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December 15, 2025

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

During a customer trial of Darktrace / EMAIL and Darktrace / IDENTITY, Darktrace detected an adversary-in-the-middle (AiTM) attack that compromised a user’s Office 365 account via a business email compromise (BEC) phishing email. Following the breach, the compromised account was used to launch both internal and external phishing campaigns.
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
Ryan Traill
Analyst Content Lead
Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with DarktraceDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
15
Dec 2025

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

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
Ryan Traill
Analyst Content Lead

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March 26, 2026

Phantom Footprints: Tracking GhostSocks Malware

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Why are attackers using residential proxies?

In today's threat landscape, blending in to normal activity is the key to success for attackers and the growing reliance on residential proxies shows a significant shift in how threat actors are attempting to bypass IP detection tools.

The increasing dependency on residential proxies has exposed how prevalent proxy services are and how reliant a diverse range of threat actors are on them. From cybercriminal groups to state‑sponsored actors, the need to bypass IP detection tools is fundamental to the success of these groups. One malware that has quietly become notorious for its ability to avoid anomaly detection is GhostSocks, a malware that turns compromised devices into residential proxies.

What is GhostSocks?

Originally marketed on the Russian underground forum xss[.]is as a Malware‑as‑a‑Service (MaaS), GhostSocks enables threat actors to turn compromised devices into residential proxies, leveraging the victim's internet bandwidth to route malicious traffic through it.

How does Ghostsocks malware work? 

The malware offers the threat actor a “clean” IP address, making it look like it is coming from a household user. This enables the bypassing of geographic restrictions and IP detection tools, a perfect tool for avoiding anomaly detection. It wasn’t until 2024, when a partnership was announced with the infamous information stealer Lumma Stealer, that GhostSocks surged into widespread adoption and alluded to who may be the author of the proxy malware.

Written in GoLang, GhostSocks utilizes the SOCKS5 proxy protocol, creating a SOCKS5 connection on infected devices. It uses a relay‑based C2 implementation, where an intermediary server sits in between the real command-and-control (C2) server and the infected device.

How does Ghostsocks malware evade detection?

To further increase evasion, the Ghostsocks malware wraps its SOCKS5 tunnels in TLS encryption, allowing its malicious traffic to blend into normal network traffic.

Early variants of GhostSocks do not implement a persistence mechanism; however, later versions achieve persistence via registry run keys, ensuring sustained proxy operational time [1].

While proxying is its primary purpose, GhostSocks also incorporates backdoor functionality, enabling malicious actors to run arbitrary commands and download and deploy additional malicious payloads. This was evident with the well‑known ransomware group Black Basta, which reportedly used GhostSocks as a way of maintaining long‑term access to victims’ networks [1].

Darktrace’s detection of GhostSocks Malware

Darktrace observed a steady increase in GhostSocks activity across its customer base from late 2025, with its Threat Research team identifying multiple incidents involving the malware. In one notable case from December 2025, Darktrace detected GhostSocks operating alongside Lumma Stealer, reinforcing that the partnership between Lumma and GhostSocks remains active despite recent attempts to disrupt Lumma’s infrastructure.

Darktrace’s first detection of GhostSocks‑related activity came when a device on the network of a customer in the education sector began making connections to an endpoint with a suspicious self‑signed certificate that had never been seen on the network before.

The endpoint in question, 159.89.46[.]92 with the hostname retreaw[.]click, has been flagged by multiple open‑source intelligence (OSINT) sources as being associated with Lumma Stealer’s C2 infrastructure [2], indicating its likely role in the delivery of malicious payloads.

Darktrace’s detection of suspicious SSL connections to retreaw[.]click, indicating an attempted link to Lumma C2 infrastructure.
Figure 1: Darktrace’s detection of suspicious SSL connections to retreaw[.]click, indicating an attempted link to Lumma C2 infrastructure.

Less than two minutes later, Darktrace observed the same device downloading the executable (.exe) file “Renewable.exe” from the IP 86.54.24[.]29, which Darktrace recognized as 100% rare for this network.

Darktrace’s detection of a device downloading the unusual executable file “Renewable.exe”.
Figure 2: Darktrace’s detection of a device downloading the unusual executable file “Renewable.exe”.

Both the file MD5 hash and the executable itself have been identified by multiple OSINT vendors as being associated with the GhostSocks malware [3], with the executable likely the backdoor component of the GhostSocks malware, facilitating the distribution of additional malicious payloads [4].

