Your Guide to Cloud Penetration Testing -PlutoSec - Cyber Security Canada

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Cloud Penetration Testing

The shift to cloud computing has been a major trend in enterprise IT over the past decade, and it shows no signs of slowing down. Today, the majority of online services operate on a cloud-native model. A remarkable 92% of organizations report using some form of cloud infrastructure, with over half of these using multiple public clouds, and 21% utilizing three or more. Cloud infrastructure provides operational convenience and efficiency, leading to enhanced productivity and lower costs compared to on-premises infrastructure. At PlutoSec, Canada’s leading penetration testing company, we recognize the importance of cloud infrastructure in driving business success.

On average, recovering from data breaches involving cloud assets costs victims nearly $5 million USD.

Securing cloud assets against internal and external threats is crucial, given the significant value of cloud systems and data. According to IBM research, data breaches involving cloud assets cost victims nearly $5 million USD on average to recover. It’s no surprise that the global cloud security market reached approximately 29.26 billion USD in 2021, with projections estimating it will grow to USD 106.02 billion by 2029, at a CAGR of 18.1%.

Although cloud solutions frequently offer convenient security features like reliable and easily deployable backups, scalable compute power, and extensive technical support documentation, there are unique security risks associated with cloud infrastructure that must be addressed. Additionally, a shortage of cloud computing skills further complicates the deployment of secure cloud systems.

Cloud penetration testing can bridge the visibility gaps that arise when deploying complex cloud-native solutions. By developing a cloud pentesting methodology based on guidance from leading IT security authorities and utilizing our highly certified and experienced in-house pentesters, PlutoSec is poised to deliver the highest level of risk assurance for cloud infrastructure. Our pentesting services meet regulatory requirements for government contracts such as FedRamp and adhere to industry standards like PCI-DSS, ISO-27001, and SOC-2. As the best penetration testing company in Canada, PlutoSec is committed to securing your cloud infrastructure.

Who Will Benefit from This Guide

MCSL  C-level executives responsible for IT security, including CISOs, CSOs, and VPs of Security

MCSL  Other high-level management, such as CEOs, Business Owners, and Business Executives

MCSL  Managed Service Providers (MSP)

MCSL  Cybersecurity Architects, Network Architects, and Network Administrators

This guide will be valuable for an organization’s leaders, including CEOs, CTOs, and CISOs, as well as other senior team members such as security managers, security engineers, network engineers, and administrators. It will also be useful for IT professionals like MSPs and providers of IaaS, PaaS, and SaaS.

What Is Cloud Penetration Testing?

Cloud penetration testing simulates real-world cyber-attacks on an organization’s cloud infrastructure, cloud-native services, applications, APIs, and enterprise components such as Infrastructure as Code (IaC), serverless computing platforms, and federated login systems. This methodology is specifically designed to address the unique threats, vulnerabilities, and risks associated with cloud environments and cloud-native services.

A cloud penetration test delivers a comprehensive report, attack narrative, and vulnerability severity assessment to help interpret the implications of each finding. Unlike traditional vulnerability scanning, which may include false positives, cloud penetration tests focus exclusively on true positive vulnerabilities within your cloud infrastructure.

The primary objective of cloud pentesting is to safeguard digital infrastructure against an ever-evolving threat landscape and provide organizations with the highest level of IT security assurance to meet their risk management needs.

Why Is Cloud Penetration Testing Essential?

Cloud infrastructure and services are rapidly becoming a key asset for enterprises of all sizes, increasing their value and associated risk. Organizations now store a wide range of applications, services, and data in the cloud, including file-sharing and productivity tools, public web applications, mobile app data, network monitoring information, log files, system backups, security services, and both employee and customer data. As a result, the cloud has become a prime target for attackers. Cloud penetration testing offers strong evidence that an organization has robust operational resilience and is safeguarded against cyber-attacks, forced disruptions, unauthorized access, data theft, malware, and ransomware.

