Blog
/
Network
/
September 6, 2021

What Are the Early Signs of a Ransomware Attack?

Discover the early signs of ransomware and how to defend against it. Often attack is the best form of defense with cybersecurity. Learn more here!
No items found.
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.
No items found.
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
06
Sep 2021

The deployment of ransomware is the endgame of a cyber-attack. A threat actor must have accomplished several previous steps – including lateral movement and privilege escalation – to reach this final position. The ability to detect and counter the early moves is therefore just as important as detecting the encryption itself.

Attackers are using diverse strategies – such as ‘Living off the Land’ and carefully crafting their command and control (C2) – to blend in with normal network traffic and evade traditional security defenses. The analysis below examines the Tactics, Techniques and Procedures (TTPs) used by many ransomware actors by unpacking a compromise which occurred at a defense contractor in Canada.

Phases of a ransomware attack

Figure 1: Timeline of the attack.

The opening: Initial access to privileged account

The first indicator of compromise was a login on a server with an unusual credential, followed by unusual admin activity. The attacker may have gained access to the username and password in a number of ways, from credential stuffing to buying them on the Dark Web. As the attacker had privileged access from the get-go, there was no need for privilege escalation.

Lateral movement

Two days later, the attacker began to spread from the initial server. The compromised server began to send out unusual Windows Management Instrumentation (WMI) commands.

It began remotely controlling four other devices – authenticating on them with a single admin credential. One of the destinations was a domain controller (DC), another was a backup server.

By using WMI – a common admin tool – for lateral movement, the attacker opted to ‘live off the land’ rather than introduce a new lateral movement tool, aiming to remain unnoticed by the company’s security stack. The unusual use of WMI was picked up by Darktrace and the timings of the unusual WMI connections were pieced together by Cyber AI Analyst.

Models:

  • New or Uncommon WMI Activity
  • AI Analyst / Extensive Chain of Administrative Connections

Establish C2

The four devices then connected to the IP 185.250.151[.]172. Three of them, including the DC and backup server, established SSL beacons to the IP using the dynamic DNS domain goog1e.ezua[.]com.

The C2 endpoints had very little open-source intelligence (OSINT) available, but it seems that a Cobalt Strike-style script had used the endpoint in the past. This suggests complex tooling, as the attacker used dynamic SSL and spoofed Google to mask their beaconing.

Interestingly, through the entirety of the attack, only these three devices used SSL connections for beaconing, while later C2 occurred over unencrypted protocols. It appears these three critical devices were treated differently to the other infected devices on the network.

Models:

  • Immediate breach of Anomalous External Activity from Critical Network Device, then several model breaches involving beaconing and SSL to dynamic DNS. (Domain Controller DynDNS SSL or HTTP was particularly specific to this activity.)

The middle game: Internal reconnaissance and further lateral movement

The attack chain took the form of two cycles of lateral movement, followed by establishing C2 at the newly controlled destinations.

Figure 2: Observed chain of lateral movement and C2.

So, after establishing C2, the DC made WMI requests to 20 further IPs over an extended period. It also scanned 234 IPs via ICMP pings, presumably in an attempt to find more hosts.

Many of these were eventually found with ransom notes, in particular when the targeted devices were hypervisors. The ransomware was likely deployed with remote commands via WMI.

Models:

  • AI Analyst / Suspicious Chain of Administrative Connections (from the initial server to the DC to the hypervisor)
  • AI Analyst / Extensive Suspicious WMI Activity (from the DC)
  • Device / ICMP Address Scan, Scanning of Multiple Devices AI Analyst incident (from the DC)

Further C2

As the second stage of lateral movement stopped, a second stage of unencrypted C2 was seen from five new devices. Each started with GET requests to the IP seen in the SSL C2 (185.250.151[.]172), which used the spoofed hostname google[.]com.

Activity started on each device with HTTP requests for a URI ending in .png, before a more consistent beaconing to the URI /books/. Eventually, the devices made POST requests to the URI /ebooks/?k= (a unique identifier for each device). All this appears to be a way of concealing a C2 beacon in what looks like plausible traffic to Google.

In this way, by encrypting some C2 connections with SSL to a Dynamic DNS domain, while crafting other unencrypted HTTP to look like traffic to google[.]com, the attacker managed to operate undetected by the company’s antivirus tools.

Darktrace identified this anomalous activity and generated a large number of external connectivity model breaches.

Models:

  • Eight breaches of Compromise / HTTP Beaconing to New Endpoint from the affected devices

Accomplish mission: Checkmate

Finally, the attacker deployed ransomware. In the ransom note, they stated that sensitive information had been exfiltrated and would be leaked if the company did not pay.

