional maintenance overhead for our small IT team.
  • AI-native from the ground up: Darktrace wasn’t just layering AI on top of an existing product; it was built with AI at its core. Their autonomous detection and response to threats immediately reduced the need for constant human supervision. In a world where cyber-attacks are increasingly sophisticated and subtle, having an AI that learns our environment and adapts in real time is invaluable.
  • Comprehensive coverage: We started with a POV focused on email security, but quickly expanded to full deployment across our entire infrastructure. Darktrace’s products now protect our email, network, and identity layers, providing visibility and defense against lateral movement and abnormal behavior that traditional tools often miss.

Integration and workflow: Smooth and simple

One of the most impressive aspects of Darktrace is how easy it was to integrate into an existing environment. For network security, it was as simple as plugging an appliance into our top-of-rack switch – no downtime, no complex configuration. For email and identity, API integrations meant we could be up and running in hours, not weeks.

This simplicity extended to day-to-day operations. Our IT team received regular security reports, and any time we had questions or needed to adjust policies, Darktrace’s support team was there with white-glove service. Their responsiveness- even in the middle of the night- gave us confidence that we had true partners, not just a vendor.

Real-world impact: Threats stopped, time saved

The results spoke for themselves. During the time with Darktrace, I did not experience any security incidents. The team slept better at night knowing that Darktrace was monitoring for anomalies and proactively blocking suspicious activity, alerting us even before we noticed anything was wrong.

A memorable example was during an Electronic Health Record (EHR) upgrade, when my team forgot to adjust the policy in advance. Darktrace’s autonomous response was so effective that it blocked our upgrade activities- proof that nothing, not even internal changes, could slip by unnoticed. This level of vigilance meant that ransomware, data exfiltration attempts, or insider threats would be detected and contained before causing harm.

While I can’t share specific ROI numbers, the value was clear: we’ve avoided costly breaches, reduced the time spent investigating alerts, and eliminated the performance drag of agent-based tools. With Darktrace layered on top of Microsoft, I’ve hit the right balance of maximum protection with minimal spending. The cost of Darktrace / EMAIL was competitive, especially when factoring in the included Managed Detection and Response (MDR) service, which provides expert human oversight on top of the AI.

Key differentiators over the competition

  • Extending visibility beyond the endpoint: Traditional host-based monitoring solutions, such as EDR, play a critical role in securing individual devices. By adding a network detection and response (NDR) layer, we gained visibility into activity across our wider digital environment, surfacing threats that move laterally, operate between devices, or bypass endpoint controls. Darktrace also stood out for its ability to learn our normal patterns of behavior and identify subtle deviations in real time, not just known indicators of compromise. Because this is delivered through passive, non-disruptive monitoring, we were able to strengthen our defenses without adding complexity or impacting performance.
  • Layered security without complexity: Darktrace elevated our Microsoft foundation without creating conflicts or requiring us to disable existing protections. This layered approach maximized our security posture without adding operational burden.
  • Expert partnership: Beyond technology, Darktrace’s team acted as true partners, guiding us through deployment, providing ongoing support, and helping us interpret findings. This partnership was as valuable as the technology itself.

Advice for other nonprofits

If you’re an IT leader in a nonprofit, my advice is simple: look for solutions that are easy to deploy, intelligent in their response, and cost-effective. Don’t settle for more endpoint based tools that overlap with what you already have. Seek out a layered approach that covers your blind spots – especially at the network and email layers- at a price point that suits your organization.

Most importantly, don’t be afraid to evaluate new solutions. Even if you’re inundated with vendor pitches, you owe it to your organization to explore options that could save you time, money, and sleepless nights.

For organizations I work at, combining Microsoft’s security stack with Darktrace’s AI-native, platform struck the right balance between protection and practicality. We gained enterprise-grade security without sacrificing performance or stretching our budget. In the end, that meant more resources for what matters most: delivering care to our patients. If you’re facing similar challenges, I encourage you to consider how Darktrace could transform your security posture, and give your team the peace of mind they deserve.

