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Akira Ransomware: How Darktrace Foiled Another Novel Ransomware Attack







Threats Landscape: New Strains of Ransomware
In the face of a seemingly never-ending production line of novel ransomware strains, security teams across the threat landscape are continuing to see a myriad of new variants and groups targeting their networks. Naturally, new strains and threat groups present unique challenges to organizations. The use of previously unseen tactics, techniques, and procedures (TTPs) means that threat actors can often completely bypass traditional rule and signature-based security solutions, thus rendering an organization’s digital environment vulnerable to attack.
What is Akira Ransomware?
One such example of a novel ransomware family is Akira, which was first observed in the wild in March 2023. Much like many other strains, Akira is known to target corporate networks worldwide, encrypting sensitive files and demanding huge sums of money to retrieve the data and stop it from being posted online [1].
In late May 2023, Darktrace observed multiple instances of Akira ransomware affecting networks across its customer base. Thanks to its anomaly-based approach to threat detection, Darktrace DETECT™ successfully identified the novel ransomware attacks and provided full visibility over the cyber kill chain, from the initial compromise to the eventual file encryptions and ransom notes. In cases where Darktrace RESPOND™ was enabled in autonomous response mode, these attacks were mitigated the early stages of the attack, thus minimizing any disruption or damage to customer networks.

Initial access and privilege escalation
The Akira ransomware group typically uses spear-phishing campaigns containing malicious downloads or links as their primary initial access vector; however, they have also been known to use Remote Desktop Protocol (RDP) brute-force attacks to access target networks [2].
While Darktrace did observe the early access activities that are detailed below, it is very likely that the actual initial intrusion happened prior to this, through targeted phishing attacks that fell outside of Darktrace’s purview. The first indicators of compromise (IoCs) that Darktrace observed on customer networks affected by Darktrace were typically unusual RDP sessions, and the use of compromised administrative credentials.
On one Darktrace customer’s network (customer A), Darktrace DETECT identified a highly privileged credential being used for the first time on an internal server on May 21, 2023. Around a week later, this server was observed establishing RDP connections with multiple internal destination devices via port 3389. Further investigation carried out by the customer revealed that this credential had indeed been compromised. On May 30, Darktrace detected another device scanning internal devices and repeatedly failing to authenticate via Kerberos.
As the customer had integrated Darktrace with Microsoft Defender, their security team received additional cyber threat intelligence from Microsoft which, coupled with the anomaly alerts provided by Darktrace, helped to further contextualize these anomalous events. One specific detail gleaned from this integration was that the anomalous scanning activity and failed authentication attempts were carried out using the compromised administrative credentials mentioned earlier.
By integrating Microsoft Defender with Darktrace, customers can efficiently close security gaps across their digital infrastructure. While Darktrace understands customer environments and provides valuable network-level insights, by integrating with Microsoft Defender, customers can further enrich these insights with endpoint-specific information and activity.
In another customer’s network (customer B), Darktrace detected a device, later observed writing a ransom note, receiving an unusual RDP connection from another internal device. The RDP cookie used during this activity was an administrative RDP cookie that appeared to have been compromised. This device was also observed making multiple connections to the domain, api.playanext[.]com, and using the user agent , AnyDesk/7.1.11, indicating the use of the AnyDesk remote desktop service.
Although this external domain does not appear directly related to Akira ransomware, open-source intelligence (OSINT) found associations with multiple malicious files, and it appeared to be associated with the AnyDesk user agent, AnyDesk/6.0.1 [3]. The connections to this endpoint likely represented the malicious use of AnyDesk to remotely control the customer’s device, rather than Akira command-and-control (C2) infrastructure or payloads. Alternatively, it could be indicative of a spoofing attempt in which the threat actor is attempting to masquerade as legitimate remote desktop service to remain undetected by security tools.
Around the same time, Darktrace observed many devices on customer B’s network making anomalous internal RDP connections and authenticating via Kerberos, NTLM, or SMB using the same administrative credential. These devices were later confirmed to be affected by Akira ransomware.
Figure 1 shows how Darktrace detected one of those internal devices failing to login via SMB multiple times with a certain credential (indication of a possible SMB/NTLM brute force), before successfully accessing other internal devices via SMB, NTLM and RDP using the likely compromised administrative credential mentioned earlier.

