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April 21, 2022

Email Compromise To Mass Phishing Campaign

Read Darktrace's in-depth analysis on the shift from business email compromise to mass phishing campaigns. Gain the knowledge to safeguard your business.
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
Shuh Chin Goh
Written by
Sam Lister
Specialist Security Researcher
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21
Apr 2022

It is common for attackers to send large volumes of malicious emails from the email accounts which they compromise. Before carrying out this mass-mailing activity, there are predictable, preparatory steps which attackers take, such as registering mass-mailing applications and creating new inbox rules. In this blog, we will provide details of an attack observed in February 2022 in which a threat actor conducted a successful mass-mailing attack at a financial company based in Africa.

Attack summary

In February 2022, an attacker attempted to infiltrate the email environment of a financial services company based in Africa. At the beginning of February, the attacker likely gained a foothold in the company’s email environment by tricking an internal user into entering the credentials of their corporate email account into a phishing page. Over the following week, the attacker used the compromised account credentials to conduct a variety of activities, such as registering a mass-mailing application and creating a new inbox rule.

After taking these preparatory steps, the attacker went on to send out large volumes of phishing emails from the internal user’s email account. The attacker consequently obtained the credentials of several further internal corporate accounts. They used the credentials of one of these accounts to carry out similar preparatory steps (registering a mass-mailing application and creating a new inbox rule). After taking these steps, the attacker again sent large volumes of phishing emails from the account. At this point, the customer requested assistance from Darktrace’s SOC to aid investigation, and the intrusion was consequently contained by the company.

Since the attacker carried out their activities using a VPN and an Amazon cloud service, the endpoints from which the activities took place did not serve as particularly helpful indicators of an attack. However, prior to sending out phishing emails from internal users’ accounts, the attacker did carry out other predictable, preparatory activities. One of the main goals of this blog is to highlight that these behaviors serve as valuable signs of preparation for mass-mailing activity.

Attack timeline

Figure 1: Timeline of the intrusion

On February 3, the attacker sent a phishing email to the corporate account of an employee. The email was sent from the corporate account of an employee at a company with business ties to the victim enterprise. It is likely that the attacker had compromised this account prior to sending the phishing email from it. The phishing email in question claimed to be an overdue payment reminder. Within the email, there was a link hidden behind the display text “view invoice”. The hostname of the phishing link’s URL was a subdomain of questionpro[.]eu — an online survey platform. The page referred to by the URL was a fake Microsoft Outlook login page.

Figure 2: Destination of phishing link within the email sent by the attacker

Antigena Email, Darktrace’s email security solution, identified the highly unusual linguistic structure of the email, given its understanding of ‘normal’ for that sender. This was reflected in an inducement shift score of 100. However, in this case, the original URL of the phishing link was rewritten by Mimecast’s URL protection service in a way which made the full URL impossible to extract. Consequently, Antigena Email did not know what the original URL of the link was. Since the link was rewritten by Mimecast’s URL protection service, the email’s recipient will have received a warning notification in their browser upon clicking the link. It seems that the recipient ignored the warning, and consequently divulged their email account credentials to the attacker.

For Antigena Email to hold an email from a user’s mailbox, it must judge with high confidence that the email is malicious. In cases where the email contains no suspicious attachments or links, it is difficult for Antigena Email to obtain such high degrees of confidence, unless the email displays clear payload-independent malicious indicators, such as indicators of spoofing or indicators of extortion. In this case, the email, as seen by Antigena Email, didn’t contain any suspicious links or attachments (since Mimecast had rewritten the suspicious link) and the email didn’t contain any indicators of spoofing or extortion.

Figure 3: The email’s high inducement shift score highlights that the email’s linguistic content and structure were unusual for the email’s sender

Shortly after receiving the email, the internal user’s corporate device was observed making SSL connections to the questionpro[.]eu phishing endpoint. It is likely that the user divulged their email account credentials during these connections.

