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May 10, 2024

Exploitation of ConnectWise ScreenConnect Vulnerabilities

Uncover the tactics used to exploit ConnectWise vulnerabilities and strategies to protect your systems.
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 Torres
Cyber Analyst
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10
May 2024

Introduction

Across an ever changing cyber landscape, it is common place for threat actors to actively identify and exploit newly discovered vulnerabilities within commonly utilized services and applications. While attackers are likely to prioritize developing exploits for the more severe and global Common Vulnerabilities and Exposures (CVEs), they typically have the most success exploiting known vulnerabilities within the first couple years of disclosure to the public.

Addressing these vulnerabilities in a timely manner reduces the effectiveness of known vulnerabilities, decreasing the pace of malicious actor operations and forcing pursuit of more costly and time-consuming methods, such as zero-day related exploits or attacking software supply chain operations. While actors also develop tools to exploit other vulnerabilities, developing exploits for critical and publicly known vulnerabilities gives actors impactful tools at a low cost they are able to use for quite some time.

Between January and March 2024, the Darktrace Threat Research team investigated one such example that involved indicators of compromise (IoCs) suggesting the exploitation of vulnerabilities in ConnectWise’s remote monitoring and management (RMM) software ScreenConnect.

What are the ConnectWise ScreenConnect vulnerabilities?

CVE-2024-1708 is an authentication bypass vulnerability in ScreenConnect 23.9.7 (and all earlier versions) that, if exploited, would enable an attacker to execute remote code or directly impact confidential information or critical systems. This exploit would pave the way for a second ScreenConnect vunerability, CVE-2024-1709, which allows attackers to directly access confidential information or critical systems [1].

ConnectWise released a patch and automatically updated cloud versions of ScreenConnect 23.9.9, while urging security temas to update on-premise versions immediately [3].

If exploited in conjunction, these vulnerabilities could allow a malicious actor to create new administrative accounts on publicly exposed instances by evading existing security measures. This, in turn, could enable attackers to assume an administrative role and disable security tools, create backdoors, and disrupt RMM processes. Access to an organization’s environment in this manner poses serious risk, potentially leading to significant consequences such as deploying ransomware, as seen in various incidents involving the exploitation of ScreenConnect [2]

Darktrace Coverage of ConnectWise Exploitation

Darktrace’s anomaly-based detection was able to identify evidence of exploitation related to CVE-2024-1708 and CVE-2024-1709 across two distinct timelines; these detections included connectivity with endpoints that were later confirmed to be malicious by multiple open-source intelligence (OSINT) vendors. The activity observed by Darktrace suggests that threat actors were actively exploiting these vulnerabilities across multiple customer environments.

In the cases observed across the Darktrace fleet, Darktrace DETECT™ and Darktrace RESPOND™ were able to work in tandem to pre-emptively identify and contain network compromises from the onset. While Darktrace RESPOND was enabled in most customer environments affected by the ScreenConnect vulnerabilities, in the majority of cases it was configured in Human Confirmation mode. Whilst in Human Confirmation mode, RESPOND will provide recommended actions to mitigate ongoing attacks, but these actions require manual approval from human security teams.

When enabled in autonomous response mode, Darktrace RESPOND will take action automatically, shutting down suspicious activity as soon as it is detected without the need for human intervention. This is the ideal end state for RESPOND as actions can be taken at machine speed, without any delays waiting for user approval.

Looking within the patterns of activity observed by Darktrace , the typical  attack timeline included:

Darktrace observed devices on affected customer networks performing activity indicative of ConnectWise ScreenConnect usage, for example connections over 80 and 8041, connections to screenconnect[.]com, and the use of the user agent “LabTech Agent”. OSINT research suggests that this user agent is an older name for ConnectWise Automate [5] which also includes ScreenConnect as standard [6].

Darktrace DETECT model alert highlighting the use of a remote management tool, namely “screenconnect[.]com”.
Figure 1: Darktrace DETECT model alert highlighting the use of a remote management tool, namely “screenconnect[.]com”.

This activity was typically followed by anomalous connections to the external IP address 108.61.210[.]72 using URIs of the form “/MyUserName_DEVICEHOSTNAME”, as well as additional connections to another external, IP 185.62.58[.]132. Both of these external locations have since been reported as potentially malicious [14], with 185.62.58[.]132 in particular linked to ScreenConnect post-exploitation activity [2].