The extensive range of services hosted in a typical organization’s cloud makes it a primary target for attackers.

Cloud infrastructure and services come with a unique set of vulnerabilities, necessitating specialized cloud penetration testing to achieve a high level of assurance. Additionally, compliance standards such as FedRamp, PCI-DSS, SOC-2, ISO-27001, and NIST CSF specifically mandate penetration testing, which should ideally focus on cloud security for protecting cloud infrastructure. Furthermore, cloud penetration testing can also help reduce the cost of cyber insurance.

The advantages of a cloud penetration testing engagement include:

MCSL  Enhanced risk assurances – Traditional vulnerability assessments do not replicate real cyber-attacks, thus failing to offer robust risk assurances. Cloud systems are intricate and require meticulous configurations to stay secure, while threat actors continuously evolve their tactics and employ innovative attack strategies to outpace defenders.

MCSL  Enhanced compliance – Partners and customers are increasingly seeking to work with companies that exhibit a strong security posture through adherence to IT security compliance standards. In some cases, compliance is a mandatory requirement for partnership and can also lead to lower cyber insurance premiums.

MCSL  Increased cost savings – Penetration testing boosts the return on security investment (ROSI) by significantly decreasing the likelihood of a cyber breach. By avoiding the substantial financial repercussions associated with ransom payments, system and data recovery, reputational damage, potential fines and lawsuits, and higher cyber insurance premiums, organizations can achieve substantial cost savings.

MCSL Peace of mind – By conducting cloud-specific penetration testing on cloud-native resources, an organization can be assured that they have achieved the highest level of confidence in their assets’ resilience to cyber-attacks and the safety of their business operations.

What Does Cloud Penetration Testing Involve?

PlutoSec’s cloud penetration testing methodology draws from industry-leading frameworks, including the SANS Penetration Testing Methodology, MITRE ATT&CK Enterprise and Cloud matrices, Azure Threat Research Matrix, and NIST SP800-115 Information Security Testing and Assessment standard. By adhering to these established frameworks, PlutoSec ensures compliance with security assessment regulations for government contracts, such as FedRamp, and industry standards like PCI-DSS, SOC-2, and ISO-27001.

Common Cloud Vulnerabilities

Cloud penetration testing should primarily involve simulated attacks targeting the most prevalent cloud vulnerabilities. Evaluating an organization’s cloud infrastructure for resilience against these common attacks ensures that attackers using readily available automated tools will not easily succeed. This approach significantly lowers the likelihood of experiencing a breach.

Here are the most frequently encountered cloud vulnerabilities

MCSL  Cloud Misconfigurations – Inexperience, neglect of IT security best practices, and the absence of static code reviews often lead to misconfigurations in production cloud services. The NSA considers cloud misconfiguration a major IT security threat, representing an easily exploitable weakness that novice attackers can target using automated tools.

MCSL External services and applications including APIs – Cloud-hosted services have an exposed attack surface that can be scanned for known vulnerabilities and targeted with both automated tools and custom exploits. It is crucial to thoroughly test these exposed surfaces and continuously monitor them for changes that could provide attackers with opportunities to exploit.

MCSL Exposed sensitive information, data, and documents –As organizations rapidly develop and deploy new digital services, security visibility can often be overlooked. This can result in sensitive data—such as passwords, encryption keys, private certificates, financial information, or trade secrets—being inadvertently exposed and accessible to unauthorized individuals. Cloud penetration testing aims to identify such unintentionally exposed data so that it can be properly secured.

MCSL Internal testing of cloud servers and services – To achieve the highest level of security assurance, it is crucial to simulate the actions an attacker might take if they successfully gain access to a system or account. A “defense in depth” strategy ensures that multiple layers of security are in place to prevent attacks from various points within the network. Internal penetration testing of cloud resources also helps reveal the potential damage an insider attack could inflict on an organization’s systems and data.

