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April 29, 2025

MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services

Tycoon 2FA uses AiTM phishing and legitimate services to bypass MFA. Darktrace AI stopped it, read the blog to learn how Self-Learning AI detects sophisticated threats.
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
Alexandra Sentenac
Cyber Analyst
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29
Apr 2025

In late 2024 and early 2025, the Darktrace Security Operations Center (SOC) investigated alerts regarding separate cases of Software-as-a-Service (SaaS) account compromises on two customer environments that presented several similarities, suggesting they were part of a wider phishing campaign.

This campaign was found to leverage the project collaboration and note-taking application, Milanote, and the Tycoon 2FA phishing kit.

Legitimate services abused

As highlighted in Darktrace's 2024 Annual Threat Report [1], threat actors are abusing legitimate services, like Milanote, in their phishing campaigns. By leveraging these trusted platforms and domains, malicious actors can bypass traditional security measures, making their phishing emails appear benign and increasing the likelihood of successful attacks.

Darktrace categorizes these senders and platforms as free content senders. These services allow users to send emails containing custom content (e.g., files) from fully validated, fixed service address belonging to legitimate corporations. Although some of these services permit full body and subject customization by attackers, the structure of these emails is generally consistent, making it challenging to differentiate between legitimate and malicious emails.

What is Tycoon 2FA?

Tycoon 2FA is an Adversary-in-the-Middle (AitM) phishing kit, first seen in August 2023 and distributed via the Phishing-as-a-Service (PhaaS) model [2]. It targets multi-factor authentication (MFA) by intercepting credentials and MFA tokens during authentication on fake Microsoft or Google login pages. The attacker captures session cookies after MFA is completed, allowing them to replay the session and access the user account, even if credentials are reset. The rise in MFA use has increased the popularity of AitM phishing kits like Tycoon 2FA and Mamba 2FA, another AiTM phishing kit investigated by Darktrace.

Initial access via phishing email

At the beginning of 2025, Darktrace observed phishing emails leveraging Milanote being sent to multiple internal recipients in an organization. In this attack, the same email was sent to 19 different users, all of which were held by Darktrace.

The subject line of the emails mentioned both a legitimate internal user of the company, the company name, as well as a Milanote board regarding a “new agreement” in German. It is a common social engineering technique to mention urgent matters, such as unpaid invoices, expired passwords, or awaiting voicemails, in the subject line to prompt immediate action from the user. However, this tactic is now widely covered in phishing awareness training, making users more suspicious of such emails. In this case, while the subject mentioned a “new agreement,” likely raising the recipient’s curiosity, the tone remained professional and not overly alarming. Additionally, the mention of a colleague and the standardized language typical of free content sender emails further helped dispel concerns regarding the email.

These emails were sent by the legitimate address support@milanote[.]com and referenced "Milanote" in the personal field of the header but originated from the freemail address “ahnermatternk.ef.od.13@gmail[.]com”. Darktrace / EMAIL recognized that none of the recipients had previously received a file share email from Milanote, making this sender unfamiliar in the customer's email environment

The emails contained several benign links to legitimate Milanote endpoints (including an unsubscribe link) which were not flagged by Darktrace. However, they also included a malicious link designed to direct recipients to a pre-filled credential harvesting page hosted on Milanote, prompting them to register for an account. Despite not blocking the legitimate Milanote links in the same email, Darktrace locked the malicious link, preventing users from visiting the credential harvester.

Credential harvesting page sent to recipients, as seen in. sandbox environment.
Figure 1: Credential harvesting page sent to recipients, as seen in. sandbox environment.

Around one minute later, one recipient received a legitimate email from Milanote confirming their successful account registration, indicating they had accessed the phishing page. This email had a lower anomaly score and was not flagged by Darktrace / EMAIL because, unlike the first email, it did not contain any suspicious links and was a genuine account registration notification. Similarly, in the malicious Milanote email, only the link leading to the phishing page was blocked, while the benign and legitimate Milanote links remained accessible, demonstrating Darktrace’s precise and targeted actioning.

A legitimate and a malicious Milanote email received by one recipient.
Figure 2: A legitimate and a malicious Milanote email received by one recipient.

Around the same time, Darktrace / NETWORK observed the same user’s device making DNS query for the domain name “lrn.ialeahed[.]com” , which has been flagged as a Tycoon 2FA domain [2], suggesting the use of this phishing platform.

