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April 26, 2020

How Cyber-Criminals Leverage AI in Attacks

Cyber attacks are relentless and ever-evolving. Learn how cyber-criminals are using AI to augment their attacks at every stage of the kill chain.
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.
Written by
Max Heinemeyer
Global Field CISO
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26
Apr 2020

Overview

The mind of an experienced and dedicated cyber-criminal works like that of an entrepreneur: the relentless pursuit of profit guides every move they make. At each step of the journey towards their objective, the same questions are asked: how can I minimize my time and resources? How can I mitigate against risk? What measures can I take which will return the best results?

Incorporating this ‘enterprise’ model into the cyber-criminal framework uncovers why attackers are turning to new technology in an attempt to maximize efficiency, and why a report from Forrester earlier this year revealed that 88% of security leaders now consider the nefarious use of AI in cyber activity to be inevitable. Over half of the responders to that same survey foresee AI attacks manifesting themselves to the public in the next twelve months – or think they are already occurring.

AI has already achieved breakthroughs in fields such as healthcare, facial recognition, voice assistance and many others. In the current cat-and-mouse game of cyber security, defenders have started to accept that augmenting their defenses with AI is necessary, with over 3,500 organizations using machine learning to protect their digital environments. But we have to be ready for the moment attackers themselves use open-source AI technology available today to supercharge their attacks.

Enhancing the attack life cycle

To a cyber-criminal ring, the benefits of leveraging AI in their attacks are at least four-fold:

  • It gives them an understanding of context
  • It helps to scale up operations
  • It makes attribution and detection harder
  • It ultimately increases their profitability

To best demonstrate how each of these factors surface themselves, we can break down the life cycle of a typical data exfiltration attempt, telling the story of how AI can augment the attacker during the campaign at every stage of the attack.

ReconnaissanceCAPTCHA breakerIntrusionShellphish and SNAP_RC2 establishmentFirstOrder and unsupervised clustering algorithmPrivilege escalationCeWL and neural networkLateral movementMITRE CALDERAMission accomplishedYahoo NSFW

Figure 1: The ‘AI toolbox’ attackers use to augment their attacks

Stage 1: Reconnaissance

In seeking to garner trust and make inroads into an organization, automated chatbots would first interact with employees via social media, leveraging profile pictures of non-existent people created by AI instead of re-using actual human photos. Once the chatbots have gained the trust of the victims at the target organization, the human attackers can gain valuable intelligence about its employees, while CAPTCHA-breakers are used for automated reconnaissance on the organization’s public-facing web pages.

Forrester estimates that AI-enabled ‘deep fakes’ will cost businesses a quarter of a billion dollars in losses in 2020.

Stage 2: Intrusion

This intelligence would then be used to craft convincing spear phishing attacks, whilst an adapted version of SNAP_R can be leveraged to create realistic tweets at scale – targeting several key employees. The tweets either trick the user into downloading malicious documents, or contain links to servers which facilitate exploit-kit attacks.

An autonomous vulnerability fuzzing engine based on Shellphish would be constantly crawling the victim’s perimeter – internet-facing servers and websites – and trying to find new vulnerabilities for an initial foothold.

Stage 3: Command and control

A popular hacking framework, Empire, allows attackers to ‘blend in’ with regular business operations, restricting command and control traffic to periods of peak activity. An agent using some form of automated decision-making engine for lateral movement might not even require command and control traffic to move laterally. Eliminating the need for command and control traffic drastically reduces the detection surface of existing malware.

Stage 4: Privilege escalation

At this stage, a password crawler like CeWL could collect target-specific keywords from internal websites and feed those keywords into a pre-trained neural network, essentially creating hundreds of realistic permutations of contextualized passwords at machine-speed. These can be automatically entered in period bursts so as to not alert the security team or trigger resets.

Stage 5: Lateral movement

Moving laterally and harvesting accounts and credentials involves identifying the optimal paths to accomplish the mission and minimize intrusion time. Parts of the attack planning can be accelerated by concepts such as from the CALDERA framework using automated planning AI methods. This would greatly reduce the time required to reach the final destination.

Stage 6: Data exfiltration

It is in this final stage where the role of offensive AI is most apparent. Instead of running a costly post-intrusion analysis operation and sifting through gigabytes of data, the attackers can leverage a neural network that pre-selects only relevant material for exfiltration. This neural network is pre-trained and therefore has a basic understanding of what valuable material constitutes and flags those for immediate exfiltration. The neural network could be based on something like Yahoo’s open-source project for content recognition.

Conclusion

Today’s attacks still require several humans behind the keyboard making guesses about the sorts of methods that will be most effective in their target network – it’s this human element that often allows defenders to neutralize attacks.

