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Insider-Bedrohungen, Lieferketten und IoT: Entschlüsselung eines modernen Cyberangriffs







It’s ten to five on a Friday afternoon. A technician has come in to perform a routine check on an electronic door. She enters the office with no issues – she works for a trusted third-party vendor, employees see her every week. She opens her laptop and connects to the Door Access Control Unit, a small Internet of Things (IoT) device used to operate the smart lock. Minutes later, trojans have been downloaded onto the company network, a crypto-mining operation has begun, and there is evidence of confidential data being exfiltrated. Where did things go wrong?
Threats in a business: A new dawn surfaces
As organizations keep pace with the demands of digital transformation, the attack surface has become broader than ever before. There are numerous points of entry for a cyber-criminal – from vulnerabilities in IoT ecosystems, to blind spots in supply chains, to insiders misusing their access to the business. Darktrace sees these threats every day. Sometimes, like in the real-world example above, which will be examined in this blog, they can occur in the very same attack.
Insider threats can use their familiarity and level of access to a system as a critical advantage when evading detection and launching an attack. But insiders don’t necessarily have to be malicious. Every employee or contractor is a potential threat: clicking on a phishing link or accidentally releasing data often leads to wide-scale breaches.
At the same time, connectivity in the workspace – with each IoT device communicating with the corporate network and the Internet on its own IP address – is an urgent security issue. Access control systems, for example, add a layer of physical security by tracking who enters the office and when. However, these same control systems imperil digital security by introducing a cluster of sensors, locks, alarm systems, and keypads, which hold sensitive user information and connect to company infrastructure.
Furthermore, a significant proportion of IoT devices are built without security in mind. Vendors prioritize time-to-market and often don’t have the resources to invest in baked-in security measures. Consider the number of start-ups which manufacture IoT – over 60% of home automation companies have fewer than ten employees.
Insider threat detected by Cyber AI
In January 2021, a medium-sized North American company suffered a supply chain attack when a third-party vendor connected to the control unit for a smart door.

Figure 1: The attack lasted 3.5 hours in total, commencing 16:50 local time.
The technician from the vendor’s company had come in to perform scheduled maintenance. They had been authorized to connect directly to the Door Access Control Unit, yet were unaware that the laptop they were using, brought in from outside of the organization, had been infected with malware.
As soon as the laptop connected with the control unit, the malware detected an open port, identified the vulnerability, and began moving laterally. Within minutes, the IoT device was seen making highly unusual connections to rare external IP addresses. The connections were made using HTTP and contained suspicious user agents and URIs.
Darktrace then detected that the control unit was attempting to download trojans and other payloads, including upsupx2.exe and 36BB9658.moe. Other connections were used to send base64 encoded strings containing the device name and the organization’s external IP address.
Cryptocurrency mining activity with a Monero (XMR) CPU miner was detected shortly afterwards. The device also utilized an SMB exploit to make external connections on port 445 while searching for vulnerable internal devices using the outdated SMBv1 protocol.
One hour later, the device connected to an endpoint related to the third-party remote access tool TeamViewer. After a few minutes, the device was seen uploading over 15 MB to a 100% rare external IP.

Figure 2: Timeline of the connections made by an example device on the days around an incident (blue). The connections associated with the compromise are a significant deviation from the device’s normal pattern of life, and result in multiple unusual activity events and repeated model breaches (orange).
Security threats in the supply chain
Cyber AI flagged the insider threat to the customer as soon as the control unit had been compromised. The attack had managed to bypass the rest of the organization’s security stack, for the simple reason that it was introduced directly from a trusted external laptop, and the IoT device itself was managed by the third-party vendor, so the customer had little visibility over it.
Traditional security tools are ineffective against supply chain attacks such as this. From the SolarWinds hack to Vendor Email Compromise, 2021 has put the nail in the coffin for signature-based security – proving that we cannot rely on yesterday’s attacks to predict tomorrow’s threats.
International supply chains and the sheer number of different partners and suppliers which modern organizations work with thus pose a serious security dilemma: how can we allow external vendors onto our network and keep an airtight system?
The first answer is zero-trust access. This involves treating every device as malicious, inside and outside the corporate network, and demanding verification at all stages. The second answer is visibility and response. Security products must shed a clear light into cloud and IoT infrastructure, and react autonomously as soon as subtle anomalies emerge across the enterprise.
IoT investigated
Darktrace’s Cyber AI Analyst reported on every stage of the attack, including the download of the first malicious executable file.

Figure 3: Example of Cyber AI Analyst detecting anomalous behavior on a device, including C2 connectivity and suspicious file downloads.
Cyber AI Analyst investigated the C2 connectivity, providing a high-level summary of the activity. The IoT device had accessed suspicious MOE files with randomly generated alphanumeric names.

Figure 4: A Cyber AI Analyst summary of C2 connectivity for a device.
Not only did the AI detect every stage of the activity, but the customer was also alerted via a Proactive Threat Notification following a high scoring model breach at 16:59, just minutes after the attack had commenced.
Stranger danger
Third parties coming in to tweak device settings and adjust the network can have unintended consequences. The hyper-connected world which we’re living in, with the advent of 5G and Industry 4.0, has become a digital playground for cyber-criminals.
In the real-world case study above, the IoT device was unsecured and misconfigured. With rushed creations of IoT ecosystems, intertwining supply chains, and a breadth of individuals and devices connecting to corporate infrastructure, modern-day organizations cannot expect simple security tools which rely on pre-defined rules to stop insider threats and other advanced cyber-attacks.
The organization did not have visibility over the management of the Door Access Control Unit. Despite this, and despite no prior knowledge of the attack type or the vulnerabilities present in the IoT device, Darktrace detected the behavioral anomalies immediately. Without Cyber AI, the infection could have remained on the customer’s environment for weeks or months, escalating privileges, silently crypto-mining, and exfiltrating sensitive company data.
Thanks to Darktrace analyst Grace Carballo for her insights on the above threat find.
Learn more about insider threats
Darktrace Modell-Erkennungen:
- Anomalous File/Anomalous Octet Stream
- Anomalous Connection/New User Agent to IP Without Hostname
- Unusual Activity/Unusual External Connectivity
- Device/Increased External Connectivity
- Anomalous Server Activity/Outgoing from Server
- Device/New User Agent and New IP
- Compliance/Cryptocurrency Mining Activity
- Compliance/External Windows Connectivity
- Anomalous File/Multiple EXE from Rare External Locations
- Anomalous File/EXE from Rare External Location
- Device/Large Number of Model Breaches
- Anomalous File/Internet Facing System File Download
- Device/Initial Breach Chain Compromise
- Device/SMB Session Bruteforce
- Device/Network Scan- Low Anomaly Score
- Device/Large Number of Connections to New Endpoint
- Anomalous Server Activity/Outgoing from Server
- Compromise/Beacon to Young Endpoint
- Anomalous Server Activity/Rare External from Server
- Device/Multiple C2 Model Breaches
- Compliance/Remote Management Tool on Server
- Anomalous Connection/Data Sent to New External Device
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More in this series
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Einblicke in das SOC-Team
Protecting Prospects: How Darktrace Detected an Account Hijack Within Days of Deployment



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

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

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

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

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

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

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

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

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

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


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


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