Figure 4: The above screenshot — obtained from Advanced Search — depicts the connections made by the account owner’s device on February 3

Between February 3 and February 7, the attacker logged into the user’s email account several times. Since these logins were carried out using a common VPN service, they were not identified as particularly unusual by Darktrace. However, during their login sessions, the attacker exhibited behavior which was highly unusual for the email account’s owner. The attacker was observed creating an inbox rule called “ _ ” on the user’s email account,[1] as well as registering and granting permissions to a mass-mailing application called Newsletter Software SuperMailer. These steps were taken by the attacker in preparation for their subsequent mass-mailing activity.

On February 7, the attacker sent out phishing emails from the user’s account. The emails were sent to hundreds of internal and external mailboxes. The email claimed to be an overdue payment reminder and it contained a questionpro[.]eu link hidden behind the display text “view invoice”. It is likely that the inbox rule created by the attacker caused all responses to this phishing email to be deleted. Attackers regularly create inbox rules on the email accounts which they compromise to ensure that responses to the malicious emails which they distribute are hidden from the accounts’ owners.[2]

Since Antigena Email does not have visibility of internal-to-internal emails, the phishing email was delivered fully weaponized to hundreds of internal mailboxes. On February 7, after the phishing email was sent from the compromised internal account, more than twenty internal devices were observed making SSL connections to the relevant questionpro[.]eu endpoint, indicating that many internal users had clicked the phishing link and possibly revealed their account credentials to the attacker.

Figure 5: The above screenshot — obtained from Advanced Search — depicts the large volume of connections made by internal devices to the phishing endpoint

Over the next five days, the attacker was observed logging into the corporate email accounts of at least six internal users. These logins were carried out from the same VPN endpoints as the attacker’s original logins. On February 11, the attacker was observed creating an inbox rule named “ , ” on one of these accounts. Shortly after, the attacker went on to register and grant permissions to the same mass-mailing application, Newsletter Software SuperMailer. As with the other account, these steps were taken by the attacker in preparation for subsequent mass-mailing activity.

Figure 6: The above screenshot — obtained from Advanced Search — outlines all of the actions involving the mass-mailing application that were taken by the attacker (accounts have been redacted)

On February 11, shortly after 08:30 (UTC), the attacker widely distributed a phishing email from this second user’s account. The phishing email was distributed to hundreds of internal and external mailboxes. Unlike the other phishing emails used by the attacker, this one claimed to be a purchase order notification, and it contained an HTML file named PurchaseOrder.html. Within this file, there was a link to a suspicious page on the public relations (PR) news site, everything-pr[.]com. After the phishing email was sent from the compromised internal account, more than twenty internal devices were observed making SSL connections to the relevant everything-pr[.]com endpoint, indicating that many internal users had opened the malicious attachment.

Figure 7: The above screenshot — obtained from Advanced Search — depicts the connections made by internal devices to the endpoint referenced in the malicious attachment

On February 11, the customer submitted an Ask the Expert (ATE) request to Darktrace’s SOC team. The guidance provided by the SOC helped the security team to contain the intrusion. The attacker managed to maintain a presence within the organization’s email environment for eight days. During these eight days, the attacker sent out large volumes of phishing emails from two corporate accounts. Before sending out these phishing emails, the attacker carried out predictable, preparatory actions. These actions included registering a mass-mailing application with Azure AD and creating an inbox rule.

Darktrace guidance

There are many learning points for this particular intrusion. First, it is important to be mindful of signs of preparation for malicious mass-mailing activity. After an attacker compromises an email account, there are several actions which they will likely perform before they send out large volumes of malicious emails. For example, they may create an inbox rule on the account, and they may register a mass-mailing application with Azure AD. The Darktrace models SaaS / Compliance / New Email Rule and SaaS / Admin / OAuth Permission Grant are designed to pick up on these behaviors.

Second, in cases where an attacker succeeds in sending out phishing emails from an internal, corporate account, it is advised that customers make use of Darktrace’s Advanced Search to identify users that may have divulged account credentials to the attacker. The phishing email sent from the compromised account will likely contain a suspicious link. Once the hostname of the link has been identified, it is possible to ask Advanced Search to display all HTTP or SSL connections to the host in question. If the hostname is www.example.com, you can get Advanced Search to display all SSL connections to the host by using the Advanced Search query, @fields.server_name:"www.example.com", and you can get Advanced Search to display all HTTP connections to the host by using the query, @fields.host:"www.example.com".

