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June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

We cover two real cases on how Darktrace stopped Microsoft 365 account takeovers by correlating insights across SaaS applications & email activity.
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
Dan Fein
VP, Product
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07
Jun 2020

‘Social engineering’. ‘Credential theft’. ‘Account takeover’. If you were a fly on the wall of a Security Operations Center in 2020, you would have heard these phrases far more often than ‘banking trojan’, ‘SQL injection’ or ‘exploit kit’. The reason for this is simple – the reality for most security teams now is that their perimeter has shifted into the cloud. Identities are being attacked more than devices.

‘Microsoft 365 account compromise’ is the current favorite, with 29% of organizations reporting a related incident in one month alone. Security teams struggle with these attacks because the evidence needed to detect them is scattered across the enterprise: they begin via email, are executed over the network, and progress in the cloud. This broad and spread out digital footprint means that following the breadcrumbs is not easy.

Darktrace’s Cyber AI Platform is designed to understand a user’s behavior as they move between devices and cloud services, tracking their activity to identify a compromise. To help understand how these attacks avoid detection, it is useful to look at a couple of examples of Microsoft Office 365 compromise detected recently in one of our customers.

Microsoft 365 compromised to launch external email threat

A Microsoft 365 account was recently compromised at a public accounting firm based in the United States. Darktrace initially picked up on several anomalies, including a sudden surge in outbound email traffic as well as the unusual login location – while the company and nearly all of its users were located in Wisconsin, an IP address located in Kansas was used to log in to the Microsoft 365 account. Along with the unusual login, a login to Microsoft Teams from the same Kansas IP address was detected.

Figure 1: Just after the new email rule was created, a Microsoft Teams 100% rare IP login occurred.

‘Impossible travel’ rules alone would have missed these anomalies, but an understanding of activity and behavior across different SaaS applications allowed Darktrace’s AI to recognize these events as one systematic case of credential theft. When the threat-actor subsequently created a new email rule, Darktrace was able to connect this event with the other anomalous behavior and understand its potentially malicious nature.

Figure 2: Darktrace’s SaaS Module noted a 100% rare IP logging into the user’s Microsoft 365 account and the creation of a new mailbox rules. All factors indicated 100% unusual SaaS activity.

Five minutes later, Antigena Email alerted on a large number of outbound emails containing a generic subject line and an attached PDF. The technology also detected that there was a clear spike in outbound emails from this user and flagged each of these emails with the “Out of Character” tag, which in this case denoted a change from normal behavior with the surge in recipients, and likely internal compromise.

Figure 3: Antigena Email detected a surge in recipients that indicated a serious breach of normal behavior for this user.

The unusual login behavior detected by Darktrace’s SaaS Module could be connected to the anomalous outbound email behavior flagged by Antigena Email, allowing the security team to see the extent of the attack and neutralize it as it emerged. It was clear that the account was being used to engage in malicious activity, as each of the 220 outbound emails used a generic subject line and contained a suspicious attachment. The security team therefore immediately disabled the compromised account.

Figure 4: A recreation of the email sent by the attacker, containing the malicious attachment.

‘Change of bank details’ sent from accounts department

When an Accounts Department’s Microsoft 365 account was compromised and used to send targeted phishing emails, Darktrace was able to track the attacker’s movement within the inbox, tying together information from Darktrace’s SaaS Module with Antigena Email’s alerts to understand the full picture of the threat and stop the attack.

The SaaS account appears to have been compromised via an inbound spear phishing attack, or some other form of attack that occurred before Darktrace began monitoring the organization. While Darktrace Cyber AI had no oversight of the initial compromise, it was still able to distinguish later attacker behavior as malicious, based on its actively evolving understanding of the organization and its workforce.

When the account user logged in from a 100% rare French IP address, Darktrace’s SaaS Module picked up on the anomaly immediately, and further detected a series of activities carried out after the unusual login. At the same time, Antigena Email noted an email being sent.

Figure 5: The login from a French IP was noted as 100% rare for this user and SaaS account.

Darktrace then identified more activity occurring from a second rare login location, a Swiss IP address. Very little email activity occurred when the account was logged in from this IP. Instead, Cyber AI saw the threat-actor using their illegitimate SaaS access to view information on the legitimate account user and files related to banking, invoices, and payments.

Antigena Email then identified a series of email communications that, when seen in the context of the SaaS account compromise, pointed to a clear threat. There were no obvious malicious attachments or links in the emails. However, the subject of the final reply was ‘Change of Bank Details’, and the email prompted a high Solicitation Inducement Score within Antigena Email, strongly implying that the malicious actor had sent emails instructing the destination to change payment details in order to route money to the attacker, instead of the company.

