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Walking through the front door: Compromises of Internet-facing systems






By virtue of their exposure, Internet-facing systems (i.e., systems which have ports open/exposed to the wider Internet) are particularly susceptible to compromise. Attackers typically compromise Internet-facing systems by exploiting zero-day vulnerabilities in applications they run. During 2021, critical zero-day vulnerabilities in the following applications were publicly disclosed:
- Microsoft Exchange
- Confluence
- GitLab
- Log4j-using applications
Internet-facing systems running these applications were consequently heavily targeted by attackers. In this post, we will provide examples of compromises of these systems observed by Darktrace’s SOC team in 2021. As will become clear, successful exploitation of weaknesses in Internet-facing systems inevitably results in such systems doing things which they do not normally do. Rather than focusing on identifying attempts to exploit these weaknesses, Darktrace focuses on identifying the unusual behaviors which inevitably ensue. The purpose of this post is to highlight the effectiveness of this approach.
Exchange server compromise
In January, researchers from the cyber security company DEVCORE reported a series of critical vulnerabilities in Microsoft Exchange which they dubbed ‘ProxyLogon’.[1] ProxyLogon consists of a server-side request forgery (SSRF) vulnerability (CVE-2021-26855) and a remote code execution (RCE) vulnerability (CVE-2021-27065). Attackers were observed exploiting these vulnerabilities in the wild from as early as January 6.[2] In April, DEVCORE researchers reported another series of critical vulnerabilities in Microsoft Exchange which they dubbed ‘ProxyShell’.[3] ProxyShell consists of a pre-authentication path confusion vulnerability (CVE-2021-34473), a privilege elevation vulnerability (CVE-2021-34523), and a post-authentication RCE vulnerability (CVE-2021-31207). Attackers were first observed exploiting these vulnerabilities in the wild in August.[4] In many cases, attackers exploited the ProxyShell and ProxyLogon vulnerabilities in order to create web shells on the targeted Exchange servers. The presence of these web shells provided attackers with the means to remotely execute commands on the compromised servers.
In early August 2021, by exploiting the ProxyShell vulnerabilities, an attacker gained the rights to remotely execute PowerShell commands on an Internet-facing Exchange server within the network of a US-based transportation company. The attacker subsequently executed a number of PowerShell commands on the server. One of these commands caused the server to make a 28-minute-long SSL connection to a highly unusual external endpoint. Within a couple of hours, the attacker managed to strengthen their foothold within the network by installing AnyDesk and CobaltStrike on several internal devices. In mid-August, the attacker got the devices on which they had installed Cobalt Strike to conduct network reconnaissance and to transfer terabytes of data to the cloud storage service, MEGA. At the end of August, the attacker got the devices on which they had installed AnyDesk to execute Conti ransomware and to spread executable files and script files to further internal devices.
In this example, the attacker’s exploitation of ProxyShell immediately resulted in the Exchange Server making a long SSL connection to an unusual external endpoint. This connection caused the model Device / Long Agent Connection to New Endpoint to breach. The subsequent reconnaissance, lateral movement, C2, external data transfer, and encryption behavior brought about by the attacker were also picked up by Darktrace’s models.