Third, it is advised that customers make use of Darktrace’s ‘watched domains’ feature[3] in cases where an attacker succeeds in sending out malicious emails from the accounts they compromise. If a hostname is added to the watched domains list, then a model named Compromise / Watched Domain will breach whenever an internal device is observed connecting to it. If Antigena Network is configured, then observed attempts to connect to the relevant host will be blocked if the hostname is added to the watched domains list with the ‘flag for Antigena’ toggle switched on. If an attacker succeeds in sending out a malicious email from an internal, corporate account, it is advised that customers add hostnames of phishing links within the email to the watched domains list and enable the Antigena flag. Doing so will cause Darktrace to identify and thwart any attempts to connect to the relevant phishing endpoints.

Figure 8: The above screenshot — obtained from the Model Editor — shows that Antigena Network prevented ten internal devices from connecting to phishing endpoints after the relevant phishing hostnames were added to the watched domains list on February 11

For Darktrace customers who want to find out more about phishing detection, refer here for an exclusive supplement to this blog.

MITRE ATT&CK techniques observed

Thanks to Paul Jennings for his contributions.

Footnotes

1. https://docs.microsoft.com/en-us/powershell/module/exchange/new-inboxrule?view=exchange-ps

2. https://www.fireeye.com/current-threats/threat-intelligence-reports/rpt-fin4.html

3. https://customerportal.darktrace.com/product-guides/main/watched-domains

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
Shuh Chin Goh
Written by
Sam Lister
Specialist Security Researcher

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August 10, 2026

9 Stages of Ransomware & How AI Responds

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Ransomware gets its name by commandeering and holding assets ransom, extorting their owner for money in exchange for discretion and full cooperation in returning exfiltrated data and providing decryption keys to allow business to resume.

Average ransom demands are skyrocketing, rising to $5.3 million in 2021, a 518% increase from the previous year. But the cost of recovering from a ransomware attack typically far exceeds the ransom payments: the average downtime after a ransomware attack is 21 days; and 66% of ransomware victims report a significant loss of revenue following a successful attack.

In this series, we break down this huge topic step by step. Ransomware is a multi-stage problem, requiring a multi-stage solution that autonomously and effectively contains the attack at any stage. Read on to discover how Self-Learning AI and Autonomous Response stops ransomware in its tracks.

1. Initial intrusion (email)

Initial entry – the first stage of a ransomware attack – can be achieved through RDP brute-forcing (exposed Internet service), malicious websites and drive-by downloads, an insider threat with company credentials, system and software vulnerabilities, or any number of other attack vectors.

But the most common initial attack vector is email. An organization’s biggest security weakness is often their people – and attackers are good at finding ways of exploiting this. Well-researched, targeted, legitimate-looking emails are aimed at employees attempting to solicit a reaction: a click of a link, an opening of an attachment, or persuading them to divulge credentials or other sensitive information.

Gateways: Stops what has been seen before

Most conventional email tools rely on past indicators of attack to try and spot the next threat. If an email comes in from a blocklisted IP address or email domain, and uses known malware that has previously been seen in the wild, the attack may be blocked.

But the reality is, attackers know the majority of defenses take this historical approach, and so constantly update their attack infrastructure to bypass these tools. By buying new domains for a few pennies each, or creating bespoke malware with just small adaptions to the code, they can outpace and outsmart the legacy approach taken by a typical email gateway.

Real-world example: Supply chain phishing attack

By contrast, Darktrace’s evolving understanding of ‘normal’ for every email user in the organization enables it to detect subtle deviations that point to a threat – even if the sender or any malicious contents of the email are unknown to threat intelligence. This is what enabled the technology to stop an attack that recently targeted McLaren Racing, with emails sent to a dozen employees in the organization each containing a malicious link. This possible precursor to ransomware bypassed conventional email tools – largely because it was sent from a known supplier – however Darktrace recognized the account hijack and held the email back.