It seems the attackers went through the banking and invoicing files in order to find a customer with a big bill to pay, then used the compromised email account to launch an outbound phishing attack, changing the billing details. With Darktrace AI correlating information within the SaaS platform and insights from Antigena Email, this targeted phishing attack could be contained before further compromise or damage could occur.

The below screenshot also indicates a series of inbox processing rules made on the compromised account, showing actions that are typical of an account takeover.

Figure 6: Darktrace’s records of new inbox rules being set up on the compromised SaaS account.

The benefits of a unified approach

These stories are all too familiar. Most security tools would not be able to take action on any one of these steps individually. But the combination reveals the tell-tale sign of a Microsoft 365 account hijack. Organizations are struggling to manage their user identities across their cloud infrastructure, and rule and policy-based detection is no longer feasible.

However, by learning identities and behavior across the enterprise, Darktrace is able to detect, and seamlessly respond, to combat these threats. Hundreds of organizations are now using Antigena Email to protect their email and cloud environments continuously, trusting it to dynamically enforce MFA, lock accounts, block network traffic, and withhold emails when necessary.

As cloud-native applications become more popular, organizations face the growing problem of separate end-to-end security solutions for each type of workload. With Antigena Email working in conjunction with Darktrace’s Enterprise Immune System, defenders can be assured that a single, unified platform is tracking every suspicious behavior, wherever it arises in the organization.

Learn more about Antigena Email

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
Dan Fein
VP, Product

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October 14, 2026

CikaBika Bot: Inside a Discord RAT

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Key Takeaways

·      Darktrace malware researchers have found an ongoing malware campaign using a document-themed lure containing a malicious LNK file and a PDF with an embedded payload.

·      The Nim based loader deploys a Rust-based remote access trojan (RAT), using a UAC bypass and DLL search-order hijacking technique targeting Microsoft Edge.

·      The RAT uses Discord for C2, creating dedicated channels to manage infected devices and execute commands.

·      CikaBika Bot supports system reconnaissance, remote command execution, screenshot capture, and file transfers.

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Introduction

In a threat landscape where attackers continue to rely on social engineering techniques to deliver malware, legitimate services are increasingly being abused to support malicious operations. Communications platforms like Discord can provide attackers with a ready-made channel for command-and-control (C2), allowing them to manage compromised devices without establishing dedicated infrastructure.

Malware researchers at Darktrace have identified a campaign distributing CikaBika, a Rust-based RAT that uses Discord for C2. The infection chain begins with a disk image and a malicious Windows shortcut. A Nim loader extracts the final payload and attempts to plant it in Microsoft Edge’s installation directory using a PowerShell UAC bypass. Once running, the RAT collects host information, registers the device with Discord, and accepts commands through a dedicated channel.

Technical Analysis

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Figure 1: Contents of Proposition_Projet.img.

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Initial access and PDF payload

The malware is packaged within a disk image named Proposition_Projet.img. Inside are a PDF titled “Presentation_Generale.pdf.pdf” and a Windows shortcut (LNK) disguised as a Word document, “Proposition_Projet_Personnalisable.docx”. The delivery method has not been confirmed; however, the filenames and document-themed lure are consistent with a phishing campaign.

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Figure 2: PowerShell command embedded in the malicious shortcut.


Opening the shortcut launches a hidden PowerShell process while displaying the PDF as a decoy. The French-language document explains how to produce a written summary or contraction of a text. In the background, PowerShell reads the PDF as bytes and uses the value at offset 239 (0x20) as an XOR key to decode an embedded executable. The resulting payload is written to %TEMP%\IfyuUapz.txt and executed using cmd /c.

Nim loader and UAC bypass

“IfyuUapz.txt” is a Nim-based loader that contains two Base64-encoded blobs: a Rust dynamic-link library (DLL)  and a PowerShell deployment script. Both are decoded and written to temporary files, referenced to within the loader as “dllFile” and “copyPs1”. The loader runs the script through a hidden PowerShell process using an encoded command, then attempts to load the DLL using Nim’s loadLib function. If loading fails, it invokes regsvr32.exe and retries.

Figure 3: Silent DLL deployer.

The PowerShell component is responsible for moving the DLL to C:\Program Files (x86)\Microsoft\Edge\Application\dbghelp.dll. It first copies the DLL to C:\Windows\Temp\dbghelp.tmp, then modifies HKCU\Software\Classes\ms-settings\shell\open\command so that launching computerdefaults.exe can trigger a command to move the staged DLL into the protected Edge directory. This is an attempt to bypass User Account Control (UAC), which depends on the target’s Windows configuration.

The script also compiles a small C# helper that calls ShowWindow to hide windows associated with Windows Settings and ApplicationFrameHost. It launches the bypass helper three times, checks for the presence of the destination DLL, and attempts to delete the temporary scripts, intermediate DLL, and associated registry changes.

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Figure 4: Legitimate msedge.exe function to load the legitimate dbghelp.dll.