Darktrace DETECT models observed for initial access and privilege escalation:
- Device / Anomalous RDP Followed By Multiple Model Breaches
- Anomalous Connection / Unusual Admin RDP Session
- New Admin Credentials on Server
- Possible SMB/NTLM Brute Force Indicator
- Unusual Activity / Successful Admin Brute-Force Activity
Internal Reconnaissance and Lateral Movement
The next step Darktrace observed during Akira ransomware attacks across the customer was internal reconnaissance and lateral movement.
In another customer’s environment (customer C), after authenticating via NTLM using a compromised credential, a domain controller was observed accessing a large amount of SMB shares it had never previously accessed. Darktrace DETECT understood that this SMB activity represented a deviation in the device’s expected behavior and recognized that it could be indicative of SMB enumeration. Darktrace observed the device making at least 196 connections to 34 unique internal IPs via port 445. SMB actions read, write, and delete were observed during those connections. This domain controller was also one of many devices on the customer’s network that was received incoming connections from an external endpoint over port 3389 using the RDP protocol, indicating that the devices were likely being remotely controlled from outside the network. While there were no direct OSINT links with this endpoint and Akira ransomware, the domain controller in question was later confirmed to be compromised and played a key role in this phase of the attack.
Moreover, this represents the second IoC that Darktrace observed that had no obvious connection to Akira, likely indicating that Akira actors are establishing entirely new infrastructure to carry out their attacks, or even utilizing newly compromised legitimate infrastructure. As Darktrace DETECT adopts an anomaly-based approach to threat detection, it can recognize suspicious activity indicative of an emerging ransomware attack based on its unusualness, rather than having to rely on previously observed IoCs and lists of ‘known-bads’.
Darktrace further observed a flurry of activity related to lateral movement around this time, primarily via SMB writes of suspicious files to other internal destinations. One particular device on customer C’s network was detected transferring multiple executable (.exe) and script files to other internal devices via SMB.
Darktrace recognized that these transfers represented a deviation from the device’s normal SMB activity and may have indicated threat actors were attempting to compromise additional devices via the transfer of malicious software.

Darktrace DETECT models observed for internal reconnaissance and lateral movement:
- Device / RDP Scan
- Anomalous Connection / SMB Enumeration
- Anomalous Connection / Possible Share Enumeration Activity
- Scanning of Multiple Devices (Cyber AI Analyst Incident)
- Device / Possible SMB/NTLM Reconnaissance
Compliance / Incoming Remote Desktop- Compliance / Outgoing NTLM Request from DC
- Unusual Activity / Internal Data Transfer
- Security Integration / Lateral Movement and Integration Detection
- Device / Anomalous SMB Followed By Multiple Model Breaches
Ransomware deployment
In the final phase of Akira ransomware attacks detected on Darktrace customer networks, Darktrace DETECT identified the file extension “.akira” being added after encryption to a variety of files on the affected network shares, as well as a ransom note titled “akira_readme.txt” being dropped on affected devices.
On customer A’s network, after nearly 9,000 login failures and 2,000 internal connection attempts indicative of scanning activity, one device was detected transferring suspicious files over SMB to other internal devices. The device was then observed connecting to another internal device via SMB and continuing suspicious file activity, such as appending files on network shares with the “.akira” extension, and performing suspicious writes to SMB shares on other internal devices.
Darktrace’s autonomous threat investigator, Cyber AI Analyst™, was able to analyze the multiple events related to this encryption activity and collate them into one AI Analyst incident, presenting a detailed and comprehensive summary of the entire incident within 10 minutes of Darktrace’s initial detection. Rather than simply viewing individual breaches as standalone activity, AI Analyst can identify the individual steps of an ongoing attack to provide complete visibility over emerging compromises and their kill chains. Not only does this bolster the network’s defenses, but the autonomous investigations carried out by AI Analyst also help to save the security team’s time and resources in triaging and monitoring ongoing incidents.