Figure 1: A snapshot of Darktrace’s Threat Visualizer surfacing the malicious email

Read the full case study

2. Initial intrusion (server-side)

With organizations rapidly expanding their Internet-facing perimeter, this increased attack surface has paved the way for a surge in brute-force and server-side attacks.

A number of vulnerabilities against such Internet-facing servers and systems have been disclosed this year, and for attackers, targeting and exploiting public-facing infrastructure is easier than ever – scanning the Internet for vulnerable systems is made simple with tools like Shodan or MassScan.

Attackers may also achieve initial intrusion via RDP brute-forcing or stolen credentials, with attackers often reusing legitimate credentials from previous data dumps. This has much higher precision and is less noisy than a classic brute-force attack.

A lot of ransomware attacks use RDP as an entry vector. This is part of a wider trend of ‘Living off the Land’: using legitimate off-the-shelf tools (abusing RDP, SMB1 protocol, or various command line tools WMI or Powershell) to blur detection and attribution by blending in with typical administrator activity. Ensuring that backups are isolated, configurations are hardened, and systems are patched is not enough – real-time detection of every anomalous action is needed.

Antivirus, firewalls and SIEMs

In cases of malware downloads, endpoint antivirus will detect these if, and only if, the malware has been seen and fingerprinted before. Firewalls typically require configuration on a per-organization basis, and often need to be modified based on the needs of the business. If the attack hits the firewall where a rule or signature does not match it, again, it will bypass the firewall.

SIEM and SOAR tools also look for known malware being downloaded, leverage pre-programmed rules and use pre-programmed responses. While these tools do look for patterns, these patterns are defined in advance, and this approach relies on a new attack to have sufficiently similar traits to attacks that have been seen before.

Real-world example: Dharma ransomware

Darktrace detected a targeted Dharma ransomware attack against a UK organization exploiting an open RDP connection through Internet-facing servers. The RDP server began receiving a large number of incoming connections from rare IP addresses on the Internet. It is highly likely that the RDP credential used in this attack had been compromised at a previous stage – either via common brute-force methods, credential stuffing attacks, or phishing. Indeed, a technique growing in popularity is to buy RDP credentials on marketplaces and skip to initial access.

Figure 2: The model breaches that fired over the course of this attack, including anomalous RDP activity

Unfortunately, in this case, without Autonomous Response installed, the Dharma ransomware attack continued until its final stages, where the security team were forced into the heavy-handed and disruptive action of pulling the plug on the RDP server midway through encryption.

Read the full case study

3. Establish foothold and C2

Whether through a successful phish, a brute-force attack, or some other method, the attacker is in. Now, they make contact with the breached device(s) and establish a foothold.

This stage allows attackers to control subsequent stages of the attack remotely. During these command and control (C2) communications, further malware may also pass from the attacker to the devices. This helps them to establish an even greater foothold within the organization and readies them for lateral movement.

Attackers can adapt malware functionality with an assortment of ready-made plug-ins, allowing them to lie low inside the business undetected. More modern and sophisticated ransomware is able to adapt by itself to the surrounding environment, and operate autonomously, blending in to regular activity even when cut off from its command and control server. These ‘self-sufficient’ ransomware strains pose a big problem for traditional defenses reliant on stopping threats solely on the grounds of its malicious external connections.

Viewing connections in isolation vs understanding the business

Conventional security tools like IDS and firewalls tend to look at connections in isolation rather than in the context of previous and potentially relevant connections, making command and control very difficult to spot.

IDS and firewalls may block ‘known-bad’ domains or use some geo-blocking, but this is where an attacker would likely leverage new infrastructure.

These tools also don’t tend to analyze for things like the periodicity, such as whether a connection is beaconing at a regular or irregular interval, or the age and rarity of the domain in the context of the environment.

With Darktrace’s evolving understanding of the digital enterprise, suspicious C2 connections and the downloads which follow them are spotted, even when conducted using regular programs or methods. The AI technology correlates multiple subtle signs of threat – a small subset of which includes anomalous connections to young and/or unusual endpoints, anomalous file downloads, incoming remote desktop, and unusual data uploads and downloads.