A non-exhaustive list of the models that breached as a result of the behavior brought about by the attacker:
- Device / Long Agent Connection to New Endpoint
- Device / ICMP Address Scan
- Anomalous Connection / SMB Enumeration
- Anomalous Server Activity / Outgoing from Server
- Compromise / Beacon to Young Endpoint
- Anomalous Server Activity / Rare External from Server
- Compromise / Fast Beaconing to DGA
- Compromise / SSL or HTTP Beacon
- Compromise / Sustained SSL or HTTP Increase
- Compromise / Beacon for 4 Days
- Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
- Unusual Activity / Enhanced Unusual External Data Transfer
- Anomalous Connection / Data Sent to Rare Domain
- Anomalous Connection / Uncommon 1 GiB Outbound
- Compliance / SMB Drive Write
- Anomalous File / Internal / Additional Extension Appended to SMB File
- Anomalous Connection / Suspicious Read Write Ratio
- Anomalous Connection / Suspicious Read Write Ratio and Unusual SMB
- Anomalous Connection / Sustained MIME Type Conversion
- Unusual Activity / Anomalous SMB Move & Write
- Unusual Activity / Unusual Internal Data Volume as Client or Server
- Device / Suspicious File Writes to Multiple Hidden SMB Shares
- Compromise / Ransomware / Suspicious SMB Activity
- Anomalous File / Internal / Unusual SMB Script Write
- Anomalous File / Internal / Masqueraded Executable SMB Write
- Device / SMB Lateral Movement
- Device / Multiple Lateral Movement Model Breaches
Confluence server compromise
Atlassian’s Confluence is an application which provides the means for building collaborative, virtual workspaces. In the era of remote working, the value of such an application is undeniable. The public disclosure of a critical remote code execution (RCE) vulnerability (CVE-2021-26084) in Confluence in August 2021 thus provided a prime opportunity for attackers to cause havoc. The vulnerability, which arises from the use of Object-Graph Navigation Language (OGNL) in Confluence’s tag system, provides attackers with the means to remotely execute code on vulnerable Confluence server by sending a crafted HTTP request containing a malicious parameter.[5] Attackers were first observed exploiting this vulnerability towards the end of August, and in the majority of cases, attackers exploited the vulnerability in order to install crypto-mining tools onto vulnerable servers.[6]
At the beginning of September 2021, an attacker was observed exploiting CVE-2021-26084 in order to install the crypto-mining tool, XMRig, as well as a shell script, onto an Internet-facing Confluence server within the network of an EMEA-based television and broadcasting company. Within a couple of hours, the attacker installed files associated with the crypto-mining malware, Kinsing, onto the server. The Kinsing-infected server then immediately began to communicate over HTTP with the attacker’s C2 infrastructure. Around the time of this activity, the server was observed using the MinerGate crypto-mining protocol, indicating that the server had begun to mine cryptocurrency.
In this example, the attacker’s exploitation of CVE-2021-26084 immediately resulted in the Confluence server making an HTTP GET request with an unusual user-agent string (one associated with curl in this case) to a rare external IP. This behavior caused the models Device / New User Agent, Anomalous Connection / New User Agent to IP Without Hostname, and Anomalous File / Script from Rare Location to breach. The subsequent file downloads, C2 traffic and crypto-mining activity also resulted in several models breaching.
A non-exhaustive list of the models which breached as a result of the unusual behavior brought about by the attacker:
- Device / New User Agent
- Anomalous Connection / New User Agent to IP Without Hostname
- Anomalous File / Script from Rare Location
- Anomalous File / EXE from Rare External Location
- Anomalous File / Internet Facing System File Download
- Device / Initial Breach Chain Compromise
- Anomalous Connection / Posting HTTP to IP Without Hostname
- Compliance / Crypto Currency Mining Activity
- Compromise / High Priority Crypto Currency Mining
- Device / Internet Facing Device with High Priority Alert
GitLab server compromise
GitLab is an application providing services ranging from project planning to source code management. Back in April 2021, a critical RCE vulnerability (CVE-2021-22205) in GitLab was publicly reported by a cyber security researcher via the bug bounty platform, HackerOne.[7] The vulnerability, which arises from GitLab’s use of ExifTool for removing metadata from image files, [8] enables attackers to remotely execute code on vulnerable GitLab servers by uploading specially crafted image files.[9] Attackers were first observed exploiting CVE-2021-22205 in the wild in June/July.[10] A surge in exploitations of the vulnerability was observed at the end of October, with attackers exploiting the flaw in order to assemble botnets.[11] Darktrace observed a significant number of cases in which attackers exploited the vulnerability in order to install crypto-mining tools onto vulnerable GitLab servers.
