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July 9, 2024

How Darktrace Detects NTLM Hash Theft

Explore Darktrace's innovative methods for detecting NTLM hash theft and safeguarding your organization from cyber threats.
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
Charlotte Thompson
Cyber Analyst
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09
Jul 2024

What is credential theft and how does it work?

What began as a method to achieve unauthorized access to an account, often driven by the curiosity of individual attackers, credentials theft become a key tactic for malicious actors and groups, as stolen login credentials can be abused to gain unauthorized access to accounts and systems. This access can be leveraged to carry out malicious activities such as data exfiltration, fraud, espionage and malware deployment.

It is therefore no surprise that the number of dark web marketplaces selling privileged credentials has increased in recent years, making it easier for malicious actors to monetize stolen credentials [1]. This, in turn, has created new opportunities for threat actors to use increasingly sophisticated tactics such as phishing, social engineering and credential stuffing in their attacks, targeting individuals, organizations and government entities alike [1].

Credential theft example

TA577 Threat Actor

TA577 is a threat actor known to leverage stolen credentials, also known as Hive0118 [2], an initial access broker (IAB) group that was previously known for delivering malicious payloads [2]. On March 4, 2024, Proofpoint reported evidence of TA577 using a new attack chain with a different aim in mind: stealing NT LAN Manager (NTLM) hashes that can be used to authenticate to systems without needing to know plaintext passwords [3].

How does TA577 steal credentials?

Proofpoint reported that this new attack chain, which was first observed on February 26 and 27, was made up of two distinct campaigns. The first campaign consisted of a phishing attack featuring tens of thousands of emails targeting hundreds of organizations globally [3]. These phishing emails often appeared as replies to previous messages (thread hijacking) and contained zipped HTML attachments that each contained a unique file hash, customized for each recipient [3]. These attached files also contained a HTTP Meta refresh function, which triggered an automatic connection to a text file hosted on external IP addresses running as SMB servers [3].

When attempting to access the text file, the server requires an SMB session authentication via NTLM. This session is initiated when a client sends an ‘SMB_COM_NEGOTIATE’ request to the server, which answers with a ‘SMB_COM_NEGOTIATE’ response.

The client then proceeds to send a ‘SMB_COM_SESSION_SETUP_ANDX’ request to start the SMB session setup process, which includes initiating the NTLM authentication process. The server responds with an ‘SMB_COM_SESSION_SETUP_ANDX’ response, which includes an NTLM challenge message [6].

The client can then use the challenge message and its own credentials to generate a response by hashing its password using an NTLM hash algorithm. The response is sent to the server in an ‘SMB_COM_SESSION_SETUP_ANDX’ request. The server validates the response and, if the authentication is successful, the server answers with a final ‘SMB_COM_SESSION_SETUP_ANDX’ response, which completes the session setup process and allows the client to access the file listed on the server [6].

What is the goal of threat actor TA577?

As no malware delivery was detected during these sessions, researchers have suggested that the aim of TA577 was not to deliver malware, but rather to take advantage of the NTLMV2 challenge/response to steal NTLM authentication hashes [3] [4]. Hashes stolen by attackers can be exploited in pass-the-hash attacks to authenticate to a remote server or service [4]. They can also be used for offline password cracking which, if successful, could be utilized to escalate privileges or perform lateral movement through a target network [4]. Under certain circumstances, these hashes could also permit malicious actors to hijack accounts, access sensitive information and evade security products [4].

The open-source toolkit Impacket, which includes modules for password cracking [5] and which can be identified by the default NTLM server challenge “aaaaaaaaaaaaaaaa”[3], was observed during the SMB sessions. This indicates that TA577 actor aim to use stolen credentials for password cracking and pass-the-hash attacks.

TA577 has previously been associated with Black Basta ransomware infections and Qbot, and has been observed delivering various payloads including IcedID, SystemBC, SmokeLoader, Ursnif, and Cobalt Strike [2].This change in tactic to follow the current trend of credential theft may indicate that not only are TA577 actors aware of which methods are most effective in the current threat landscape, but they also have monetary and time resources needed to create new methods to bypass existing detection tools [3].  

Darktrace’s Coverage of TA577 Activity

On February 26 and 27, coinciding with the campaign activity reported by Proofpoint, Darktrace/Email™ observed a surge of inbound emails from numerous suspicious domains targeting multiple customer environments. These emails consistently included zip files with seemingly randomly generated names, containing HTLM content and links to an unusual external IP address [3].

A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Figure 1: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.
Figure 2: Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.

The URL of these links contained an unusually named .txt file, which corresponds with Proofpoint reports of the automatic connection to a text file hosted on an external SMB server made when the attachment is opened [3].

A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.
Figure 3: A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.

Darktrace identified devices on multiple customer networks connecting to external SMB servers via the SMB protocol. It understood this activity was suspicious as the SMB protocol is typically reserved for internal connections and the endpoint in question had never previously been observed on the network.

The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
Figure 4: The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
External Sites Summary highlighting the rarity of the external SMB server.
Figure 5: External Sites Summary highlighting the rarity of the external SMB server.
External Sites Summary highlightin that the SMB server is geolocated in Moldova.
Figure 6: External Sites Summary highlightin that the SMB server is geolocated in Moldova.