Once they are detected as a threat, Darktrace's Autonomous Response halts these connections and downloads, while allowing normal business activity to continue.

Real-world example: WastedLocker attack

When a WastedLocker ransomware attack hit a US agricultural organization, Darktrace immediately detected the initial unusual SSL C2 activity (based on a combination of destination rarity, JA3 unusualness and frequency analysis). Antigena (on this occasion configured in passive mode, and therefore not granted permission to take autonomous action) suggested instantly blocking the C2 traffic on port 443 and parallel internal scanning on port 135.

Figure 3: The Threat Visualizer reveals the action Antigena would have taken

When beaconing was later observed to bywce.payment.refinedwebs[.]com, this time over HTTP to /updateSoftwareVersion, Antigena escalated its response by blocking the further C2 channels.

Figure 4: Antigena escalates its response

Read the full case study

4. Lateral movement

Once an attacker has established a foothold within an organization, they begin to increase their knowledge of the wider digital estate and their presence within it. This is how they will find and access the files which they will ultimately attempt to exfiltrate and encrypt. It begins reconnaissance: scanning the network; building up a picture of its component devices; identifying the location of the most valuable assets.

Then the attacker begins moving laterally. They infect more devices and look to escalate their privileges – for instance, by obtaining admin credentials – thereby increasing their control over the environment. Once they have obtained authority and presence within the digital estate, they can progress to the final stages of the attack.

Modern ransomware has built-in functions that allow it to search automatically for stored passwords and spread through the network. More sophisticated strains are designed to build themselves differently in different environments, so the signature is constantly changing and it’s harder to detect.

Legacy tools: A blunt response to known threats

Because they rely upon static rules and signatures, legacy solutions struggle to prevent lateral movement and privilege escalation without also impeding essential business operations. Whilst in theory, an organization leveraging firewalls and NAC internally with proper network segmentation and a perfect configuration could prevent cross-network lateral movement, maintaining a perfect balance between protective and disruptive controls is near impossible.

Some organizations rely on Intrusion Prevent Systems (IPS) to deny network traffic when known threats are detected in packets, but as with previous stages, novel malware will evade detection, and this requires the database to be constantly updated. These solutions also sit at the ingress/egress points, limiting their network visibility. An Intrusion Detection System (IDS) may sit out-of-line, but doesn’t have response capabilities.

A self-learning approach

Darktrace’s AI learns ‘self’ for the organization, enabling it to detect suspicious activity indicative of lateral movement, regardless of whether the attacker uses new infrastructure or ‘lives off the land’. Potential unusual activity that Darktrace detects includes unusual scanning activity, unusual SMB, RDP, and SSH activity. Other models that fire at this stage include:

  • Suspicious Activity on High-Risk Device
  • Numeric EXE in SMB Write
  • New or Uncommon Service Control

Autonomous Response then takes targeted action to stop the threat at this stage, blocking anomalous connections, enforcing the infected device’s ‘pattern of life’, or enforcing the group ‘pattern of life’ – automatically clustering devices into peer groups and preventing a device from doing anything its peer group hasn’t done.

Where malicious behavior persists, and only if necessary, Darktrace will quarantine an infected device.

Real-world example: Unusual chain of RDP connections

At an organization in Singapore, one compromised server led to the creation of a botnet, which began moving laterally, predominantly by establishing chains of unusual RDP connections. The server then started making external SMB and RPC connections to rare endpoints on the Internet, in an attempt to find further vulnerable hosts.

Other lateral movement activities detected by Darktrace included the repeated failing attempts to access multiple internal devices over the SMB file-sharing protocol with a range of different usernames, implying brute-force network access attempts.

Figure 5: Darktrace’s Cyber AI Analyst reveals suspicious TCP scanning followed by a suspicious chain of administrative RDP connections

Read the full case study

5. Data exfiltration

In the past, ransomware was simply about encrypting an operating system and network files.

In a modern attack, as organizations insure against malicious encryption by becoming increasingly diligent with data backups, threat actors have moved towards ‘double extortion’, where they exfiltrate key data and destroy backups before the encryption takes place. Exfiltrated data is used to blackmail organizations, with attackers threatening to publish sensitive information online or sell it on to the organization’s competitors if they are not paid.