Figure 2: Darktrace DETECT model alert highlighting the unusual connection to 185.62.58[.]132 via port 8041.
Figure 2: Darktrace DETECT model alert highlighting the unusual connection to 185.62.58[.]132 via port 8041.
Figure 3: Darktrace DETECT model alert highlighting connections to 108.61.210[.]72 using a new user agent and the “/MyUserName_DEVICEHOSTNAME” URI.
Figure 3: Darktrace DETECT model alert highlighting connections to 108.61.210[.]72 using a new user agent and the “/MyUserName_DEVICEHOSTNAME” URI.

Same Exploit, Different Tactics?  

While the majority of instances of ConnectWise ScreenConnect exploitation observed by Darktrace followed the above pattern of activity, Darktrace was able to identify some deviations from this.

In one customer environment, Darktrace’s detection of post-exploitation activity began with the same indicators of ScreenConnect usage, including connections to screenconnect[.]com via port 8041, followed by connections to unusual domains flagged as malicious by OSINT, in this case 116.0.56[.]101 [16] [17]. However, on this deployment Darktrace also observed threat actors downloading a suspicious AnyDesk installer from the endpoint with the URI “hxxp[:]//116.0.56[.]101[:]9191/images/Distribution.exe”.

Figure 4: Darktrace DETECT model alert highlighting the download of an unusual executable file from 116.0.56[.]101.
Figure 4: Darktrace DETECT model alert highlighting the download of an unusual executable file from 116.0.56[.]101.

Further investigation by Darktrace’s Threat Research team revealed that this endpoint was associated with threat actors exploiting CVE-2024-1708 and CVE-2024-1709 [1]. Darktrace was additionally able to identify that, despite the customer being based in the United Kingdom, the file downloaded came from Pakistan. Darktrace recognized that this represented a deviation from the device’s expected pattern of activity and promptly alerted for it, bringing it to the attention of the customer.

Figure 5: External Sites Summary within the Darktrace UI pinpointing the geographic locations of external endpoints, in this case highlighting a file download from Pakistan.
Figure 5: External Sites Summary within the Darktrace UI pinpointing the geographic locations of external endpoints, in this case highlighting a file download from Pakistan.

Darktrace’s Autonomous Response

In this instance, the customer had Darktrace enabled in autonomous response mode and the post-exploitation activity was swiftly contained, preventing the attack from escalating.

As soon as the suspicious AnyDesk download was detected, Darktrace RESPOND applied targeted measures to prevent additional malicious activity. This included blocking connections to 116.0.56[.]101 and “*.56.101”, along with blocking all outgoing traffic from the device. Furthermore, RESPOND enforced a “pattern of life” on the device, restricting its activity to its learned behavior, allowing connections that are considered normal, but blocking any unusual deviations.

Figure 6: Darktrace RESPOND enforcing a “pattern of life” on the offending device after detecting the suspicious AnyDesk download.
Figure 6: Darktrace RESPOND enforcing a “pattern of life” on the offending device after detecting the suspicious AnyDesk download.
Figure 7: Darktrace RESPOND blocking connections to the suspicious endpoint 116.0.56[.]101 and “*.56.101” following the download of the suspicious AnyDesk installer.
Figure 7: Darktrace RESPOND blocking connections to the suspicious endpoint 116.0.56[.]101 and “*.56.101” following the download of the suspicious AnyDesk installer.

The customer was later able to use RESPOND to manually quarantine the offending device, ensuring that all incoming and outgoing traffic to or from the device was prohibited, thus preventing ay further malicious communication or lateral movement attempts.

Figure 8: The actions applied by Darktrace RESPOND in response to the post-exploitation activity related to the ScreenConnect vulnerabilities, including the manually applied “Quarantine device” action.

Conclusion

In the observed cases of the ConnectWise ScreenConnect vulnerabilities being exploited across the Darktrace fleet, Darktrace was able to pre-emptively identify and contain network compromises from the onset, offering vital protection against disruptive cyber-attacks.

While much of the post-exploitation activity observed by Darktrace remained the same across different customer environments, important deviations were also identified suggesting that threat actors may be adapting their tactics, techniques and procedures (TTPs) from campaign to campaign.

While new vulnerabilities will inevitably surface and threat actors will continually look for novel ways to evolve their methods, Darktrace’s Self-Learning AI and behavioral analysis offers organizations full visibility over new or unknown threats. Rather than relying on existing threat intelligence or static lists of “known bads”, Darktrace is able to detect emerging activity based on anomaly and respond to it without latency, safeguarding customer environments whilst causing minimal disruption to business operations.

Credit: Emma Foulger, Principal Cyber Analyst for their contribution to this blog.

