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Inside the SOC

Outlaw Returns: Uncovering Returning Features and New Tactics

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27
Jul 2023
27
Jul 2023

What is Outlaw Cryptocurrency Mining Operation?

The cybersecurity community has been aware of the threat of Outlaw cryptocurrency mining operation, and its affiliated activities since as early as 2018. Despite its prominence, Outlaw remains largely elusive to researchers and analysts due to its ability to adapt its tactics, procedures, and payloads.

Outlaw gained notoriety in 2018 as security researchers began observing the creation of affiliated botnets.[1][2]  Researchers gave Outlaw  its name based on the English translation of the “Haiduc” tool observed during their initial activity on compromised devices.[3],[4] By 2019, much of the initial Outlaw activity  focused on the targeting of Internet of Things (IoT) devices and other internet facing servers, reportedly focusing operations in China and on Chinese devices.[5],[6]  From the outset, mining operations featured as a core element of botnets created by the group.[7] This initial focus may have been a sign of caution by threat actors or a preliminary means of testing procedures and operation efficacy. Regardless, Outlaw actors inevitably expanded scope, targeting larger organizations and a wider range of internet facing devices across geographic scope.

Following a short period of inactivity, security researchers began to observe new Outlaw activity, showcasing additional capabilities such as the ability to kill existing crypto-mining processes on devices, thereby reclaiming devices already compromised by crypto-jacking. [8],[9]

Latest News on Outlaw

Although the more recently observed incidents of Outlaw did demonstrate some new tactics, many of its procedures remained the same, including its unique bundling of payloads that combine crypto-mining and botnet capabilities. [10] In conjunction, the continued use of mining-specific payloads and growth of affiliated botnets has bolstered the belief that Outlaw actors historically prioritizes financial gain, in lieu of overt political objectives.

Given the tendency for malicious actors to share tools and capabilities, true attribution of threat or threat group is extremely difficult in the wild. As such, a genuine survey of activity from the group across a customer base has not always been possible. Therefore, we will present an updated look into more recent activity associated with Outlaw detected across the Darktrace customer base.  

Darktrace vs Outlaw

Since late 2022, Darktrace has observed a rise in probable cyber incidents involving indicators of compromise (IoCs) associated with Outlaw. Given its continued prevalence and relative dearth of information, it is essential to take a renewed look at the latest campaign activity associated with threats like Outlaw to avoid making erroneous assumptions and to ensure the threat posed is correctly characterized.

While being aware of previous IoCs and tactics known to be employed in previous campaigns will go some way to protecting against future Outlaw attacks, it is paramount for organizations to arm themselves with an autonomous intelligent decision maker that can identify malicious activity, based on recognizing deviations from expected patterns of behavior, and take preventative action to effectively defend against such a versatile threat.

Darktrace’s anomaly-based approach to threat detection means it is uniquely positioned to detect novel campaign activity by recognizing subtle deviations in affected devices’ behavior that would have gone unnoticed by traditional security tools relying on rules, signatures and known IoCs.

Outlaw Attack Overview & Darktrace Coverage

From late 2022 through early 2023, Darktrace identified multiple cyber events involving IP addresses, domains, and payloads associated with Outlaw on customer networks. In this recent re-emergence of campaign activity, Darktrace identified numerous attack vectors and IoCs that had previously been associated with Outlaw, however it also observed significant deviations from previous campaigns.

Returning Features

As outlined in a previous blog, past iterations of Outlaw compromises include four identified, distinct phases:

1. Targeting of internet facing devices via SSH brute-forcing

2. Initiation of crypto-mining operations

3. Download of shell script and/or botnet malware payloads

4. Outgoing external SSH scanning to propagate the botnet

Nearly all affected devices analyzed by Darktrace were tagged as internet facing, as identified in previous campaigns, supporting the notion that Outlaw continues to focus on easily exposed devices. In addition to this, Darktrace observed three other core returning features from previous Outlaw campaigns in affected devices between late 2022 and early 2023:

1. Gzip and/or Script Download

2. Beaconing Activity (Command and Control)

3. Crypto-mining

Gzip and/or Script Download

Darktrace observed numerous devices downloading the Dota malware, a strain that is previously known to have been associated with the Outlaw botnet, as either a gzip file or a shell script from rare external hosts.

In some examples, IP addresses that provided the payload were flagged by open-source intelligence (OSINT) sources as having engaged in widespread SSH brute-forcing activities. While the timing of the payload transfer to the device was not consistent, download of gzip files featured prominently during directly observed or potentially affiliated activity. Moreover, Darktrace detected multiple devices performing HTTP requests for shell scripts (.sh) according to detected connection URIs. Darktrace DETECT was able to identify these anomalous connections due to the rarity of the endpoint, payloads, and connectivity for the devices.

Figure 1: Darktrace Cyber AI Analyst technical details summary from an incident during the analysis timeframe that highlights a breach device retrieving the anomalous shell scripts using wget.