Modern ransomware variants also look for cloud file storage repositories such as Box, Dropbox, and others.

Many of these incidents aren’t public, because if IP is stolen, organizations are not always legally required to disclose it. However, in the case of customer data, organizations are obligated by law to disclose the incident and face the additional burden of compliance files – and we’ve seen these mount in recent years (Marriot, $23.8 million; British Airways, $26 million; Equifax, $575 million). There’s also the reputational blow associated with having to inform customers that a data breach has occurred.

Legacy tools: The same old story

For those that have been following, the narrative by now will sound familiar: to stop a ransomware attack at this stage, most defenses rely on either pre-programmed definitions of 'bad' or have rules constructed to combat different scenarios put organizations in a risky, never-ending game of cat and mouse.

A firewall and proxy might block connections based on pre-programmed policies based on specific endpoints or data volumes, but it’s likely an attacker will ‘live off the land’ and utilize a service that is generally allowed by the business.

The effectiveness of these tools will vary according to data volumes: they might be effective for ‘smash and grab’ attacks using known malware, and without employing any defense evasion techniques, but are unlikely to spot ‘low and slow’ exfiltration and novel or sophisticated strains.

On the other hand, because by nature it involves a break from expected behavior, even less conspicuous, low and slow data exfiltration is detected by Darktrace and stopped with Darktrace's Autonomos Response. No confidential files are lost, and attackers are unable to extort a ransom payment through blackmail.

Real-world example: Unusual chain of RDP connections

It becomes more difficult to find examples of Darktrace stopping ransomware at these later stages, as the threat is usually contained before it gets this far. This is the double-edged sword of effective security – early containment makes for bad storytelling! However, we can see the effects of a double extortion ransomware attack on an energy company in Canada. The organization had the Enterprise Immune System but no Antigena, and without anyone actively monitoring Darktrace’s AI detections, the attack was allowed to unfold.

The attacker managed to connect to an internal file server and download 1.95TB of data. The device was also seen downloading Rclone software – an open-source tool, which was likely applied to sync data automatically to the legitimate file storage service pCloud. Following the completion of the data exfiltration, the device ‘serverps’ finally began encrypting files on 12 devices with the extension *.06d79000. As with the majority of ransomware incidents, the encryption happened outside of office hours – overnight in local time – to minimize the chance of the security team responding quickly.

Read the full details of the attack

It should be noted that the exact order of the stages 3–5 above is not set in stone, and varies according to attack. Sometimes data is exfiltrated and then there is further lateral movement, and additional C2 beaconing. This entire period is known as the ‘dwell time’. Sometimes it takes place over only a few days, other times attackers may persist for months, slowly gathering more intel and exfiltrating data in a ‘low and slow’ fashion so as to avoid detection from rule-based tools that are configured to flag any single data transfer over a certain threshold. Only through a holistic understanding of malicious activity over time can a technology spot this level of activity and allow the security team to remove the threat before it reaches the latter and most damaging stages of ransomware.

6. Data encryption

Using either symmetric encryption, asymmetric encryption, or a combination of the two, attackers attempt to render as much data unusable in the organization’s network as they can before the attack is detected.

As the attackers alone have access to the relevant decryption keys, they are now in total control of what happens to the organization’s data.

Pre-programmed response and disruption

There are many families of tools that claim to stop encryption in this manner, but each contain blind spots which enable a sophisticated attacker to evade detection at this crucial stage. Where they do take action, it is often highly disruptive, causing major shutdowns and preventing a business from continuing its usual operations.

Internal firewalls prevent clients from accessing servers, so once an attacker has penetrated to servers using any of the techniques outlined above, they have complete freedom to act as they want.

Similarly, antivirus tools look only for known malware. If the malware has not been detected until this point, it is highly unlikely the antivirus will act here.