Once the user had entered their details in the credential harvester, it is likely that they were presented a document hosted on Milanote that contained the final payload link – likely hidden behind text instructing users to access a “new agreement” document.

External research indicates that the user was likely directed to a Cloudflare Turnstile challenge meant to reroute unwanted traffic, such as automated security scripts and penetration testing tools [2] [3]. After these checks and other background processes are completed, the user is directed to the final landing page. In this case, it was likely a fake login prompt hosted on the attacker’s server, where the user is asked to authenticate to their account using MFA. By burrowing malicious links and files in this manner, threat actors can evade analysis by traditional security email gateways, effectively bypassing their protection.

Darktrace’s analysis of the structure and word content of the phishing emails resulted in an 82% probability score that the email was malicious, and the email further received a 67% phishing inducement score, representing how closely the structure and word content of the emails compared to typical phishing emails.

All these unusual elements triggered multiple alerts in Darktrace / EMAIL, focusing on two main suspicious aspects: a new, unknown sender with no prior correspondence with the recipients or the environment, and the inclusion of a link to a previously unseen file storage solution.

Milanote phishing email as seen within Darktrace / EMAIL.
Figure 3: Milanote phishing email as seen within Darktrace / EMAIL.

After detecting the fifth email, the “Sender Surge” model alert was triggered in Darktrace / EMAIL due to a significant number of recipients being emailed by this new suspicious sender in a short period. These recipients were from various departments across the customer’s organization, including sales, marketing, purchasing, and production. Darktrace / EMAIL determined that the emails were sent to a highly unusual group of internal recipients, further raising doubts about the business legitimacy.

Darktrace / EMAIL suggested actions to contain the attack by holding all Milanote phishing emails back from recipient’s inboxes, except for the detailed email with locked links. However, autonomous actions were not enabled at the time, allowing the initial email to reach recipients' inboxes, providing a brief window for interaction. Unfortunately, during this window, one recipient clicked on the Milanote payload link, leading to the compromise of their account.

SaaS account takeover

About three minutes after the malicious Milanote email was received, Darktrace / IDENTITY detected an unusual login to the email recipient’s SaaS account. The SaaS actor was observed accessing files from their usual location in Germany, while simultaneously, a 100% rare login occurred from a location in the US that had never been seen in the customer’s environment before. This login was also flagged as suspicious by Microsoft 365, triggering a 'Conditional Access Policy' that required MFA authentication, which was successfully completed.

Tycoon 2FA adnimistration panel login page dated from October 2023 [3].
Figure 4: Tycoon 2FA adnimistration panel login page dated from October 2023 [3].

Despite the successful authentication, Darktrace / IDENTITY recognized that the login from this unusual location, coupled with simultaneous activity in another geographically distant location, were highly suspicious. Darktrace went on to observe MFA-validated logins from three separate US-based IP addresses: 89.185.80[.]19, 5.181.3[.]68, and 38.242.7[.]252. Most of the malicious activity was performed from the latter, which is associated with the Hide My Ass (HMA) VPN network [5].

Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
Figure 5: Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
Darktrace’s detection of the suspicious login following successful MFA authentication.
Figure 6: Darktrace’s detection of the suspicious login following successful MFA authentication.

Following this, the malicious actor accessed the user’s inbox and created a new mailbox rule named “GTH” that deleted any incoming email containing the string “milanote” in the subject line or body. Rules like this are a common technique used by attackers to leverage compromised accounts for launching phishing campaigns and concealing replies to phishing emails that might raise suspicions among legitimate account holders. Using legitimate, albeit compromised, accounts to send additional phishing emails enhances the apparent legitimacy of the malicious emails. This tactic has been reported as being used by Tycoon 2FA attackers [4].

The attacker accessed over 140 emails within the legitimate user’s inbox, including both the inbox and the “Sent Items” folder. Notably, the attacker accessed five emails in the “Sent Items” folder and modified their attachments. These emails were mainly related to invoices, suggesting the threat actor may have been looking to hijack those email threads to send fake invoices or replicate previous invoice emails.

Darktrace’s Cyber AI AnalystTM launched autonomous investigations into the individual events surrounding this suspicious activity. It connected these separate events into a single, broad account takeover incident, providing the customer with a clearer view of the ongoing compromise.

Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
Figure 7: Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
Cyber AI Analyst investigation of suspicious activities performed by the attacker.
Figure 8: Cyber AI Analyst investigation of suspicious activities performed by the attacker.

Darktrace's response

Within three minutes of the first unusual login alert, Darktrace’s Autonomous Response intervened, disabling the compromised user account for two hours.

As the impacted customer was subscribed to the Managed Threat Detection Service, Darktrace’s SOC team investigated the activity further and promptly alerted the customer’s security team. With the user’s account still disabled by Autonomous Response, the attack was contained, allowing the customer’s security team valuable time to investigate and remediate. Within ten minutes of receiving the alert from Darktrace’s SOC, they reset the user’s password, closed all active SaaS sessions, and deleted the malicious email rule. Darktrace’s SOC further supported the customer through the Security Operations Service Support service by providing information about the data accessed and identifying any other affected users.

Autonomous Response actions carried out by Darktrace / IDENTITY to contain the malicious activity
Figure 9: Autonomous Response actions carried out by Darktrace / IDENTITY to contain the malicious activity.

A wider Milanote phishing campaign?

Around a month before this compromise activity, Darktrace alerted another customer to similar activities involving two compromised user accounts. These accounts created new inbox rules named “GFH” and “GVB” to delete all incoming emails containing the string “milanote” in their subject line and/or body.

The phishing emails that led to the compromise of these user accounts were similar to the ones discussed above. Specifically, these emails were sent via the Milanote platform and referenced a “new agreement” (in Spanish) being shared by a colleague. Additionally, the payload link included in the phishing emails showed the same UserPrincipalName (UPN) attribute (i.e., click?upn=u001.qLX9yCzR), which has been seen in other Milanote phishing emails leveraging Tycoon 2FA reported by OSINT sources [6]. Interestingly, in some cases, the email also referenced a “new agreement” in Portuguese, indicating a global campaign.

Based on the similarities in the rule’s naming convention and action, as well as the similarities in the phishing email subjects, it is likely that these were part of the same campaign leveraging Milanote and Tycoon 2FA to compromise user accounts. Since its introduction, the Tycoon 2FA phishing kit has undergone several enhancements to increase its stealth and obfuscation methods, making it harder for security tools to detect. For example, the latest versions contain special source code to obstruct web page analysis by defenders, prevent users from copying meaningful text from the phishing webpages, and disable the right-click menu to prevent offline analysis [4].

Conclusion

Threat actors are continually employing new methods to bypass security detection tools and measures. As highlighted in this blog, even robust security mechanisms like MFA can be compromised using AitM phishing kits. The misuse of legitimate services such as Milanote for malicious purposes can help attackers evade traditional email security solutions by blurring the distinction between legitimate and malicious content.

This is why security tools based on anomaly detection are crucial for defending against such attacks. However, user awareness is equally important. Delays in processing can impact the speed of response, making it essential for users to be informed about these threats.

[related-resource]

Appendices

References

[1] https://www.darktrace.com/resources/annual-threat-report-2024

[2] https://www.validin.com/blog/tycoon_2fa_analyzing_and_hunting_phishing-as-a-service_domains

[3] https://blog.sekoia.io/tycoon-2fa-an-in-depth-analysis-of-the-latest-version-of-the-aitm-phishing-kit/#h-iocs-amp-technical-details

[4] https://blog.barracuda.com/2025/01/22/threat-spotlight-tycoon-2fa-phishing-kit

[5] https://spur.us/context/38.242.7.252    

[6] https://any.run/report/5ef1ac94e4c6c1dc35579321c206453aea80d414108f9f77abd2e2b03ffbd658/be5351d9-53c0-470b-8708-ee2e29300e70

Indicators of Compromise (IoCs)

IoC         Type      Description + Probability

89.185.80[.]19 - IP Address - Malicious login

5.181.3[.]68 - IP Address -Malicious login

38.242.7[.]252 - IP Address - Malicious login and new email inbox rule creation -  Hide My Ass VPN

lrn.ialeahed[.]com – Hostname - Likely Tycoon 2FA domain

Darktrace Model Detections

Email alerts

Platforms / Free Content Sender + High Sender Surge

Platforms / Free Content Sender + Sender Surge

Platforms / Free Content Sender + Unknown Initiator

Platforms / Free Content Sender

Platforms / Free Content Sender + First Time Recipient

Unusual / New Sender Surge

Unusual / Sender Surge

Antigena Anomaly / High Antigena Anomaly

Association / Unknown Sender

History / New Sender

Link / High Rarity Link to File Storage

Link/ Link To File Storage

Link / Link to File Storage + Unknown Sender

Link / Low Link Association

Platforms / Free Content Sender + First Time Initiator

Platforms / Free Content Sender + Unknown Initiator + Freemail

Platforms / Free Content Sender Link

Unusual / Anomalous Association

Unusual / Unlikely Recipient Association

IDENTITY

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Compromise / Login from Rare High Risk Endpoint