On October 29, an attacker successfully exploited CVE-2021-22205 on an Internet-facing GitLab server within the network of a UK-based education provider. The organization was trialing Darktrace when this incident occurred. The attacker installed several executable files and shell scripts onto the server by exploiting the vulnerability. The attacker communicated with the compromised server (using unusual ports) for several days, before making the server transfer large volumes of data externally and download the crypto-mining tool, XMRig, as well as the botnet malware, Mirai. The server was consequently observed making connections to the crypto-mining pool, C3Pool.
In this example, the attacker’s exploitation of the vulnerability in GitLab immediately resulted in the server making an HTTP GET request with an unusual user-agent string (one associated with Wget in this case) to a rare external IP. The models Anomalous Connection / New User Agent to IP Without Hostname and Anomalous File / EXE from Rare External Location breached as a result of this behavior. The attacker’s subsequent activity on the server over the next few days resulted in frequent model breaches.
A non-exhaustive list of the models which breached as a result of the attacker’s activity on the server:
- Anomalous Connection / New User Agent to IP Without Hostname
- Anomalous File / EXE from Rare External Location
- Anomalous File / Multiple EXE from Rare External Locations
- Anomalous File / Internet Facing Device with High Priority Alert
- Anomalous File / Script from Rare Location
- Anomalous Connection / Application Protocol on Uncommon Port
- Anomalous Connection / Anomalous SSL without SNI to New External
- Device / Initial Breach Chain Compromise
- Unusual Activity / Unusual External Data to New IPs
- Anomalous Server Activity / Outgoing from Server
- Device / Large Number of Model Breaches from Critical Network Device
- Anomalous Connection / Data Sent to Rare Domain
- Compromise / Suspicious File and C2
- Unusual Activity / Enhanced Unusual External Data Transfer
- Compliance / Crypto Currency Mining Activity
- Compliance / High Priority Crypto Currency Mining
- Anomalous File / Zip or Gzip from Rare External Location
- Compromise / Monero Mining
- Device / Internet Facing Device with High Priority Alert
- Anomalous Server Activity / Rare External from Server
- Compromise / Slow Beaconing Activity To External Rare
- Compromise / Beaconing Activity To External Rare
- Compromise / HTTP Beaconing to Rare Destination
- Compromise / High Volume of Connections with Beacon Score
- Anomalous File / Numeric Exe Download
Log4j server compromise
On December 9 2021, a critical RCE vulnerability (dubbed ‘Log4Shell’) in version 2 of Apache’s Log4j was publicly disclosed by researchers at LunaSec.[12] As a logging library present in potentially millions of Java applications,[13] Log4j constitutes an obscured, yet ubiquitous feature of the digital world. The vulnerability (CVE-2021-44228), which arises from Log4j’s Java Naming and Directory Interface (JNDI) Lookup feature, enables an attacker to make a vulnerable server download and execute a malicious Java class file. To exploit the vulnerability, all the attacker must do is submit a specially crafted JNDI lookup request to the server. The fact that Log4j is present in so many applications and that the exploitation of this vulnerability is so simple, Log4Shell has been dubbed the ‘most critical vulnerability of the last decade’.[14] Attackers have been exploiting Log4Shell in the wild since at least December 1.[15] Since then, attackers have been observed exploiting the vulnerability to install crypto-mining tools, Cobalt Strike, and RATs onto vulnerable servers.[16]
On December 10, one day after the public disclosure of Log4Shell, an attacker successfully exploited the vulnerability on a vulnerable Internet-facing server within the network of a US-based architecture company. By exploiting the vulnerability, the attacker managed to get the server to download and execute a Java class file named ‘Exploit69ogQNSQYz.class’. Executing the code in this file caused the server to download a shell script file and a file related to the Kinsing crypto-mining malware. The Kinsing-infected server then went on to communicate over HTTP with a C2 server. Since the customer was using the Proactive Threat Notification (PTN) service, they were immediately alerted to this activity, and the server was subsequently quarantined, preventing crypto-mining activity from taking place.