Appendices

Darktrace Model Coverage

DETECT Models

Compromise / Agent Beacon (Medium Period)

Compromise / Agent Beacon (Long Period)

Anomalous File / EXE from Rare External Location

Device / New PowerShell User Agent

Anomalous Connection / Powershell to Rare External

Anomalous Connection / New User Agent to IP Without Hostname

User / New Admin Credentials on Client

Device / New User Agent

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Compromise / Suspicious Request Data

Compliance / Remote Management Tool On Server

Anomalous File / Anomalous Octet Stream (No User Agent)

RESPOND Models

Antigena / Network::External Threat::Antigena Suspicious File Block

Antigena / Network::External Threat::Antigena File then New Outbound Block

Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block

Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block

Antigena / Network::Significant Anomaly::Antigena Controlled and Model Breach

Antigena / Network::Insider Threat::Antigena Unusual Privileged User Activities Block

Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Pattern of Life Block

List of IoCs

IoC - Type - Description + Confidence

185.62.58[.]132 – IP- IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

108.61.210[.]72- IP - IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

116.0.56[.]101    - IP - IP linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

/MyUserName_ DEVICEHOSTNAME – URI - URI linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

/images/Distribution.exe – URI - URI linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

24780657328783ef50ae0964b23288e68841a421 - SHA1 Filehash - Filehash linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

a21768190f3b9feae33aaef660cb7a83 - MD5 Filehash - Filehash linked with threat actors exploiting CVE-2024-1708 and CVE-2024-17091

MITRE ATT&CK Mapping

Technique – Tactic – ID - Sub-technique of

Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

Web Services      - RESOURCE DEVELOPMENT - T1583.006 - T1583

Drive-by Compromise - INITIAL ACCESS - T1189 – NA

Ingress Tool Transfer   - COMMAND AND CONTROL - T1105 - NA

Malware - RESOURCE DEVELOPMENT - T1588.001- T1588

Exploitation of Remote Services - LATERAL MOVEMENT - T1210 – NA

PowerShell – EXECUTION - T1059.001 - T1059

Pass the Hash      - DEFENSE EVASION, LATERAL MOVEMENT     - T1550.002 - T1550

Valid Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078 – NA

Man in the Browser – COLLECTION - T1185     - NA

Exploit Public-Facing Application - INITIAL ACCESS - T1190         - NA

Exfiltration Over C2 Channel – EXFILTRATION - T1041 – NA

IP Addresses – RECONNAISSANCE - T1590.005 - T1590

Remote Access Software - COMMAND AND CONTROL - T1219 – NA

Lateral Tool Transfer - LATERAL MOVEMENT - T1570 – NA

Application Layer Protocol - COMMAND AND CONTROL - T1071 – NA

References:

[1] https://unit42.paloaltonetworks.com/connectwise-threat-brief-cve-2024-1708-cve-2024-1709/  

[2] https://www.huntress.com/blog/slashandgrab-screen-connect-post-exploitation-in-the-wild-cve-2024-1709-cve-2024-1708    

[3] https://www.huntress.com/blog/a-catastrophe-for-control-understanding-the-screenconnect-authentication-bypass

[4] https://www.speedguide.net/port.php?port=8041  

[5] https://www.connectwise.com/company/announcements/labtech-now-connectwise-automate

[6] https://www.connectwise.com/solutions/software-for-internal-it/automate

[7] https://www.securityweek.com/slashandgrab-screenconnect-vulnerability-widely-exploited-for-malware-delivery/

[8] https://arcticwolf.com/resources/blog/cve-2024-1709-cve-2024-1708-follow-up-active-exploitation-and-pocs-observed-for-critical-screenconnect-vulnerabilities/https://success.trendmicro.com/dcx/s/solution/000296805?language=en_US&sfdcIFrameOrigin=null

[9] https://www.connectwise.com/company/trust/security-bulletins/connectwise-screenconnect-23.9.8

[10] https://socradar.io/critical-vulnerabilities-in-connectwise-screenconnect-postgresql-jdbc-and-vmware-eap-cve-2024-1597-cve-2024-22245/

[11] https://www.trendmicro.com/en_us/research/24/b/threat-actor-groups-including-black-basta-are-exploiting-recent-.html

[12] https://otx.alienvault.com/indicator/ip/185.62.58.132

[13] https://www.virustotal.com/gui/ip-address/185.62.58.132/community

[14] https://www.virustotal.com/gui/ip-address/108.61.210.72/community

[15] https://otx.alienvault.com/indicator/ip/108.61.210.72

[16] https://www.virustotal.com/gui/ip-address/116.0.56[.]101/community

[17] https://otx.alienvault.com/indicator/ip/116.0.56[.]101

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 Torres
Cyber 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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