Stopping encryption autonomously

Even if familiar tools and methods are used to conduct it, Autonomous Response can enforce the normal ‘pattern of life’ for devices attempting encryption, without using static rules or signatures. This action can be taken independently or via integrations with native security controls, maximizing the return on other security investments. With a targeted Autonomous Response, normal business operations can continue while encryption is prevented.

7. Ransom note

It is important to note that in the stages before encryption, this ransomware attack is not yet “ransomware”. Only at this stage does it gets its name.

A ransom note is deployed. The attackers request payment in return for a decryption key and threaten the release of sensitive exfiltrated data. The organization must decide whether to pay the ransom or lose their data, possibly to their competition or the public. The average demand made by ransomware threat actors rose in 2021 to $5.3 million, with meat processing company JBS paying out $11 million and DarkSide receiving over $90 million in Bitcoin payments following the Colonial Pipeline incident.

All of the stages up until this point represent a typical, traditional ransomware attack. But ransomware is shifting from indiscriminate encryption of devices to attackers targeting business disruption in general, using multiple techniques to hold their victims to ransom. Additional methods of extortion include not only data exfiltration, but corporate domain hijack, deletion or encryption of backups, attacks against systems close to industrial control systems, targeting company VIPs… the list goes on.

Sometimes, attackers will just skip straight from stage 2 to 6 and jump straight to extortion. Darktrace recently stopped an email attack which showed an attacker bypassing the hard work and attempting to jump straight to extortion in an email. The attacker claimed to have compromised the organization’s sensitive data, requesting payment in bitcoin for its same return. Whether or not the claims were true, this attack shows that encryption is not always necessary for extortion, and this type of harassment exists in multiple forms.

Figure 6: Darktrace holds back the offending email, protecting the recipient and organization from harm

As with the email example we explored in the first post of this series, Darktrace/Email was able to step in and stop this email where other email tools would have let it through, stopping this potentially costly extortion attempt.

Whether through encryption or some other kind of blackmail, the message is the same every time. Pay up, or else. At this stage, it’s too late to start thinking about any of the options described above that were available to the organization, that would have stopped the attack in its earliest stages. There is only one dilemma. “To pay or not to pay” – that is the question.

Often, people believe their payment troubles are over after the ransom payment stage, but unfortunately, it’s just beginning to scratch the surface…

8. Clean-up

Efforts are made to try to secure the vulnerabilities which allowed the attack to happen initially – the organization should be conscious that approximately 80% of ransomware victims will in fact be targeted again in the future.

Legacy tools largely fail to shed light on the vulnerabilities which allowed the initial breach. Like searching for a needle in an incomplete haystack, security teams will struggle to find useful information within the limited logs offered by firewalls and IDSs. Antivirus solutions may reveal some known malware but fail to spot novel attack vectors.

With Darktrace’s Cyber AI Analyst, organizations are given full visibility over every stage of the attack, across all coverage areas of their digital estate, taking the mystery out of ransomware attacks. They are also able to see the actions that would have been taken to halt the attack by Darktrace RESPOND.

9. Recovery

The organization begins attempts to return its digital environment to order. Even if it has paid for a decryption key, many files may remain encrypted or corrupted. Beyond the costs of the ransom payment, network shutdowns, business disruption, remediation efforts, and PR setbacks all incur hefty financial losses.

The victim organization may also suffer additional reputation costs, with 66% of victims reporting a significant loss of revenue following a ransomware attack, and 32% reporting losing C-level talent as a direct result from ransomware.

Conclusion

While the high-level stages described above are common in most ransomware attacks, the minute you start looking at the details, you realize every ransomware attack is different.

As many targeted ransomware attacks come through ransomware affiliates, the Tools, Techniques and Procedures (TTPs) displayed during intrusions vary widely, even when the same ransomware malware is used. This means that even comparing two different ransomware attacks using the same ransomware family, you are likely to encounter completely different TTPs. This makes it impossible to predict what tomorrow’s ransomware will look like.

This is the nail in the coffin for traditional tooling which is based on historic attack data. The above examples demonstrate that Self-Learning technology and Autonomous Response is the only solution that stops ransomware at every stage, across email and network.

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About the author
Dan Fein
VP, Product

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August 7, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product | Darktrace
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