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September 20, 2022

Modern Extortion: Detecting Data Theft From the Cloud

Darktrace highlights a handful of data theft incidents on shared cloud platforms, showing that cloud computing can be a vulnerable place for modern extortion.
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
Adrianne Marques
Senior Research Analyst
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20
Sep 2022

Ransomware Industry

The ransomware industry has benefitted from a number of factors in recent years: inadequate cyber defenses, poorly regulated cryptocurrency markets, and geopolitical tensions have allowed gangs to extort increasingly large ransoms while remaining sheltered from western law enforcement [1]. However, one of the biggest success stories of the ransomware industry has been the adaptability and evolution of attacker TTPs (tactics, techniques and procedures). The WannaCry and NotPetya attacks of 2017 popularized a form of ransomware which used encryption algorithms to hold data to ransom in exchange for a decryption key. Last year in 2021, almost all ransomware strains evolved to use double extortion tactics: holding stolen data to ransom as well as encrypted data [2]. Now, some ransomware gangs have dropped encryption entirely, and are using data theft as their sole means of extortion. 

Using data theft for extortion is not new. In 2020 the Finnish psychotherapy center Vastaamo had over 40,000 patient records stolen. Impacted patients were told that their psychiatric transcripts would be published online if they failed to pay a Bitcoin ransom. [3]. A later report by BlackFog in May 2021 predicted data theft extortion would become one of the key emerging cybersecurity trends that year [4]. Adoption of offline back-ups and endpoint detection had made encryption harder, while a large-scale move to Cloud and SaaS platforms offered new vectors for data theft. By moving from data encryption to data exfiltration, ransomware attackers pivoted from targeting data availability within the CIA triad (Confidentiality, Integrity, Availability) to threatening data confidentiality.

In November 2021, Darktrace detected a data theft incident following the compromise of two SaaS accounts within an American tech customer’s Office365 environment. The client was a longstanding user of Darktrace DETECT/Network, and was in the process of expanding their coverage by trialing Darktrace DETECT+RESPOND/ Apps + Cloud.

Attack Overview

On November 23rd 2021, an Ask the Expert (ATE) ticket was raised prompting investigation into a breached SaaS model, ‘SaaS / Access / Unusual External Source for SaaS Credential Use’, and the activities of a user (censored as UserA) over the prior week.

1. Office365: UserA 

The account UserA had been logging in from an unusual location in Nigeria on November 21st. At the time of the incident there were no flags of malicious activity from this IP in widely used OSINT sources. It is also highly probable the attacker was not located in Nigeria but using Nigerian infrastructure in order to hide their true location. Regardless, the location of the login from this IP and ASN was considered highly unusual for users within the customer’s digital estate. The specific user in question most commonly accessed their account from IP ranges located in the US.

Figure 1: In the Geolocation tab of the External Sites Summary on the SaaS Console, UserA was seen logging in from Nigeria when previous logins were exclusively from USA

Further investigation revealed an additional anomaly in the Outlook Web activity of UserA. The account was using the Firefox browser to access their account for the first time in at least 4 weeks (the maximum period for which the customer stored such data). SaaS logs detailing the access of confidential folders and other suspicious actions were identified using the Advanced Search (AS) query:

@fields.saas_actor:"UserA@[REDACTED]" AND @fields.saas_software:"Firefox"

Most actions were ‘MailItemsAccessed’ events originating from IPs located in Nigeria [5,6] and one other potentially malicious IP located in the US [7].

‘MailItemsAccessed’ is part of the new Advanced Audit functionality from Microsoft and can be used to determine when email data is accessed by mail protocols and clients. A bind mail access type denotes an individual access to an email message [8]. 

