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April 10, 2023

Detecting Malicious Email Activity & AI Impersonating

Discover how two different phishing attempts from some known and unknown senders used a payroll diversion and credential sealing box link to harm users.
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
Isabelle Cheong
Cyber Security Analyst
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10
Apr 2023

Social engineering has become widespread in the cyber threat landscape in recent years, and the near-universal use of social media today has allowed attackers to research and target victims more effectively. Social engineering involves manipulating users to carry out actions such as revealing sensitive information like login credentials or credit card details. It can also lead to user account compromises, causing huge disruption to an organization’s digital estate. 

As people use social media platforms not only for personal reasons, but also for business purposes, attackers gain information they can exploit in social engineering attacks. For example, a threat actor may attempt to impersonate a known individual or legitimate service to take advantage of a user’s established trust. This is a highly successful method of social engineering because mimicking known contacts makes it difficult for traditional security tools that rely on deny-lists to detect the attack.

In October 2022, Darktrace identified and responded to two separate malicious email campaigns in which threat actors attempted to impersonate known contacts in an effort to compromise customer devices. As it learns the normal behavior of every user in the email system, Darktrace was able to instantly detect these threats and mitigate them autonomously, preventing significant disruption to the customer networks.

Payroll Diversion Fraud Attempt Impersonating a Former Employee 

While a customer in the Canadian energy sector was trialing Darktrace in October 2022, Darktrace/Email™ identified a suspicious email seemingly sent from an employee within the organization. The email was sent to the Senior Director of Human Resources (HR) with a subject line of “Change in payroll Direct Deposit.” The email requested a change in bank account information for an employee. However, Darktrace recognized that the sender was using a free mail address that contained random letters, indicating it may have been algorithmically generated. Since this incident occurred during a trial, Darktrace/Email was not configured to take action. Otherwise, it would have prevented the email from landing in the inbox. In this case though, the email went through, bypassing all other security tools in place.

Although the email was from an unknown sender, the HR director believed the email could have been legitimate as the employee who appeared to be the sender had left the organization seven days prior and no longer had access to their corporate email account. However, after reviewing it in the Darktrace/Email dashboard, the customer grew suspicious and contacted the former employee directly to verify if the request was legitimate. The former employee validated the suspicions by confirming they had sent no such email.

Further investigation by the customer revealed that the former employee had been vocal about their departure on various social media platforms. This gave threat actors valuable information to believably impersonate the former employee and defraud the organization. 

Such attempts to target organizations’ HR departments and divert payroll are common tactics for cyber-criminals and are often identified by Darktrace/Email across the customer base. Darktrace/Email is able to instantly identify the indicators associated with these spoofing attempts and immediately bring them to the attention of the customer’s security team. 

Using Legitimate File Sharing Service to Share a Phishing Link 

On October 7, 2022, a customer in the Singaporean construction sector was targeted by a phishing campaign attempting to impersonate a law firm known to the organization. Almost 200 employees received an email with the subject line “Accepted: Valuation Agreement.” 

Figure 1: Sample of an UI view of the message held showing anomaly indicators, history, association, and validation.

Four days earlier, Darktrace observed communication between another email address associated with the law firm and an employee of the customer. Darktrace/Email noted that it was the first time this correspondent had sent emails to the customer. 

Figure 2: Metrics showing how well the sender’s domain is known within the digital environment.

The emails contained a highly unusual link to a file sharing service, (hxxps://ssvilvensstokes[.]app[.]box[.]com/notes), hidden behind the text “PREVIEW OR PRINT COPY OF DOCUMENT HERE.” Darktrace analysts investigated this event further and found that around 30 similar URLs had been identified as suspicious using OSINT security tools in October 2022, suggesting the customer was not the only target of this phishing campaign.

Figure 3: Preview of the phishing email’s body.
Figure 4: Darktrace’s evaluation of the link contained in the phishing email.

Additional OSINT work revealed that the link directed to a website which appeared to host a PDF file named “Valuation Agreement.” The recipient would then be prompted to follow another link (hulking-citrine-krypton[.]glitch[.]me), again hidden behind the text “OPEN OR ACCESS DOCUMENT HERE” to view the file. Subsequently, the user would be prompted to enter their Microsoft 365 credentials. 

Figure 5: The page displayed when the phishing link was clicked, viewed in a sandbox environment.
Figure 6: Example of a page shown when recipient clicks the second link, accessing “hulking-citrine-krypton[.]glitch[.]me”. 

This page contained the text “This document has been scanned for viruses by Norton Antivirus Security.” This is another example of threat actors’ employing social engineering techniques by impersonating well-known brands, such as established security vendors, to gain the trust of users and increase their likelihood of success.

It is highly probable that a real employee of the law firm had their account hijacked and that a malicious actor was exploiting it to send out these phishing emails en masse as part of a supply chain attack. In such cases, malicious actors rely on their targets’ trust of known contacts to not question departures from their normal conversations. 

Darktrace was able to instantly detect multiple anomalies in these emails, despite the fact that they were seemingly sent by known correspondents. The activity detected automatically triggered model breaches associated with unexpected and visually prominent links. As a result, Darktrace/Email responded by locking the link, stopping users from being able to click it.

Darktrace subsequently identified additional emails from this sender attempting to target other recipients within the company, triggering the model breaches associated with a surge in email sending indicative of a phishing campaign. In response, Darktrace/Email autonomously acted and filed these emails as junk. As more emails were detected across the customer’s environment, the anomaly score of the sender increased and Darktrace ultimately held back over 160 malicious emails, safeguarding recipients from potential account compromise.           

The following Darktrace/Email models were breached throughout the course of this phishing campaign:

  • Unusual/Sender Surge 
  • Unusual/Undisclosed Recipients 
  • Antigena Anomaly 
  • Association/Unlikely Recipient Association 
  • Link/Low Link Association 
  • Link/Visually Prominent Link 
  • Link/Visually Prominent Link Unexpected For Sender 
  • Unusual/New Sender Wide Distribution
  • Unusual/Undisclosed Recipients + New Address Known Domain

Conclusion

Social engineering plays a role in many of the major threats challenging current email cyber security, as attackers can use it to manipulate users into transferring money, revealing credentials, clicking malicious links, and more. 

The above threat stories happened before language generating AI became mainstream with the release of ChatGPT in December 2022. Now, it is even easier for malicious actors to generate sophisticated social engineering emails. By using social media posts as input, social engineering emails written by generative AI can be highly targeted and produced at scale. They often avoid the flags users are trained to look for, like poor grammar and spelling mistakes, and can hide payloads or forgo them entirely.

To mitigate the risk of possible social engineering attempts, it is recommended that organizations implement social media policies that advise employees to be cautious of what they post online and enact procedures to verify if fund transfer requests are legitimate.

Yet these policies are not enough on their own. Darktrace/Email can identify suspicious email traits, whether an email is sent from a known correspondent or an unknown sender. With Self-Learning AI, it knows an organization’s users better than any impersonator could. In this way, Darktrace/Email detects anomalies within emails and neutralizes malicious components at machine-speed, stopping attacks at their earliest stages, before employees fall victim. 

Appendices

List of Indicators of Compromise (IoCs)

Domain:

hxxps://ssvilvensstokes[.]app[.]box[.]com/notes/*?s=* - 1st external link (seen in email)

hxxps://hulking-citrine-krypton[.]glitch[.]me/flk.html - 2nd external link, masked behind “OPEN OR ACCESS DOCUMENT HERE”

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
Isabelle Cheong
Cyber Security Analyst

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June 2, 2026

Stopping Stealth Attacks with Precision: How Núclea Prevented a Breach Without Disruption

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Núclea is a Brazilian data and technology company that supports the country’s financial system by delivering digital services exclusively to banks and financial institutions. Operating in an environment where trust, availability, and data integrity are critical, the company faces a threat landscape that has evolved rapidly—particularly with the rise of AI-driven cyberattacks.

Brazil has experienced a wave of successful cyber incidents targeting financial institutions, many of them enabled by insiders or compromised credentials. The result was a noticeable shift in attacker strategy: instead of focusing on end customers, threat actors began targeting the institutions and platforms that underpin the financial ecosystem itself.

“Attacks became far more directed and contextual,” explains Guilherme, who leads incident response within Núclea’s security platform engineering team. “They weren’t noisy or obviously malicious—they were precise, patient, and designed to blend into normal operations.”

That precision was on full display in January 2026, when Núclea faced one of the most convincing phishing attacks the team had seen.

A real attack, built on trust and context

The attack began with a seemingly routine email.

It was sent from a real Brazilian government institution, using legitimate infrastructure and valid credentials that were later confirmed to have been compromised. Núclea had an established, ongoing relationship with this organization, and the email’s language, tone, and subject matter aligned perfectly with the type of communication the recipient team handled every day.

Attached to the email was a PDF document containing content that looked entirely legitimate.

The problem? A single URL embedded inside that PDF.

“The message itself was correct. The sender was real. The context was familiar. Even the document content made sense,” Guilherme explains. “There was just one small element that didn’t belong.”

That small detail was enough to initiate a full attack chain.

What the attackers were trying to do

If clicked, the URL would have downloaded a malicious payload designed to:

  • Collect information about the user and device
  • Identify where the system was located within the financial ecosystem
  • Install remote access tools to maintain control
  • Deploy an infostealer to extract sensitive data
  • Execute anti-forensic scripts to erase traces of the intrusion

In other words, it was a carefully engineered operation designed for persistence and stealth, not immediate disruption.

The attack also employed urgency—a classic social engineering technique. When the link didn’t open as expected, employees requested assistance from the security team, insisting the document was important and needed to be accessed quickly.

This is precisely the kind of scenario where traditional security tools struggle: almost everything about the interaction is legitimate.

Where Darktrace made the difference

Instead of blocking the entire message or relying on known indicators of compromise, Darktrace focused on behavioral context.

Darktrace recognized:

  • That the sending organization was normally trusted
  • That the communication pattern matched historical behavior
  • That the PDF content itself was not suspicious

But it also identified that the URL embedded within the document deviated from established behavioral patterns.

Rather than disrupting business operations, Darktrace took precise action: it rewrote the URL, preventing the malicious download while leaving the rest of the email untouched.

“When we analyzed it afterward, it became clear how dangerous the attack would have been,” says Guilherme. “But it never progressed—because Darktrace acted at exactly the right point.”

Subsequent forensic analysis confirmed the payload’s malicious intent. The attack never succeeded.

Precision over disruption

For Núclea, this incident reinforced a critical lesson: modern attacks don’t always look malicious—they hide within normal activity.

“What stands out to me is the precision,” Guilherme says. “Darktrace doesn’t rely on big, obvious signals. It’s effective in situations that fall outside the standard patterns we all know.”

Building resilience in a high trust ecosystem

For Núclea, cybersecurity is not just a defensive measure—it’s a business enabler.

Availability failures or successful breaches in the financial ecosystem can have immediate, large-scale consequences, from financial loss to reputational damage. Preventing those outcomes protects not just Núclea, but its partners and customers as well.

“Cyber resilience means keeping the business running—even under attack,” Guilherme explains. “And that requires people, processes, and technology working together.”

As AI continues to accelerate both attacks and defenses, the role of security is evolving. Precision, behavioral understanding, and intelligent automation are no longer optional—they’re essential.

“The easy days were yesterday,” Guilherme says. “The challenges ahead are bigger. We need to be prepared—internally and with partners that help us build resilience.”

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June 1, 2026

効率化の裏にあるリスク:AI導入が製造現場にもたらす見えない脆弱性

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AIエージェントが製造業に与える影響

製造業界のセキュリティチームやIT担当者は、生産を守り、稼働時間を維持し、重要資産を保護するという絶え間ないプレッシャー下にあります。そしてAIは非常に大きなチャンスとともに、新たなサイバーリスクももたらしています。製造業全体で、AIはワークフローや意思決定に組み込まれつつあり、自律型AIエージェントが従業員やシステムに代わって行動する場面が増えています。

エージェント型システムは独立して行動できるため強力ですが、その同じ自律性がサイバーリスク、運用上のリスクも生み出します。エージェントは広範な権限を持ち、複雑なタスクの実行、意思決定、ツールや外部システムとのやり取りを、ほとんどまたは全く人間の介入なしに行うことができます。

あらかじめ定義されたタスクを実行する従来のAIモデルとは異なり、AIエージェントは高度なテクニックを使用して人間の意思決定プロセスを模倣することにより、新たな課題に動的に適応し、また自らの判断に基づいて意思決定し、アクションを実行します。彼らは業務の上では従業員のように見えますが、人間が持つ判断力、倫理観、または行動の結果に対する恐れが欠けています。これは、サイバー犯罪者によって簡単に操られる可能性があることを意味しており、OTネットワーク全体に埋め込まれたAIエージェントは、データ漏洩をはるかに超える脅威を生み出します。たとえば、BMWでは、AI は溶接プロセスのエラーの発生を識別するのに使われています。同社のスパータンバーグ(米サウスカロライナ州)の工場では、すべてのSUVフレーム上の300-400個のスタッドの溶接をAIが監視し、スタッドの配置間違いや欠陥を検知し直ちに修正します。このAIシステムが破損すれば壊滅的な品質管理問題につながる恐れがあります。

製造全体にエージェント型AIシステムを導入することについて多くのセキュリティチームはさまざまな懸念を示しています。ダークトレースの行ったAIサイバーセキュリティの現状調査では、製造業のセキュリティプロフェッショナルの78%が従業員によるAIエージェントの利用に懸念を抱いており、これは彼らの最も大きな危惧でした。それに続く問題点が従業員によるCopilotやChatGPT等の生成AIツールの使用であり、製造業のセキュリティプロフェッショナルの76%が懸念を抱いていました。これらのツールがますます多くのビジネスデータやプロセスにアクセスし、組織内でより多くの自律性を持つようになるにつれ、エージェントのアクティビティがほとんど可視化されていない現在、セキュリティチームにおいては機密データの露出(60%)や偶発的なポリシーおよび規制違反(59%)への懸念が高まっています。

