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Using Self-Learning AI to defend against zero-day and N-day attacks






Key Terms:
Zero-day | A recently discovered security vulnerability in computer software that has no currently available fix or patch. Its name come from the reality that vendors have “zero days” to act and respond.
N-day | A vulnerability that emerges in computer software in which a vendor is aware and may have already issued (or are currently working on) a patch or fix. Active exploits often already exist and await abuse by nefarious actors.
Traditional security solutions often apply signature-based-detection when identifying cyber threats, helping to defend against legacy attacks but consequently missing novel ones. Therefore, security teams often lend a lot of focus to ensuring that the risk of zero-day vulnerabilities is reduced [1]. As explored in this blog, however, organizations can face just as much of a risk from n-day attacks, since they invite the most attention from malicious actors [2]. This is due in part to the reduced complexity, cost and time invested in researching and finding new exploits compared with that found when attackers exploit zero-days.
This blog will examine both a zero-day and n-day attack that two different Darktrace customers faced in the fall of 2021. This will include the activity Darktrace detected, along with the steps taken by Darktrace/Network to intervene. It will then compare the incidents, discuss the possible dangers of third-party integrations, and assess the deprecation of legacy security tools.
Revisiting zero-day attacks
Zero-days are among the greatest concerns security teams face in the era of modern technology and networking. Defending critical systems from zero-day compromises is a task most legacy security solutions are often unable to handle. Due to the complexity of uncovering new security flaws and developing elaborate code that can exploit them, these attacks are often carried out by funded or experienced groups such as nation-state actors and APTs. One of history’s most prolific zero-days, ‘Stuxnet’, sent security teams worldwide into a global panic in 2010. This involved a widespread attack on Iranian nuclear infrastructure and was widely accepted to be a result of nation-state actors [3]. The Stuxnet worm took advantage of four zero-day exploits, compromising over 200,000 devices and physically damaging around 10% of the 9,000 critical centrifuges at the Natanz nuclear site.
More recently, 2021 saw the emergence of several critical zero-day vulnerabilities within SonicWall’s product suite [4]. SonicWall is a security hardware manufacturer that provides hardware firewall devices, unified threat management, VPN gateways and network security solutions. Some of these vulnerabilities lie within their Secure Mobile Access (SMA) 100 series (for example, CVE-2019-7481, CVE-2021-20016 and CVE-2021-20038 to name a few). These directly affected VPN devices and often allowed attackers easy remote access to company devices. CVE-2021-20016 in particular incorporates an SQL-Injection vulnerability within SonicWall’s SSL VPN SMA 100 product line [5]. If exploited, this defect would allow an unauthenticated remote attacker to perform their own malicious SQL query in order to access usernames, passwords and other session related information.
The N-day underdog
The shadow cast by zero-day attacks often shrouds that of n-day attacks. N-days, however, often pose an equal - if not greater - risk to the majority of organizations, particularly those in industrial sectors. Since these vulnerabilities have fixes available, all of the hard work around research is already done; malicious actors only need to view proof of concepts (POCs) or, if proficient in coding, reverse-engineer software to reveal code-changes (binary diffing) in order to exploit these security flaws in the wild. These vulnerabilities are typically attributed to opportunistic hackers and script-kiddies, where little research or heavy lifting is required.
August 2021 gave rise to a critical vulnerability in Atlassian Confluence servers, namely CVE-2021-26084 [6]. Confluence is a widely used collaboration wiki tool and knowledge-sharing platform. As introduced and discussed a few months ago in a previous Darktrace blog, this vulnerability allows attackers to remotely execute code on internet-facing servers after exploiting injection vulnerabilities in Object-Graph Navigation Language (OGNL). Whilst Confluence had patches and fixes available to users, attackers still jumped on this opportunity and began scanning the internet for signs of critical devices serving this outdated software [7]. Once identified, they would exploit the vulnerability, often installing crypto mining software onto the device. More recently, Darktrace explored a new vulnerability (CVE-2022-26134), disclosed midway through 2022, that affected Confluence servers and data centers using similar techniques to that found in CVE-2021-26084 [8].
SonicWall in the wild – 1. Zero-day attack
At the beginning of August 2021, Darktrace prevented an attack from taking place within a European automotive customer’s environment (Figure 1). The attack targeted a vulnerable internet-facing SonicWall VPN server, and while the attacker’s motive remains unclear, similar historic events suggest that they intended to perform ransomware encryption or data exfiltration.

