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June 21, 2018

Unsupervised Machine Learning and JA3 for Enhanced Security

Unlock the true power of Darktrace's algorithms. Learn how JA3 enhances cybersecurity defenses with unique TLS/SSL fingerprints & unsupervised machine learning.
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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21
Jun 2018

Introducing JA3

JA3 is a methodology for fingerprinting Transport Layer Security applications. It was first posted on GitHub in June 2017 and is the work of Salesforce researchers John Althouse, Jeff Atkinson, and Josh Atkins. The JA3 TLS/SSL fingerprints created can overlap between applications but are still a great Indicator of Compromise (IoC). Fingerprinting is achieved by creating a hash of 5 decimal fields of the Client Hello message that is sent in the initial stages of an TLS/SSL session.

JA3 is an interesting approach to the increasing usage of encryption in networks. There is also a clear uptick in cyber-attacks using encrypted command and control (C2) channels – such as HTTPS – for malware communication.

The benefits of JA3 for enhancing rules-and-signatures security

These near-unique fingerprints can be used to enhance traditional cyber security approaches such as whitelisting, deny-listing, and searching for IoCs.

Let’s take the following JA3 hash for example: 3e860202fc555b939e83e7a7ab518c38. According to one of the public lists that maps JA3s to applications, this JA3 hash is associated with the ‘hola_svc’ application. This is the infamous Hola VPN solution that is non-compliant in most enterprise networks. On the other hand, the following hash is associated with the popular messenger software Slack: a5aa6e939e4770e3b8ac38ce414fd0d5. Traditional cyber security tools can use these hashes like traditional signatures to search for instances of them in data sets or trying to deny-list malicious ones.

While there is some merit to this approach, it comes with all the known limitations of rules-and-signatures defenses, such as the overlaps in signatures, the inability to detect unknown threats, as well as the added complexity of having to maintain a database of known signatures.

JA3 in Darktrace

Darktrace creates JA3 hashes for every TLS/SSL connection it encounters. This is incredibly powerful in a number of ways. First, the JA3 can add invaluable context to a threat hunt. Second, Darktrace can also be queried to see if a particular JA3 was encountered in the network, thus providing actionable intelligence during incident response if JA3 IoCs are known to the incident responders.

Things become much more interesting once we apply our unsupervised machine learning to JA3: Darktrace’s AI algorithms autonomously detect which JA3s are anomalous for the network as a whole and which JA3s are unusual for specific devices.

It basically tells a cyber security expert: This JA3 (3e860202fc555b939e83e7a7ab518c38) has never been seen in the network before and it is only used by one device. It indicates that an application, which is used by nobody else on the network, is initiating TLS/SSL connections. In our experience, this is most often the case for malware or non-compliant software. At this stage, we are observing anomalous behavior.

Darktrace’s AI combines these IoCs (Unusual Network JA3, Unusual Device JA3, …) with many other weak indicators to detect the earliest signs of an emerging threat, including previously unknown threats, without using rules or hard-coded thresholds.

Catching Red-Teams and domain fronting with JA3

The following is an example where Darktrace detected a Red-Team’s C2 communication by observing anomalous JA3 behavior.

The unsupervised machine learning algorithms identified a desktop device using a JA3 that was 100% unusual for the network connecting to an external domain using a Let’s Encrypt certificate, which, along with self-signed certificates, is often abused by malicious actors. As well as the JA3, the domain was also 100% rare for the network – nobody else visited it:

It turned out that a Red-Team had registered a domain that was very similar to the victim’s legitimate domain: www.companyname[.]com (legitimate domain) vs. www.companyname[.]online (malicious domain). This was intentionally done to avoid suspicion and human analysis. Over a 7-day period in a 2,000-device environment, this was the only time that Darktrace flagged unusual behavior of this kind.

As the C2 traffic was encrypted (therefore no intrusion detection was possible on the payload) and the domain was non-suspicious (no reputation-based deny-listing worked), this C2 had remained undetected by the rest of the security stack.

Combining unsupervised machine learning with JA3 is incredibly powerful for the detection of domain fronting. Domain fronting is a popular technique to circumvent censorship and to hide C2 traffic. While some infrastructure providers take action to prevent domain fronting on their end, it is still prevalent and actively used by attackers.

The only agreed-upon method within wide parts of the cyber-security community to detect domain fronting appears to be TLS/SSL inspection. This usually involved breaking up encrypted communication to inspect the clear-text payloads. While this works, it commonly involves additional infrastructure, network restructuring and comes with privacy issues – especially in the context of GDPR.

Unsupervised machine learning makes the detection of domain fronting without having to break up encrypted traffic possible by combining unusual JA3 detection with other anomalies such as beaconing. A good start for a domain fronting threat hunt? A device beaconing to an anomalous CDN with an unusual JA3 hash.

Conclusion

JA3 is not a silver bullet to pre-empt malware compromise. As a signature-based solution, it shares the same limitations of all other defenses that rely on pre-identified threats or deny-lists: having to play a constant game of catch-up with innovative attackers. However, as a novel means of identifying TLS/SSL applications, JA3 hashing can be leveraged as a powerful network behavioral indicator, an additional metric that can flag the use of unauthorized or risky software, or as a means of identifying emerging malware compromises in the initial stages of C2 communication. This is made possible through the power of unsupervised machine learning.

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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December 22, 2025

The Year Ahead: AI Cybersecurity Trends to Watch in 2026

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Introduction: 2026 cyber trends

Each year, we ask some of our experts to step back from the day-to-day pace of incidents, vulnerabilities, and headlines to reflect on the forces reshaping the threat landscape. The goal is simple:  to identify and share the trends we believe will matter most in the year ahead, based on the real-world challenges our customers are facing, the technology and issues our R&D teams are exploring, and our observations of how both attackers and defenders are adapting.  