In addition to analyzing and compiling Darktrace DETECT model breaches, AI Analyst also leveraged the host-level insights provided by Microsoft Defender to enrich its investigation into the encryption event. By using the Security Integration model breaches, AI Analyst can retrieve timestamp and device details from a Defender alert and further investigate any unusual activity surrounding the alert to present a full picture of the suspicious activity.
In customer B’s environment, following the unusual RDP sessions and rare external connections using the AnyDesk user agent, an affected device was later observed writing around 2,000 files named "akira_readme.txt" to multiple internal SMB shares. This represented the malicious actor dropping ransom notes, containing the demands and extortion attempts of the actors.


As a result of this ongoing activity, an Enhanced Monitoring model breach, a high-fidelity DETECT model type that detects activities that are more likely to be indicative of compromise, was escalated to Darktrace’s Security Operations Center (SOC) who, in turn were able to further investigate and triage this ransomware activity. Customers who have subscribed to Darktrace’s Proactive Threat Notification (PTN) service would receive an alert from the SOC team, advising urgent follow up action.
Darktrace DETECT models observed during ransomware deployment:
- Security Integration / Integration Ransomware Incident
- Security Integration / High Severity Integration Detection
- Security Integration / Integration Ransomware Detected
- Device / Suspicious File Writes to Multiple Hidden SMB Shares
- Compliance / SMB Drive Write
- Compromise / Ransomware / Suspicious SMB Activity (Proactive Threat Notification Alerted by the Darktrace SOC)
- Anomalous File / Internal / Additional Extension Appended to SMB File
- Anomalous File / Internal / Unusual SMB Script Write
- Compromise / Ransomware / Ransom or Offensive Words Written to SMB
- Anomalous Server Activity /Write to Network Accessible WebRoot
- Anomalous Server Activity /Write to Network Accessible WebRoot
Darktrace RESPOND
When Darktrace is configured in autonomous response mode, RESPOND is able to follow up successful threat identifications by DETECT with instant autonomous actions that stop malicious actors in their tracks and prevent them from achieving their end goals.
In the examples of Darktrace customers affected by Akira outlined above, only customer A had RESPOND enabled in autonomous response mode during their ransomware attack. The autonomous response capability of Darktrace RESPOND helped the customer to minimize disruption to the business through multiple targeted actions on devices affected by ransomware.
One action carried out by RESPOND was to block all on-going traffic from affected devices. In doing so, Darktrace effectively shuts down communications between devices affected by Akira and the malicious infrastructure used by threat actors, preventing the spread of data on the client network or threat actor payloads.
Another crucial RESPOND action applied on this customer’s network was combat Akira was to “Enforce a Pattern of Life” on affected devices. This action is designed to prevent devices from performing any activity that would constitute a deviation from their expected behavior, while allowing them to continue their ‘usual’ business operations without causing any disruption.
While the initial intrusion of the attack on customer A’s network likely fell outside of the scope of Darktrace’s visibility, Darktrace RESPOND was able to minimize the disruption caused by Akira, containing the ransomware and allowing the customer to further investigate and remediate.
Darktrace RESPOND model breaches:
- Antigena / Network / External Threat / Antigena Ransomware Block
- Antigena / Network / External Threat / Antigena Suspicious Activity Block
- Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block
- Antigena / Network / External Threat / Antigena Suspicious Activity Block
- Antigena / Network / External Threat / Antigena File then New Outbound Block
- Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block
- Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
- Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
- Antigena / Network /Insider Threat /Antigena SMB Enumeration Block
Schlussfolgerung
Novel ransomware strains like Akira present a significant challenge to security teams across the globe due to the constant evolution of attack methods and tactics, making it huge a challenge for security teams to stay up to date with the most current threat intelligence.
Therefore, it is paramount for organizations to adopt a technology designed around an intelligent decision maker able to identify unusual activity that could be indicative of a ransomware attack without depending solely on rules, signatures, or statistic lists of malicious IoCs.
Darktrace DETECT identified Akira ransomware at every stage of the attack’s kill chain on multiple customer networks, even when threat actors were utilizing seemingly legitimate services (or spoofed versions of them) to carry out malicious activity. While this may have gone unnoticed by traditional security tools, Darktrace’s anomaly-based detection enabled it to recognize malicious activity for what it was. When enabled in autonomous response mode, Darktrace RESPOND is able to follow up initial detections with machine-speed preventative actions to stop the spread of ransomware and minimize the damage caused to customer networks.
There is no silver bullet to defend against novel cyber-attacks, however Darktrace’s anomaly-based approach to threat detection and autonomous response capabilities are uniquely placed to detect and respond to cyber disruption without latency.
Credit to: Manoel Kadja, Cyber Analyst, Nahisha Nobregas, SOC Analyst.
Appendices
IOC - Type - Description/Confidence
202.175.136[.]197 - External destination IP -Incoming RDP Connection
api.playanext[.]com - External hostname - Possible RDP Host
.akira - File Extension - Akira Ransomware Extension
akira_readme.txt - Text File - Akira Ransom Note
AnyDesk/7.1.11 - User Agent -AnyDesk User Agent
MITRE ATT&CK Mapping
Tactic & Technique
DISCOVERY
T1083 - File and Directory Discovery
T1046 - Network Service Scanning
T1135 - Network Share Discovery
RECONNAISSANCE
T1595.002 - Vulnerability Scanning
CREDENTIAL ACCESS, COLLECTION
T1557.001 - LLMNR/NBT-NS Poisoning and SMB Relay
DEFENSE EVASION, LATERAL MOVEMENT
T1550.002 - Pass the Hash
DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS
T1078 - Valid Accounts
DEFENSE EVASION
T1006 - Direct Volume Access
LATERAL MOVEMENT
T1563.002 - RDP Hijacking
T1021.001 - Remote Desktop Protocol
T1080 - Taint Shared Content
T1021.002 - SMB/Windows Admin Shares
INITIAL ACCESS
T1190 - Exploit Public-Facing Application
T1199 - Trusted Relationship
PERSISTENCE, INITIAL ACCESS
T1133 - External Remote Services
PERSISTENCE
T1505.003 - Web Shell
IMPACT
T1486 - Data Encrypted for Impact
References
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Protecting Prospects: How Darktrace Detected an Account Hijack Within Days of Deployment