Figure 2: AS logs shows UserA had not used Firefox to access Office365 for at least 4 weeks prior to the unusual login on the 21st November

Below are details of the main suspicious SaaS activities: 

·      Time: 2021-11-21 09:05:25 - 2021-11-22 16:57:39 UTC

·      SaaS Actor: UserA@[REDACTED]

·      SaaS Service: Office365

·      SaaS Service Product: Exchange

·      SaaS Software: Firefox

·      SaaS Office365 Parent Folders:

          o   \Accounts/Passwords
          o   \Invoices
          o   \Sent Items
          o   \Inbox
          o   \Recoverable Items\Deletions

·      SaaS Event:

          o   MailItemsAccessed
          o   UserLoggedIn
          o   Update

·      SaaS Office365 Mail Access Type: Bind (47 times)

·      Source IP addresses:

          o   105.112.59[.]83
          o   105.112.36[.]212
          o   154.6.17[.]16
          o   45.130.83[.]129

·      SaaS User Agents: 

          o   Client=OWA;Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:80.0) Gecko/20100101 Firefox/80.0;
          o   Mozilla/5.0 (Windows NT 10.0; Win64; x64; rv:80.0) Gecko/20100101 Firefox/80.0

·      Total SaaS logs: 57 

At the start of the month on the 5th November, the user had also been seen logging in from a potentially malicious endpoint [9] in Europe, performing ‘MailItemsAccessed’ and ‘Updates’ events with subjects and a resource location related to invoices and wire transfers from the Sent items folder. This suggests the initial compromise had been earlier in the month, giving the threat actor time to make preparations for the final stages of the attack.

Figure 3: Event log showing the activity of UserA from IP 45.135.187[.]108 

2. Office365: UserB 

Looking into the model breach ‘SaaS / Access / Suspicious Credential Use And Login User-Agent’, it was seen that a second account, UserB, was also observed logging in from a rare and potentially malicious location in Bangladesh [7]. Similar to UserA, this user had previously logged in exclusively from the USA, and no other accounts within the digital estate had been observed interacting with the Bangladeshi IP address. The login event appeared to bypass MFA (Multi-factor Authentication) and a suspicious user agent, BAV2ROPC, was used. Against misconfigured accounts, this Microsoft user agent is commonly used by attackers to bypass MFA on Office365. It targets Exchange’s Basic Authentication (normally used in POP3/IMAP4 conditions) and results in an OAuth flow which circumvents the additional password security brought by MFA [10].  

During the session, additional resources were accessed which appear to be associated with bill and invoice payments. In addition, on the 4th November, two new suspicious email rules named “..” were created from rare IPs (107.10.56[.]48 and 76.189.202[.]66). This type of behavior is commonly seen during SaaS compromises to delete or forward emails. Typically, an email rule created by a human user will be named to reflect the change being made, such as ‘Move emails from Legal to Urgent’. In contrast, malicious email rules are often short and undescriptive. The rule “..” is likely to blend in without arousing suspicion, while also being easy for the attacker to create and remember. 

Details of these rule changes are as follows:

·      Time: 2021-11-04 13:25:06, 2021-11-05 15:50:00 [UTC]
·      SaaS Service: Office365
·      SaaS Service Product: Exchange
·      SaaS Status Message: True
·      SaaS Source IP addresses: 107.10.56[.]48, 76.189.202[.]66
·      SaaS Account Name: O365
·      SaaS Actor: UserB@[REDACTED]
·      SaaS Event: SetInboxRule
·      SaaS Office365 Modified Property Names:
          o   AlwaysDeleteOutlookRulesBlob, Force, Identity, MoveToFolder, Name, FromAddressContainsWords, StopProcessingRules
          o   AlwaysDeleteOutlookRulesBlob, Force, Identity, Name, FromAddressContainsWords, StopProcessingRules
·      SaaS Resource Name: .. 

During cloud account compromises, attackers will often use sync operations to download emails to their local email client. During the operations, these clients typically download a large set of mail items from the cloud to a local computer. If the attacker is able to sync all mail items to their mail client, the entire mailbox can be compromised. The attacker is able to disconnect from the account and review and search the email without generating additional event logs. 