Darktrace was unable to confirm the definite tactics, techniques and procedures (TTPs) used by the attacker to compromise the customer’s environment, as the device was compromised before Darktrace installation and coverage. However, from looking at recently disclosed SonicWall VPN vulnerabilities and patterns of behaviour, it is likely CVE-2021-20016 played a part. At some point after this initial infection, it is also believed the device was able to move laterally to a domain controller (DC) using administrative credentials; it was this server that then initiated the anomalous activity that Darktrace detected and alerted on.
On August 5th 2021 , Darktrace observed this compromised domain controller engaging in unusual ICMP scanning - a protocol used to discover active devices within an environment and create a map of an organization’s network topology. Shortly after, the infected server began scanning devices for open RDP ports and enumerating SMB shares using unorthodox methods. SMB delete and HTTP requests (over port 445 and 80 respectively) were made for files named delete.me in the root directory of numerous network shares using the user agent Microsoft WebDAV. However, no such files appeared to exist within the environment. This may have been the result of an attacker probing devices in the network in an effort to see their responses and gather information on properties and vulnerabilities they could later exploit.
Soon the infected DC began establishing RDP tunnels back to the VPN server and making requests to an internal DNS server for multiple endpoints relating to exploit kits, likely in an effort to strengthen the attacker’s foothold within the environment. Some of the endpoints requested relate to:
- EternalBlue vulnerability
- Petit Potam NTLM hash attack tool
- Unusual GitHub repositories
- Unusual Python repositories
The DC made outgoing NTLM requests to other internal devices, implying the successful installation of Petit Potam exploitation tools. The server then began performing NTLM reconnaissance, making over 1,000 successful logins under ‘Administrator’ to several other internal devices. Around the same time, the device was also seen making anonymous SMBv1 logins to numerous internal devices, (possibly symptomatic of the attacker probing machines for EternalBlue vulnerabilities).
Interestingly, the device also made numerous failed authentication attempts using a spoofed credential for one of the organization’s security managers. This was likely in an attempt to hide themselves using ‘Living off the Land’ (LotL) techniques. However, whilst the attacker clearly did their research on the company, they failed to acknowledge the typical naming convention used for credentials within the environment. This ultimately backfired and made the compromise more obvious and unusual.
In the morning of the following day, the initially compromised VPN server began conducting further reconnaissance, engaging in similar activity to that observed by the domain controller. Until now, the customer had set Darktrace RESPOND to run in human confirmation mode, meaning interventions were not made autonomously but required confirmation by a member of the internal security team. However, thanks to Proactive Threat Notifications (PTNs) delivered by Darktrace’s dedicated SOC team, the customer was made immediately aware of this unusual behaviour, allowing them to apply manual Darktrace RESPOND blocks to all outgoing connections (Figure 2). This gave the security team enough time to respond and remediate before serious damage could be done.

Confluence in the wild – 2. N-day attack
Towards the end of 2021, Darktrace saw a European broadcasting customer leave an Atlassian Confluence internet-facing server unpatched and vulnerable to crypto-mining malware using CVE-2021-26084. Thanks to Darktrace, this attack was entirely immobilized within only a few hours of the initial infection, protecting the organization from damage (Figure 3).

On midday on September 1st 2021, an unpatched Confluence server was seen receiving SSL connections over port 443 from a suspicious new endpoint, 178.238.226[.]127. The connections were encrypted, meaning Darktrace was unable to view the contents and ascertain what requests were being made. However, with the disclosure of CVE-2021-26084 just 7 days prior to this activity, it is likely that the TTPs used involved injecting OGNL expressions to Confluence server memory; allowing the attacker to remotely execute code on the vulnerable server.
Immediately after successful exploitation of the Confluence server, the infected device was observed making outgoing HTTP GET requests to several external endpoints using a new user agent (curl/7.61.1). Curl was used to silently download and configure multiple suspicious files relating to XMRig cryptocurrency miner, including ld.sh, XMRig and config.json. Subsequent outgoing connections were then made to europe.randomx-hub.miningpoolhub[.]com · 172.105.210[.]117 using the JSON-RPC protocol, seen alongside the mining credential maillocal.confluence (Figure 4). Only 3 seconds after initial compromise, the infected device began attempting to mine cryptocurrency using the Minergate protocol but was instantly and autonomously blocked by Darktrace RESPOND. This prevented the server from abusing system resources and generating profits for the attacker.