Cloud Migration Expanding the Attack Surface
Cloud migration is here to stay – accelerated by pandemic lockdowns, there has been an ongoing increase in the use of public cloud services, and Gartner has forecasted worldwide public cloud spending to grow around 20%, or by almost USD 600 billion [1], in 2023. With more and more organizations utilizing cloud services and moving their operations to the cloud, there has also been a corresponding shift in malicious activity targeting cloud-based software and services, including Microsoft 365, a prominent and oft-used Software-as-a-Service (SaaS).
With the adoption and implementation of more SaaS products, the overall attack surface of an organization increases – this gives malicious actors additional opportunities to exploit and compromise a network, necessitating proper controls to be in place. This increased attack surface can leave organization’s open to cyber risks like cloud misconfigurations, supply chain attacks and zero-day vulnerabilities [2]. In order to achieve full visibility over cloud activity and prevent SaaS compromise, it is paramount for security teams to deploy sophisticated security measures that are able to learn an organization’s SaaS environment and detect suspicious activity at the earliest stage.
Darktrace Immediately Detects Hijacked Account
In May 2023, Darktrace observed a chain of suspicious SaaS activity on the network of a customer who was about to begin their trial of Darktrace/Cloud™ and Darktrace/Email™. Despite being deployed on the network for less than a week, Darktrace DETECT™ recognized that the legitimate SaaS account, belonging to an executive at the organization, had been hijacked. Darktrace/Email was able to provide full visibility over inbound and outbound mail and identified that the compromised account was subsequently used to launch an internal spear-phishing campaign.
If Darktrace RESPOND™ were enabled in autonomous response mode at the time of this compromise, it would have been able to take swift preventative action to disrupt the account compromise and prevent the ensuing phishing attack.
Account Hijack Attack Overview
Unusual External Sources for SaaS Credentials
On May 9, 2023, Darktrace DETECT/Cloud detected the first in a series of anomalous activities performed by a Microsoft 365 user account that was indicative of compromise, namely a failed login from an external IP address located in Virginia.