Following this detection, Darktrace’s Autonomous Response capability recommended a blocking action for the device in an early attempt to stop the malicious file download. In this instance, Darktrace was configured in Human Confirmation Mode, meaning the customer’s security team was required to manually apply any mitigative response actions. Had Autonomous Response been fully enabled at the time of the attack, the connections to 86.54.24[.]29 would have been blocked, rendering the malware ineffective at reaching its C2 infrastructure and halting any further malicious communication.

 Darktrace’s Autonomous Response capability suggesting blocking the suspicious connections to the unusual endpoint from which the malicious executable was downloaded.
Figure 3: Darktrace’s Autonomous Response capability suggesting blocking the suspicious connections to the unusual endpoint from which the malicious executable was downloaded.

As the attack was able to progress, two days later the device was detected downloading additional payloads from the endpoint www.lbfs[.]site (23.106.58[.]48), including “Setup.exe”, “,.exe”, and “/vp6c63yoz.exe”.

Darktrace’s detection of a malicious payload being downloaded from the endpoint www.lbfs[.]site.
Figure 4: Darktrace’s detection of a malicious payload being downloaded from the endpoint www.lbfs[.]site.

Once again, Darktrace recognized the anomalous nature of these downloads and suggested that a “group pattern of life” be enforced on the offending device in an attempt to contain the activity. By enforcing a pattern of life on a device, Darktrace restricts its activity to connections and behaviors similar to those performed by peer devices within the same group, while still allowing it to carry out its expected activity, effectively preventing deviations indicative of compromise while minimizing disruption. As mentioned earlier, these mitigative actions required manual implementation, so the activity was able to continue. Darktrace proceeded to suggest further actions to contain subsequent malicious downloads, including an attempt to block all outbound traffic to stop the attack from progressing.

An overview of download activity and the Autonomous Response actions recommended by Darktrace to block the downloads.
Figure 5: An overview of download activity and the Autonomous Response actions recommended by Darktrace to block the downloads.

Around the same time, a third executable download was detected, this time from the hostname hxxp[://]d2ihv8ymzp14lr.cloudfront.net/2021-08-19/udppump[.]exe, along with the file “udppump.exe”.While GhostSocks may have been present only to facilitate the delivery of additional payloads, there is no indication that these CloudFront endpoints or files are functionally linked to GhostSocks. Rather, the evidence points to broader malicious file‑download activity.

Shortly after the multiple executable files had been downloaded, Darktrace observed the device initiating a series of repeated successful connections to several rare external endpoints, behavior consistent with early-stage C2 beaconing activity.

Cyber AI Analyst’s investigation

Darktrace’s detection of additional malicious file downloads from malicious CloudFront endpoints.
Figure 7: Darktrace’s detection of additional malicious file downloads from malicious CloudFront endpoints.

Throughout the course of this attack, Darktrace’s Cyber AI Analyst carried out its own autonomous investigation, piecing together seemingly separate events into one wider incident encompassing the first suspicious downloads beginning on December 4, the unusual connectivity to many suspicious IPs that followed, and the successful beaconing activity observed two days later. By analyzing these events in real-time and viewing them as part of the bigger picture, Cyber AI Analyst was able to construct an in‑depth breakdown of the attack to aid the customer’s investigation and remediation efforts.

Cyber AI Analyst investigation detailing the sequence of events on the compromised device, highlighting its extensive connectivity to rare endpoints, the related malicious file‑download activity, and finally the emergence of C2 beaconing behavior.
Figure 8: Cyber AI Analyst investigation detailing the sequence of events on the compromised device, highlighting its extensive connectivity to rare endpoints, the related malicious file‑download activity, and finally the emergence of C2 beaconing behavior.

Conclusion

The versatility offered by GhostSocks is far from new, but its ability to convert compromised devices into residential proxy nodes, while enabling long‑term, covert network access—illustrates how threat actors continue to maximise the value of their victims’ infrastructure. Its growing popularity, coupled with its ongoing partnership with Lumma, demonstrates that infrastructure takedowns alone are insufficient; as long as threat actors remain committed to maintaining anonymity and can rapidly rebuild their ecosystems, related malware activity is likely to persist in some form.