Both accounts UserA and UserB were observed using ‘MailItemsAccessed’ sync operations between the 1st and 23rd November when this attack occurred. However, based on the originating IP of the sync operations, the activity is likely to have been initiated by the legitimate, US-based users. Once the security team were able to confirm the events were expected and legitimate, they could establish that the contents of the mailbox were not a part of the data breach. 

Accomplish Mission

After gaining access to the Office365 accounts, sensitive data was downloaded by the attackers to their local system. Either on or before 14th December, the attacker had seemingly uploaded the documents onto a data leak website. In total, 130MB of data had been made available for download in two separate packages. The packages included audit and accounting financial documents, with file extensions such as DB, XLSX, and PDF.

Figure 4: The two data packages uploaded by the attacker and the extracted contents

In a sample of past SaaS activity of UserA, the subject and attachments appear related to the ‘OUTSTANDING PREPAY WIRES 2021’ excel document found from the data leak website in Figure 4, suggesting a further possibility that the account was associated with the leaked data. 

Historic SaaS activity associated with UserA: 

·      Time: 2021-11-05 21:21:18 [UTC]
·      SaaS Office365 Logon Type: Owner
·      Protocol: OFFICE365
·      SaaS Account Name: O365
·      SaaS Actor: UserA@[REDACTED].com
·      SaaS Event: Send
·      SaaS Service: Office365
·      SaaS Service Product: Exchange
·      SaaS Status Message: Succeeded
·      SaaS Office365 Attachment: WIRE 2021.xlsx (92406b); image.png (9084b); image.png (1454b); image.png (1648b); image.png (1691b); image.png (1909b); image.png (2094b)
·      SaaS Office365 Subject: Wires 11/8/21
·      SaaS Resource Location: \Drafts
·      SaaS User Agent: Client=OWA;Action=ViaProxy 

Based on the available evidence, it is highly likely that the data packages contain the data stolen during the account compromise the previous month.  

Once the credentials of an Office365 account are stolen, an attacker can not only access the user's mailbox, but also a full range of Office365 applications such as SharePoint folders, Teams Chat, or files in the user's OneDrive [11]. For example, files shared in Teams chat are stored in OneDrive for Business in a folder named Microsoft Teams Chat Files in the default Document library on SharePoint. One of the files visible on the data leak website, called ‘[REDACTED] CONTRACT.3.1.2020.pdf’, was also observed in the default document folder of a third user account (UserC) within the victim organization, suggesting the compromised accounts may have been able to access shared files stored on other accounts by moving laterally via other O365 applications such as Teams. 

One example can be seen in the below AS logs: 

·      Time: 2021-11-11 01:58:35 [UTC]
·      SaaS Resource Type: File
·      Protocol: OFFICE365
·      SaaS Account Name: 0365
·      SaaS Actor: UserC@[REDACTED]
·      SaaS Event: FilePreviewed
·      SaaS Service Product: OneDrive
·      SaaS Metric: ResourceViewed
·      SaaS Office365 Application Name: Media Analysis and Transformation Service
·      SaaS Office365 File Extension: pdf
·      SaaS Resource Location: https://[REDACTED]-my.sharepoint.com/personal/userC_[REDACTED]_com/Documents/Microsoft Teams Chat Files/[REDACTED] CONTRACT 3.1.2020.pdf
·      SaaS Resource Name: [REDACTED] CONTRACT 3.1.2020.pdf
·      SaaS Service: Office365
·      SaaS Service Product: OneDrive
·      SaaS User Agent: OneDriveMpc-Transform_Thumbnail/1.0 

In the period between the 1st and 30th November, the customer’s Darktrace DETECT/Apps trial had raised multiple high-level alerts associated with SaaS account compromise, but there was no evidence of file encryption.  

Establish Foothold 

Looking back at the start of the attack, it is unclear exactly how the attacker evaded the customer’s pre-existing security stack. At the time of the incident, the victim was using a Barracuda email gateway and Microsoft 365 Threat Management for their cloud environment. 

