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January 30, 2023

Qakbot Resurgence in the Cyber Landscape

Stay informed on the evolving threat Qakbot. Protect yourself from the Qakbot resurgence! Learn more from our Darktrace AI Cybersecurity experts!
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
Nahisha Nobregas
SOC Analyst
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30
Jan 2023

In June 2022, Darktrace observed a surge in Qakbot infections across its client base. The detected Qakbot infections, which in some cases led to the delivery of secondary payloads such as Cobalt Strike and Dark VNC, were initiated through novel delivery methods birthed from Microsoft’s default blocking of XL4 and VBA macros in early 2022 [1]/[2]/[3]/[4] and from the public disclosure in May 2022 [5] of the critical Follina vulnerability (CVE-2022-30190) in Microsoft Support Diagnostic Tool (MSDT). Despite the changes made to Qakbot’s delivery methods, Qakbot infections still inevitably resulted in unusual patterns of network activity. In this blog, we will provide details of these network activities, along with Darktrace/Network’s coverage of them. 

Qakbot Background 

Qakbot emerged in 2007 as a banking trojan designed to steal sensitive data such as banking credentials.  Since then, Qakbot has developed into a highly modular triple-threat powerhouse used to not only steal information, but to also drop malicious payloads and to serve as a backdoor. The malware is also versatile, with its delivery methods regularly changing in response to the changing threat landscape.  

Threat actors deliver Qakbot through email-based delivery methods. In the first half of 2022, Microsoft started rolling out versions of Office which block XL4 and VBA macros by default. Prior to this change, Qakbot email campaigns typically consisted in the spreading of deceitful emails with Office attachments containing malicious macros.  Opening these attachments and then enabling the macros within them would lead users’ devices to install Qakbot.  

Actors who deliver Qakbot onto users’ devices may either sell their access to other actors, or they may leverage Qakbot’s capabilities to pursue their own objectives [6]. A common objective of actors that use Qakbot is to drop Cobalt Strike beacons onto infected systems. Actors will then leverage the interactive access provided by Cobalt Strike to conduct extensive reconnaissance and lateral movement activities in preparation for widespread ransomware deployment. Qakbot’s close ties to ransomware activity, along with its modularity and versatility, make the malware a significant threat to organisations’ digital environments.

Activity Details and Qakbot Delivery Methods

During the month of June, variationsof the following pattern of network activity were observed in several client networks:

1.     User’s device contacts an email service such as outlook.office[.]com or mail.google[.]com

2.     User’s device makes an HTTP GET request to 185.234.247[.]119 with an Office user-agent string and a ‘/123.RES' target URI. The request is responded to with an HTML file containing a exploit for the Follina vulnerability (CVE-2022-30190)

3.     User’s device makes an HTTP GET request with a cURL User-Agent string and a target URI ending in ‘.dat’ to an unusual external endpoint. The request is responded to with a Qakbot DLL sample

4.     User’s device contacts Qakbot Command and Control servers over ports such as 443, 995, 2222, and 32101

In some cases, only steps 1 and 4 were seen, and in other cases, only steps 1, 3, and 4 were seen. The different variations of the pattern correspond to different Qakbot delivery methods.

Figure 1: Geographic distribution of Darktrace clients affected by Qakbot

Qakbot is known to be delivered via malicious email attachments [7]. The Qakbot infections observed across Darktrace’s client base during June were likely initiated through HTML smuggling — a method which consists in embedding malicious code into HTML attachments. Based on open-source reporting [8]-[14] and on observed patterns of network traffic, we assess with moderate to high confidence that the Qakbot infections observed across Darktrace’s client base during June 2022 were initiated via one of the following three methods:

  • User opens HTML attachment which drops a ZIP file on their device. ZIP file contains a LNK file, which when opened, causes the user's device to make an external HTTP GET request with a cURL User-Agent string and a '.dat' target URI. If successful, the HTTP GET request is responded to with a Qakbot DLL.
  • User opens HTML attachment which drops a ZIP file on their device. ZIP file contains a docx file, which when opened, causes the user's device to make an HTTP GET request to 185.234.247[.]119 with an Office user-agent string and a ‘/123.RES' target URI. If successful, the HTTP GET request is responded to with an HTML file containing a Follina exploit. The Follina exploit causes the user's device to make an external HTTP GET with a '.dat' target URI. If successful, the HTTP GET request is responded to with a Qakbot DL.
  • User opens HTML attachment which drops a ZIP file on their device. ZIP file contains a Qakbot DLL and a LNK file, which when opened, causes the DLL to run.

