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December 7, 2021

Conti Ransomware Strategies in Modern Cybercrime

Uncover the strategies behind the Conti ransomware gang's double extortion methods and what it means for businesses facing 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
Justin Fier
SVP, Red Team Operations
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07
Dec 2021

In a previous blog, we outlined how the Ryuk ransomware strain developed by Russian hacking group ‘Wizard Spider’ has fallen into the hands of small-time cyber criminals.

Wizard Spider – who allegedly operate with support from the Russian government and remain under investigation by the FBI and Interpol – adopted Ryuk ransomware’s successor ‘Conti’ in 2020. Conti affects all Windows operating systems and has been involved in more than 400 incidents. Wizard Spider were soon rebranded in cyber press as the ‘Conti Ransomware Gang’, though the group does not necessarily see itself as a ‘gang’. It prefers to present itself as a business.

The ransomware bubble

Ransomware has become a multibillion-dollar industry – and the Conti Ransomware Gang reportedly made up 15% of it in 2020. With this scale of income, groups like Conti find themselves adopting some crude imitations of legitimate business practice. This corporate mimicry dictates that their victims be called ‘customers’, their extortion attempts ‘negotiations’ and their criminal peers ‘affiliates’. They even publish ‘press releases’ via a dedicated Dark Web site.

The gang’s Ransomware-as-a-Service ‘business model’ consists of employing affiliates, training them in Conti ransomware’s deployment and management, and then taking 30% of the profits themselves. With exact profits known only to the malware writers and not the affiliates, however, the percentage Conti takes is often much higher than the 30% they claim.

There may not be checks and regulations in place to address fraud in the cyber underworld, but one business complication which Conti have not been able to escape is that of the disgruntled employee.

Unhappy with the malpractice of their superiors, an underpaid affiliate leaked the Conti Ransomware Gang’s training materials and the IP addresses for their Cobalt Strike C2 servers in August 2021, declaring, “they recruit suckers and divide the money among themselves”.

Meanwhile, the US Government has also been taking action to try to disrupt the profit margins of groups like the Conti Ransomware Gang, going as far as to impose sanctions on cryptocurrency exchanges seen as facilitating ransomware transactions. However, leaks and legislation have proved far from fatal for Conti.

The reality is that these actions have not lost the Conti Ransomware Gang any of its so-called “customers”, and where there are customers there is profit. Any individual or organization entrusting their cyber security to conventional, rules-based measures is in their target market.

Darktrace’s AI recently detected a Conti attack conducted along the lines of one of the methods outlined in the August leak. The target organization – a US transportation company – was trialing Darktrace but, without Darktrace’s Autonomous Response set in active mode, the attack was allowed to go ahead. In examining how it progressed, however, it should become clear not only how threatening double extortion ransomware attacks like this one can be, but also how effectively they can be stopped by Darktrace at each stage of the attack.

Figure 1: Timeline of the attack

Conti Ransomware Gang diversifies the ransomware playbook

A single uninstalled Microsoft patch had left the target organization with dangerous ProxyShell vulnerabilities. Conti exploited these vulnerabilities, quickly gaining the rights to remotely execute Exchange PowerShell commands on the company’s server and steadily broadened its presence within the digital environment. This is a relatively new approach for the Conti Ransomware Gang, who previously relied upon phishing attacks and firewall exploits. By diversifying its approach, it stays ahead of patches and intelligence.

Two weeks after the initial breach, C2 connections were made to an unusual endpoint located in Finland using an SSL client which appeared innocuous but was 100% rare for the organization. Had Autonomous Response been set in active mode, Darktrace would have shut the connections down at this very early stage.

The IP address of this suspicious endpoint has since been identified as a Conti IoC (Indicator of Compromise), allowing it to be incorporated into rules-based security solutions. This would have done little good for the company in question, however, which was breached weeks before this intelligence was made available.

As Conti continued to conduct internal reconnaissance and move laterally through the company’s digital environment, Darktrace detected further unusual activity. The suspicious Finnish endpoint then employed new ‘Living off the Land’ techniques, installing the usually legitimate tools AnyDesk and Cobalt Strike onto various parts of the environment.

