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Why the 'Air Gap' is Not Enough to Keep Your OT Systems Resilient







At a Glance:
- Air gaps reduce cyber risk, but they do not prevent modern cyber attacks
- Having visibility into an air-gapped network is better than assuming your defenses are impenetrable and having zero visibility
- Darktrace can provide visibility and resiliency without jeopardizing the integrity of the air gap
What is an 'Air Gap'?
Information technology (IT) needs to fluidly connect with the outside world in order channel a flow of digital information across everything from endpoints and email systems to cloud and hybrid infrastructures. At the same time, this high level of connectivity makes IT systems particularly vulnerable to cyber-attacks.
Operational technology (OT), which controls the operations of physical processes, are considerably more sensitive. OT often relies on a high degree of regularity to maintain continuity of operations. Even the slightest disturbance can lead to disastrous results. Just a few seconds of delay on a programmable logic controller (PLC), for example, can significantly disrupt a manufacturing assembly line, leading to downtime at a considerable cost. In worst-case scenarios, disruptions to OT can even threaten human safety.
An air gap is a ‘digital moat’ where data cannot enter or leave OT environments unless it is transferred manually.
Organizations with OT have traditionally tried to reconcile this conflict between IT and OT by attempting to separate them completely. Essentially, the idea is to let IT do what IT does best — facilitate activities like communication and data transfer at rapid speeds, thus allowing people to connect with each other and access information and applications in an efficient capacity. But at the same time, erect an air gap between IT and OT so that any cyber threats that slip into IT systems do not then spread laterally into highly sensitive, mission-critical OT systems. This air gap is essentially a ‘digital moat’ where data cannot enter or leave OT environments unless it is transferred manually.
Limitations of the Air Gap
The air gap approach makes sense, but it is far from perfect. First, many organizations that believe they have completely air-gapped systems in fact have unknown points of IT/OT convergence, that is, connections between IT and OT networks of which they are unaware.
Many organizations today are also intentionally embracing IT/OT convergence to reap the benefits of digital transformation of their OT, in what is often called Industry 4.0. Examples include the industrial cloud (or ICSaaS), the industrial internet of things (IIoT), and other types of cyber-physical systems that offer increased efficiency and expanded capabilities when compared to more traditional forms of OT. Organizations may also embrace IT/OT convergence due to a lack of human capital, as convergence can make processes simpler and more efficient.
Even when an organization does have a true air gap (which is nearly impossible to confirm without full visibility across IT and OT environments), the fact is that there are a variety of ways for attackers to ‘jump the air gap'. Full visibility across IT and OT ecosystems in a single pane of glass is thus essential for organizations seeking to secure their OT. This is not only to illuminate any points of IT/OT convergence and validate the fact that an air gap exists in the first place, but also to see when an attack slips through the air gap.
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Air Gap Attack Vectors
Even a perfect air gap will be vulnerable to a variety of different attack vectors, including (but not limited to) the following:
- Physical compromise: An adversary bypasses physical security and gains access directly to the air-gapped network devices. Physical access is by far the most effective and obvious technique.
- Insider threats: Someone who is part of an organization and has access to air-gapped secure systems intentionally or unintentionally compromises a system.
- Supply chain compromise: A vendor with legitimate access to air-gapped systems unwittingly is compromised and brings infected devices into a network.
- Misconfiguration: Misconfiguration of access controls or permissions allows an attacker to access the air-gapped system through a separate device on the network.
- Social engineering (media drop): If an attacker was able to successfully conduct a malicious USB/media drop and an employee was to use that media within the air-gapped system, the network could be compromised.
- Other advanced tactics: Thermal manipulation, covert surface vibrations, LEDs, ultrasonic transmissions, radio signals, and magnetic fields are among a range of advanced tactics documented and demonstrated by researchers at Ben Gurion University.