The usage of these delivery methods illustrate how threat actors are adopting to a post-macro world [4], with their malware delivery techniques shifting from usage of macros-embedding Office documents to usage of container files, Windows Shortcut (LNK) files, and exploits for novel vulnerabilities. 

The Qakbot infections observed across Darktrace’s client base did not only vary in terms of their delivery methods — they also differed in terms of their follow-up activities. In some cases, no follow-up activities were observed. In other cases, however, actors were seen leveraging Qakbot to exfiltrate data and to deliver follow-up payloads such as Cobalt Strike and Dark VNC.  These follow-up activities were likely preparation for the deployment of ransomware. Darktrace’s early detection of Qakbot activity within client environments enabled security teams to take actions which likely prevented the deployment of ransomware. 

Darktrace Coverage 

Users’ interactions with malicious email attachments typically resulted in their devices making cURL HTTP GET requests with empty Host headers and target URIs ending in ‘.dat’ (such as as ‘/24736.dat’ and ‘/noFindThem.dat’) to rare, external endpoints. In cases where the Follina vulnerability is believed to have been exploited, users’ devices were seen making HTTP GET requests to 185.234.247[.]119 with a Microsoft Office User-Agent string before making cURL HTTP GET requests. The following Darktrace DETECT/Network models typically breached as a result of these HTTP activities:

  • Device / New User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Device / New User Agent and New IP
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Numeric Exe Download 

These DETECT models were able to capture the unusual usage of Office and cURL User-Agent strings on affected devices, as well as the downloads of the Qakbot DLL from rare external endpoints. These models look for unusual activity that falls outside a device’s usual pattern of behavior rather than for activity involving User-Agent strings, URIs, files, and external IPs which are known to be malicious.

When enabled, Darktrace RESPOND/Network autonomously intervened, taking actions such as ‘Enforce group pattern of life’ and ‘Block connections’ to quickly intercept connections to Qakbot infrastructure. 

Figure 2: This ‘New User Agent to IP Without Hostname’ model breach highlights an example of Darktrace’s detection of a device attempting to download a file containing a Follina exploit
Figure 3: This ‘New User Agent to IP Without Hostname’ model breach highlights an example of Darktrace’s detection of a device attempting to download Qakbot
Figure 4: The Event Log for an infected device highlights the moment a connection to the endpoint outlook.office365[.]com was made. This was followed by an executable file transfer detection and use of a new User-Agent, curl/7.9.1

After installing Qakbot, users’ devices started making connections to Command and Control (C2) endpoints over ports such as 443, 22, 990, 995, 1194, 2222, 2078, 32101. Cobalt Strike and Dark VNC may have been delivered over some of these C2 connections, as evidenced by subsequent connections to endpoints associated with Cobalt Strike and Dark VNC. These C2 activities typically caused the following Darktrace DETECT/Network models to breach: 

  • Anomalous Connection / Application Protocol on Uncommon Port
  • Anomalous Connection / Multiple Connections to New External TCP Port
  • Compromise / Suspicious Beaconing Behavior
  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Compromise / Large Number of Suspicious Successful Connections
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / SSL or HTTP Beacon
  • Anomalous Connection / Rare External SSL Self-Signed
  • Anomalous Connection / Anomalous SSL without SNI to New External
  • Compromise / SSL Beaconing to Rare Destination
  • Compromise / Suspicious TLS Beaconing To Rare External
  • Compromise / Slow Beaconing Activity To External Rare
Figure 5: This Device Event Log illustrates the Command and Control activity displayed by a Qakbot-infected device

The Darktrace DETECT/Network models which detected these C2 activities do not look for devices making connections to known, malicious endpoints. Rather, they look for devices deviating from their ordinary patterns of activity, making connections to external endpoints which internal devices do not usually connect to, over ports which devices do not normally connect over. 

In some cases, actors were seen exfiltrating data from Qakbot-infected systems and dropping Cobalt Strike in order to conduct extensive discovery. These exfiltration activities typically caused the following models to breach:

  • Anomalous Connection / Data Sent to Rare Domain
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Low and Slow Exfiltration to IP
  • Unusual Activity / Unusual External Data to New Endpoints

The reconnaissance and brute-force activities carried out by actors typically resulted in breaches of the following models:

  • Device / ICMP Address Scan
  • Device / Network Scan
  • Anomalous Connection / SMB Enumeration
  • Device / New or Uncommon WMI Activity
  •  Unusual Activity / Possible RPC Recon Activity
  • Device / Possible SMB/NTLM Reconnaissance
  •  Device / SMB Lateral Movement
  •  Device / Increase in New RPC Services
  •  Device / Spike in LDAP Activity
  • Device / Possible SMB/NTLM Brute Force
  • Device / SMB Session Brute Force (Non-Admin)
  • Device / SMB Session Brute Force (Admin)
  • Device / Anomalous NTLM Brute Force