In the afternoon, the malware persisted with its infection. The compromised server began making successive HTTP GET requests to a new rare endpoint 195.19.192[.]28 using the same curl user agent (Figures 5 & 6). These requests were for executable and dynamic library files associated with Kinsing malware (but fortunately were also blocked by Darktrace RESPOND). Kinsing is a malware strain found in numerous attack campaigns which is often associated with crypto-jacking, and has appeared in previous Darktrace blogs [9].

The attacker then began making HTTP POST requests to an IP 185.154.53[.]140, using the same curl user agent; likely a method for the attacker to maintain persistence within the network and establish a foothold using its C2 infrastructure. The Confluence server was then again seen attempting to mine cryptocurrency using the Minergate protocol. It made outgoing JSON-RPC connections to a different new endpoint, 45.129.2[.]107, using the following mining credential: ‘42J8CF9sQoP9pMbvtcLgTxdA2KN4ZMUVWJk6HJDWzixDLmU2Ar47PUNS5XHv4Kmfdh8aA9fbZmKHwfmFo8Wup8YtS5Kdqh2’. This was once again blocked by Darktrace RESPOND (Figure 7).


The final activity seen from this device involved the download of additional shell scripts over HTTP associated with Kinsing, namely spre.sh and unk.sh, from 194.38.20[.]199 and 195.3.146[.]118 respectively (Figure 8). A new user agent (Wget/1.19.5 (linux-gnu)) was used when connecting to the latter endpoint, which also began concurrently initiating repeated connections indicative of C2 beaconing. These scripts help to spread the Kinsing malware laterally within the environment and may have been the attacker's last ditch efforts at furthering their compromise before Darktrace RESPOND blocked all connections from the infected Confluence server [11]. With Darktrace RESPOND's successful actions, the customer’s security team were then able to perform their own response and remediation.