Credit to Isabel Evans (Cyber Analyst), Gernice Lee (Associate Principal Analyst & Regional Consultancy Lead – APJ)
Edited by Ryan Traill (Content Manager)

Appendices

References

1.    https://bloo.io/research/malware/ghostsocks

2.    https://www.virustotal.com/gui/domain/retreaw.click/community

3.    https://synthient.com/blog/ghostsocks-from-initial-access-to-residential-proxy

4.    https://www.joesandbox.com/analysis/1810568/0/html

5. https://www.virustotal.com/gui/url/fab6525bf6e77249b74736cb74501a9491109dc7950688b3ae898354eb920413

Darktrace Model Detections

Real-time Detection Models

Anomalous Connection / Suspicious Self-Signed SSL

Anomalous Connection / Rare External SSL Self-Signed

Anomalous File / EXE from Rare External Location

Anomalous File / Multiple EXE from Rare External Locations

Compromise / Possible Fast Flux C2 Activity

Compromise / Large Number of Suspicious Successful Connections

Compromise / Large Number of Suspicious Failed Connections

Compromise / Sustained SSL or HTTP Increase

Autonomous Response Models

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

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

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

Antigena / Network / Significant Anomaly / Antigena Alerts Over Time Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

MITRE ATT&CK Mapping

Tactic – Technique – Sub-Technique

Resource Development – T1588 - Malware

Initial Access - T1189 - Drive-by Compromise

Persistence – T1112 – Modify Registry

Command and Control – T1071 – Application Layer Protocol

Command and Control – T1095 – Non-application Layer Protocol

Command and Control – T1071 – Web Protocols

Command and Control – T1571 – Non-Standard Port

Command and Control – T1102 – One-Way Communication

List of Indicators of Compromise (IoCs)

86.54.24[.]29 - IP - Likely GhostSocks C2

http[://]86.54.24[.]29/Renewable[.]exe - Hostname - GhostSocks Distribution Endpoint

http[://]d2ihv8ymzp14lr.cloudfront[.]net/2021-08-19/udppump[.]exe - CDN - Payload Distribution Endpoint

www.lbfs[.]site - Hostname - Likely C2 Endpoint

retreaw[.]click - Hostname - Lumma C2 Endpoint

alltipi[.]com - Hostname - Possible C2 Endpoint

w2.bruggebogeyed[.]site - Hostname - Possible C2 Endpoint

9b90c62299d4bed2e0752e2e1fc777ac50308534 - SHA1 file hash – Likely GhostSocks payload

3d9d7a7905e46a3e39a45405cb010c1baa735f9e - SHA1 file hash - Likely follow-up payload

10f928e00a1ed0181992a1e4771673566a02f4e3 - SHA1 file hash - Likely follow-up payload

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About the author
Gernice Lee
Associate Principal Analyst & Regional Consultancy Lead

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March 24, 2026

Darktrace Unites Human Behavior and Threat Detection Across Email, Slack, Teams, and Zoom

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The communication attack surface is expanding

Modern attackers no longer focus solely on inboxes, they target people and the productivity systems where work actually happens. Meanwhile, the boundary between internal and external usage of tools is becoming blurrier everyday – turning the entire workplace into the attack surface. In 2025, identity compromise emerged as the single most consistent threat across the global threat landscape, as observed by Darktrace research across our entire customer base. Over 70% of incidents in the US involved SaaS/M365 account compromise and phishing or email-based social engineering, making credential abuse the single most effective initial access vector.

Despite this upward trend, investment in existing security awareness training (SAT) isn’t moving the needle on reducing risk. 84% of organizations still measure success through completion rates1, even though completion of standard training correlates with less than 2% real improvement in risky behavior.2 By prioritizing completion, organizations reward time spent rather than meaningful engagement, yet time in training doesn’t translate to retention or real-world decision-making. This compliance-first approach has left the workforce unprepared for the threats they actually face.

At the same time, attacks have evolved. Highly personalized, AI-generated campaigns now move fluidly across email, Slack, Teams, Zoom, and beyond, blending channels and even targeting systems directly through techniques like prompt injection. This new reality demands a different approach: one that treats people and the tools they use as a single ecosystem, where behavior and detection continuously inform and strengthen each other.

Only an adaptive communication security system can keep pace with the speed, creativity, and cross channel nature of today’s threats. 

Ushering in the adaptive era of workplace security

With this release, Darktrace brings together our new behavior-driven training solution with email detection, cross-channel visibility, and platform-level insights. Powered by Self-Learning AI, it delivers protection across both people and the communication tools they rely on every day, including email, Slack, Teams, and Zoom.

Each component learns from the others – training adapts to real user behavior, detection evolves across channels, and response is continuously refined – creating a powerful feedback loop that strengthens resilience and improves accuracy against today’s AI-driven threats.