Just a few minutes later, Darktrace observed the same user credential being used to successfully login from the same unusual IP address, with multi-factor authentication (MFA) requirements satisfied.

A few hours after this, the user credential was once again used to login from a different city in the state of Virginia, with MFA requirements successfully met again. Around the time of this activity, the SaaS user account was also observed previewing various business-related files hosted on Microsoft SharePoint, behavior that, taken in isolation, did not appear to be out of the ordinary and could have represented legitimate activity.
The following day, May 10, however, there were additional login attempts observed from two different states within the US, namely Texas and Florida. Darktrace understood that this activity was extremely suspicious, as it was highly improbable that the legitimate user would be able to travel over 2,500 miles in such a short period of time. Both login attempts were successful and passed MFA requirements, suggesting that the malicious actor was employing techniques to bypass MFA. Such MFA bypass techniques could include inserting malicious infrastructure between the user and the application and intercepting user credentials and tokens, or by compromising browser cookies to bypass authentication controls [3]. There have also been high-profile cases in the recent years of legitimate users mistakenly (and perhaps even instinctively) accepting MFA prompts on their token or mobile device, believing it to be a legitimate process despite not having performed the login themselves.
New Email Rule
On the evening of May 10, following the successful logins from multiple US states, Darktrace observed the Microsoft 365 user creating a new inbox rule, named “.’, in Microsoft Outlook from an IP located in Florida. Threat actors are often observed naming new email rules with single characters, likely to evade detection, but also for the sake of expediency so as to not expend any additional time creating meaningful labels.
In this case the newly created email rules included several suspicious properties, including ‘AlwaysDeleteOutlookRulesBlob’, ‘StopProcessingRules’ and “MoveToFolder”.
Firstly, ‘AlwaysDeleteOutlookRulesBlob’ suppresses or hides warning messages that typically appear if modifications to email rules are made [4]. In this case, it is likely the malicious actor was attempting to implement this property to obfuscate the creation of new email rules.
The ‘StopProcessingRules’ rule meant that any subsequent email rules created by the legitimate user would be overridden by the email rule created by the malicious actor [5]. Finally, the implementation of “MoveToFolder” would allow the malicious actor to automatically move all outgoing emails from the “Sent” folder to the “Deleted Items” folder, for example, further obfuscating their malicious activities [6]. The utilization of these email rule properties is frequently observed during account hijackings as it allows attackers to delete and/or forward key emails, delete evidence of exploitation and launch phishing campaigns [7].
In this incident, the new email rule would likely have enabled the malicious actor to evade the detection of traditional security measures and achieve greater persistence using the Microsoft 365 account.

Account Update
A few hours after the creation of the new email rule, Darktrace observed the threat actor successfully changing the Microsoft 365 user’s account password, this time from a new IP address in Texas. As a result of this action, the attacker would have locked out the legitimate user, effectively gaining full access over the SaaS account.

Phishing Emails
The compromised SaaS account was then observed sending a high volume of suspicious emails to both internal and external email addresses. Darktrace was able to identify that the emails attempting to impersonate the legitimate service DocuSign and contained a malicious link prompting users to click on the text “Review Document”. Upon clicking this link, users would be redirected to a site hosted on Adobe Express, namely hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/.
Adobe Express is a free service that allows users to create web pages which can be hosted and shared publicly; it is likely that the threat actor here leveraged the service to use in their phishing campaign. When clicked, such links could result in a device unwittingly downloading malware hosted on the site, or direct unsuspecting users to a spoofed login page attempting to harvest user credentials by imitating legitimate companies like Microsoft.

The malicious site hosted on Adobe Express was subsequently taken down by Adobe, possibly in response to user reports of maliciousness. Unfortunately though, platforms like this that offer free webhosting services can easily and repeatedly be abused by malicious actors. Simply by creating new pages hosted on different IP addresses, actors are able to continue to carry out such phishing attacks against unsuspecting users.
In addition to the suspicious SaaS and email activity that took place between May 9 and May 10, Darktrace/Email also detected the compromised account sending and receiving suspicious emails starting on May 4, just two days after Darktrace’s initial deployment on the customer’s environment. It is probable that the SaaS account was compromised around this time, or even prior to Darktrace’s deployment on May 2, likely via a phishing and credential harvesting campaign similar to the one detailed above.