For the organization I work in, combining Microsoft with Darktrace delivered a clear step-change in our security posture. Microsoft provided the foundation, while Darktrace’s behavioral intelligence added visibility into the unknown, surfacing emerging threats based on deviations in real-time activity, not just known indicators.

The result was enterprise-grade protection without added overhead, allowing us to stay focused on patient outcomes, not security operations. For organizations facing similar pressures, this layered approach offers a smarter, more efficient path to securing modern environments.

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Mice Chen
Chief Information Security Officer

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June 25, 2026

Shadow AI Detection: The First Step Toward Securing AI

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Why shadow AI is emerging  

Imagine you’re an employee under pressure, deadlines stacking up, repetitive tasks piling higher by the day. You find a free AI tool online that promises to automate the work in seconds; no approvals are needed. It feels like a simple win, paste in some data, write a quick prompt, and move faster.

But in that moment, something changed.  

Sensitive customer information is entered into a tool your organization doesn’t monitor, doesn’t govern, and can’t see and suddenly, that data is no longer where it should be, and no one knows where it’s gone.

This is the reality of Shadow AI: employees using unsanctioned AI tools to move faster, while unintentionally creating risk that exists entirely outside visibility and control.  

This is not just a one off case, research across businesses indicate that nearly half of employees report using unsanctioned AI tools, often prioritizing speed and productivity over security. Additionally, 51% of employees report connecting AI tools to work systems or apps without IT approval, creating significant operational risk where the average cost of security incidents in organizations with a high level of shadow AI usage can reach $670k.

While shadow AI is often top of mind for security professionals, it is just one component of how AI use can increase risk. Understanding and managing shadow AI use should be considered as part of a broader, comprehensive risk management strategy that aims to secure AI systems, including human and agent identities, interactions, human-AI partnerships, and behaviors operating across the digital enterprise from visibility and governance through detection, response, and recovery.  

Effective risk management calls for a layered and interdisciplinary strategy. It requires addressing issues across governance and visibility; identity, access and agent control, data security and privacy, secure MLOps / LLMOps, runtime security, behavior-based detection, autonomous response and recovery.  

This blog explores a specific governance and visibility use case linked to shadow AI and reveals the challenges it presents as well as the defensive strategies that security teams can adopt.

Why shadow AI is hard to detect  

When it comes to AI, what organizations can easily see does not always reflect the full scope of AI activity occurring within the tools, applications, and workflows used across an enterprise. As a result, organizations using traditional rule-based methods to flag unusual activity may struggle to distinguish unsanctioned AI usage from legitimate operational behavior, particularly as SaaS applications, APIs, and orchestration layers increasingly have AI embedded into normal business workflows. Identifying threats using previously observed intelligence or depending on hard to maintain allow and block lists does not provide a dynamic enough strategy to manage risk. Also, many organizations are focusing on identifying Shadow AI in their governed infrastructure, like gateways, endpoints, or SASE, which is foundational. But, organizations require visibility and Shadow AI detection across all networked infrastructure from on-prem, hybrid, data centers, and cloud infrastructure that may not have endpoint agent visibility. This uncovers the utilization of MCP, data flows, and autonomous agents across these domains.

For example, employees interact with AI assistants across approved SaaS platforms every day. However, browser extensions and other types of plug-ins can route prompts that include enterprise data to embedded AI services in ways that are not visible to the security team. AI enabled workflows may invoke multiple APIs, orchestration layers, and cloud services behind the scenes, making it difficult for traditional security tooling to determine where data is processed, stored, or retransmitted. Because much of this activity occurs within trusted browser sessions and encrypted SaaS traffic, conventional network monitoring, DLP, and application allowlisting controls often lack the context needed to accurately identify or govern these interactions

Identifying AI tools in the environment is one part of the equation. Understanding the behavior surrounding their use is where the real challenge lies. An AI application is not inherently risky, but the way users or other assets interact with it may be. Sensitive data exposure, abnormal access patterns, and misuse of AI-assisted workflows often appear legitimate in isolation and only become visible through behavioral analysis across the broader environment.  