MCSL Containers and pods – Security contexts establish privilege and access control settings for Kubernetes Pods, other Infrastructure as Code (IaC) platforms, and containers. Misconfigurations can lead to unauthorized access to applications, services, or the underlying virtual environment, a vulnerability known as “virtual machine (VM) escape.” Additionally, IaC and container configurations are frequently sourced from third parties, and their security settings are not always thoroughly tested to identify potential weaknesses.

MCSL Identity and access management (IAM) – Using common or weak passwords can enable an attacker to swiftly gain unauthorized access to an account. Additionally, default accounts with widely known credentials may be exposed, inactive accounts might remain active, or API keys and PKI certificates could be publicly leaked, leading to compromised authentication systems.

MCSL Amazon Lambda, Azure Function, and Google Cloud Function vulnerabilities – Serverless computing platforms automatically execute code and manage the underlying cloud infrastructure in response to event triggers. Because these platforms provide direct access to cloud computing resources, they must be monitored and subjected to vulnerability assessments to safeguard against potential exploitation.

OWASP Top 10 Cloud Security Risks

The OWASP Top 10 Cloud Security Risks is a leading industry framework for assessing potential security gaps in cloud IT operations. It aims to enhance visibility into an organization’s cloud security posture by identifying vulnerabilities related to governance, regulatory compliance, policies, and business continuity planning (BCP).

MCSL Accountability and Data Ownership – Identifies issues related to data ownership as defined by existing contracts between the organization and the cloud service provider, and outlines the mechanisms for protecting cloud data, including backup and recovery processes.

MCSL User Identity Federation – Ensures that users are accurately identified across cloud computing platforms to minimize the attack surface, prevent exposures due to misconfigurations, and control access to privileged resources.

MCSL Regulatory Compliance – Laws can significantly affect an organization’s confidentiality and availability. It is crucial to understand how compliance and national regulations apply to cloud infrastructure based on its geographical location.

MCSL Business Continuity and Resiliency – An organization’s capacity to maintain service during an outage is essential. Therefore, it is important for the organization to work closely with its cloud service provider to ensure a robust disaster recovery and business continuity plan is established for emergencies.

MCSL User Privacy and Secondary Usage of Data – Data stored on a cloud-based platform is a high-value target for hackers and must be safeguarded with secure access controls and the principle of least privilege. This protection is essential throughout the entire data lifecycle, as data may move across multiple clouds and be shared between different owners.

 

MCSL Service and Data Integration – Protecting data-in-transit with cloud-based solutions is crucial to prevent sensitive data exposure, compromise of company information, and potential fines, lawsuits, and reputational damage. Ensuring that data is transmitted using secure protocols and encryption is essential.

MCSL Multi-Tenancy and Physical Security – Multi-tenant environments pose significant security risks if resources in the cloud are not properly segmented to ensure the isolation of each tenant’s data. While multi-tenancy helps reduce costs, some data is too sensitive to be exposed in such shared environments, making it advisable to negotiate private cloud solutions with the cloud IaaS provider.

MCSL Incidence Analysis and Forensic Support – Cloud environments pose unique challenges for forensic analysis, which is essential for maintaining security. This analysis is crucial for network detection, prevention security, and investigations by security operation centers into potential cyber incidents. Inadequate forensic analysis capabilities could leave an organization without a clear understanding of the true impact of a cyber attack.

MCSL Infrastructure Security – Fundamental network security best practices, such as regular vulnerability assessments and the application of security patches and updates, are also relevant for cloud infrastructure. Implementing robust network security in the cloud is even more crucial due to the publicly accessible nature of the cloud attack surface.

MCSL Non-Production Environment Exposure – While the cloud offers a convenient solution for deploying staging, testing, and development environments, it is essential to implement stringent standards to prevent unauthorized access, as these environments are generally less secure than production ones. It is important to minimize the attack surface of these environments by removing any sensitive user information, trade secrets, or unnecessary code.