Darktrace Coverage
As the customer was soon to begin their trial period, Darktrace RESPOND was set in “human confirmation” mode, meaning that any preventative RESPOND actions required manual application by the customer’s security team.
If Darktrace RESPOND had been enabled in autonomous response mode during this incident, it would have taken swift mitigative action by logging the suspicious user out of the SaaS account and disabling the account for a defined period of time, in doing so disrupting the attack at the earliest possible stage and giving the customer the necessary time to perform remediation steps. As it was, however, these RESPOND actions were suggested to the customer’s security team for them to manually apply.

Nevertheless, with Darktrace DETECT/Cloud in place, visibility over the anomalous cloud-based activities was significantly increased, enabling the swift identification of the chain of suspicious activities involved in this compromise.
In this case, the prospective customer reached out to Darktrace directly through the Ask the Expert (ATE) service. Darktrace’s expert analyst team then conducted a timely and comprehensive investigation into the suspicious activity surrounding this SaaS compromise, and shared these findings with the customer’s security team.
Schlussfolgerung
Ultimately, this example of SaaS account compromise highlights Darktrace’s unique ability to learn an organization’s digital environment and recognize activity that is deemed to be unexpected, within a matter of days.
Due to the lack of obvious or known indicators of compromise (IoCs) associated with the malicious activity in this incident, this account hijack would likely have gone unnoticed by traditional security tools that rely on a rules and signatures-based approach to threat detection. However, Darktrace’s Self-Learning AI enables it to detect the subtle deviations in a device’s behavior that could be indicative of an ongoing compromise.
Despite being newly deployed on a prospective customer’s network, Darktrace DETECT was able to identify unusual login attempts from geographically improbable locations, suspicious email rule updates, password changes, as well as the subsequent mounting of a phishing campaign, all before the customer’s trial of Darktrace had even begun.
When enabled in autonomous response mode, Darktrace RESPOND would be able to take swift preventative action against such activity as soon as it is detected, effectively shutting down the compromise and mitigating any subsequent phishing attacks.
With the full deployment of Darktrace’s suite of products, including Darktrace/Cloud and Darktrace/Email, customers can rest assured their critical data and systems are protected, even in the case of hybrid and multi-cloud environments.
Credit: Samuel Wee, Senior Analyst Consultant & Model Developer
Appendices
References
[2] https://www.upguard.com/blog/saas-security-risks
[4] https://learn.microsoft.com/en-us/powershell/module/exchange/disable-inboxrule?view=exchange-ps
[7] https://blog.knowbe4.com/check-your-email-rules-for-maliciousness
Darktrace Model Detections
Darktrace DETECT/Cloud and RESPOND Models Breached:
SaaS / Access / Unusual External Source for SaaS Credential Use
SaaS / Unusual Activity / Multiple Unusual External Sources for SaaS Credential
Antigena / SaaS / Antigena Unusual Activity Block (RESPOND Model)
SaaS / Compliance / New Email Rule
Antigena / SaaS / Antigena Significant Compliance Activity Block
SaaS / Compromise / Unusual Login and New Email Rule (Enhanced Monitoring Model)
Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)
SaaS / Compromise / SaaS Anomaly Following Anomalous Login (Enhanced Monitoring Model)
SaaS / Compromise / Unusual Login and Account Update
Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)
IoC – Type – Description & Confidence
hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/ - Domain – Probable Phishing Page (Now Defunct)
37.19.221[.]142 – IP Address – Unusual Login Source
35.174.4[.]92 – IP Address – Unusual Login Source
MITRE ATT&CK Mapping
Tactic - Techniques
INITIAL ACCESS, PRIVILEGE ESCALATION, DEFENSE EVASION, PERSISTENCE
T1078.004 – Cloud Accounts
DISCOVERY
T1538 – Cloud Service Dashboards
CREDENTIAL ACCESS
T1539 – Steal Web Session Cookie
RESOURCE DEVELOPMENT
T1586 – Compromise Accounts
PERSISTENCE
T1137.005 – Outlook Rules