Darktrace Coverage: N- vs Zero-days
In the SonicWall case the attacker was unable to achieve their actions on objectives (thanks to Darktrace's intervention). However, this incident displayed tactics of a more stealthy and sophisticated attacker - they had an exploited machine but waited for the right moment to execute their malicious code and initiate a full compromise. Due to the lack of visibility over attacker motive, it is difficult to deduce what type of actor led to this intrusion. However, with the disclosure of a zero-day vulnerability (CVE-2021-20016) not long before this attack, along with a seemingly dormant initially compromised device, it is highly possible that it was carried out by a sophisticated cyber criminal or gang.
On the other hand, the Confluence case engaged in a slightly more noisy approach; it dropped crypto mining malware on vulnerable devices in the hope that the target’s security team did not maintain visibility over their network or would merely turn a blind eye. The files downloaded and credentials observed alongside the mining activity heavily imply the use of Kinsing malware [11]. Since this vulnerability (CVE-2021-26084) emerged as an n-day attack with likely easily accessible POCs, as well as there being a lack of LotL techniques and the motive being long term monetary gain, it is possible this attack was conducted by a less sophisticated or amateur actor (script-kiddie); one that opportunistically exploits known vulnerabilities in internet-facing devices in order to make a quick profit [12].
Whilst Darktrace RESPOND was enabled in human confirmation mode only during the start of the SonicWall attack, Darktrace’s Cyber AI Analyst still offered invaluable insight into the unusual activity associated with the infected machines during both the Confluence and SonicWall compromises. SOC analysts were able to see these uncharacteristic behaviours and escalate the incident through Darktrace’s PTN and ATE services. Analysts then worked through these tickets with the customers, providing support and guidance and, in the SonicWall case, quickly helping to configure Darktrace RESPOND. In both scenarios, Darktrace RESPOND was able to block abnormal connections and enforce a device’s pattern of life, affording the security team enough time to isolate the infected machines and prevent further threats such as ransomware detonation or data exfiltration.
Concluding thoughts and dangers of third-party integrations
Organizations with internet-facing devices will inevitably suffer opportunistic zero-day and n-day attacks. While little can be done to remove the risk of zero-days entirely, ensuring that organizations keep their systems up to date will at the very least help prevent opportunistic and script-kiddies from exploiting n-day vulnerabilities.
However, it is often not always possible for organizations to keep their systems up to date, especially for those who require continuous availability. This may also pose issues for organizations that rely on, and put their trust in, third party integrations such as those explored in this blog (Confluence and SonicWall), as enforcing secure software is almost entirely out of their hands. Moreover, with the rising prevalence of remote working, it is essential now more than ever that organizations ensure their VPN devices are shielded from external threats, guidance on which has been released by the NSA/CISA [13].
These two case studies have shown that whilst organizations can configure their networks and firewalls to help identify known indicators of compromise (IoC), this ‘rearview mirror’ approach will not account for, or protect against, any new and undisclosed IoCs. With the aid of Self-Learning AI and anomaly detection, Darktrace can detect the slightest deviation from a device’s normal pattern of life and respond autonomously without the need for rules and signatures. This allows for the disruption and prevention of known and novel attacks before irreparable damage is caused- reassuring security teams that their digital estates are secure.
Thanks to Paul Jennings for his contributions to this blog.
Appendices: SonicWall (Zero-day)
Darktrace model detections
· AIA / Suspicious Chain of Administrative Credentials
· Anomalous Connection / Active Remote Desktop Tunnel
· Anomalous Connection / SMB Enumeration
· Anomalous Connection / Unusual Internal Remote Desktop
· Compliance / High Priority Compliance Model Breach
· Compliance / Outgoing NTLM Request from DC
· Device / Anomalous RDP Followed By Multiple Model Breaches
· Device / Anomalous SMB Followed By Multiple Model Breaches
· Device / ICMP Address Scan
· Device / Large Number of Model Breaches
· Device / Large Number of Model Breaches from Critical Network Device
· Device / Multiple Lateral Movement Model Breaches (PTN/Enhanced Monitoring model)
· Device / Network Scan
· Device / Possible SMB/NTLM Reconnaissance
· Device / RDP Scan
· Device / Reverse DNS Sweep
· Device / SMB Session Bruteforce
· Device / Suspicious Network Scan Activity (PTN/Enhanced Monitoring model)
· Unusual Activity / Possible RPC Recon Activity
Darktrace RESPOND (Antigena) actions (as displayed in example)
· Antigena / Network / Manual / Quarantine Device
MITRE ATT&CK Techniques Observed

IoCs

Appendices: Confluence (N-day)
Darktrace model detections
· Anomalous Connection / New User Agent to IP Without Hostname
· Anomalous Connection / Posting HTTP to IP Without Hostname
· Anomalous File / EXE from Rare External Location
· Anomalous File / Script from Rare Location
· Compliance / Crypto Currency Mining Activity
· Compromise / High Priority Crypto Currency Mining (PTN/Enhanced Monitoring model)
· Device / Initial Breach Chain Compromise (PTN/Enhanced Monitoring model)
· Device / Internet Facing Device with High Priority Alert
· Device / New User Agent
Darktrace RESPOND (Antigena) actions (displayed in example)
· Antigena / Network / Compliance / Antigena Crypto Currency Mining Block
· Antigena / Network / External Threat / Antigena File then New Outbound Block
· Antigena / Network / External Threat / Antigena Suspicious Activity Block
· Antigena / Network / External Threat / Antigena Suspicious File Block
· Antigena / Network / Significant Anomaly / Antigena Block Enhanced Monitoring
MITRE ATT&CK Techniques Observed

IOCs


References:
[1] https://securitybrief.asia/story/why-preventing-zero-day-attacks-is-crucial-for-businesses
[3] https://www.wired.com/2014/11/countdown-to-zero-day-stuxnet/
[4] https://cve.mitre.org/cgi-bin/cvekey.cgi?keyword=SonicWall+2021
[5] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-20016
[6] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2021-26084
[8] https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2022-26134
[9] https://attack.mitre.org/software/S0599/
[10] https://www.virustotal.com/gui/ip-address/195.19.192.28/detection
[11] https://sysdig.com/blog/zoom-into-kinsing-kdevtmpfsi/
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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.
Conclusion
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.
Conclusion
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.