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June 28, 2021

Post-Mortem Analysis of a SQL Server Exploit

Learn about the post-mortem analysis of a SQL Server exploit. Discover key insights and strategies to enhance your cybersecurity defenses.
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
Max Heinemeyer
Global Field CISO
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28
Jun 2021

While SaaS and IoT devices are increasingly popular vectors of intrusion, server-side attacks remain a serious threat to organizations worldwide. With sophisticated vulnerability scanning tools, attackers can now pinpoint security flaws in seconds, finding points of entry across the attack surface. Human security teams often struggle to keep pace with the constant wave of newly documented vulnerabilities and patches.

Darktrace recently stopped a targeted cyber-attack by an unknown attacker. After the initial entry, the attacker exploited an unpatched vulnerability (CVE-2020-0618), granting a low-privileged credential the ability to remotely execute code. This enabled the attacker to spread laterally and eventually establish a foothold in the system by creating a new user account.

The server-side attack cycle: authenticates user; scans network; infects three servers; downloads malware; c2 traffic; creates new user.

Figure 1: Overview of the server-side attack cycle.

This blog breaks down the intrusion and explores how Darktrace’s Autonomous Response technology took three surgical actions to halt the attacker’s movements.

Unknown threat actors exploit a vulnerability

Initial compromise

At a financial firm in Canada with around 3,000 devices, Cyber AI detected the use of a new credential, ‘parents’. The attacker used this credential to access the company’s internal environment through the VPN. From there, the credential authenticated to a desktop using NT LAN Manager (NTLM). No further suspicious activity was observed.

NTLM is a popular attack vector for cyber-criminals as it is vulnerable to multiple methods of compromise, including brute-force and ‘pass the hash’. The initial access to the credential could have been obtained via phishing before Darktrace had been deployed.

Figure 2: The credential was first observed on the device five days prior to reconnaissance. The attacker performed reconnaissance and lateral movement for two days, until the compromised devices were taken down.

Internal reconnaissance

Five days later, the ‘parents’ credential was seen logging onto the desktop. The desktop began scanning the network – over 80 internal IPs – on Port 443 and 445.

Shortly after the scan, the device used Nmap to attempt to establish SMBv1 sessions to 139 internal IPs, using guest / user credentials. 79 out of the 278 sessions were successful, all using the login.

Figure 3: New failed internal connections performed by an initially infected desktop, in a similar incident. The graph highlights a surge in failed internal connections and model breaches.

The network scan was the first stage after intrusion, enabling the attacker to find out which services were running, before looking for unpatched vulnerabilities.

Nmap has multiple built-in functionalities which are often exploited for reconnaissance and lateral movement. In this case, it was being used to establish the SMBv1 sessions to the domain controller, saving the attacker from having to initiate SMBv1 sessions with each destination one by one. SMBv1 has well-known vulnerabilities and best practice is to disable it where possible.

Lateral movement

The desktop began controlling services (svcctl endpoint) on a SQL server. It was observed both creating and starting services (CreateServiceW, StartServiceW).

The desktop then initiated an unencrypted HTTP connection to a SQL Reporting server. This was the first HTTP connection between the two devices and the first time the user agent had been seen on the device.

A packet capture of the connection reveals a POST that is seen in an exploit of CVE-2020-0613. This vulnerability is a deserialization issue, whereby the server mishandles carefully crafted page requests and allows low-privileged accounts to establish a reverse shell and remotely execute code on the server.

Figure 4: A partial PCAP of the HTTP connection. The traffic matches the CVE-2020-0618 exploit, which enables Remote Code Execution (RCE) in SQL Server Reporting Services (SSRS).

Most movements were seen in East-West traffic, with readily-available remote procedure call (RPC) methods. Such connections are abundant in systems. Without learning an organization’s ‘pattern of life’, it would have been near-impossible to highlight the malicious connections.

Cyber AI detected connections to the svcctl endpoint, via the DCE-RPC endpoint. This is called the 'service control' endpoint and is used to remotely control running processes on a device.

During the lateral movement from the desktop, the HTTP POST request revealed that the desktop was exploiting CVE-2020-0613. The attacker had managed to find and exploit an existing vulnerability which hadn’t been patched.

Darktrace was the only tool which alerted to the HTTP connection, revealing this underlying (and concluding) exploit. The AI determined that the user agent was unusual for the device and for the wider organization, and that the connection was highly anomalous. This connection would have gone otherwise amiss, since HTTP connections are common in most digital environments.

Because the attacker on the desktop used readily-available tools and protocols, such as Nmap, DCE-RPC, and HTTP, the device went undetected by all the other cyber defenses. However, Cyber AI noticed multiple scanning and lateral movement anomalies – triggering high-fidelity detections which would have been alerted to with Proactive Threat Notifications.

Command and control (C2) communication

The next day, the attacker connected to an SNMP server from the VPN. The connection used the ‘parents’ RDP cookie.