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Darktrace/Email in Action: Why AI-Driven Email Security is the Best Defense Against Sustained Phishing Campaigns
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Stopping the bad while allowing the good
Since its inception, email has been regarded as one of the most important tools for businesses, revolutionizing communication and allowing global teams to become even more connected. But besides organizations heavily relying on email for their daily operations, threat actors have also recognized that the inbox is one of the easiest ways to establish an initial foothold on the network.
Today, not only are phishing campaigns and social engineering attacks becoming more prevalent, but the level of sophistication of these attacks are also increasing with the help of generative AI tools that allow for the creation of hyper-realistic emails with minimal errors, effectively lowering the barrier to entry for threat actors. These diverse and stealthy types of attacks evade traditional email security tools based on rules and signatures, because they are less likely to contain the low-sophistication markers of a typical phishing attack.
In a situation where the sky is the limit for attackers and security teams are lean, how can teams equip themselves to tackle these threats? How can they accurately detect increasingly realistic malicious emails and neutralize these threats before it is too late? And importantly, how can email security block these threats while allowing legitimate emails to flow freely?
Instead of relying on past attack data, Darktrace’s Self-Learning AI detects the slightest deviation from a user’s pattern of life and responds autonomously to contain potential threats, stopping novel attacks in their tracks before damage is caused. It doesn’t define ‘good’ and ‘bad’ like traditional email tools, rather it understands each user and what is normal for them – and what’s not.
This blog outlines how Darktrace/Email™ used its understanding of ‘normal’ to accurately detect and respond to a sustained phishing campaign targeting a real-life company.
Responding to a sustained phishing attack
Over the course of 24 hours, Darktrace detected multiple emails containing different subjects, all from different senders to different recipients in one organization. These emails were sent from different IP addresses, but all came from the same autonomous system number (ASN).

The emails themselves had many suspicious indicators. All senders had no prior association with the recipient, and the emails generated a high general inducement score. This score is generated by structural and non-specific content analysis of the email – a high score indicates that the email is trying to induce the recipient into taking a particular action, which may lead to account compromise.
Additionally, each email contained a visually prominent link to a file storage service, hidden behind a shortened bit.ly link. The similarities across all these emails pointed to a sustained campaign targeting the organization by a single threat actor.


With all these suspicious indicators, many models were breached. This drove up the anomaly score, causing Darktrace/Email to hold all suspicious emails from the recipients’ inboxes, safeguarding the recipients from potential account compromise and disallowing the threats from taking hold in the network.
Imagining a phishing attack without Darktrace/Email
So what could have happened if Darktrace had not withheld these emails, and the recipients had clicked on the links? File storage sites have a wide variety of uses that allow attackers to be creative in their attack strategy. If the user had clicked on the shortened link, the possible consequences are numerous. The link could have led to a login page for unsuspecting victims to input their credentials, or it could have hosted malware that would automatically download if the link was clicked. With the compromised credentials, threat actors could even bypass MFA, change email rules, or gain privileged access to a network. The downloaded malware might also be a keylogger, leading to cryptojacking, or could open a back door for threat actors to return to at a later time.


The limits of traditional email security tools
Secure email gateways (SEGs) and static AI security tools may have found it challenging to detect this phishing campaign as malicious. While Darktrace was able to correlate these emails to determine that a sustained phishing campaign was taking place, the pattern among these emails is far too generic for specific rules as set in traditional security tools. If we take the characteristic of the freemail account sender as an example, setting a rule to block all emails from freemail accounts may lead to more legitimate emails being withheld, since these addresses have a variety of uses.
With these factors in mind, these emails could have easily slipped through traditional security filters and led to a devastating impact on the organization.
Schlussfolgerung
As threat actors step up their attacks in sophistication, prioritizing email security is more crucial than ever to preserving a safe digital environment. In response to these challenges, Darktrace/Email offers a set-and-forget solution that continuously learns and adapts to changes in the organization.
Through an evolving understanding of every environment in which it is deployed, its threat response becomes increasingly precise in neutralizing only the bad, while allowing the good – delivering email security that doesn’t come at the expense of business growth.