Vulnerabilities of Air-Gapped Systems
Aside from susceptibility to advanced techniques, tactics, and procedures (TTPs) such as thermal manipulation and magnetic fields, more common vulnerabilities associated with air-gapped environments include factors such as unpatched systems going unnoticed, lack of visibility into network traffic, potentially malicious devices coming on the network undetected, and removable media being physically connected within the network.
Once the attack is inside OT systems, the consequences can be disastrous regardless of whether there is an air gap or not. However, it is worth considering how the existence of the air gap can affect the time-to-triage and remediation in the case of an incident. For example, the existence of an air gap may seriously limit an incident response vendor’s ability to access the network for digital forensics and response.
Kremlin Hackers Jumping the Air Gap
In 2018, the U.S. Department of Homeland Security (DHS) issued an alert documenting the TTPs used by Russian threat actors known as Dragonfly and Energetic Bear. Further reporting alleged that these groups ‘jumped the air gap,’ and, concerningly, gained the ability to disable the grid at the time of their choosing.
These attackers successfully gained access to sensitive air-gapped systems across the energy sector and other critical infrastructure sectors by targeting vendors and suppliers through spear-phishing emails and watering hole attacks. These vendors had legitimate access to air-gapped systems, and essentially brought the infection into these systems unintentionally when providing support services such as patch deployment.
This incident reveals that even if a sensitive OT system has complete digital isolation, this robust air gap still cannot fully eliminate one of the greatest vulnerabilities of any system—human error. Human error would still hold if an organization went to the extreme of building a faraday cage to eliminate electromagnetic radiation. Air-gapped systems are still vulnerable to social engineering, which exploits human vulnerabilities, as seen in the tactics that Dragonfly and Energetic Bear used to trick suppliers, who then walked the infection right through the front door.
Ideally, a technology would be able to identify an attack regardless of whether it is caused by a compromised supplier, radio signal, or electromagnetic emission. By spotting subtle deviations from a device, human, or network’s normal ‘pattern of life’, Self-Learning AI detects even the most nuanced forms of threatening behavior as they emerge — regardless of the source or cause of the threat.
Darktrace/OT for Air-Gapped Environments
Darktrace/OT for air-gapped environments is a physical appliance that deploys directly to the air-gapped system. Using raw digital data from an OT network to understand the normal pattern of life, Darktrace/OT does not need any data or threat feeds from external sources because the AI builds an innate understanding of self without third-party support.
Because all data-processing and analytics are performed locally on the Darktrace appliance, there is no requirement for Darktrace to have a connection out to the internet. As a result, Darktrace/OT provides visibility and threat detection to air-gapped or highly segmented networks without jeopardizing their integrity. If a human or machine displays even the most nuanced forms of threatening behavior, the solution can illuminate this in real time.
Security professionals can then securely access Darktrace alerts from anywhere within the network, using a web browser and encrypted HTTPS, and in line with your organization’s network policies.

With this deployment, Darktrace offers all the critical insights demonstrated in other Darktrace/OT deployments, including (but not limited to) the following:
- Illuminating all points of IT/OT convergence, including unknown points of IT/OT convergence in ‘air gapped’ environments
- OT network visibility across all Purdue Levels to the field controller level
- OT asset inventory
- CVE tracking
- Identification of new devices on the network, first seen devices, and last seen active devices
- Threat response and incident reporting that the IT team, security professionals, operators, and engineering can easily read
Organizations seeking to validate whether they have an air gap in the first place and maintain the air gap as their IT and OT environments evolve will greatly benefit from the comprehensive visibility and continuous situational awareness offered by Darktrace’s Self-Learning AI. Also, organizations looking to poke holes in their air gap to embrace the benefits of IT/OT convergence will find that Self-Learning AI’s vigilance spots cyber-attacks that slip through.
Whatever your organizations goals—be it embracing IIoT or creating a full-blown DMZ—by learning ‘you’, Darktrace’s Self-Learning AI can help you achieve them safely and securely.
Credit to: Daniel Simonds and Oakley Cox for their contribution to this blog.
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A l'intérieur du SOC
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.