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.

Written by

David Ison

Cyber Analyst

Written by

Ryan Traill

Content Manager - Digital Customer Success

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

David Ison

Cyber Analyst

Written by

Ryan Traill

Content Manager - Digital Customer Success

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

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 / EMAIL^TM and Darktrace / IDENTITY^TM 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.

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”.

Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.

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.

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.

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

Content Manager - Digital Customer Success

Inside the SOC

Written by

David Ison

Cyber Analyst

Written by

Ryan Traill

Content Manager - Digital Customer Success

•

September 30, 2026

Angel Arribas Lopez

Associate Principal Cyber Analyst

•

September 24, 2026

Sam Lister

Specialist Security Researcher

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Blog

AI

October 5, 2026

AI-Assisted Attacks Still Leave a Behavioral Trace

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

IoC	Type	Description + Confidence
onedrive[.]cv	Hostname	Likely C2 server
138.124.123[.]87	IP Address	Possible C2 server
hXXp://onedrive[.]cv/Downloads/CURP/ReportFinal.%E2%80%AE%E1%BA%9D%D4%81%EF%BD%90.scr	URI	Possible payload
google.services[.]ug	Hostname	Likely C2 server
77.110.127[.]205	IP Address	Likely C2 server
google.services[.]ug:57666	Hostname + Port	Likely C2 communication
google.services[.]ug:57888	Hostname + Port	Likely C2 communication
google.services[.]ug:56001	Hostname + Port	Likely C2 communication

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Case 2

IoC	Type	Description + Confidence
192.229.115[.]229	IP Address	Likely C2 communication

About the author

Angel Arribas Lopez

Associate Principal Cyber Analyst

Blog

Network

October 5, 2026

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

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