Cloud Security: Addressing Common CISO Challenges with Advanced Solutions
This blog highlights how Darktrace / CLOUD leverages self-learning AI to tackle critical cloud security challenges—such as misconfigurations, hybrid environment complexity, securing productivity suites, and agent fatigue—by providing unified visibility, intelligent monitoring, and real-time threat response to empower organizations with proactive protection.
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
Adam Stevens
Director of Product, Cloud Security
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28
Nov 2024
Cloud adoption is a cornerstone of modern business with its unmatched potential for scalability, cost efficiency, flexibility, and net-zero targets around sustainability. However, as organizations migrate more workloads, applications, and sensitive data to the cloud it introduces more complex challenges for CISO’s. Let’s dive into the most pressing issues keeping them up at night—and how Darktrace / CLOUD provides a solution for each.
1. Misconfigurations: The Silent Saboteur
Misconfigurations remain the leading cause of cloud-based data breaches. In 2023 alone over 80% of data breaches involved data stored in the cloud.1 Think open storage buckets or overly permissive permissions; seemingly minor errors that are easily missed and can snowball into major disasters. The fallout of breaches can be costly—both financially and reputationally.
How Darktrace / CLOUD Helps:
Darktrace / CLOUD continuously monitors your cloud asset configurations, learning your environment and using these insights to flag potential misconfigurations. New scans are triggered when changes take place, then grouped and prioritised intelligently, giving you an evolving and prioritised view of vulnerabilities, best practice and mitigation strategies.
2. Hybrid Environments: The Migration Maze
Many organizations are migrating to the cloud, but hybrid setups (where workloads span both on-premises and cloud environments) create unique challenges and visibility gaps which significantly increase complexity. More traditional and most cloud native security tooling struggles to provide adequate monitoring for these setups.
How Darktrace / CLOUD Helps:
Provides the ability to monitor runtime activity for both on-premises and cloud workloads within the same user interface. By leveraging the right AI solution across this diverse data set, we understand the behaviour of your on-premises workloads and how they interact with cloud systems, spotting unusual connectivity or data flow activity during and after the migration process.
This unified visibility enables proactive detection of anomalies, ensures seamless monitoring across hybrid environments, and provides actionable insights to mitigate risks during and after the migration process.
3. Securing Productivity Suites: The Last Mile
Cloud productivity suites like Microsoft 365 (M365) are essential for modern businesses and are often the first step for an organization on a journey to Infrastructure as a Service (IaaS) or Platform as a Service (PaaS) use cases. They also represent a prime target for attackers. Consider a scenario where an attacker gains access to an M365 account, and proceeds to; access sensitive emails, downloading files from SharePoint, and impersonating the user to send phishing emails to internal employees and external partners. Without a system to detect these behaviours, the attack may go unnoticed until significant damage is done.
How Darktrace helps:
Darktrace’s Active AI platform integrates with M365 and establishes an understanding of normal business activity, enabling the detection of abnormalities across its suite including Email, SharePoint and Teams. By identifying subtle deviations in behaviour, such as:
• Unusual file accesses
• Anomalous login attempts from unexpected locations or devices.
• Suspicious email forwarding rules created by compromised accounts.
Darktrace’s Autonomous Response can act precisely to block malicious actions, by disabling compromised accounts and containing threats before they escalate. Precise actions also ensure that critical business operations are maintained even when a response is triggered.
4. Agent Fatigue: The Visibility Struggle
To secure cloud environments, visibility is critical. If you don’t know what’s there, how can you secure it? Many solutions require agents to be deployed on every server, workload, and endpoint. But managing and deploying agents across sprawling hybrid environments can be both complex and time-consuming when following change controls, and especially as cloud resources scale dynamically.
How Darktrace / CLOUD Helps:
Darktrace reduces or eliminates the need for widespread agent deployment. Its agentless by default, integrating directly with cloud environments and providing instant visibility without the operational headache. Darktrace ensures coverage with minimal friction. By intelligently graphing the relationships between assets and logically grouping your deployed Cloud resources, you are equipped with real-time visibility to quickly understand and protect your environment.
So why Darktrace / CLOUD?
Darktrace’s Self-Learning AI redefines cloud security by adapting to your unique environment, detecting threats as they emerge, and responding in real-time. From spotting misconfigurations to protecting productivity suites and securing hybrid environments. Darktrace / CLOUD simplifies cloud security challenges without adding operational burdens.
From Chaos to Clarity
Cloud security doesn’t have to be a game of endless whack-a-mole. With Darktrace / CLOUD, CISOs can achieve the visibility, control, and proactive protection they need to navigate today’s complex cloud ecosystems confidently.
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.
Cloud Security Evolution: Why Security Teams are Taking the Lead
While many internal teams contribute to general cloud hygiene, the security team has increasingly taken the lead on cloud security. Learn how AI-powered cloud detection and response tools can help these teams with new responsibilities.
Pallavi Singh
Product Marketing Manager, OT Security & Compliance
Fusing Vulnerability and Threat Data: Enhancing the Depth of Attack Analysis
This blog highlights how vulnerability data, collected using Cado's new vulnerability discovery feature, can be fused with threat data to help deepen the understanding of an attack, as well as guide remediation efforts.