Beaconing Activity – Command and Control (C2) Endpoint

Across all Outlaw activity identified by Darktrace, devices engaged in some form of beaconing behavior, rather than one-off connections to IPs associated with Outlaw. While the use of application protocol was not uniform, repeated connectivity to rare external IP addresses related to Outlaw occurred across many analyzed incidents. Darktrace’s Self-Learning AI understood that this beaconing activity represented devices deviating from their expected patterns of life and was able to bring it to the immediate attention of customer security teams.

Figure 2: Model breach log details showing sustained, repeated connectivity to Outlaw affiliated endpoint over port 443, indicating potential C2 activity.

Crypto-mining

In almost every incident of Outlaw identified across the fleet, Darktrace detected some form of cryptocurrency mining activity. Devices affected by Outlaw were consistently observed making anomalous connections to external endpoints associated with crypto-mining operations. Furthermore, the Minergate protocol appeared consistently across hosts; even when devices did not make direct crypto-mining commands, such hosts attempted connections to external entities that were known to support crypto-mining operations.

Figure 3: Advanced Search results showing a sudden spike in mining activity from a device observed connecting to Outlaw-affiliated IP addresses. Such crypto-mining activity was observed consistently across analyzed incidents.

Is Outlaw Using New Tactics?

While in the past, Outlaw activity was identified through a systematic kill chain, recent investigations conducted by Darktrace show significant deviations from this.

For instance, affected devices do not necessarily follow the previously outlined kill chain directly as they did previously. Instead, Darktrace observed affected devices exhibiting these phases in differing orders, repeating steps, or missing out attack phases entirely.

It is essential to study such variation in the kill chain to learn more about the threat of Outlaw and how threat actors are continuing to use it is varying ways. These discrepancies in kill chain elements are likely impacted by visibility into the networks and devices of Darktrace customers, with some relevant activity falling outside of Darktrace’s purview. This is particularly true for internet-exposed devices and hosts that repeatedly performed the same anomalous activity (such as making Minergate requests). Moreover, some devices involved in Outlaw activity may have already been compromised prior to Darktrace’s visibility into the network. As such, these conclusions must be evaluated with a degree of uncertainty.

SSH Activity

Although external SSH connectivity was apparent in some of the incidents detected by Darktrace, it was not directly related to brute-forcing activity. Affected devices did receive anomalous incoming SSH connections, however, wide ranging SSH failed connectivity following the initiation of mining operations by compromised devices was not readily apparent across analyzed compromises. Connections over port 22 were more frequently associated with beaconing and/or C2 activity to endpoints associated with Outlaw, than with potential brute-forcing. As such, Darktrace could not, with high confidence correlate such SSH activity to brute-forcing. This could suggest that threat actors are now portioning or rotation of botnet devices for different operations, for example dividing between botnet expansion and mining operations.

Command line tools

In cases of Outlaw investigated by Darktrace, there was also a degree of variability involving the tools used to retrieve payloads. On the networks of customers affected by Outlaw, Darktrace DETECT identified the use of user agents and command line tools that it considered to be out of character for the network and its devices.

When retrieving the Dota malware payload or shell script data, compromised devices frequently relied on numerous versions of wget and curl user agents. Although the use of such tools as a tactic cannot be definitively linked to the crypto-mining campaign, the employment of varying and/or outdated native command line tools attests to the procedural flexibility of Outlaw campaigns, and its potential for continued evolution.

Figure 4: Breach log data showing use of curl and wget tools to connect to IP addresses associated with Outlaw.

Outlaw in 2023

Given Outlaw’s widespread notoriety and its continued activities, it is likely to remain a prominent threat to organizations and security teams across the threat landscape in 2023 and beyond.

As Darktrace has observed within its customer base from late 2022 through early 2023, activity linked with the Outlaw cryptocurrency mining campaign continues to transpire, offering security teams and research a renewed look at how it has evolved and adapted over the years. While many of its features and tactics appear to have remained consistent, Darktrace has identified numerous signs of Outlaw deviating from its previously known activities.

While relying on previously established IoCs and known tactics from previous campaigns will go some way to protecting an organization’s network from Outlaw compromises, there is a greater need than ever to go further than this. Rather than depending on a list of known-bads or traditional signatures and rules, Darktrace’s anomaly-based approach to threat detection and unparallel autonomous response capabilities mean it is uniquely positioned to DETECT and RESPOND to Outlaw activity, regardless of how it evolves in the future.