Conclusion

June 2022 saw Qakbot swiftly mould itself in response to Microsoft's default blocking of macros and the public disclosure of the Follina vulnerability. The evolution of the threat landscape in the first half of 2022 caused Qakbot to undergo changes in its delivery methods, shifting from delivery via macros-based methods to delivery via HTML smuggling methods. The effectiveness of these novel delivery methods where highlighted in Darktrace's client base, where large volumes of Qakbot infections were seen during June 2022. Leveraging Self-Learning AI, Darktrace DETECT/Network was able to detect the unusual network behaviors which inevitably resulted from these novel Qakbot infections. Given that the actors behind these Qakbot infections were likely seeking to deploy ransomware, these detections, along with Darktrace RESPOND/Network’s autonomous interventions, ultimately helped to protect affected Darktrace clients from significant business disruption.  

Appendices

List of IOCs

References

[1] https://techcommunity.microsoft.com/t5/excel-blog/excel-4-0-xlm-macros-now-restricted-by-default-for-customer/ba-p/3057905

[2] https://techcommunity.microsoft.com/t5/microsoft-365-blog/helping-users-stay-safe-blocking-internet-macros-by-default-in/ba-p/3071805

[3] https://learn.microsoft.com/en-us/deployoffice/security/internet-macros-blocked

[4] https://www.proofpoint.com/uk/blog/threat-insight/how-threat-actors-are-adapting-post-macro-world

[5] https://twitter.com/nao_sec/status/1530196847679401984

[6] https://www.microsoft.com/security/blog/2021/12/09/a-closer-look-at-qakbots-latest-building-blocks-and-how-to-knock-them-down/

[7] https://www.zscaler.com/blogs/security-research/rise-qakbot-attacks-traced-evolving-threat-techniques

[8] https://www.esentire.com/blog/resurgence-in-qakbot-malware-activity

[9] https://www.fortinet.com/blog/threat-research/new-variant-of-qakbot-spread-by-phishing-emails

[10] https://twitter.com/pr0xylife/status/1539320429281615872

[11] https://twitter.com/max_mal_/status/1534220832242819072

[12] https://twitter.com/1zrr4h/status/1534259727059787783?lang=en

[13] https://isc.sans.edu/diary/rss/28728

[14] https://www.fortiguard.com/threat-signal-report/4616/qakbot-delivered-through-cve-2022-30190-follina

Credit to:  Hanah Darley, Cambridge Analyst Team Lead and Head of Threat Research and Sam Lister, Senior Cyber Analyst

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
Nahisha Nobregas
SOC Analyst

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May 5, 2026

How email-delivered prompt injection attacks can target enterprise AI – and why it matters

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What are email-delivered prompt injection attacks?

As organizations rapidly adopt AI assistants to improve productivity, a new class of cyber risk is emerging alongside them: email-delivered AI prompt injection. Unlike traditional attacks that target software vulnerabilities or rely on social engineering, this is the act of embedding malicious or manipulative instructions into content that an AI system will process as part of its normal workflow. Because modern AI tools are designed to ingest and reason over large volumes of data, including emails, documents, and chat histories, they can unintentionally treat hidden attacker-controlled text as legitimate input.  

At Darktrace, our analysis has shown an increase of 90% in the number of customer deployments showing signals associated with potential prompt injection attempts since we began monitoring for this type of activity in late 2025. While it is not always possible to definitively attribute each instance, internal scoring systems designed to identify characteristics consistent with prompt injection have recorded a growing number of high-confidence matches. The upward trend suggests that attackers are actively experimenting with these techniques.

Recent examples of prompt injection attacks

Two early examples of this evolving threat are HashJack and ShadowLeak, which illustrate prompt injection in practice.

HashJack is a novel prompt injection technique discovered in November 2025 that exploits AI-powered web browsers and agentic AI browser assistants. By hiding malicious instructions within the URL fragment (after the # symbol) of a legitimate, trusted website, attackers can trick AI web assistants into performing malicious actions – potentially inserting phishing links, fake contact details, or misleading guidance directly into what appears to be a trusted AI-generated output.

ShadowLeak is a prompt injection method to exfiltrate PII identified in September 2025. This was a flaw in ChatGPT (now patched by OpenAI) which worked via an agent connected to email. If attackers sent the target an email containing a hidden prompt, the agent was tricked into leaking sensitive information to the attacker with no user action or visible UI.