From Containment to Remediation: Darktrace / CLOUD & Cado Reducing MTTR
Darktrace / CLOUD combines with Cado’s automated forensics capture to achieve rapid containment and deep investigative capabilities. Learn more about accelerating MTTR here.
MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services
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.
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.
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.
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.
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].
Figure 5: Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
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.
Figure 7: Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
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.
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.
As threat actors become more adept at targeting and disabling EDR agents, relying solely on endpoint detection leaves critical blind spots.
Network detection and response (NDR) offers the visibility and resilience needed to catch what EDR can’t especially in environments with unmanaged devices or advanced threats that evade local controls.
This blog explores how threat actors can disable or bypass EDR-based XDR solutions and demonstrates how Darktrace’s approach to NDR closes the resulting security gaps with Self-Learning AI that enables autonomous, real-time detection and response.
Threat actors see local security agents as targets
Recent research by security firms has highlighted ‘EDR killers’: tools that deliberately target EDR agents to disable or damage them. These include the known malicious tool EDRKillShifter, the open source EDRSilencer, EDRSandblast and variants of Terminator, and even the legitimate business application HRSword.
The attack surface of any endpoint agent is inevitably large, whether the software is challenged directly, by contesting its local visibility and access mechanisms, or by targeting the Operating System it relies upon. Additionally, threat actors can readily access and analyze EDR tools, and due to their uniformity across environments an exploit proven in a lab setting will likely succeed elsewhere.
With the local EDR agent silently disabled or evaded, how will the threat be discovered?
What are the limitations of relying solely on EDR?
Cyber attackers will inevitably break through boundary defences, through innovation or trickery or exploiting zero-days. Preventive measures can reduce but not completely stop this. The attackers will always then want to expand beyond their initial access point to achieve persistence and discover and reach high value targets within the business. This is the primary domain of network activity monitoring and NDR, which includes responsibility for securing the many devices that cannot run endpoint agents.
In the insights from a CISA Red Team assessment of a US CNI organization, the Red Team was able to maintain access over the course of months and achieve their target outcomes. The top lesson learned in the report was:
“The assessed organization had insufficient technical controls to prevent and detect malicious activity. The organization relied too heavily on host-based endpoint detection and response (EDR) solutions and did not implement sufficient network layer protections.”
This proves that partial, isolated viewpoints are not sufficient to track and analyze what is fundamentally a connected problem – and without the added visibility and detection capabilities of NDR, any downstream SIEM or MDR services also still have nothing to work with.
Why is network detection & response (NDR) critical?
An effective NDR finds threats that disable or can’t be seen by local security agents and generally operates out-of-band, acquiring data from infrastructure such as traffic mirroring from physical or virtual switches. This means that the security system is extremely inaccessible to a threat actor at any stage.
An advanced NDR such as Darktrace / NETWORK is fully capable of detecting even high-end novel and unknown threats.
Detecting exploitation of Ivanti CS/PS with Darktrace / NETWORK
On January 9th 2025, two new vulnerabilities were disclosed in Ivanti Connect Secure and Policy Secure appliances that were under malicious exploitation. Perimeter devices, like Ivanti VPNs, are designed to keep threat actors out of a network, so it's quite serious when these devices are vulnerable.
An NDR solution is critical because it provides network-wide visibility for detecting lateral movement and threats that an EDR might miss, such as identifying command and control sessions (C2) and data exfiltration, even when hidden within encrypted traffic and which an EDR alone may not detect.
Darktrace initially detected suspicious activity connected with the exploitation of CVE-2025-0282 on December 29, 2024 – 11 days before the public disclosure of the vulnerability, this early detection highlights the benefits of an anomaly-based network detection method.
Throughout the campaign and based on the network telemetry available to Darktrace, a wide range of malicious activities were identified, including the malicious use of administrative credentials, the download of suspicious files, and network scanning in the cases investigated.
Darktrace / NETWORK’s autonomous response capabilities played a critical role in containment by autonomously blocking suspicious connections and enforcing normal behavior patterns. At the same time, Darktrace Cyber AI Analyst™ automatically investigated and correlated the anomalous activity into cohesive incidents, revealing the full scope of the compromise.
This case highlights the importance of real-time, AI-driven network monitoring to detect and disrupt stealthy post-exploitation techniques targeting unmanaged or unprotected systems.
Unlocking adaptive protection for evolving cyber risks
Darktrace / NETWORK uses unique AI engines that learn what is normal behavior for an organization’s entire network, continuously analyzing, mapping and modeling every connection to create a full picture of your devices, identities, connections, and potential attack paths.
With its ability to uncover previously unknown threats as well as detect known threats Darktrace is an essential layer of the security stack. Darktrace has helped secure customers against attacks including 2024 threat actor campaigns against Fortinet’s FortiManager , Palo Alto firewall devices, and more.
Stay tuned for part II of this series which dives deeper into the differences between NDR types.
Credit to Nathaniel Jones VP, Security & AI Strategy, FCISO & Ashanka Iddya, Senior Director of Product Marketing for their contribution to this blog.
![Tycoon 2FA adnimistration panel login page dated from October 2023 [3].](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6807b3eb07498494e192803a_Screenshot%202025-04-22%20at%208.20.57%E2%80%AFAM.png)