SaaS / Access / M365 High Risk Level Login

SaaS / Compromise / Login From Rare Endpoint While User Is Active

SaaS / Access / MailItemsAccessed from Rare Endpoint

SaaS / Unusual Activity / Multiple Unusual SaaS Activities

SaaS / Unusual Activity / Multiple Unusual External Sources For SaaS Credential

SaaS / Compliance / Anomalous New Email Rule

SaaS / Compromise / Unusual Login and New Email Rule

SaaS / Compromise / SaaS Anomaly Following Anomalous Login

Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block

Antigena / SaaS / Antigena Unusual Activity Block

Antigena / SaaS / Antigena Suspicious SaaS and Email Activity Block

Cyber AI Analyst Incident

Possible Hijack of Office365 Account

MITRE ATT&CK Mapping

Tactic – Technique

DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - Cloud Accounts

INITIAL ACCESS - Phishing

CREDENTIAL ACCESS - Steal Web Session Cookie

PERSISTENCE - Account Manipulation

PERSISTENCE - Outlook Rules

RESOURCE DEVELOPMENT - Email Accounts

RESOURCE DEVELOPMENT - Compromise Accounts

Experts breakdown of Identity Security in the Cloud Era

This white paper discusses the current identity threat landscape and how defenders can adopt new tools to better secure their users and data.

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
Alexandra Sentenac
Cyber Analyst

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July 13, 2026

Security After Signatures: Operating in a World of Pre‑CVE Disclosure Exploitation, Collapsed Trust Boundaries, and Autonomous Systems

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Three shifts have reshaped what it means to defend an enterprise securely.  

First, exploitation often begins before defenders have a Common Vulnerabilities and Exposures (CVE) identifier, a security advisory, or an entry in the Cybersecurity and Infrastructure Security Agency's (CISA) Known Exploited Vulnerabilities (KEV) catalog.

Secondly, the trust boundary has moved beyond the network edge into identities, tokens, APIs, and Software-as-a-Service (SaaS) workflows.  

Third, an increasing share of business activity is executed through automation, integrations, and AI agent-like systems that can act faster than teams can verify intent.  

If your security model still relies on detecting known bad artefacts, triaging isolated alerts, and waiting for confirmation before acting, you are already behind the threat.  

This is not a failure of security teams; it’s a failure of the operating model to keep pace with how the environment has changed.

A SOC built around alerts and signatures assumes that malicious activity will eventually surface as an event. In real incidents, however, the decisive evidence is rarely a single event. Instead, it is a chain of individually explainable actions that only appears malicious once you connect the dots across identity, non-human identity, cloud, email, SaaS, operational technology (OT), and network telemetry.

The defenders succeeding today observe behaviors, link them into sequences, understand what those sequences mean, and contain impact before the full story unfolds. That is the operating model the current threat environment demands.  

Exploitation before disclosure

The first shift is the straightforward: the time to exploit has dropped to nearly zero.  

In one example, Darktrace observed a sequence of subtle but strategically significant anomalies within a customer environment that later aligned with exploitation of CVE‑2025‑0994 in Trimble Cityworks by likely Chinese-nexus threat actors. Behavioral indicators were visible at least 18 days before public disclosure, with related anomalies emerging 40 to 50 days earlier during the intrusion window.  

This case illustrates a familiar pattern: clusters of weak‑signal anomalies combing to form an actionable picture of intrusion long before a CVE is published. Such activity reflects long‑horizon, option‑preserving operator models often associated with mature state‑linked activity.  

Figure 1: Darktrace’s detection of malicious exploitation of CVE 2025-0994, later tied to Chinese-nexus threat actors targeting critical national infrastructure (CNI) in the US, weeks before public disclosure.

Throughout 2025 and 2026, Darktrace has continued to observe the value of anomaly-based detections across a range of incidents.