外部からのAIによる脅威も急激に進化

製造業を変革しているのと同じAIの能力が、サイバー攻撃の形も変貌させています。

AIにより攻撃者は偵察を自動化し、標的をより高度に絞り込み、リアルタイムで適応できるようになっています。かつては人手による作業と時間を要していたことが、今では継続的かつ大規模に実行できるようになりました。そして、製造業はすでにその影響を実感しています。当社が調査した製造業のセキュリティプロフェッショナルの76%は、すでにAIを活用した脅威の影響を受けており、90%がAIによってソーシャルエンジニアリング攻撃の成功率が高まっていると回答しています。

また、攻撃のテクニック自体も進化しています。製造業界全体で、AIを利用した攻撃の経路の多様化に対する懸念が高まっています。特にリアルタイムで進化する適応型マルウェアについて、調査対象の製造業のセキュリティプロフェッショナルの半数近く(49%)が懸念しており、これは全産業の平均よりも9%高い数値です。AIを使った適応型マルウェアに続くその他の懸念には次が含まれます:

  • 自動化された脆弱性スキャンとエクスプロイトチェイニング(48%):Anthropicの新しいMythos AIモデルにより脆弱性探索が深刻化する中で、この問題は一層差し迫ったものとなっています。
  • 超パーソナライズされたフィッシングキャンペーン(46%):フィッシングは依然としてハッカーの主力兵器の1つであり、AIによってフィッシングメールはより説得力が高く検知困難なものとなり、その効果は増幅されました。

これは単に攻撃の量の増加だけでなく、攻撃の展開につれて静的な防御が対応できるよりも速く進化する脅威への変化なのです。

こうした認識が高まっているにもかかわらず、製造業の多くはまだこの変化に対応する準備ができていません。半数以上(51%)がAI駆動の脅威への準備が十分にできていないと回答し、AIの導入を管理する正式なポリシーを持っている組織はわずか37%でした。  

可視性、コンテキスト、およびガードレールを通じてAIのセキュリティを確保

これらの問題に対処するためにAIイノベーションを遅らせる必要はありません。それには、AIと同じスピードと規模で動作できる、これまでとは異なるアプローチのセキュリティが必要です。具体的には、製造業がAIの力を活用する上で、次の3つの優先課題が浮上しています。

可視性はすべての土台  

AIがどこで使用されているか、何にアクセスできるか、そしてITおよびOT環境にわたってどのように動作するかを理解する必要があります。それがなければ、リスクを測定したり管理したりすることはできません。ダークトレースの調査において、製造業のセキュリティプロフェッショナルの91%が、AIを信頼する前に、それがどのように意思決定を行うかを理解する必要があると回答したのは当然のことです。OT環境においてこのことはさらに重要です。稼働の中断は安全や環境、財務、および評判に大きな影響を及ぼすからです。

可視性をアクションにつなげるにはコンテキストが必要  

AIによって形作られる環境において、正常とされる挙動は絶えず変化します。つまり、脅威を検知するにはビヘイビアベースのアプローチが必要なのです。組織全体で生活パターンを理解し、わずかな逸脱をリアルタイムに検知すること- これは従来のセキュリティとリスク管理に対するアプローチからの根本的な変化です。

エージェントからの露出を防ぐガードレール  

AIシステムがより大きな責任を担うようになるなかで、組織はAIが何をできるか、そしていつ独立して行動できるかについて、明確な境界を設ける必要があります。これらのコントロールは何かがあってから適用されるのではなく、システム自体に組み込んでおかなければなりません。  

製造業のITおよびOT環境におけるAIエージェントのセキュリティ

エージェント型AIの出現は製造業を変革し、次世代のオペレーションを支える一方で、脅威ランドスケープも一変させています。これは単なる脅威の増加ではなく、自律型システムへの移行、挙動の絶え間ない変化、そしてマシンスピードで進行するリスクです。AIを活用しつつリスクを管理するという課題に取り組む組織にとって、可視性、コンテキスト、ガードレールはセキュリティの基盤となります。

Darktraceはこの基盤を実現することにより、製造業の安全なAIアプローチ構築を支援します。ITおよびOT環境全体を可視化し、異常なアクティビティに対するリアルタイムの検知および対応を提供することにより、従業員が使用するプロンプトや構築するエージェントから、それらのエージェントの環境全体での動作に至るまで、AIアクティビティの理解を可能にします。これにより、AIの導入を拡大する製造業はコントロールを犠牲にすることなくイノベーションの基盤を構築することができます。

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About the author
Dr. Oakley Cox-Robinson
Senior Director of Product
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