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March 19, 2020

5 Security Risks Companies Face Transitioning to Remote Work

Discover 5 security risks companies face with remote work employees. Protect against email scams, weakened security controls, errors, and insider threats.
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
Andrew Tsonchev
VP, Security & AI Strategy, Field CISO
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19
Mar 2020

As we all adjust to working remotely, security teams across the world are grappling with a very serious challenge. Almost overnight our companies have changed. Well established procedures are being rewritten, best practices quickly rethought, and policies stretched to breaking point.

Business transformation is always a security risk. New technology and working practices need new security measures; but normally this risk is managed carefully, and over time. COVID-19 has not afforded us that luxury. For some businesses the scale and speed of this change will be unprecedented. It is also very public; attackers are aware of the situation and already exploiting it. Below are some of the most serious threats that security teams will face over the coming weeks.

1. Email scams

Change brings novelty, and novelty brings opportunity for scammers. In the last 48 hours, internal security teams will have been racing to roll out essential remote working tools. Links to download new software, changes to how we authenticate services. When you do not know what to expect, employee training on spotting social engineering goes out the window. Both employees and IT departments should be wary of unexpected calls and requests:

“Hi, I’m calling from IT, can you please read out your 2FA code to me to confirm that you have been transitioned to the new Duo system?”

“Hi, I’ve forgotten my O365 password, can you please email a reset code to my personal Gmail?”

Such requests may be legitimate and may need to be resolved outside normal channels. The onus will be on individuals to be cautious, apply common sense and validate as appropriate.

There will also be ample opportunity for spear phishers to impersonate third-parties and clients:

“Hi John, I need to reschedule our meeting next week to be remote. Please see the link below for an invite to the Zoom call.”

These risks will be exacerbated by the simultaneous relaxing of security controls in order to facilitate the use of non-standard web conferencing software and the sharing of files by email. Attackers will have both the opportunity and the means.

2. Weakened security controls

The weakening of security controls goes far beyond relaxing firewall rules and email policy. Many existing layers of security will not apply to remote workers. Employees suddenly taking their work computer home with them will find themselves stripped of protection as they trade the office network for their home Wi-Fi. Without internet proxy, NAC, IDS and NGFW, client devices will now be sitting exposed on potentially unsecured networks amongst potentially compromised devices. Endpoint security will have to bear the full brunt of protection.

Internal network security may be compromised as well; employees might need access to resources previously only accessible on a wired network in one location. To make it reachable over VPN, internal segmentation might need to be flattened. This will open the door to malware spread and lateral movement. Client certificate authentication protecting web services might need to be turned off to enable BYOD working for employees that don’t have a company laptop.

These changes must be scrupulously logged, and dependencies understood. The extra weight will have to be carried elsewhere: perhaps host AV policies can be tightened to compensate for lack of network protection, perhaps employee devices can be reconfigured to use a secure external DNS provider instead of the on-prem DNS server.

3. Attacks on remote-working infrastructure

Beyond the weakening of existing controls, spinning up new infrastructure will bring fresh risks. In January we saw a spate of attacks on web-facing Citrix infrastructure. Companies will be rapidly deploying VPN gateways, transitioning to Sharepoint and expanding their internet-facing perimeter. This rapidly increased attack surface will need monitoring and protecting. Security teams should be on heightened alert for brute force and server-side attacks. DDoS protection will also become more important than ever; for many companies this will be the first time that a DDoS attack could cripple their business by preventing remote workers from accessing services over the internet. We should expect to see a sharp rise in both of these forms of attack immediately.

4. Errors and creative solutions

“Put it in an S3 bucket.”

“Let’s use join.me instead.”

“I’ll send it to you over WeTransfer.”

Both IT, and individual employees, will face blockers. There won’t be an authorized solution for their needs, and those needs may well be extremely urgent. At a time when businesses are extremely worried about their financial position and ability to operate, there will be pressure to throw caution to the wind and protect ‘business as usual’. This pressure may even come from the top. Security leadership must do the best they can to both push back against rash decisions and provide creative solutions.

Well-meaning employees will get creative, and responsibility will be delegated to team leaders to “do what it takes”. It may be impossible for security to police this centrally but monitoring vigilance will be required to spot risky behavior and non-compliance. This is easier said than done; the SOC will be asked to monitor for incidents in a sea of change. Existing use-cases and rules will not apply, and companies will need a more proactive and dynamic approach to detection and response.

5. Malicious insiders and malicious housemates

Unfortunately, there will be some within our companies that want to kick us while we are down. Sudden remote working is a godsend to malicious insiders. Data can now be easily taken from a company device over USB within the privacy of their own home. Security monitoring may be crippled or disabled entirely. This risk is harder to address. It may not be eliminable, but it can be balanced against the need for productivity and access to data.

We should also be wary of those around us. We all hope we can trust the people we live with. But from a company perspective, employee homes are zero-trust environments. Confidential conversations will now be conducted within range of eavesdroppers. Intellectual property will be visible on screens and monitors in living rooms around the world. This risk is greater for younger demographics likely to be house-sharing, but it remains for all workers; delivery personnel, visitors to the house – they could all potentially steal a company laptop from the kitchen room table. Education of employees in particular risk groups will be key.

Finding direction in a sea of digital change

All of the above changes and risks create a monitoring nightmare for SOCs. We are entering into a period of digital unknown, where change will be the new normal. Data flows and topology will change. New technology and services will be deployed. Logging formats will be different. The SIEM use-cases that took 12 months to develop will need to be scrapped overnight. For the next few weeks, business practice will shift rapidly.

Static defenses and rules will not be able to keep up, no matter how diligently and rapidly we rewrite them. How will you spot a malicious login attempt to O365 in your audit logs now that connections are coming from thousands of different locations around the world? Companies need to leverage technology that can allow them to continue to operate amidst uncertainty without choking productivity at this critical time. More critical still, containing those threats is of paramount importance – it won’t be feasible to entirely quarantine an infected machine if it cannot be re-imaged or replaced for days.

AI systems that can continuously evolve and adapt to change will provide the best chance of detecting misconfigurations, attacks, and risky behavior – when you don’t know what to look for, you need technology that is able to identify patterns and quantify risks for you. Autonomous Response technology can also surgically intervene to halt malicious activity when teams can’t be there to stop it, protecting devices and systems whilst allowing essential operations to continue unaffected.

Evolutions: Meeting the challenge head-on

Confronting these threats will not be easy. It will require a mixture of hard work, creativity, and new technology, alongside an openness to new ways of working and a willingness to embrace dynamic, proactive defense, instead of traditional rigid policies. However, placing trust in defensive systems to autonomously protect employees will be the single most effective way of maintaining resilience and security when our static defenses have failed us.

At Darktrace we are working hard to help our customers get even more value from their Cyber AI platform throughout this difficult time, and ease workloads of busy security teams. We know that with the right tools and technologies – from Autonomous Response and Cyber AI Analyst, through to the Darktrace Mobile App – these teams will be able to navigate these stormy waters. In this unprecedented period of uncertainty, the need for security that evolves in step with your changing digital business has never been greater.

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
Andrew Tsonchev
VP, Security & AI Strategy, Field CISO

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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About the author
Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

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AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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