During these connections, Darktrace observed multiple devices establishing an SMB session to this server via a NTLM challenge/response, representing the potential theft of the credentials used in this session. During this session, some devices also attempted to access an unusually named .txt file, further indicating that the affected devices were trying to access the .txt file hosted on external SMB servers [3].

Packet captures (PCAPs) of these sessions show the default NTLM server challenge, indicating the use of Impacket, suggesting that the captured NTLM hashes were to be used for password cracking or pass-the-hash-attacks [3]

PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.
Figure 7: PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.

Conclusions

Ultimately, Darktrace’s suite of products effectively detected and alerted for multiple aspects of the TA577 attack chain and NTLM hash data theft activity across its customer base. Darktrace/Email was able to uncover the inbound phishing emails that served as the initial access vector for TA577 actors, while Darktrace DETECT identified the subsequent external connections to unusual external locations and suspicious SMB sessions.

Furthermore, Darktrace’s anomaly-based approach enabled it to detect suspicious TA577 activity across the customer base on February 26 and 27, prior to Proofpoint’s report on their new attack chain. This showcases Darktrace’s ability to identify emerging threats based on the subtle deviations in a compromised device’s behavior, rather than relying on a static list of indicators of compromise (IoCs) or ‘known bads’.

This approach allows Darktrace to remain one step ahead of increasingly adaptive threat actors, providing organizations and their security teams with a robust AI-driven solution able to safeguard their networks in an ever-evolving threat landscape.

Credit to Charlotte Thompson, Cyber Analyst, Anna Gilbertson, Cyber Analyst.

References

1)    https://www.sentinelone.com/cybersecurity-101/what-is-credential-theft/

2)    https://malpedia.caad.fkie.fraunhofer.de/actor/ta577

3)    https://www.proofpoint.com/us/blog/threat-insight/ta577s-unusual-attack-chain-leads-ntlm-data-theft

4)    https://www.bleepingcomputer.com/news/security/hackers-steal-windows-ntlm-authentication-hashes-in-phishing-attacks/

5)    https://pawanjswal.medium.com/the-power-of-impacket-a-comprehensive-guide-with-examples-1288f3a4c674

6)    https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-nlmp/c083583f-1a8f-4afe-a742-6ee08ffeb8cf

7)    https://www.hivepro.com/threat-advisory/ta577-targeting-windows-ntlm-hashes-in-global-campaigns/

Darktrace Model Detections

Darktrace/Email

·       Attachment / Unsolicited Archive File

·       Attachment / Unsolicited Attachment

·       Link / New Correspondent Classified Link

·       Link / New Correspondent Rare Link

·       Spoof / Internal User Similarities

Darktrace DETECT

·       Compliance / External Windows Communications

Darktrace RESPOND

·       Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

IoCs

IoC - Type - Description

176.123.2[.]146 - IP address -Likely malicious SMB Server

89.117.2[.]33 - IP address - Likely malicious SMB Server

89.117.1[.]161 - IP address - Likely malicious SMB Server

104.129.20[.]167 - IP address - Likely malicious SMB Server

89.117.1[.]160 - IP address - Likely malicious SMB Server

85.239.33[.]149 - IP address - Likely malicious SMB Server

89.117.2[.]34 - IP address - Likely malicious SMB Server

146.19.213[.]36 - IP address - Likely malicious SMB Server

66.63.188[.]19 - IP address - Likely malicious SMB Server

103.124.104[.]76 - IP address - Likely malicious SMB Server

103.124.106[.]224 - IP address - Likely malicious SMB Server

\5aohv\9mn.txt - SMB Path and File - SMB Path and File

\hvwsuw\udrh.txt - SMB Path and File - SMB Path and File

\zkf2rj4\VmD.txt = SMB Path and File - SMB Path and File

\naams\p3aV.txt - SMB Path and File - SMB Path and File

\epxq\A.txt - SMB Path and File - SMB Path and File

\dbna\H.txt - SMB Path and File - SMB Path and File

MAGNAMSB.zip – Filename - Phishing Attachment

e751f9dddd24f7656459e1e3a13307bd03ae4e67 - SHA1 Hash - Phishing Attachment

OMNIS2C.zip  - Filename - Phishing Attachment

db982783b97555232e28d5a333525118f10942e1 - SHA1 Hash - Phishing Attachment

aaaaaaaaaaaaaaaa - NTLM Server Challenge -Impacket Default NTLM Challenge

MITRE ATT&CK Tactics, Techniques and Procedures (TTPs)

Tactic - Technique

TA0001            Initial Access

TA0002            Execution

TA0008            Lateral Movement

TA0003            Persistence

TA0005            Defense Evasion

TA0006            Credential Access

T1021.002       SMB/Windows Admin Shares

T1021  Remote Services

T1566.001       Spearfishing Attachment

T1566  Phishing

T1204.002       Malicious File

T1204  User Execution

T1021.002       SMB/Windows Admin Shares

T1574  Hijack Execution Flow

T1021  Remote Services

T1555.004       Windows Credential Manager

T1555  Credentials from Password Stores

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
Charlotte Thompson
Cyber Analyst

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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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