CVE CVE Public Disclosure Date Darktrace Detection Date Days Between Detection of Exploitation and CVE Public Disclosure
CVE 2025 0994
(Trimble City Works)
2025-02-06 2025-01-19 18 Days
CVE 2025-24183
(Apache)
2025-03-10 2025-02-18 20 days
CVE 2025-10035
(Fortra GoAnywhere)
2025-09-18 2025-09-11 7 days

Identity is the real control plane

The second shift is that identity has replaced perimeter as the primary control plane. As Darktrace’s Annual Threat Report 2026 illustrated, identity remains the main challenge in defending against modern intrusions. A clear example is the Adversary-in-the-Middle (AiTM) case published by Darktrace in December 2025. A phishing email led to the compromise of an Office 365 account. Session hijacking bypassed multi-factor authentication (MFA), and the compromised account was used for follow-on phishing and persistence activities including the creation of malicious email rules.  

Every step in that sequence mattered. A successful login alone does not prove legitimacy. An inbox rule, on its own, may not appear catastrophic. Mail activity, viewed in isolation, may seem operationally normal. But the behavioral chain tells a different story: credential theft, token abuse, persistence, and onward compromise through a trusted identity.  

This is why the question is no longer “Did the user authenticate successfully”. The more important question is, “Does this identity action make sense right now, in this context, given what came before it?” The AiTM case shows how identity can be compromised. In practice, however, attacks rarely remained confined to identity alone.  

In another Darktrace case, a compromised SaaS account triggered activity across the email, SaaS, and network layers, including inbox rule changes, phishing propagation, and connections to suspicious infrastructure. Viewed in isolation, none of these events were decisive. Together, however,  they formed a behavioral sequence that revealed the intrusion, with the full attack story automatically correlated and surfaced to defenders by Darktrace’s Cyber AI Analyst.  

Figure 2: Cyber AI Analyst correlated and appended additional events to the incident, including other users who connected to the suspicious redirect link after outbound phishing emails were sent.

AI accelerates the threat  

The third shift is the one many teams still underestimate: trusted tooling, integrations, and AI agent-like systems can create actions that appear legitimate but are strategically dangerous.  

The shift becomes clearer when examining how governments are now framing AI risk. In 2026, guidance published by CISA, UK’s National Cyber Security Centre (NCSC) and Five Eyes partners warned that agentic systems expand attack surfaces, accumulate privilege, and can behave in ways that are difficult to predict or explain [1]. The advice is simple: assume unexpected behavior and design controls around it.  

The real risk is not AI usage. It is unknown autonomy: systems with credentials, data access, and action paths that can execute workflow steps without sufficient behavioral validation, traceability, or human oversight. Darktrace’s Model Context Protocol (MCP) risk analysis provides a useful framework for understanding this challenge. Over-privileged agents, content injection, and tool abuse become high-consequence risks when connected systems can dynamically retrieve data, execute actions, and communicate externally.  

Whether security teams like it or not, AI is already in the enterprise. It will help drive innovation, but it will also be abused, whether accidentally or maliciously. In each of the cases below, AI either scaled the attacker, built the tooling, or existed within the environment as something to exploit or misuse.

1. AI as an Attack Multiplier

In one campaign targeting Mexican government entities, a single operator used commercial AI platforms to generate exploits, automate reconnaissance, and process large volumes of data, compressing work that would traditionally have required an entire team into a single workflow [2].  

Darktrace is also observing this trend further down the stack. In one case, Darktrace identified AI-generated malware exploiting React2Shell, where an attacker used a Large Language Model (LLM) to produce working exploit code and deploy it at scale.  

[darktrace.com], [darktrace.com]

2. AI as an Attack Surface

Attempted AI exploitation is now appearing within customer environments. In one case involving an automation technology manufacturer, a compromised LLM proxy was seemingly used as a stepping stone to access additional AI services. When that attempt failed, the attacker pivoted to cryptomining.

What is clear is that the AI layer has already become an asset worth probing, exploiting, and pivoting through. It is also clear that defenders benefit from rapidly understanding how these activities connect. In this case, Cyber AI Analyst automatically pieced together the intrusion, while Darktrace’s Managed Threat Detection service alerted to the customer, enabling the activity to be contained before it could progress further.