Immediately after the RDP connection began, the server connected to Pastebin and downloaded small amounts of encrypted data. Pastebin was likely being used as a vector to drop malicious scripts onto the device.

The SNMP server then started controlling services (svcttl) on the SQL server: again, creating and starting services.

Following this, both the SQL server and the SNMP server made a high volume of SSL connections to a rare external domain. One upload to the destination was around 21 MB, but otherwise the connections were mostly the same packet size. This, among other factors, indicated that the destination was being used as a C2 server.

Figure 5: Example Cyber AI Analyst investigation into beaconing activity by a SQL server.

With just one compromised credential, the attacker was now connecting to the VPN and infecting multiple servers on the company’s internal network.

The attacker dropped scripts onto the host using Pastebin. Darktrace alerted on this because Pastebin is highly rare for the organization. In fact, these connections were the first time it had been seen. Most security tools would miss this, as Pastebin is a legitimate site and would not be blocked by open-source intelligence (OSINT).

Even if a lesser-known Pastebin alternative had been used – say, in an environment where Pastebin was blocked on the firewall but the alternative not — Darktrace would have picked up on it in exactly the same way.

The C2 beaconing endpoint – dropbox16[.]com – has no OSINT information available online. The connections were on Port 443 and nothing about them was notable except from their rarity on the company’s system. Darktrace sent alerts because of its high rarity, rather than relying on known signatures.

Achieve persistence

After another Pastebin pull, the attacker attempted to maintain a greater foothold and escalate privileges by creating a new user using the SamrCreateUser2InDomain operation (endpoint: samr).

To establish persistence, the attacker now created a new user through a specific DCE-RPC command to the domain controller. This was highly unusual activity for the device, and was given a 100% anomaly score for ‘New or Uncommon Occurrence’.

If Darktrace had not alerted on this activity, the attacker would have continued to access files and make further inroads in the company, extracting sensitive data and potentially installing ransomware. This could have led to sensitive data loss, reputational damage, and financial losses for the company.

The value of Autonomous Response

The organization had Antigena in passive mode, so although it was not able to respond autonomously, we have visibility into the actions that it would have taken.

Antigena would have taken three actions on the initially infected desktop, as shown in the table below. The actions would have taken effect immediately in response to the first scan and the first service control requests.

During the two days of reconnaissance and lateral movement activity, these were the only steps Antigena suggested. The steps were all directly relevant to the intrusion – there was no attempt to block anything unrelated to the attack, and no other Antigena actions were triggered during this period.

By surgically blocking connections on specific ports during the scanning activity and enforcing the ‘pattern of life’ on the infected desktop, Antigena would have paralyzed the attacker’s reconnaissance efforts.

Furthermore, unusual service control attempts performed by the device would have been halted, minimizing the damage to the targeted destination.

Antigena would have delivered these blocks directly or via whatever integration was most suitable for the customer, such as firewall integrations or NAC integrations.

Lessons learned

The threat story above demonstrates the importance of controlling the access granted to low-privileged credentials, as well as remaining up-to-date with security patches. Since such attacks take advantage of existing network infrastructure, it is extremely difficult to detect these anomalous connections without the use of AI.

There was a delay of several days between the initial use of the ‘parents’ credentials and the first signs of lateral movement. This dormancy period – between compromise and the start of internal activities – is commonly seen in attacks. It likely indicates that the attacker was checking initially if their access worked, and then re-visiting the victim for further compromise once their schedule allowed for it.

Stopping a server-side attack

This compromise is reflective of many real-life intrusions: attacks cannot be easily attributed and are often conducted by sophisticated, unidentified threat actors.

Nevertheless, Darktrace managed to detect each stage of the attack cycle: initial compromise, reconnaissance, lateral movement, established foothold, and privilege escalation, and had Antigena been in active mode, it would have blocked these connections, and even prevented the initial desktop from ever exploiting the SQL vulnerability, which allowed the attacker to execute code remotely.

One day later, after seeing the power of Autonomous Response, the company decided to deploy Antigena in active mode.

Thanks to Darktrace analyst Isabel Finn for her insights on the above threat find.

Darktrace model detections:

  • Device / Anomalous Nmap SMB Activity
  • Device / Network Scan - Low Anomaly Score
  • Device / Network Scan
  • Device / ICMP Address Scan
  • Device / Suspicious Network Scan Activity
  • Anomalous Connection / New or Uncommon Service Control
  • Device / Multiple Lateral Movement Model Breaches
  • Device / New User Agent To Internal Server
  • Compliance / Pastebin
  • Device / Repeated Unknown RPC Service Bind Errors
  • Anomalous Server Activity / Rare External from Server
  • Compromise / Unusual Connections to Rare Lets Encrypt
  • User / Anomalous Domain User Creation Or Addition To Group

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
Max Heinemeyer
Global Field CISO

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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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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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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