A series of SSL connections were made to AnyDesk endpoints and external hosts, one of which lasted 95 hours, indicating an active remote session conducted by one of Conti’s affiliates. At this stage, Darktrace had 10 distinct reasons to suspect an imminent attack.

Conti News: Closing the deal with double extortion ransomware

Double extortion has become the Conti Ransomware Gang’s new favourite sales tactic. If you refuse to pay its ransom, Conti will not only take your most important files from you, but also exfiltrate and publish them using its dedicated ‘Conti News’ website, or sell them directly to your competitors.

Having expanded their reach across the transport company’s network, the Conti affiliate began rapidly exfiltrating large quantities of company data to Conti’s preferred cloud storage site, MEGA. Over four days, more than 3TB of data was uploaded, and then encrypted.

To avoid detection by a human security team, encryption was launched at close to midnight – Conti’s ‘business’ does not respect business hours. When the company’s security team returned to work the next day, they were met with a ransom note.

This attack was able to progress because Darktrace was only being trialed at this stage and was therefore allowed to detect threats but not to take action against them. With Autonomous Response employed in active mode, this ransomware attack would have ended in the very early stages, when Darktrace detected its first suspicious connections.

Nonetheless, the Cyber AI Analyst was able to investigate and connect the dots of the attack automatically, making the organization’s remediation efforts drastically quicker and easier than they would have been without even this partial Darktrace deployment.

Figure 2: Cyber AI Analyst generated this incident report following the initiation of data exfiltration

How the Conti Ransomware Gang evades cyber intelligence

Security systems that rely on human intelligence to detect threats fit Conti’s ideal customer profile perfectly. By adapting and diversifying their approach, moving from Ryuk to Conti, and from spear phishing and firewall exploits to this new ProxyShell approach, Conti stay ahead of regulations and hold on to their vulnerable customer base.

Even if the Conti Ransomware Gang is brought down by leaks or legislation, other groups will rise to fill the gap in the market, eager for their own cut of the illicit gains. If these groups are to be truly stopped, they must be made unprofitable.

The US government has tried to do this by imposing fines upon ransom payers, but companies still often consider the losses involved in not recovering their data too great. As I have argued previously, ‘to pay or not to pay,’ is not the question we should be asking.

If you’re deciding whether to pay or not to pay, you’re already too far down the line. Darktrace stops groups like Conti at the first encounter. As this case has shown, Darktrace’s Self-Learning AI is able to identify threats weeks before human analysts and threat intelligence can do the same, and neutralize them at every stage of an attack with Autonomous Response.

Thanks to Darktrace analyst Sam Lister for his insights on the above threat find.

Darktrace model detections:

  • Device / Long Agent Connection to New Endpoint
  • Device / ICMP Address Scan
  • Anomalous Connection / SMB Enumeration
  • Anomalous Server Activity / Outgoing from Server
  • Compromise / Beacon to Young Endpoint
  • Anomalous Server Activity / Rare External from Server
  • Compromise / Fast Beaconing to DGA
  • Compromise / SSL or HTTP Beacon
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Beacon for 4 Days
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Compliance / SMB Drive Write
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Connection / Suspicious Read Write Ratio
  • Anomalous Connection / Suspicious Read Write Ratio and Unusual SMB
  • Anomalous Connection / Sustained MIME Type Conversion
  • Unusual Activity / Anomalous SMB Move & Write
  • Unusual Activity / Unusual Internal Data Volume as Client or Server
  • Device / Suspicious File Writes to Multiple Hidden SMB Shares
  • Compromise / Ransomware / Suspicious SMB Activity
  • Anomalous File / Internal / Unusual SMB Script Write
  • Anomalous File / Internal / Masqueraded Executable SMB Write
  • Device / SMB Lateral Movement
  • Device / Multiple Lateral Movement Model Breaches

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
Justin Fier
SVP, Red Team Operations

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December 18, 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.

[related-resource]

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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