What’s the risk of email-delivered prompt injection attacks?

Enterprise AI assistants often have complete visibility across emails, documents, and internal platforms. This means an attacker does not need to compromise credentials or move laterally through an environment. If successful, they can influence the AI to retrieve relevant information seamlessly, without the labor of compromise and privilege escalation.

The first risk is data exfiltration. In a prompt injection scenario, malicious instructions may be embedded within an ordinary email. As in the ShadowLeak attack, when AI processes that content as part of a legitimate task, it may interpret the hidden text as an instruction. This could result in the AI disclosing sensitive data, summarizing confidential communications, or exposing internal context that would otherwise require significant effort to obtain.

The second risk is agentic workflow poisoning. As AI systems take on more active roles, prompt injection can influence how they behave over time. An attacker could embed instructions that persist across interactions, such as causing the AI to include malicious links in responses or redirect users to untrusted resources. In this way, the attacker inserts themselves into the workflow, effectively acting as a man-in-the-middle within the AI system.

Why can’t other solutions catch email-delivered prompt injection attacks?

AI prompt injection challenges many of the assumptions that traditional email security is built on. It does not fit the usual patterns of phishing, where the goal is to trick a user into clicking a link or opening an attachment.  

Most security solutions are designed to detect signals associated with user engagement: suspicious links, unusual attachments, or social engineering cues. Prompt injection avoids these indicators entirely, meaning there are fewer obvious red flags.

In this case, the intention is actually the opposite of user solicitation. The objective is simply for the email to be delivered and remain in the inbox, appearing benign and unremarkable. The malicious element is not something the recipient is expected to engage with, or even notice.

Detection is further complicated by the nature of the prompts themselves. Unlike known malware signatures or consistent phishing patterns, injected prompts can vary widely in structure and wording. This makes simple pattern-matching approaches, such as regex, unreliable. A broad rule set risks generating large numbers of false positives, while a narrow one is unlikely to capture the diversity of possible injections.

How does Darktrace catch these types of attacks?

The Darktrace approach to email security more generally is to look beyond individual indicators and assess context, which also applies here.  

For example, our prompt density score identifies clusters of prompt-like language within an email rather than just single occurrences. Instead of treating the presence of a phrase as a blocking signal, the focus is on whether there is an unusual concentration of these patterns in a way that suggests injection. Additional weighting can be applied where there are signs of obfuscation. For example, text that is hidden from the user – such as white font or font size zero – but still readable by AI systems can indicate an attempt to conceal malicious prompts.

This is combined with broader behavioral signals. The same communication context used to detect other threats remains relevant, such as whether the content is unusual for the recipient or deviates from normal patterns.

Ask your email provider about email-delivered AI prompt injection

Prompt injection targets not just employees, but the AI systems they rely on, so security approaches need to account for both.

Though there are clear indications of emerging activity, it remains to be seen how popular prompt injection will be with attackers going forward. Still, considering the potential impact of this attack type, it’s worth checking if this risk has been considered by your email security provider.

Questions to ask your email security provider

  • What safeguards are in place to prevent emails from influencing AI‑driven workflows over time?
  • How do you assess email content that’s benign for a human reader, but may carry hidden instructions intended for AI systems?
  • If an email contains no links, no attachments, and no social engineering cues, what signals would your platform use to identify malicious intent?

Visit the Darktrace / EMAIL product hub to discover how we detect and respond to advanced communication threats.  

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product

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May 5, 2026

Mythos vs Ethos: Defending in an Era of AI‑Accelerated Vulnerability Discovery

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Anthropic’s Mythos and what it means for security teams

Recent attention on systems such as Anthropic Mythos highlights a notable problem for defenders. Namely that disclosure’s role in coordinating defensive action is eroding.

As AI systems gain stronger reasoning and coding capability, their usefulness in analyzing complex software environments and identifying weaknesses naturally increases. What has changed is not attacker motivation, but the conditions under which defenders learn about and organize around risk. Vulnerability discovery and exploitation increasingly unfold in ways that turn disclosure into a retrospective signal rather than a reliable starting point for defense.

Faster discovery was inevitable and is already visible

The acceleration of vulnerability discovery was already observable across the ecosystem. Publicly disclosed vulnerabilities (CVEs) have grown at double-digit rates for the past two years, including a 32% increase in 2024 according to NIST, driven in part by AI even prior to Anthropic’s Mythos model. Most notably XBOW topped the HackerOne US bug bounty leaderboard, marking the first time an autonomous penetration tester had done so.  