In 2025, we saw generative AI and early agentic systems moving from limited pilots into more widespread adoption across enterprises. Generative AI tools became embedded in SaaS products and enterprise workflows we rely on every day, AI agents gained more access to data and systems, and we saw glimpses of how threat actors can manipulate commercial AI models for attacks. At the same time, expanding cloud and SaaS ecosystems and the increasing use of automation continued to stretch traditional security assumptions.

Looking ahead to 2026, we’re already seeing the security of AI models, agents, and the identities that power them becoming a key point of tension – and opportunity -- for both attackers and defenders. Long-standing challenges and risks such as identity, trust, data integrity, and human decision-making will not disappear, but AI and automation will increase the speed and scale of the cyber risk.  

Here's what a few of our experts believe are the trends that will shape this next phase of cybersecurity, and the realities organizations should prepare for.  

Agentic AI is the next big insider risk

In 2026, organizations may experience their first large-scale security incidents driven by agentic AI behaving in unintended ways—not necessarily due to malicious intent, but because of how easily agents can be influenced. AI agents are designed to be helpful, lack judgment, and operate without understanding context or consequence. This makes them highly efficient—and highly pliable. Unlike human insiders, agentic systems do not need to be socially engineered, coerced, or bribed. They only need to be prompted creatively, misinterpret legitimate prompts, or be vulnerable to indirect prompt injection. Without strong controls around access, scope, and behavior, agents may over-share data, misroute communications, or take actions that introduce real business risk. Securing AI adoption will increasingly depend on treating agents as first-class identities—monitored, constrained, and evaluated based on behavior, not intent.

-- Nicole Carignan, SVP of Security & AI Strategy

Prompt Injection moves from theory to front-page breach

We’ll see the first major story of an indirect prompt injection attack against companies adopting AI either through an accessible chatbot or an agentic system ingesting a hidden prompt. In practice, this may result in unauthorized data exposure or unintended malicious behavior by AI systems, such as over-sharing information, misrouting communications, or acting outside their intended scope. Recent attention on this risk—particularly in the context of AI-powered browsers and additional safety layers being introduced to guide agent behavior—highlights a growing industry awareness of the challenge.  

-- Collin Chapleau, Senior Director of Security & AI Strategy

Humans are even more outpaced, but not broken

When it comes to cyber, people aren’t failing; the system is moving faster than they can. Attackers exploit the gap between human judgment and machine-speed operations. The rise of deepfakes and emotion-driven scams that we’ve seen in the last few years reduce our ability to spot the familiar human cues we’ve been taught to look out for. Fraud now spans social platforms, encrypted chat, and instant payments in minutes. Expecting humans to be the last line of defense is unrealistic.

Defense must assume human fallibility and design accordingly. Automated provenance checks, cryptographic signatures, and dual-channel verification should precede human judgment. Training still matters, but it cannot close the gap alone. In the year ahead, we need to see more of a focus on partnership: systems that absorb risk so humans make decisions in context, not under pressure.

-- Margaret Cunningham, VP of Security & AI Strategy

AI removes the attacker bottleneck—smaller organizations feel the impact

One factor that is currently preventing more companies from breaches is a bottleneck on the attacker side: there’s not enough human hacker capital. The number of human hands on a keyboard is a rate-determining factor in the threat landscape. Further advancements of AI and automation will continue to open that bottleneck. We are already seeing that. The ostrich approach of hoping that one’s own company is too obscure to be noticed by attackers will no longer work as attacker capacity increases.  

-- Max Heinemeyer, Global Field CISO

SaaS platforms become the preferred supply chain target

Attackers have learned a simple lesson: compromising SaaS platforms can have big payouts. As a result, we’ll see more targeting of commercial off-the-shelf SaaS providers, which are often highly trusted and deeply integrated into business environments. Some of these attacks may involve software with unfamiliar brand names, but their downstream impact will be significant. In 2026, expect more breaches where attackers leverage valid credentials, APIs, or misconfigurations to bypass traditional defenses entirely.

-- Nathaniel Jones, VP of Security & AI Strategy

Increased commercialization of generative AI and AI assistants in cyber attacks

One trend we’re watching closely for 2026 is the commercialization of AI-assisted cybercrime. For example, cybercrime prompt playbooks sold on the dark web—essentially copy-and-paste frameworks that show attackers how to misuse or jailbreak AI models. It’s an evolution of what we saw in 2025, where AI lowered the barrier to entry. In 2026, those techniques become productized, scalable, and much easier to reuse.  

-- Toby Lewis, Global Head of Threat Analysis

Conclusion

Taken together, these trends underscore that the core challenges of cybersecurity are not changing dramatically -- identity, trust, data, and human decision-making still sit at the core of most incidents. What is changing quickly is the environment in which these challenges play out. AI and automation are accelerating everything: how quickly attackers can scale, how widely risk is distributed, and how easily unintended behavior can create real impact. And as technology like cloud services and SaaS platforms become even more deeply integrated into businesses, the potential attack surface continues to expand.  

Predictions are not guarantees. But the patterns emerging today suggest that 2026 will be a year where securing AI becomes inseparable from securing the business itself. The organizations that prepare now—by understanding how AI is used, how it behaves, and how it can be misused—will be best positioned to adopt these technologies with confidence in the year ahead.

Learn more about how to secure AI adoption in the enterprise without compromise by registering to join our live launch webinar on February 3, 2026.  

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December 22, 2025

Why Organizations are Moving to Label-free, Behavioral DLP for Outbound Email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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