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The legitimate msedge.exe has a delay-loaded dependency on dbghelp.dll, and the malicious DLL exports a subset of the functions associated with Microsoft’s debugging library. The attacker appears to be exploiting this dependency through DLL search-order hijacking. However, it does not export every function in Edge’s delay-import table, meaning its compatibility with the host is incomplete. The observed code establishes the intended sideloading route, rather than proving that Edge successfully loaded the planted DLL.

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Rust RAT payload

Figure 5: Discord configuration within the RAT.

The malicious dbghelp.dll (IfyuUapz.txt) is a Rust-based RAT. At startup, the RAT registers the compromised device with Discord and begins collecting information about the host. Its reconnaissance routine gathers system details, runs tasklist to enumerate processes, executes ipconfig to obtain network configuration, and attempts to take a screenshot. The resulting artifacts include tasklist_startup.txt, network_info.txt, and screenshot.png.

Figure 6: Network configuration notification in Discord channel.

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Figure 7: Network configuration output from network_info.txt.

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Discord C2

The RAT uses Discord channels to send commands and report results. The operator can send commands to the device’s channel and receive the resulting output in the same conversation. This gives the attacker an interactive command interface without having to operate and maintain a dedicated C2 server.

Figure 8: Commands available in Discord.

The command set includes !shell for remote command execution; !sysinfo and !info for host details; !isOn for status checks; !tasklist and !ps for process enumeration; and !kill for process termination. File-transfer commands include !upload and !download. Additional strings and command handlers reference screenshots (!src), camera access (!camera), streaming (!stream), and broadcasting (!broadcast).

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Figure 9: Device registration in Discord.

During device registration, the malware retrieves the victim’s public IP address using ipify.com. The registration message records the device ID, hostname, registration time, private and public IP addresses, status, uptime, and the Discord channel assigned to that device.

Operator activity and exfiltration

Figure 10: Powershell commands sent through Discord to exfiltrate data.

Once a device is registered, the attacker can issue commands through its dedicated Discord channel. In the observed activity, the attacker compressed a directory into a ZIP and exfiltrated it using ngrok.

Figure 11: Download command to retrieve a document from the target.

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The operator can also use !download to retrieve files from target. The example above displays a request for a specific document on the victim’s desktop. The requested file is then returned through the device’s Discord channel, giving the attacker a direct way to store and access selected data.

Conclusion

CikaBika Bot demonstrates how attackers continue to rely on social engineering techniques to deliver malware. Although the initial distribution method has not been confirmed, the use of a disk image containing a shortcut disguised as a Word document, alongside a legitimate-looking PDF, suggests the campaign was designed for phishing.

While Nim is less commonly encountered than C in Windows malware, it has increasingly appeared in malicious tooling. In this case, Nim is used to unpack and deploy a Rust-based RAT, adding another layer to the infection chain.

Once installed, CikaBika Bot uses Discord as its C2 platform, allowing the attacker to manage compromised devices, execute commands, and retrieve files without maintaining dedicated C2 infrastructure. The observed use of Discord channels for individual victims, alongside additional data exfiltration through ngrok, shows how legitimate services can be repurposed to support malicious operations.

Credit to Tara Gould (Malware Research Lead)

Indicators of Compromise (IoCs)

Presentation_Generale.pdf.pdf - eeb52cb95113a131c2c7713c17872da6

Proposition_Projet_Personnalisable.docx.lnk - 62e3e85eca78a0cd7e6669e9f33d936d

dbghelp.dll - c66858718d883bcfb9ce2c19b59f96c9

IfyuUapz.txt - 2deb724a709b0b892248405323350e9b

MITRE ATTACK

T1204.002 – User Execution: Malicious File
T1036.007 – Masquerading: Double File Extension
T1059.001 – PowerShell
T1027 – Obfuscated Files or Information
T1140 – Deobfuscate/Decode Files or Information
T1548.002 – Bypass User Account Control
T1112 – Modify Registry
T1574.001 – DLL Search Order Hijacking
T1036.005 – Masquerading: Match Legitimate Resource Name or Location
T1082 – System Information Discovery
T1016 – System Network Configuration Discovery
T1057 – Process Discovery
T1113 – Screen Capture
T1059.003 – Command and Scripting Interpreter: Windows Command Shell
T1102.002 – Web Service: Bidirectional Communication
T1560.001 – Archive Collected Data: Archive via Utility
T1567 – Exfiltration Over Web Service
T1070.004 – Indicator Removal: File Deletion
T1218.010 – Regsvr32
T1005 – Data from Local System
T1074.001 – Data Staged: Local Data Staging
T1041 – Exfiltration Over C2 Channel
T1564.003 – Hide Artifacts: Hidden Window
T1027.013 – Encrypted/Encoded File

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About the author
Tara Gould
Malware Research Lead

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October 5, 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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