In this example, the attacker’s exploitation of the zero-day vulnerability immediately resulted in the vulnerable server making an HTTP GET request with an unusual user-agent string (one associated with Java in this case) to a rare external IP. The models Anomalous Connection / Callback on Web Facing Device and Anomalous Connection / New User Agent to IP Without Hostname breached as a result of this behavior. The device’s subsequent file downloads and C2 activity caused several Darktrace models to breach.
A non-exhaustive list of the models which breached as a result of the unusual behavior brought about by the attacker:
- Anomalous Connection / Callback on Web Facing Device
- Anomalous Connection / New User Agent to IP Without Hostname
- Anomalous File / Internet Facing System File Download
- Anomalous File / Script from Rare External Location
- Device / Initial Breach Chain Compromise
- Anomalous Connection / Posting HTTP to IP Without Hostname
Round-up
It is inevitable that attackers will attempt to exploit zero-day vulnerabilities in applications running on Internet-facing devices. Whilst identifying these attempts is useful, the fact that attackers regularly exploit new zero-days makes the task of identifying attempts to exploit them akin to a game of whack-a-mole. Whilst it is uncertain which zero-day vulnerability attackers will exploit next, what is certain is that their exploitation of it will bring about unusual behavior. No matter the vulnerability, whether it be a vulnerability in Microsoft Exchange, Confluence, GitLab, or Log4j, Darktrace will identify the unusual behaviors which inevitably result from its exploitation. By identifying unusual behaviors displayed by Internet-facing devices, Darktrace thus makes it almost impossible for attackers to successfully exploit zero-day vulnerabilities without being detected.
For Darktrace customers who want to find out more about detecting potential compromises of internet-facing devices, refer here for an exclusive supplement to this blog.
Thanks to Andy Lawrence for his contributions.
Footnotes
1. https://devco.re/blog/2021/08/06/a-new-attack-surface-on-MS-exchange-part-1-ProxyLogon/
2. https://www.volexity.com/blog/2021/03/02/active-exploitation-of-microsoft-exchange-zero-day-vulnerabilities/
3. https://www.zerodayinitiative.com/blog/2021/8/17/from-pwn2own-2021-a-new-attack-surface-on-microsoft-exchange-proxyshell
4. https://www.rapid7.com/blog/post/2021/08/12/proxyshell-more-widespread-exploitation-of-microsoft-exchange-servers/
5. https://www.kaspersky.co.uk/blog/confluence-server-cve-2021-26084/23376/
6. https://www.bleepingcomputer.com/news/security/atlassian-confluence-flaw-actively-exploited-to-install-cryptominers/
7. https://hackerone.com/reports/1154542
8. https://security.humanativaspa.it/gitlab-ce-cve-2021-22205-in-the-wild/
9.https://about.gitlab.com/releases/2021/04/14/security-release-gitlab-13-10-3-released/
10. https://www.rapid7.com/blog/post/2021/11/01/gitlab-unauthenticated-remote-code-execution-cve-2021-22205-exploited-in-the-wild/
11. https://www.hackmageddon.com/2021/12/16/1-15-november-2021-cyber-attacks-timeline/
12. https://www.lunasec.io/docs/blog/log4j-zero-day/
13. https://www.csoonline.com/article/3644472/apache-log4j-vulnerability-actively-exploited-impacting-millions-of-java-based-apps.html
14. https://www.theguardian.com/technology/2021/dec/10/software-flaw-most-critical-vulnerability-log-4-shell
15. https://www.rapid7.com/blog/post/2021/12/15/the-everypersons-guide-to-log4shell-cve-2021-44228/
16. https://www.microsoft.com/security/blog/2021/12/11/guidance-for-preventing-detecting-and-hunting-for-cve-2021-44228-log4j-2-exploitation/
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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.