Figure 3: Cyber AI Analyst's investigation into a compromised LLM proxy that was abused for cryptomining activity.

AI as a trusted but dangerous actor

This does not require a cinematic vision of “rogue AI.” The Salesloft incident provides a more grounded example, where AI and automation operate with legitimate access but served malicious intent. In that case, attackers abused compromised OAuth tokens associated with the Drift AI chat agent to export significant volumes of data from Salesforce environments.  

The activity resembled legitimate API usage and relied on trusted SaaS integrations rather than malware or other obvious signs of intrusion. That is precisely the challenge. Traditional security controls are good at detecting forced entry, but far less effective when a trusted application integration behaves in a way that is technically permitted yet operationally harmful.  

In these scenarios, the security challenge shifts from validating access to validating behavior.

This is what that looks like in practice: AI-linked identities executing legitimate actions that require behavioral validation rather than access validation.

Figure 4: Darktrace / SECURE AI highlights anomalous activity across AI identities, surfacing critical behavior that requires validation and containment.

Early observations from Darktrace / SECURE AI deployments reinforce this reality. Across Darktrace's observed fleet, AI service connections per deployment increased 13% during the first half of 2026, reaching over 16 million connections overall. The typical organisation now interacts with seven different AI providers, evidence that AI is no longer operating at the edges of the enterprise. It is increasingly woven into day-to-day business activity.

The most common risks are not compromised models or advanced AI attacks. Instead, they stem from employees and business functions exposing sensitive information through entirely legitimate-looking interactions. Darktrace has observed repeated submission of personally identifiable information (PII), tax information, identification documents, and medical data into LLM prompts, alongside widespread use of unsanctioned (shadow) AI services and growing AI activity from mobile devices.  

For defenders, the challenge is increasingly one of context: understanding when legitimate business use crosses into material risk, while preserving privacy and user trust.

Conclusion

Across all three shifts, the pattern is the same: behavior precedes understanding. Security teams are not losing because adversaries have become invisible. An increasingly outdated security model assumes that malicious activity will reveal itself cleanly and early. It no longer does.  

In 2026 and beyond, defenders win by understanding behavioral sequences, continuously validating trust, and acting before certainty becomes hindsight. That is security after signatures. That is security in the AI era.

Credit to: Daniel Levy, Threat Hunting Data Scientist

Edited by: Ryan Traill, Content Manager

References

[1] https://www.cyber.gov.au/business-government/secure-design/artificial-intelligence/careful-adoption-of-agentic-ai-services  

[2]https://www.latimes.com/business/story/2026-02-26/hacker-used-anthropics-claude-ai-to-steal-mexican-government-data

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Nathaniel Jones
VP, Security & AI Strategy, Field CISO

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July 9, 2026

When AI Infrastructure Becomes Part of the Attack Surface

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AI Infrastructure and the Evolving Attack Surface

As organizations deploy generative AI into production environments, a new layer of infrastructure has emerged inside enterprise cloud environments: AI gateways.

What is an AI gateway?

AI gateways are systems that sit between users, applications, and foundation models, often holding privileged cloud permissions and managing access to AI services at scale.

Because of that role, AI gateways are becoming an increasingly important part of the enterprise attack surface. A compromise may provide attackers with access not only to compute resources, but also to cloud identities, model services, sensitive prompts, and other connected systems.

This blog examines how Darktrace investigated a compromised AI gateway connected to Amazon Bedrock services that was subsequently observed communicating with cryptomining infrastructure. Based on its configuration and associated Identity and Access Management (IAM) role, the instance appeared to function as a gateway to Amazon Bedrock-hosted AI services. Following suspected compromise activity, the host was observed communicating repeatedly with known cryptomining infrastructure before subsequently being shut down. Darktrace detected and escalated the activity through its Enhanced Monitoring and Managed Threat Detection services.

While the ultimate impact in this case appeared to be unauthorized cryptomining, the incident is notable because of where it occurred. The compromised asset sat at the intersection of cloud infrastructure, identity, and AI services. Recent research has highlighted how AI gateways such as LiteLLM can become attractive targets due to their ability to centralize credentials, model access, and cloud permissions. Although Darktrace found no evidence linking this activity directly to publicly disclosed LiteLLM vulnerabilities, the incident demonstrates why organizations should treat AI infrastructure as part of their critical attack surface rather than as a standalone application tier [1].