Offensive AI will make detecting and responding to attacks far more difficult. Open-source research and projects exist today which can be leveraged to augment every phase of the attack lifecycle. This means that the speed, scale, and contextualization of attacks will exponentially increase. Traditional security controls are already struggling to detect attacks that have never been seen before in the wild – be it malware without known signatures, new command and control domains, or individualized spear phishing emails. There is no chance that traditional tools will be able to cope with future attacks as this becomes the norm and easier to realize than ever before.

To stay ahead of this next wave of attacks, AI is becoming a necessary part of the defender’s stack, as no matter how well-trained or how well-staffed, humans alone will no longer be able to keep up. Hundreds of organizations are already using Autonomous Response to fight back against new strains of ransomware, insider threats, previously unknown techniques, tools and procedures, and many other threats. Cyber AI technology allows human responders to take stock and strategize from behind the front line. A new age in cyber defense is just beginning, and the effect of AI on this battleground is already proving fundamental.

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.
Written by
Max Heinemeyer
Global Field CISO

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May 21, 2025

Evaluating Email Security: How to Select the Best Solution for Your Organization

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When evaluating email security solutions, it’s crucial to move beyond marketing claims and focus on real-world performance. One of the most effective ways to achieve this is through an A/B comparison approach – a side-by-side evaluation of vendors based on consistent, predefined criteria.

This method cuts through biases, reveals true capability differences, and ensures that all solutions are assessed on a level playing field. It’s not just about finding an objectively good solution – it’s about finding the best solution for your organization’s specific needs.

An A/B comparison approach is particularly effective for three main reasons:

  1. Eliminates bias: By comparing solutions under identical conditions, it’s easier to spot differences in performance without the fog of marketing jargon.
  2. Highlights real capabilities: Direct side-by-side testing exposes genuine strengths and weaknesses, making it easier to judge which features are impactful versus merely decorative.
  3. Encourages objective decision-making: This structured method reduces emotional or brand-driven decisions, focusing purely on metrics and performance.

Let’s look at the key factors to consider when setting up your evaluation to ensure a fair, accurate, and actionable comparison.

Deployment: Setting the stage for fair evaluation

To achieve a genuine comparison, deployment must be consistent across all evaluated solutions:

  • Establish the same scope: All solutions should be granted identical visibility across relevant tenants and domains to ensure parity.
  • Set a concrete timeline: Deploy and test each solution with the same dataset, at the same points in time. This allows you to observe differences in learning periods and adaptive capabilities.

Equal visibility and synchronized timelines prevent discrepancies that could skew your understanding of each vendor’s true capabilities. But remember – quicker results might not equal better learning or understanding!

Tuning and configurations: Optimizing for real-world conditions

Properly tuning and configuring each solution is critical for fair evaluation:

  • Compare on optimal performance: Consult with each vendor to understand what optimal deployment looks like for their solution, particularly if machine learning is involved.
  • Consider the long term: Configuration adjustments should be made with long-term usage in mind. Short-term fixes can mask long-term challenges.
  • Data visibility: Ensure each solution can retain and provide search capabilities on all data collected throughout the evaluation period.

These steps guarantee that you are comparing fully optimized versions of each platform, not underperforming or misconfigured ones.

Evaluation: Applying consistent metrics

Once deployment and configurations are aligned, the evaluation itself must be consistent, to prevent unfair scoring and help to identify true differences in threat detection and response capabilities.

  • Coordinate your decision criteria: Ensure all vendors are measured against the same set of criteria, established before testing begins.
  • Understand vendor threat classification: Each vendor may have different ways of classifying threats, so be sure to understand these nuances.
  • Maintain communication: If results seem inaccurate, engage with the vendors. Their response and remediation capabilities are part of the evaluation.

Making a decision: Look beyond the metrics

When it comes to reviewing the performance of each solution, it’s important to both consider and look beyond the raw data. This is about choosing the solution that best aligns with your specific business needs, which may include factors and features not captured in the results.

  • Evaluate based on results: Consider accuracy, threats detected, precision, and response effectiveness.
  • Evaluate beyond results: Assess the overall experience, including support, integrations, training, and long-term alignment with your security strategy.
  • Review and communicate: Internally review the findings and communicate them back to the vendors.

Choosing the right email security solution isn’t just about ticking boxes, it’s about strategic alignment with your organization’s goals and the evolving threat landscape. A structured, A/B comparison approach will help ensure that the solution you select is truly the best fit.