The technical frontier for AI capabilities has been described elsewhere as jagged, and the implication is that Mythos is exceptional but not unique in this capability. While Mythos appears to make significant progress in complex vulnerability analysis, many other models are already able to find and exploit weaknesses to varying degrees.  

What matters here is not which model performs best, but the fact that vulnerability discovery is no longer a scarce or tightly bounded capability.

The consequence of this shift is not simply earlier discovery. It is a change in the defender-attacker race condition. Disclosure once acted as a rough synchronization point. While attackers sometimes had earlier knowledge, disclosure generally marked the moment when risk became visible and defensive action could be broadly coordinated. Increasingly, that coordination will no longer exist. Exploitation may be underway well before a CVE is published, if it is published at all.

Why patch velocity alone is not the answer

The instinctive response to this shift is to focus on patching faster, but treating patch velocity as the primary solution misunderstands the problem. Most organizations are already constrained in how quickly they can remediate vulnerabilities. Asset sprawl, operational risk, testing requirements, uptime commitments, and unclear ownership all limit response speed, even when vulnerabilities are well understood.

If discovery and exploitation now routinely precede disclosure, then patching cannot be the first line of defense. It becomes one necessary control applied within a timeline that has already shifted. This does not imply that organizations should patch less. It means that patching cannot serve as the organizing principle for defense.

Defense needs a more stable anchor

If disclosure no longer defines when defense begins, then defense needs a reference point that does not depend on knowing the vulnerability in advance.  

Every digital environment has a behavioral character. Systems authenticate, communicate, execute processes, and access resources in relatively consistent ways over time. These patterns are not static rules or signatures. They are learned behaviors that reflect how an organization operates.

When exploitation occurs, even via previously unknown vulnerabilities, those behavioral patterns change.

Attackers may use novel techniques, but they still need to gain access, create processes, move laterally, and will ultimately interact with systems in ways that diverge from what is expected. That deviation is observable regardless of whether the underlying weakness has been formally named.

In an environment where disclosure can no longer be relied on for timing or coordination, behavioral understanding is no longer an optional enhancement; it becomes the only consistently available defensive signal.

Detecting risk before disclosure

Darktrace’s threat research has consistently shown that malicious activity often becomes visible before public disclosure.

In multiple cases, including exploitation of Ivanti, SAP NetWeaver, and Trimble Cityworks, Darktrace detected anomalous behavior days or weeks ahead of CVE publication. These detections did not rely on signatures, threat intelligence feeds, or awareness of the vulnerability itself. They emerged because systems began behaving in ways that did not align with their established patterns.

This reflects a defensive approach grounded in ‘Ethos’, in contrast to the unbounded exploration represented by ‘Mythos’. Here, Mythos describes continuous vulnerability discovery at speed and scale. Ethos reflects an understanding of what is normal and expected within a specific environment, grounded in observed behavior.

Revisiting assume breach

These conditions reinforce a principle long embedded in Zero Trust thinking: assume breach.

If exploitation can occur before disclosure, patching vulnerabilities can no longer act as the organizing principle for defense. Instead, effective defense must focus on monitoring for misuse and constraining attacker activity once access is achieved. Behavioral monitoring allows organizations to identify early‑stage compromise and respond while uncertainty remains, rather than waiting for formal verification.

AI plays a critical role here, not by predicting every exploit, but by continuously learning what normal looks like within a specific environment and identifying meaningful deviation at machine speed. Identifying that deviation enables defenders to respond by constraining activity back towards normal patterns of behavior.

Not an arms race, but an asymmetry

AI is often framed as fueling an arms race between attackers and defenders. In practice, the more important dynamic is asymmetry.

Attackers operate broadly, scanning many environments for opportunities. Defenders operate deeply within their own systems, and it’s this business context which is so significant. Behavioral understanding gives defenders a durable advantage. Attackers may automate discovery, but they cannot easily reproduce what belonging looks like inside a particular organization.

A changed defensive model

AI‑accelerated vulnerability discovery does not mean defenders have lost. It does mean that disclosure‑driven, patch‑centric models no longer provide a sufficient foundation for resilience.

As vulnerability volumes grow and exploitation timelines compress, effective defense increasingly depends on continuous behavioral understanding, detection that does not rely on prior disclosure, and rapid containment to limit impact. In this model, CVEs confirm risk rather than define when defense begins.

The industry has already seen this approach work in practice. As AI continues to reshape both offense and defense, behavioral detection will move from being complementary to being essential.

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About the author
Andrew Hollister
Principal Solutions Engineer, Cyber Technician
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