Why cryptomining remains a common cloud post-compromise activity

Cryptomining can be a lucrative post-compromise activity in cloud environments. After gaining access to a cloud asset, attackers may deploy mining software to abuse the victim’s compute resources for financial gain. This type of activity is likely to be opportunistic, targeting exposed services, weak credentials, leaked access keys, vulnerable applications, or misconfigured cloud workloads.

A typical cloud cryptomining intrusion may involve:

  • Identifying exposed or vulnerable cloud infrastructure
  • Gaining access through exposed services, credentials, or application weaknesses
  • Downloading and executing mining software
  • Establishing repeated outbound connectivity to mining pool infrastructure
  • Continuing to consume compute resources until the activity is detected and disrupted

The notable element in this case is not the cryptomining alone, but where it occurred: on cloud infrastructure supporting AI-related activity. This shows how assets used to enable AI services can still be exposed to familiar cloud compromise risks.

Investigating a compromised AI gateway connected to Amazon Bedrock

On June 12, 2026, Darktrace observed activity consistent with active cryptomining from an Amazon Web Service (AWS) EC2 instance named LiteLLM-Proxy. The instance appeared to support LiteLLM activity and was associated with an instance profile that had access to Amazon Bedrock resources.

AI gateways are designed to centralize access to large language models, often handling authentication, routing, logging, and policy enforcement for AI applications. From a security perspective, they also aggregate cloud permissions, model access, and application workflows into a single control point. As a result, compromise of an AI gateway can have implications beyond the affected host itself.

While the exact initial access vector could not be confirmed, the activity appears to follow a sequence often seen in compromises of internet-facing systems: brute-forced access, payload delivery, and repeated outbound connectivity to mining pool infrastructure.

Stage 1: Internet-exposed SSH enabled initial access

Prior to the observed cryptomining activity, the LiteLLM-Proxy EC2 instance appeared to be externally exposed over SSH, with port 22 open to 0.0.0.0/0.

Figure 1: Darktrace’s misconfiguration alert EC2 instance allowing all inbound traffic to SSH port 22.

Prior to the cryptomining activity, Darktrace observed a large volume of inbound connection attempts to the instance over port 22 from external IP addresses, predominantly from 145.241.123[.]102, suggesting brute-force activity [2]. Many of these connections were short-lived, lasting only a few seconds, indicating scanning or failed login attempts.

Figure 2: Darktrace’s detection of unusual incoming connection attempts to the device over port 22.

The available telemetry did not confirm whether any inbound SSH connection resulted in successful authentication, preventing this activity from being confirmed as the initial access vector. However, the combination of public SSH exposure, inbound connections from external IP addresses, and subsequent miner activity suggests that SSH was a plausible access path.

Stage 2: XMRig malware downloaded to the AI gateway

Before the first observed connection to the mining pool, the EC2 instance downloaded 3.42 MB of data over an HTTP connection on port 80 to the external endpoint, 185.62.1[.]8, which appears to host a ZIP file containing XMRig crypto-mining malware [3][4]. As host-level logs were not available, Darktrace could not confirm how the miner was executed or whether the earlier SSH activity directly enabled payload delivery. However, the timing of the download, followed shortly by repeated mining pool connectivity, supported the assessment that the instance had been compromised and was being used for unauthorized compute activity.

Stage 3 – Compromised AI gateway communicates with cryptomining infrastructure

Just a few minutes later, Darktrace observed the LiteLLM-Proxy EC2 instance connecting to the hostname pool.hasvault[.]pro over HTTPs on port 443. Following the initial connection, repeated outbound connectivity to the same hostname was observed. This pattern is consistent with active cryptomining pool communication, where a compromised host communicates with mining infrastructure to receive work and submit results.

This activity triggered the Enhanced Monitoring model “Compromise / High Priority Crypto Currency Mining”, which was escalated to the customer by Darktrace’s SOC. The activity was also summarized by Darktrace’s Cyber AI Analyst, which grouped the relevant events into a single investigation narrative, helping to identify the repeated mining pool connectivity from the affected cloud asset.

Figure 3: Cyber AI Analyst’s investigation of the cryptocurrency mining activity.

The use of HTTPS over port 443 is notable because, when viewed in isolation, this traffic may not appear inherently suspicious. In this case, however, the destination, volume of connections, and lack of similar activity provided the behavioral context needed to identify the communication as suspicious.