Credit to: Adam Potter, Cyber Analyst, Nahisha Nobregas, SOC Analyst, and Ryan Traill, Threat Content Lead

Relevant DETECT Model Breaches:

Compliance / Incoming SSH  

Device / New User Agent and New IP

Device / New User Agent  

Anomalous Connection / New User Agent to IP Without Hostname  

Compromise / Crypto Currency Mining Activity  

Anomalous File / Internet Facing System File Download  

Anomalous Server Activity / New User Agent from Internet Facing System  

Anomalous File / Zip or Gzip from Rare External Location  

Anomalous File / Script from Rare External Location  

Anomalous Connection / Multiple Failed Connections to Rare Endpoint  

Compromise / Large Number of Suspicious Failed Connections  

Anomalous Server Activity / Outgoing from Server  

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Indicators of Compromise

Indicator - Type - Description

/dota3.tar.gz​

File  URI​

Outlaw  payload​

/tddwrt7s.sh​

File  URI​

Outlaw  payload​

73e5dbafa25946ed636e68d1733281e63332441d​

SHA1  Hash​

Outlaw  payload​

debian-package[.]center​

Hostname​

Outlaw  C2 endpoint​

161.35.236[.]24​

IP  address​

Outlaw  C2 endpoint​

138.68.115[.]96​

IP  address​

Outlaw C2  endpoint​

67.205.134[.]224​

IP  address​

Outlaw C2  endpoint​

138.197.212[.]204​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]59 ​

IP  address​

Possible  Outlaw C2 endpoint​

45.9.148[.]117​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]125​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]129​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]99 ​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]234​

IP  address​

Possible  Outlaw C2 endpoint​

45.9.148[.]236​

IP  address​

Possible  Outlaw C2 endpoint​

159.203.102[.]122​

IP  address​

Outlaw C2  endpoint​

159.203.85[.]196​

IP  address​

Outlaw C2  endpoint​

159.223.235[.]198​

IP  address​

Outlaw C2  endpoint​

MITRE ATT&CK Mapping

Tactic -Technique

Initial Access -T1190  Exploit - Public Facing Application

Command and Control - T1071 - Application - Layer Protocol

T1071.001 - Application Layer Protocol: Web Protocols

Impact - T1496 Resource Hijacking

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INSIDE THE SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
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Adam Potter
Cyber Analyst
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Inside the SOC

Protecting Prospects: How Darktrace Detected an Account Hijack Within Days of Deployment

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28
Sep 2023

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.

Figure 1: The failed login notice, as seen in Darktrace DETECT/Cloud. The notice includes additional context about the failed login attempt to the SaaS account.

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.

Figure 2: The “Unusual External Source for SaaS Credential Use” model breach summary, showing the successful login to the SaaS user account (with MFA), from the rare external IP address.

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.

Figure 3: Screenshot of the “New Email Rule” model breach. The Office365 properties associated with the newly modified Microsoft Outlook inbox rule, “.”, are highlighted in red.

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.

Figure 4: The model breach event log showing the user password and token change updates performed by the compromised 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.

Figure 5: Screenshot of the phishing email, containing a malicious link hidden behind the “Review Document” text. The embedded link directs to a now-defunct page that was hosted on Adobe Express.

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.

Figure 6: Event logs of the compromised SaaS user, here seen breaching several Darktrace/Email model breaches on 4th May.

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.

Figure 7: Example of Darktrace RESPOND notices, in response to the anomalous user activity.

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

[1] https://www.gartner.com/en/newsroom/press-releases/2022-10-31-gartner-forecasts-worldwide-public-cloud-end-user-spending-to-reach-nearly-600-billion-in-2023

[2] https://www.upguard.com/blog/saas-security-risks

[3] https://www.microsoft.com/en-us/security/blog/2022/11/16/token-tactics-how-to-prevent-detect-and-respond-to-cloud-token-theft/

[4] https://learn.microsoft.com/en-us/powershell/module/exchange/disable-inboxrule?view=exchange-ps

[5] https://learn.microsoft.com/en-us/dotnet/api/microsoft.exchange.webservices.data.ruleactions.stopprocessingrules?view=exchange-ews-api

[6] https://learn.microsoft.com/en-us/dotnet/api/microsoft.exchange.webservices.data.ruleactions.movetofolder?view=exchange-ews-api

[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

Probability yardstick used to communicate the probability that statements or explanations given are correct.
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About the author
Min Kim
Cyber Security Analyst

Blog

Email

Darktrace/Email in Action: Why AI-Driven Email Security is the Best Defense Against Sustained Phishing Campaigns

Photo of man checking emails on laptopDefault blog imageDefault blog image
26
Sep 2023

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).

Figure 1: The sender freemail addresses and subject lines all followed a certain format. The subject lines followed the format of “<First name> <Last name>”, possibly to induce curiosity. The senders were all freemail accounts and contained first names, last names and some numbers, showing the attempts to make these email addresses appear legitimate.

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.

Figure 2: One of the emails is shown above. Like all the other emails, it contained a highly suspicious and shortened link.
Figure 3: In another one of the emails, the link observed had similar characteristics. But this email stands out from the rest. The sender's name seems to be randomly set – the 3 alphabets are close to each other on the keyboard.

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.

Figure 4: Darktrace/Email highlights suspicious link characteristics and provides an option to preview the pages.
Figure 5: At the point of writing, both links could not be reached. This could be because they were one-time unique links created specifically for the user, and can no longer be accessed once the campaign has ceased.

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.

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