What Shadow AI visibility does and doesn’t show

Comprehensive Shadow AI visibility allows organizations to answer several important questions:

  • What types of AI are we using? What AI platforms, agents, MCP clients/servers, and services are active across the enterprise?  
  • Who is using AI services? Which users, business units, or systems are interacting with those AI services?  
  • Is our data safe? Is sensitive or regulated data being exposed through prompts, workflows, or integrations?  
  • Are AI systems behaving as expected? Are AI systems behaving anomalously or operating outside approved governance processes?  
  • Are our AI systems under attack? Is an attacker attempting to manipulate prompts, influence agent behavior, or abuse AI-enabled workflows?

Answering these questions is foundational to broader AI governance efforts. However, it is limited to helping teams understand initial interactions and fails to offer insight into dependencies and outcomes that are critical to securing AI across an enterprise.  

Deeper visibility that includes the ability to understand dependencies and outcomes are not always available in AI security point products. Answering the questions below requires understanding runtime behavior and operational outcomes:  

  • What actions did the AI interaction trigger?  
  • What systems, applications, or data did it access? Did the AI operate beyond its intended permissions or scope?  
  • Could a low-risk interaction lead to high-risk outcomes?  
  • What is the risk and context understanding of an anomalous activity to assist in prioritization of analysis and autonomous response action?

The distinction between these two sets of questions offers two different layers of AI security. The first set of questions focuses on discovery and interaction visibility. The second set focuses on providing visibility that includes the context and outcomes that are critical for managing follow-on risks associated with obfuscated downstream activities.  

Together, these layers help organizations move beyond simply identifying AI usage toward understanding how AI behaves operationally across the enterprise.

How organizations are addressing shadow AI

Most organizations still approach shadow AI as an application control problem, relying on policies, browser restrictions, and allow/block lists. However, AI adoption is evolving faster than most governance processes can realistically keep pace with. New assistants, plugins, and embedded AI features appear continuously, creating pressure to enable business productivity while simultaneously containing risk.  

Existing governance processes were designed for a more traditional SaaS adoption cycle, where new applications could be reviewed, approved, and monitored over longer time horizons. AI adoption operates differently. New capabilities can appear overnight inside existing platforms employees already use, making it difficult for security and governance teams to maintain an accurate understanding of enterprise AI exposure. This means that many organizations are experiencing significant operational overhead, particularly in large environments where AI usage is decentralized across teams, departments, and third-party services.  

Where should organizations start when securing their AI systems?

Shadow AI identification is an on-going critical component for AI Risk/Governance Boards as well as security organizations. As organizations seek AI certifications like ISO 42001 AI Management Systems, visibility into all AI adoption from enterprise use to custom innovation and development is crucial. Shadow AI identification provides organizations with the visibility needed to decide whether an AI tool should be brought into governed environments to reduce data loss (DLP) risks or whether policies should be established and enforced to restrict their use.

As organizations rapidly innovate and adopt AI, they are taking on more and more risk. Organizations need to have a strategy in place to mitigate the assumed risk, especially with third-party adoption. Visibility, monitoring, governance enforcement, behavioral-based detection of non-deterministic systems, and autonomous investigation and containment becomes critical to mitigating the risk of AI systems.  

How Darktrace secures AI and shadow AI

Attackers are using AI to move faster, scale tactics, and make threats more adaptive and convincing. Internally, organizations are grappling with new forms of risk created by generative AI, autonomous agents, shadow AI, and increasingly complex digital environments.

Darktrace helps organizations protect both people and AI in a world where AI is now central to how business gets done. Darktrace / SECURE AI helps organizations discover and control shadow AI by surfacing unsanctioned or unexpected AI activity where it appears – including MCP detections, distinguishing misuse of legitimate tools and unapproved services, and applying policy to contain data exposure while guiding users toward sanctioned options.

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About the author
Nicole Carignan
SVP, Security & AI Strategy, Field CISO
Your data. Our AI.
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