Stage 4: Managed Threat Detection identifies active resource abuse

The cryptomining activity was received by Darktrace’s Managed Threat Detection service and reviewed by Darktrace’s SOC. Following review, the activity was escalated to the customer. This escalation provided the customer with timely notification of active resource abuse in the AWS environment.

Stage 5: Suspicious IAM activity suggests possible cloud credential misuse

Separately, on June 13, Darktrace observed suspicious activity originating from an additional IAM user.

Figure 4: Darktrace’s Advanced Search highlighting suspicious activity performed by a second IAM user.

First, the user was observed attempting the “GetSendQuota” event, an action that had not performed by the account within at least the previous three months. Additionally, the source IP address of this command appeared to be 14.176.1[.]47, geolocated in Vietnam, whereas activity for this user had mostly been seen from Amazon IP addresses. Furthermore, the AWS CLI was also observed being used for this activity, which was also unusual for the user. This was detected by the model “IaaS / Unusual Activity / Unusual AWS CLI Activity”.

Figure 5: Darktrace’s detection of the “GetSendQuota” event.

Further suspicious activity was observed from the IAM user using the long-term access key. Notably, failed “InvokeModel” and “ListFoundationModels” commands were detected, suggesting attempted interaction with Amazon Bedrock services, including model enumeration or invocation. While this may suggest relation to the LiteLLM compromise observed the previous day, there is insufficient evidence to conclusively link the two events.

The attempted “CreateUser” command was also notable because the requested username appeared low-meaning, which may indicate an attempt to establish persistence by creating a new account. This activity triggered the model “IaaS / Admin / New AWS User Account Creation”.

Figure 6: Darktrace’s detection of the “CreateUser” event.

Even without a confirmed link between the two incidents, the IAM activity remains significant. It demonstrates the importance of incorporating workload both telemetry and control-plane telemetry into cloud compromise investigations. While the EC2 cryptomining activity indicated compute resource abuse, the IAM activity suggested potential credential compromise or misuse involving long-term access keys, along with attempted cloud service abuse.

Key lessons for securing AI infrastructure

This incident was notable not because of the cryptomining activity itself, but because of where it occurred. The compromised system appeared to function as an AI gateway with access to Amazon Bedrock services, placing it at the intersection of cloud infrastructure, identity, and AI operations. As organizations deploy AI capabilities into production environments, these platforms are becoming part of the same attack surface that adversaries already target through exposed services, credential theft, and cloud misconfigurations.

While the exact intrusion path could not be confirmed, and no definitive link was established between the compromised workload and the suspicious IAM activity observed during the investigation, both events reinforce a broader reality: AI infrastructure must be secured as part of the wider cloud environment rather than treated as a separate technology stack.

In this case, the most obvious sign of compromise was communication with cryptomining infrastructure. The more important lesson is that Darktrace’s behavioral analysis revealed risk surrounding a privileged AI-enabled asset before the full scope of the incident was understood. As AI gateways increasingly concentrate cloud permissions, model access, and application workflows, defenders will need to focus less on individual alerts and more on understanding how behaviors connect across workloads, identities, and services.

Credit to Angel Arribas Lopez (Associate Principal Cyber Analyst), Nathaniel Jones (Field CISO/VP Threat Research), Emma Foulger (Global Threat Ops),  and Mark Turner (Security Researcher)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

·       Compromise / High Priority Crypto Currency Mining

·       Compromise / Monero Mining

·       Device / Internet Facing Device with High Priority Alert

·       IaaS / Unusual Activity / Unusual AWS CLI Activity

·       IaaS / Admin / New AWS User Account Creation

MITRE ATT&CK Mapping

Initial Access – External Remote Services – T1133

Initial Access – Valid Accounts – T1078

Execution – Command and Scripting Interpreter – T1059

Persistence – Create Account – T1136

Discovery – Cloud Service Discovery – T1526

Impact – Resource Hijacking – T1496

References

[1] https://docs.litellm.ai/blog/security-update-march-2026

[2] https://www.abuseipdb.com/check/145.241.123.102

[3] https://urlscan.io/search/#185.62.1.8

[4] https://www.virustotal.com/gui/file/85de36ff66fae9f4b059cbedf6d36e017ebc26c828f99f911a96e78636f21200/community

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About the author
Angel Arribas Lopez
Associate Principal Cyber Analyst
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