However, this was a lie. Darktrace confirmed that no data had been exfiltrated, as the C2 communications had sent far too little data. Lying about data exfiltration in order to extort a ransom is a common tactic for attackers, and visibility is crucial to determine whether a threat actor is bluffing.

In addition, Antigena – Darktrace’s Autonomous Response technology – blocked an internal download from one of the servers compromised in the first round of lateral movement, because it was an unusual incoming data volume for the client device. This was most likely the attacker attempting to transfer data in preparation for the end goal, so the block may have prevented this data from being moved for exfiltration.

Figure 3: Antigena model breach.

Figure 4: Device is blocked from SMB communication with the compromised server three seconds later.

Models:

  • Unusual Incoming Data Volume
  • High Volume Server Data Transfer

Unfortunately, Antigena was not active on the majority of the devices involved in the incident. If in active mode, Antigena would have stopped the early stages of this activity, including the unusual administrative logins and beaconing. The customer is now working to fully configure Antigena, so they benefit from 24/7 Autonomous Response.

Cyber AI Analyst investigates

Darktrace’s AI spotted and reported on beaconing from several devices including the DC, which was the highest scoring device for unusual behavior at the time of the activity. It condensed this information into three incidents – ‘Possible SSL Command and Control’, ‘Extensive Suspicious Remote WMI Activity’, and ‘Scanning of Remote Devices’.

Crucially, Cyber AI Analyst not only summarized the admin activity from the DC but also linked it back to the first device through an unusual chain of administrative connections.

Figure 5: Cyber AI Analyst incident showing a suspicious chain of administrative connections linking the first device in the chain of connections to a hypervisor where a ransom note was found via the compromised DC, saving valuable time in the investigation. It also highlights the credential common to all of the lateral movement connections.

Finding lateral movement chains manually is a laborious process well suited to AI. In this case, it enabled the security team to quickly trace back to the device which was the likely source of the attack and find the common credential in the connections.

Play the game like a machine

To get the full picture of a ransomware attack, it is important to look beyond the final encryption to previous phases of the kill chain. In the attack above, the encryption itself did not generate network traffic, so detecting the intrusion at its early stages was vital.

Despite the attacker ‘Living off the Land’ and using WMI with a compromised admin credential, as well as spoofing the common hostname google[.]com for C2 and applying dynamic DNS for SSL connections, Darktrace was able to identify all the stages of the attack and immediately piece them together into a meaningful security narrative. This would have been almost impossible for a human analyst to achieve without labor-intensive checking of the timings of individual connections.

With ransomware infections becoming faster and more frequent, with the threat of offensive AI looming closer and the Dark Web marketplace thriving, with security teams drowning under false positives and no time left on the clock, AI is now an essential part of any security solution. The board is set, the time is ticking, the stakes are higher than ever. Your move.

Thanks to Darktrace analyst Daniel Gentle for his insights on the above threat find.

IoCs:

IoCComment185.250.151[.]172IP address used for both HTTP and SSL C2goog1e.ezua[.]comDynamic DNS Hostname used for SSL C2

Darktrace model detections:

  • AI Analyst models:
  • Extensive Suspicious WMI Activity
  • Suspicious Chain of Administrative Connections
  • Scanning of Multiple Devices
  • Possible SSL Command and Control
  • Meta model:
  • Device / Large Number of model breaches
  • External connectivity models:
  • Anonymous Server Activity / Domain Controller DynDNS SSL or HTTP
  • Compromise / Suspicious TLS Beaconing to Rare External
  • Compromise / Beaconing Activity To External Rare
  • Compromise / SSL to DynDNS
  • Anomalous Server Activity / External Activity from Critical Network Device
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Suspicious Beaconing Behaviour
  • Compromise / HTTP Beaconing to New Endpoint
  • Internal activity models:
  • Device / New or Uncommon WMI Activity
  • User / New Admin Credentials on Client
  • Device / ICMP Address Scan
  • Anomalous Connection / Unusual Incoming Data Volume
  • Unusual Activity / High Volume Server Data Transfer

No items found.
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.
No items found.

More in this series

No items found.

Blog

/

Email

/

December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

Man at laptopDefault blog imageDefault blog image

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]

Continue reading
About the author
Carlos Gray
Senior Product Marketing Manager, Email

Blog

/

Email

/

December 17, 2025

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

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with DarktraceDefault blog imageDefault blog image

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

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI