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April 1, 2023

Cyber Security Threats - Email Compromise With Generative AI

Discover how generative AI is impacting email attacks and what companies can do to prepare for more sophisticated and targeted attacker 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
Max Heinemeyer
Global Field CISO
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01
Apr 2023

Email communications in the era of generative AI

Today’s headlines on cyber security attacks are dominated by serious breaches that cripple critical national infrastructure providers, wreak geopolitical havoc through nation state espionage, and create paralyzing financial demands through extortion and ransomware. But how do these breaches occur in the first place, and why do they keep happening?

Social engineering – specifically malicious cyber campaigns delivered via email - remain the primary source of an organization’s vulnerability to attack. A recent survey conducted by Darktrace to 6,700 global cross-industry professionals across the UK, US, Australia, France, Germany, and Netherlands, found almost a third (30%) have fallen victim to a fraudulent email. The risk, as ever, seems to be uncontrollably on the rise – 70% of respondents have noticed an increase in the frequency of malicious emails in the last six months. 

At the end of last year, I wrote about how widespread accessibility to generative AI has compounded the problem, leading to likely efficiency gains for skilled threat actors launching email attacks. Just a few weeks ago, we published research which demonstrated that while the number of email attacks across our own customer base has remained steady since ChatGPT’s release, those that rely on tricking victims into clicking malicious links have declined, while linguistic complexity, including text volume, punctuation, and sentence length among others, have increased. This indicates that cyber-criminals may be redirecting their focus to crafting more sophisticated social engineering scams that exploit user trust delivered over email. 

Our latest findings, conducted by Darktrace Research, today reveal a 135% increase in ‘novel social engineering attacks’ across thousands of active Darktrace/Email customers from January to February 2023, corresponding with the widespread adoption of ChatGPT. A novel social engineering phishing email is an email attack that shows a strong linguistic deviation – semantically and syntactically – compared to other phishing emails. The trend suggests that generative AI, such as ChatGPT, is providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale.

Organizations are already well aware of the danger novel threats pose – globally, 82% of respondents reported are concerned that hackers can use generative AI to create scam emails that are indistinguishable from genuine communication.

Navigating the trust deficit 

Employees are being exploited continuously through their primary means of communication - email. Given that humans, and our psychology, are at the heart of the problem, organizations have scrambled to develop awareness and training programs that are delivered routinely to employees in an attempt to help them defend themselves and their organization. While a defense-in-depth approach is generally a good practice to follow, the value of security awareness training, teaching employees to spot attempts at social engineering delivered in text format, is diminishing rapidly. This problem has become especially evident now that we find ourselves in a world where ‘bad’ emails look all but undistinguishable to the human eye from ‘good’ emails. 

Over emphasizing the responsibility of employees poses a business challenge as well as a security problem: a bloated trust deficit. In times of economic uncertainty, business success is predicated on employee productivity, creativity, and efficiency. All three of these are squashed when employees treat the communication they receive, both internal and external, with forensic suspicion and mistrust. 

As generative AI becomes more mainstream – across images, audio, video, and text – we anticipate that this erosion of trust in digital communication will only continue. What happens to the workplace if an employee is left questioning their own perception when communicating with their manager or a colleague, who they can see and hear over a video conference call, but who may be an entirely fictitious creation?

The way forward

The future lies in a partnership between artificial intelligence and human beings where the algorithms are responsible for determining whether communication is malicious or benign, thereby taking the burden of responsibility off the human. In turn, humans can pursue activities that drive productivity and performance. Current training and awareness programs, coupled with traditional email security technologies which assume that knowledge of past attacks will help predict campaigns, are not sustainable in this rapidly evolving landscape. 

Our research reveals that traditional email security tools that rely on knowledge of past threats, take an average of thirteen days from an attack being launched on a victim to that attack being detected. This leaves defenders vulnerable for almost two weeks if they rely solely on traditional tools. When this statistic is contextualized against the 135% increase we’ve seen in novel social engineering campaigns, the inefficiency of ‘attack centric’ email security is made perfectly evident. If we don’t know how to define entirely new and unique attacks, how can we ever hope to recognize them based on past attacks? 

A deep understanding of ‘you’ is needed in the face of these radical changes to the email threat landscape. Instead of trying to predict attacks, an understanding of your employees’ behavior, based from their email inbox, is needed to create patterns of life for every email user: their relationships, tone and sentiments and hundreds of other data points. By leveraging AI to combat email security threats, we not only reduce risk, but revitalize organizational trusts and contribute to business outcomes.

Ironically, generative AI may be worsening the social engineering challenge, but AI that knows you, could be the parry. 

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
Max Heinemeyer
Global Field CISO

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September 30, 2026

AI-Assisted Attacks Still Leave a Behavioral Trace  

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Key Insights

  • Darktrace identified behavioral indicators associated with two campaigns linked to AI-assisted threat activity, highlighting the growing role of AI in modern cyber-attacks.
  • Observed activity involved suspicious WebDAV file transfers, disguised executable downloads, beaconing to rare infrastructure, unusual process execution, and communications with C2 infrastructure linked to active intrusion campaigns.

Introduction

Just as organizations are incorporating AI into their operations to take advantage of its benefits, threat actors are doing the same, creating new challenges for defenders.

Much of the discussion around AI risk has focused on the expanding attack surface created by AI systems within organizations. These systems are often granted privileged access and heightened permissions to carry out their duties, introducing new security risks and unintended consequences.

At the same time, threat actors are learning to leverage AI to enable malicious activities such as vulnerability discovery, exploit creation, and progressing through the Cyber Kill Chain more quickly. By accelerating development, adaptation, and scaling, AI enables attackers to operate more efficiently while making some capabilities more accessible to less skilled operators.

Whether AI is the target or the enabler, the resulting activity still manifests through networks, identities, endpoints and cloud services. Those interactions create observable signals that defenders can investigate, regardless of how the attack was developed.

AI as part of the attacker’s workflow

Darktrace has previously documented how threat actors are increasingly incorporating AI into offensive operations [1]. Two recent investigations from open-source intelligence (OSINT) illustrate this. In both cases, researchers identified the role of AI within malicious operations. Separately, Darktrace detected activity in customer environments that aligned with the infrastructure and techniques reported in those campaigns. These perspectives provide a view of both attacker workflow and operational consequences.

Although AI played different roles in each campaign, it did not remove the need for the attackers to interact with their targets. Payloads still had to be delivered, processes executed, and command-and-control (C2) connections established, creating behavioral anomalies that Darktrace was able to identify.

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Case 1: A Mexican government impersonation campaign with LLM-assisted malware development

Rapid7 reported on a malware delivery operation that used generative AI to assist development, testing, documentation and refinement of attacker infrastructure. Between May and June 2026, Darktrace similarly observed two chains of suspicious activity across customer environments in the Americas that exhibited clear similarities in behavior.

In both cases Darktrace observed:

  • WebDAV communication with onedrive[.]cv·138.124.123[.]87, retrieving a file from the path /Downloads/CURP/
  • Transfer of a masqueraded .scr executable
  • Subsequent communication with google.services[.]ug·77.110.127[.]205 over unusual high ports
  • Additional Darktrace detections correlating the unusual behavior seen spanning payload delivery and C2 communication
  • Darktrace’s Autonomous Response capability alerted across multiple stages of the attack

The infrastructure and behavior observed by Darktrace closely aligned with a campaign reported by Rapid7, in which a WebDAV malware delivery environment was exposed. Rapid7 assessed that threat actors had used generative AI to support the development, testing, documentation and refinement of the operation. The observed activity also aligned with reporting on a campaign in which impersonation of Mexico’s government Unique Population Registry Code (CURP) identity-record service led to delivery of PureRAT, a .NET-based information stealer and remote access trojan (RAT) [2]. The infrastructure overlap and consistent behavioural sequence provides strong alignment and offers a view of how an AI-assisted development pipeline ultimately manifested inside target environments.

Case 2: A suspected China-linked intrusion campaign with AI-assisted automation

In July 2026, Hunt.io published research into a suspected China-based intrusion operation targeting government and financial services organizations [3]. Material recovered from exposed attacker infrastructure by Hunt.io indicated that Claude Code and DeepSeek-v4-pro were being used as active components of the attacker’s workflow. According to the research, the models supported activities including attack reasoning, script generation, execution, exploit adaptation, and phishing-page development.

The investigation identified 192.229.115[.]229 and 192.229.115[.]230 as infrastructure associated with suspected TencShell operations and a possible second C2 framework known as Gshell [3].

Darktrace identified likely related activity within a financial services customer environment involving a newly observed laptop running the Windows 11 Pro operating system. Over a six-day period in July, the device made repeated outbound connections to 192.229.115[.]229 over port 8083.

Darktrace recognized the destination was highly rare for the environment, and the connectivity exhibited beaconing characteristics. During the same timeframe, Darktrace also identified suspicious process behavior associated with process chains involving svchost.exe and cmd.exe. The device repeatedly communicated with infrastructure identified in the Hunt.io research while exhibiting beaconing characteristics and suspicious process activity, strengthening the assessment that the activity likely was associated with the same operation.

Unlike many previous examples of AI-assisted cybercrime, the Hunt.io investigation provided rare visibility into how large language models were being incorporated directly into operational workflows rather than being used solely for content generation. Darktrace, meanwhile, observed how activity associated with that operation ultimately manifested inside a target environment, providing a complementary view of its operational impact.

Operational consequences of AI-assisted attacks

These investigations provide two complementary perspectives on AI-assisted cyber operations. OSINT research revealed how AI was incorporated into attacker workflows, while Darktrace observed the resulting activity within customer environments.

Although AI played different roles in each campaign, it did not remove the need for attackers to interact with their targets, deliver payloads, execute processes, and communicate with C2, all of which generated observable signals.

In these cases, Darktrace identified suspicious file delivery, unusual process behavior, beaconing activity, and communication with rare external infrastructure that aligned with campaigns later linked to AI-assisted operations. While AI may influence how attacks are developed, adapted, and scaled, it does not make them operationally invisible.

For defenders, the broader lesson extends beyond these specific campaigns. As AI becomes increasingly embedded within both enterprise operations and attacker workflows, understanding what a model was asked to do is often less important than understanding the actions it ultimately took and the consequences those actions produced. Whether the actor is human, AI-assisted, or increasingly autonomous, activity still manifests through identities, endpoints, applications, cloud services and network infrastructure.

Credit to Angel Arribas Lopez (Associate Principal Cyber Analyst), Emma Foulger (Global Threat Research Operations Lead), Nathaniel Jones, SVP Global Threat Intelligence
Edited by Ryan Traill (Content Manager)

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Appendices

Darktrace Model Detections

Case 1

Anomalous File / Masqueraded File Transfer from New External Endpoint

Anomalous File / Script from Rare External Location

Anomalous File / EXE from Rare External Location

Anomalous File / Script and EXE from Rare External

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Anomalous Connection / Rare External SSL Self-Signed

Compromise / New or Repeated to Unusual SSL Port

Compromise / Large Number of Suspicious Failed Connections

Device / Initial Attack Chain Activity

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

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

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

Case 2

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Compromise / High Volume of Connections with Beacon Score

Compromise / Large Number of Suspicious Failed Connections

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Indicators of Compromise (IoCs)

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Case 1

                                                                                                                                                                                                                                                 
IoCTypeDescription + Confidence
onedrive[.]cvHostnameLikely C2 server
138.124.123[.]87IP AddressPossible C2 server
hXXp://onedrive[.]cv/Downloads/CURP/ReportFinal.%E2%80%AE%E1%BA%9D%D4%81%EF%BD%90.scrURIPossible payload
google.services[.]ugHostnameLikely C2 server
77.110.127[.]205IP AddressLikely C2 server
google.services[.]ug:57666Hostname + PortLikely C2 communication
google.services[.]ug:57888Hostname + PortLikely C2 communication
google.services[.]ug:56001Hostname + PortLikely C2 communication

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Case 2

IoC Type Description + Confidence
192.229.115[.]229 IP Address Likely C2 communication
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About the author
Angel Arribas Lopez
Associate Principal Cyber Analyst

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September 30, 2026

A Chain Reaction: Blockchain-Hosted Infostealer Campaign Targets Windows and macOS

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Key Insights

  • Darktrace detected a blockchain-hosted infostealer campaign targeting Windows and macOS devices across multiple customer environments.
  • The campaign combined ClickFix social engineering with trusted services and decentralized blockchain infrastructure to support malware delivery and C2 activity.
  • Compromised devices were observed connecting to rare and unusual external endpoints, including DGA C2 domains, blockchain-related endpoints, and cryptocurrency mining infrastructure.
  • The activity was associated with information-stealing malware strains including Atomic macOS Stealer (AMOS), Lumma, Rhadamanthys, Vidar, and Phexia.
  • Darktrace identified anomalous device behavior, beaconing patterns, rare external connections, cryptomining activity, and suspicious TLS/SSL communications without relying solely on prior knowledge or static indicators of compromise.
  • The campaign highlights how attackers are increasingly using legitimate and decentralized infrastructure to make detection, disruption, and attribution more challenging for defenders.

The Infostealer Ecosystem

The information stealer malware ecosystem continues to grow in value for threat actors across the digital threat landscape. Infostealers are increasingly delivered through Malware-as-a-Service (MaaS) operating models, distributed through affiliate networks, and designed to withstand infrastructure takedowns. This resilience was demonstrated by the recent takedown of Lumma Stealer malicious domains by Microsoft’s Digital Crimes Unit (DCU) [1].

Infostealers are used to gather and exfiltrate sensitive information, including non-human identity (NHI) data, from compromised systems across cloud, Software-as-a-Service (SaaS), Virtual Private Network (VPN), and development environments. They can also support ransomware operations by expanding the credentials and access paths available to threat actors, contributing to the high volume of identity-based attacks observed across the broader threat landscape [2][3].

Darktrace’s Observations of ClickFix and Infostealers

Throughout 2026, Darktrace has observed multiple campaigns using ClickFix social engineering to trick users into carrying out malicious actions and downloading initial payloads, including information stealers. More recently, Darktrace’s Threat Research team identified a specific ClickFix campaign involving a blockchain-hosted infostealer targeting Windows and macOS devices.

Darktrace identified affected customer environments across Europe, the United States, Asia, and the Middle East where blockchain-hosted infostealer malware appears to have been delivered to compromised systems following likely ClickFix-driven initial access. Darktrace investigated the activity and found that decentralized blockchain infrastructure, alongside widely trusted legitimate services, was used to support malware delivery and information theft across Windows and macOS systems.

Following initial access, compromised systems established C2 communication, with C2 configuration and payloads hosted on public blockchain infrastructure. The ultimate objective appears to be credential and cryptocurrency theft through the deployment of information stealers such as Atomic macOS Stealer (AMOS), Lumma, Rhadamanthys, and Vidar [5][6][7].

Darktrace’s Investigation

Affected devices across the Darktrace customer base were observed making outbound connections to rare external endpoints in patterns consistent with beaconing and C2 activity. Darktrace primarily detected devices making repeated connections to algorithmically generated domains (DGA) such as hf98x4d[.]site [8]. In many cases, these domains were linked through open-source intelligence (OSINT) to information-stealing malware families including AMOS and Phexia [5][6][7][8][9].

In multiple cases, devices were also observed connecting to blockchain-related endpoints, such as polygon[.]drpc[.]org, as well as legitimate public services, including GitHub. The use of decentralized blockchain infrastructure and trusted services such as GitHub to facilitate malware distribution and C2 activity can make disruption and attribution significantly more difficult for defenders.

Darktrace also detected a significant proportion of impacted devices making outbound connections to cryptocurrency mining infrastructure associated with the legitimate open-source XMRig mining software and the HashVault mining pool, including pool.hashvault[.]pro and donate[.]ssl[.]xmrig[.]com, which were abused by the attackers, indicating, including pool.hashvault[.]pro and donate[.]ssl[.]xmrig[.]com, indicating active cryptomining on compromised systems.

In one case, mining activity was observed before and during connections to the DGA endpoint hf98x4d[.]site. Due to its highly anomalous nature, Darktrace's Real-Time AI Analyst autonomously investigated the activity as it occurred, correlating the two events into a single cryptocurrency mining incident and providing comprehensive visibility into the broader attack.

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Figure 1: Real-Time AI Analyst investigation of suspicious SSL and C2 communications with hf98x4d[.]site over port 443.

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Figure 2: Real-Time AI Analyst investigation into cryptocurrency mining activity involving pool[.]hashvault[.]pro over SSL on port 443.

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Around the same time, Darktrace identified the same device initiating connections to the GitHub endpoint release-assets[.]githubusercontent[.]com while continuing to make repeated connections to hf98x4d[.]site.

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Figure 3: Darktrace's detection of an affected device connecting to a GitHub endpoint between repeated connections to the anomalous external endpoint hf98x4d[.]site.

On the network of another customer, Darktrace observed an affected device making highly unusual outbound connections consistent with beaconing activity. The device initiated multiple connections over port 443 to the external hostname polygon[.]drpc[.]org. According to OSINT, this hostname is a Remote Procedure Call (RPC) endpoint provided by dRPC, a legitimate service enabling decentralized applications (dApps), cryptocurrency wallets, and developer tools to interact with the Polygon blockchain [10].

The same device was later observed making repeated TLS/SSL connections to the previously mentioned DGA C2 domain. In addition, it made outbound connections to the external IP 195.242.214[.]34 over destination port 51820, an endpoint associated with the ProtonVPN service. Collectively, these connections to blockchain-related infrastructure, the DGA C2 domain, and ProtonVPN-associated infrastructure suggested the device had been affected by the campaign.

Conclusion

This campaign demonstrates how attackers can combine ClickFix social engineering with trusted services and decentralized blockchain infrastructure to create a resilient, cross-platform malware delivery chain. By using services such as GitHub alongside blockchain RPC endpoints and rapidly replaceable DGA domains, the activity can blend into legitimate traffic while making infrastructure disruption and attribution more difficult.

For defenders, it’s a reminder that trusted infrastructure does not automatically mean trusted activity. Security teams should look for the behaviors surrounding these connections, including unusual outbound communication, repeated beaconing, unexpected access to blockchain services, suspicious TLS/SSL activity and cryptomining. In this campaign, Darktrace identified and correlated these deviations without depending solely on previously known indicators, providing visibility as affected devices moved between legitimate services, decentralized infrastructure and malicious C2 endpoints

Credit to Nahisha Nobregas (Associate Principal Cyber Analyst), Manoel Kadja (Senior Cyber Analyst)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

▪ Compromise / Beaconing Activity To External Rare

▪ Compromise / Beacon to Young Endpoint

▪ Compromise / Fast Beaconing to DGA

▪ Compromise / High Volume of Connections with Beacon Score

▪ Compromise / DGA Beacon

▪ Compromise / Slow Beaconing Activity To External Rare

▪ Compromise / Agent Beacon (Long Period)

▪ Compromise / Agent Beacon (Medium Period)

▪ Compromise / Sustained SSL or HTTP Increase

▪ Compromise / Large Number of Suspicious Failed Connections

▪ Compromise / SSL Beaconing to Rare Destination

▪ Compromise / Beacon for 4 Days

▪ Compromise / High Priority Crypto Currency Mining

▪ Compromise / Monero Mining

▪ Device / Long Agent Connection to New Endpoint

▪ Device / New Connections On Suspicious Port

▪ Anomalous Connection / High Volume of Connections to Rare Domain

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List of Indicators of Compromise (IoCs)

 
Indicator Description
hf98x4d[.]site C2 Endpoint (Hostname)
sj98xe4[.]xyz C2 Endpoint (Hostname)
citcix6[.]xyz C2 Endpoint (Hostname)
bduwih8[.]pro C2 Endpoint (Hostname)

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MITRE ATT&CK Mapping

 
Tactic (ID) Technique
Persistence (T1176) Browser Extensions (T1176.001)
Persistence (T1176) Software Extensions
Command and Control (T1071) Web Protocols (T1071.001)
Command and Control (T1568) Domain Generation Algorithms (T1568.002)
Command and Control (T1071) Application Layer Protocol
Command and Control (T1102) One-Way Communication (T1102.003)
Command and Control (T1571) Non-Standard Port
Command and Control (T1104) Multi-Stage Channels
Command and Control (T1573) Encrypted Channel
Command and Control (T1008) Fallback Channels
Initial Access ICS (T0862) Supply Chain Compromise
Command and Control ICS (T0885) Commonly Used Port
Collection (T1185) Browser Session Hijacking
Impact (T1496) Compute Hijacking (T1496.001)
Impact (T1496) Resource Hijacking
Command and Control (T1071) Publish/Subscribe Protocols (T1071.001)
Lateral Movement (T1210) Exploitation of Remote Services

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References:

1.        https://www.microsoft.com/en-us/security/blog/2025/05/21/lumma-stealer-breaking-down-the-delivery-techniques-and-capabilities-of-a-prolific-infostealer/

2.        https://spycloud.com/resource/report/spycloud-annual-identity-exposure-report-2026/

3.        https://www.darktrace.com/blog/why-trust-is-the-new-attack-surface-darktraces-mid-year-threat-update-2026

4.        https://www.darktrace.com/blog/unpacking-clickfix-darktraces-detection-of-a-prolific-social-engineering-tactic

5.        https://abekweng.medium.com/inside-a-blockchain-hosted-malware-campaign-targeting-windows-and-macos-f5bcdeffed66

6.        https://cloud.google.com/blog/topics/threat-intelligence/unc5142-etherhiding-distribute-malware

7.        https://haveibeensquatted.com/blog/from-typosquatting-to-macos-backdoor-clickfix-blockchain-c2

8.        https://www.virustotal.com/gui/domain/hf98x4d.site/community

9.        https://x.com/FABO97662188/status/2074125545026244795

10.  https://www.virustotal.com/gui/url/b0e5c51a411065864119c305fddf218b7c120731f655932cc1c3307ad5b43f94/gti-summary

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About the author
Nahisha Nobregas
SOC Analyst
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