Darktrace detected no indication the accounts were compromised via credential bruteforcing, which would have enabled the attacker to bypass the Azure Active Directory smart lockout (if enabled). The credentials may have been harvested via a phishing campaign which successfully evaded the list of known ‘bad’ domains maintained by their email gateway.  

Upon gaining access to the account, the Microsoft Defender for Cloud Apps anomaly detection policies would have been expected to raise an alert [12]. In this instance, the unusual login from Nigeria occurred over 16 hours after the previous login from the US, potentially evading anomaly detection policies such as the ‘Impossible Travel’ rule. 

Figure 5: Event log showing the user accessing mail from USA a day before the suspicious usage from Nigeria 

Darktrace Coverage

Darktrace DETECT 

Throughout this event, high scoring model breaches associated with the attack were visible in the customer’s SaaS Console. In addition, there were two Cyber AI Analyst incidents for ‘Possible Account Hijack’ associated with the two compromised SaaS Office365 accounts, UserA and UserB. The visibility given by Darktrace DETECT also enabled the security team to confirm which files had been accessed and were likely part of the data leak.

Figure 6: Example Cyber AI Analyst incident of UserB SaaS Office365 account

Darktrace RESPOND

In this incident, the attackers successfully compromised O365 accounts in order to exfiltrate customer data. Whilst Darktrace RESPOND/Apps was being trialed and suggested several actions, it was configured in human confirmation mode. The following RESPOND/Apps actions were advised for these activities:  

·      ‘Antigena [RESPOND] Unusual Access Block’ triggered by the successful login from an unusual IP address, would have actioned the ‘Block IP’ inhibitor, preventing access to the account from the unusual IP for up to 24 hours
·      ‘Suspicious Source Activity Block’, triggered by the suspicious user agent used to bypass MFA, would have actioned the ‘Disable User’ inhibitor, disabling the user account for up to 24 hours 

During this incident, Darktrace RESPOND/Network was being used in fully autonomous mode in order to prevent the threat actor from pivoting into the network. The security team were unable to conclusively say if any attempts by the attacker to do this had been made. 

Concluding Thoughts  

Data theft extortion has become a widely used attack technique, and ransomware gangs may increasingly use this technique alone to target organizations without secure data encryption and storage policies.  

This case study describes a SaaS data theft extortion incident which bypassed MFA and existing security tools. The attacker appeared to compromise credentials without bruteforce activity, possibly with the use of social engineering through phishing. However, from the first new login, Darktrace DETECT identified the unusual credential use in spite of it being an existing account. Had Darktrace RESPOND/Apps been configured, it would have autonomously responded to halt this login and prevent the attacker from accomplishing their data theft mission.

Thanks to Oakley Cox, Brianna Leddy and Shuh Chin Goh for their contributions.

Appendices

References 

[1] https://securelist.com/new-ransomware-trends-in-2022/106457/

[2] https://www.itpro.co.uk/security/ransomware/367624/the-rise-of-double-extortion-ransomware

[3] https://www.malwarebytes.com/blog/news/2020/10/vastaamo-psychotherapy-data-breach-sees-the-most-vulnerable-victims-extorted

[4] https://www.blackfog.com/shift-from-ransomware-to-data-theft-extortion/

[5] https://www.abuseipdb.com/check/105.112.59.83

[6] https://www.abuseipdb.com/check/105.112.36.212

[7] https://www.abuseipdb.com/check/45.130.83.129

[8] https://docs.microsoft.com/en-us/microsoft-365/compliance/mailitemsaccessed-forensics-investigations?view=o365-worldwide

[9] https://www.abuseipdb.com/check/45.135.187.108

[10] https://www.virustotal.com/gui/ip-address/45.137.20.65/details

[11] https://tidorg.com/new-bec-phishing-attack-steals-office-365-credentials-and-bypasses-mfa/

[12] https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/responding-to-a-compromised-email-account?view=o365-worldwide

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
Adrianne Marques
Senior Research Analyst

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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.

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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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