For a full checklist of the features and capabilities to compare, as well as how to perform a commercial and technical evaluation, check out the full Buyer’s Checklist for Evaluating Email Security.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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May 21, 2025

Adapting to new USCG cybersecurity mandates: Darktrace for ports and maritime systems

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What is the Marine Transportation System (MTS)?

Marine Transportation Systems (MTS) play a substantial roll in U.S. commerce, military readiness, and economic security. Defined as a critical national infrastructure, the MTS encompasses all aspects of maritime transportation from ships and ports to the inland waterways and the rail and roadways that connect them.

MTS interconnected systems include:

  • Waterways: Coastal and inland rivers, shipping channels, and harbors
  • Ports: Terminals, piers, and facilities where cargo and passengers are transferred
  • Vessels: Commercial ships, barges, ferries, and support craft
  • Intermodal Connections: Railroads, highways, and logistics hubs that tie maritime transport into national and global supply chains

The Coast Guard plays a central role in ensuring the safety, security, and efficiency of the MTS, handling over $5.4 trillion in annual economic activity. As digital systems increasingly support operations across the MTS, from crane control to cargo tracking, cybersecurity has become essential to protecting this lifeline of U.S. trade and infrastructure.

Maritime Transportation Systems also enable international trade, making them prime targets for cyber threats from ransomware gangs to nation-state actors.

To defend against growing threats, the United States Coast Guard (USCG) has moved from encouraging cybersecurity best practices to enforcing them, culminating in a new mandate that goes into effect on July 16, 2025. These regulations aim to secure the digital backbone of the maritime industry.

Why maritime ports are at risk

Modern ports are a blend of legacy and modern OT, IoT, and IT digitally connected technologies that enable crane operations, container tracking, terminal storage, logistics, and remote maintenance.

Many of these systems were never designed with cybersecurity in mind, making them vulnerable to lateral movement and disruptive ransomware attack spillover.

The convergence of business IT networks and operational infrastructure further expands the attack surface, especially with the rise of cloud adoption and unmanaged IoT and IIoT devices.

Cyber incidents in recent years have demonstrated how ransomware or malicious activity can halt crane operations, disrupt logistics, and compromise safety at scale threatening not only port operations, but national security and economic stability.

Relevant cyber-attacks on maritime ports

Maersk & Port of Los Angeles (2017 – NotPetya):
A ransomware attack crippled A.P. Moller-Maersk, the world’s largest shipping company. Operations at 17 ports, including the Port of Los Angeles, were halted due to system outages, causing weeks of logistical chaos.

Port of San Diego (2018 – Ransomware Attack):
A ransomware attack targeted the Port of San Diego, disrupting internal IT systems including public records, business services, and dockside cargo operations. While marine traffic was unaffected, commercial activity slowed significantly during recovery.

Port of Houston (2021 – Nation-State Intrusion):
A suspected nation-state actor exploited a known vulnerability in a Port of Houston web application to gain access to its network. While the attack was reportedly thwarted, it triggered a federal investigation and highlighted the vulnerability of maritime systems.

Jawaharlal Nehru Port Trust, India (2022 – Ransomware Incident):
India’s largest container port experienced disruptions due to a ransomware attack affecting operations and logistics systems. Container handling and cargo movement slowed as IT systems were taken offline during recovery efforts.

A regulatory shift: From guidance to enforcement

Since the Maritime Transportation Security Act (MTSA) of 2002, ports have been required to develop and maintain security plans. Cybersecurity formally entered the regulatory fold in 2020 with revisions to 33 CFR Part 105 and 106, requiring port authorities to assess and address computer system vulnerabilities.

In January 2025, the USCG finalized new rules to enforce cybersecurity practices across the MTS. Key elements include (but are not limited to):

  • A dedicated cyber incident response plan (PR.IP-9)
  • Routine cybersecurity risk assessments and exercises (ID.RA)
  • Designation of a cybersecurity officer and regular workforce training (section 3.1)
  • Controls for access management, segmentation, logging, and encryption (PR.AC-1:7)
  • Supply chain risk management (ID.SC)
  • Incident reporting to the National Response Center

Port operators are encouraged to align their programs with the NIST Cybersecurity Framework (CSF 2.0) and NIST SP 800-82r3, which provide comprehensive guidance for IT and OT security in industrial environments.

How Darktrace can support maritime & ports

Unified IT + OT + Cloud coverage

Maritime ports operate in hybrid environments spanning business IT systems (finance, HR, ERP), industrial OT (cranes, gates, pumps, sensors), and an increasing array of cloud and SaaS platforms.

Darktrace is the only vendor that provides native visibility and threat detection across OT/IoT, IT, cloud, and SaaS environments — all in a single platform. This means:

  • Cranes and other physical process control networks are monitored in the same dashboard as Active Directory and Office 365.
  • Threats that start in the cloud (e.g., phishing, SaaS token theft) and pivot or attempt to pivot into OT are caught early — eliminating blind spots that siloed tools miss.

This unification is critical to meeting USCG requirements for network-wide monitoring, risk identification, and incident response.

AI that understands your environment. Not just known threats

Darktrace’s AI doesn’t rely on rules or signatures. Instead, it uses Self-Learning AI TM that builds a unique “pattern of life” for every device, protocol, user, and network segment, whether it’s a crane router or PLC, SCADA server, Workstation, or Linux file server.

  • No predefined baselines or manual training
  • Real-time anomaly detection for zero-days, ransomware, and supply chain compromise
  • Continuous adaptation to new devices, configurations, and operations

This approach is critical in diverse distributed OT environments where change and anomalous activity on the network are more frequent. It also dramatically reduces the time and expertise needed to classify and inventory assets, even for unknown or custom-built systems.

Supporting incident response requirements

A key USCG requirement is that cybersecurity plans must support effective incident response.

Key expectations include:

  • Defined response roles and procedures: Personnel must know what to do and when (RS.CO-1).
  • Timely reporting: Incidents must be reported and categorized according to established criteria (RS.CO-2, RS.AN-4).
  • Effective communication: Information must be shared internally and externally, including voluntary collaboration with law enforcement and industry peers (RS.CO-3 through RS.CO-5).
  • Thorough analysis: Alerts must be investigated, impacts understood, and forensic evidence gathered to support decision-making and recovery (RS.AN-1 through RS.AN-5).
  • Swift mitigation: Incidents must be contained and resolved efficiently, with newly discovered vulnerabilities addressed or documented (RS.MI-1 through RS.MI-3).
  • Ongoing improvement: Organizations must refine their response plans using lessons learned from past incidents (RS.IM-1 and RS.IM-2).

That means detections need to be clear, accurate, and actionable.

Darktrace cuts through the noise using AI that prioritizes only high-confidence incidents and provides natural-language narratives and investigative reports that explain:

  • What’s happening, where it’s happening, when it’s happening
  • Why it’s unusual
  • How to respond

Result: Port security teams often lean and multi-tasked can meet USCG response-time expectations and reporting needs without needing to scale headcount or triage hundreds of alerts.

Built-for-edge deployment

Maritime environments are constrained. Many traditional SaaS deployment types often are unsuitable for tugboats, cranes, or air-gapped terminal systems.

Darktrace builds and maintains its own ruggedized, purpose-built appliances and unique virtual deployment options that:

  • Deploy directly into crane networks or terminal enclosures
  • Require no configuration or tuning, drop-in ready
  • Support secure over-the-air updates and fleet management
  • Operate without cloud dependency, supporting isolated and air-gapped systems

Use case: Multiple ports have been able to deploy Darktrace directly into the crane’s switch enclosure, securing lateral movement paths without interfering with the crane control software itself.

Segmentation enforcement & real-time threat containment

Darktrace visualizes real-time connectivity and attack pathways across IT, OT, and IoT it and integrates with firewalls (e.g., Fortinet, Cisco, Palo Alto) to enforce segmentation using AI insights alongside Darktrace’s own native autonomous and human confirmed response capabilities.

Benefits of autonomous and human confirmed response:

  • Auto-isolate rogue devices before the threat can escalate
  • Quarantine a suspicious connectivity with confidence operations won’t be halted
  • Autonomously buy time for human responders during off-hours or holidays
  • This ensures segmentation isn't just documented but that in the case of its failure or exploitation responses are performed as a compensating control

No reliance on 3rd parties or external connectivity

Darktrace’s supply chain integrity is a core part of its value to critical infrastructure customers. Unlike solutions that rely on indirect data collection or third-party appliances, Darktrace:

  • Uses in-house engineered sensors and appliances
  • Does not require transmission of data to or from the cloud

This ensures confidence in both your cyber visibility and the security of the tools you deploy.

See examples here of how Darktrace stopped supply chain attacks:

Readiness for USCG and Beyond

With a self-learning system that adapts to each unique port environment, Darktrace helps maritime operators not just comply but build lasting cyber resilience in a high-threat landscape.

Cybersecurity is no longer optional for U.S. ports its operationally and nationally critical. Darktrace delivers the intelligence, automation, and precision needed to meet USCG requirements and protect the digital lifeblood of the modern port.

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About the author
Daniel Simonds
Director of Operational Technology
Your data. Our AI.
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