Introducing: Unified training and email security for a self-improving email defense

Our brand new product, Darktrace / Adaptive Human Defense, closes the gap between human behavior and email security to continuously strengthen both people and defenses. Each user receives personalized training that adapts to their own inbox activity and skill level, with learning delivered directly within the flow of their day-to-day email interactions.

By learning from each user’s interactions with security training, it adapts security responses, creating a closed-loop system where training reinforces detection and detection informs training. Let’s look at some of the benefits.

  • Reduce successful phishing at the source with contextual Just in Time coaching: Contextual coaching appears directly in real email threads the moment risky behavior is detected, so habits change where mistakes actually happen. Configurable triggers and group policies target the right users, reducing repeated errors and administrative overhead.
  • Adaptive phishing simulations that progress automatically with each user: Embedded simulations vary in their degree of realism, from generic phishing to generative AI-enabled spear phishing. Users progress through the difficulty levels based on their performance to give an accurate picture of their phishing preparedness.  
  • Native email security integration turns human behavior into quantified risk: The native email security integration allows engagement, links clicked, and question success signals to flow back into / EMAIL recipes and models, so detection and response adapt automatically as users learn.  
  • Actionable risk and trend analytics beyond completion rates: Analytics that surface repeat offenders, high-value targets, and measurable exposure, moving beyond completion metrics to give leaders actionable insights tied to real behavior.

Learn more about / Adaptive Human Defense in the product solution brief.

Industry-first cross-channel full-message analysis for email, Slack, Teams, and Zoom

Darktrace now brings full-message analysis to Email, Slack, Teams, Zoom, and even generative AI prompts. The same leading behavioral analysis from EMAIL extends to every message, tracing intent, tone, relationships, and conversation flow across all communication activity for a complete understanding of every user interaction.

By correlating messaging and collaboration activity with email and account environments, cross-channel analysis reveals multi-domain attack paths and follows both users and threats as a single, continuous narrative – delivering better context to improve detection across the entire organization.

  • Eliminate cross-channel blind spots: Detect phishing, malware, account takeovers, and conversational manipulation across email and collaboration platforms, so attackers can’t exploit Slack, Teams, or Zoom as a new entry point. Unified behavioral analysis gives security teams a coherent, single view, for no more fragmented, channel-specific gaps.
  • Spot generative AI prompt injection attacks before they manipulate assistants: Dedicated models surface threats targeting corporate AI assistants – like ShadowLeak and Hashjack – before they can silently manipulate workflows, reducing risk before static filters catch up.

Learn more about Darktrace’s messaging security offering in the product solution brief.

Industry-first DMARC with bi-directional ASM and email security integration

Darktrace transforms domain protection by linking DMARC, attack surface intelligence, and email security into a single, continuously evolving workflow. Instead of treating domain authentication and exposure as separate tasks, this unified approach shows not just where domains are vulnerable, but how attackers are actively exploiting them.

  • Fix authentication weaknesses faster: SPF, DKIM, DMARC configurations, and external exposure data are analyzed together, giving teams clear guidance to correct weaknesses before they can be abused. Deep bidirectional integration with attack surface intelligence reduces impersonation risk at the source.
  • Accelerate email investigations: DMARC context is embedded directly into email workflows, enriching triage with authentication posture, internal/external sender lists, and seamless pivots between email and domain intelligence for faster, more accurate investigations.

Committed to innovation

These updates are part of a broader Darktrace release, which also includes:

Join our Live Launch Event on April 14, 2026.

Join us for an exclusive announcement event where Darktrace, the leader in AI-native cybersecurity, will be announcing our latest innovations, including  a demo of our new product / Adaptive Human Defense, an exclusive conversation with a Darktrace customer, and a deep dive into the Darktrace ActiveAI Security Portal.  

Register here.

References

[1] 84% of organizations still measure security awareness training success through completion rates, a vanity metric with no correlation to behavior change. (Source:  NIST Awareness Effectiveness Study, Forrester 2025)

[2] 'Limited benefit from embedded phishing training. Using randomized controlled trials and statistical modeling, embedded training provides a statistically-significant reduction in average failure rate, but of only 2%.' Ho, G., Mirian, A., Luo, E., Tong, K., Lee, E., Liu, L., Longhurst, C. A., Dameff, C., Savage, S., & Voelker, G. M. (2025). Understanding the Efficacy of Phishing Training in Practice. Proceedings of the 2025 IEEE Symposium on Security and Privacy.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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