Kubernetes Security Assessment

Kubernetes (or K8s) is an open-source Infrastructure as Code (IaC) platform that facilitates the automatic deployment and management of cloud VPS and containerized applications. It has rapidly become a key component of cloud architecture due to its capabilities in optimizing load balancing and automating the deployment of VMs, containers, and enterprise applications. From 2020 to 2021, the number of Kubernetes engineers grew by 67%, reaching nearly 4 million, and Kubernetes now represents 31% of all enterprise backends.

Penetration testing Kubernetes demands extensive technical knowledge and experience with its configuration, operation, and management. It should encompass tactics aimed at identifying vulnerabilities in the following areas:

  • Configuration

  • Identity and access management (IAM)

  • Multi-tenancy & pod security

  • Container image security

  • Exposed secrets such as authentication keys or plain text passwords

Restrictions on Penetration Testing Cloud Infrastructure

Cloud service providers have stringent policies that specify which penetration testing activities are permitted on their infrastructure. Some providers also require advance notice of any planned testing before it begins. It is essential for the penetration testing team to thoroughly review and comply with these policies throughout the engagement. Violating a cloud provider’s policies during testing could result in severe penalties for the organization, including potential termination of service.

Here are some penetration testing activities that are typically prohibited:

  • Virtual machine escape

  • DOS and DDoS attacks

  • Any type of illegal activity

  • Phishing or social engineering the cloud provider’s employees

  • Deploying trojans, ransomware, or other known malware strains

  • Other violations of the cloud provider’s acceptable use policy

How Does Cloud Penetration Testing Differ from Infrastructure Penetration Testing?

The primary difference between Cloud Penetration Testing and Infrastructure Penetration Testing is that the hardware assets involved in a cloud pentesting engagement are owned by a cloud Infrastructure as a Service (IaaS) provider, not the target organization. This distinction introduces limitations not present in traditional Infrastructure Penetration Testing, due to the service level agreements (SLAs) and acceptable use policies of the IaaS provider.

Otherwise, the tactical approach to Cloud Penetration Testing involves all the techniques used in Infrastructure Penetration Testing, along with additional cloud-specific methods. Additionally, because cloud infrastructure is off-premises, physical penetration testing techniques are not required.

Cloud Penetration Testing With Plutosec

PlutoSec provides top-tier professional cloud penetration testing services. Our team of over 20 in-house penetration testers all hold at least an OSCP certification, and we handle all pentesting activities internally without outsourcing to third parties. Additionally, PlutoSec is SOC-2 Type II accredited and compliant with Canada Data Residency requirements.

Although many free and fully automated “pentesting tools” are available for quickly scanning applications or environments for vulnerabilities, they fall short of providing the high level of security assurance needed for enterprise risk management. These tools do not accurately simulate an organization’s ability to handle a real-world cyber-attack. PlutoSec’s penetration testing process relies on 95% manual testing, which is crucial for identifying the most potentially risky vulnerabilities targeted by real-world adversaries. By prioritizing manual testing, we ensure that our reports are free from false positives, as each vulnerability is directly verified.

PlutoSec is committed to excellence in client communication, providing IT security findings in both general terms and detailed technical descriptions. Our reports include insights into vulnerabilities, associated threat intelligence, and recommended mitigation steps. With a team of over 20 in-house testers, PlutoSec is prepared for rapid engagement starts and offers flexible retesting schedules to accommodate client needs.

What You Can Expect from a Cloud Penetration Test

Each Cloud Penetration Test starts with a consulting phase to establish the scope and rules of engagement (RoE). This phase outlines which assets of the target organization will be tested, the types of vulnerabilities the testing team will focus on exploiting, the communication channels between the target and testing entities, and the severity thresholds that would necessitate halting the testing process and immediately reporting critical findings.

Following the initial consultation, the pentesting engagement proceeds according to IT industry-standard methodologies. The testing activities culminate in a report that summarizes the findings. This report includes a technical description of the exploitation process, a thorough severity assessment of each vulnerability, and detailed remediation steps.

PlutoSec’s Cloud Penetration Testing methodology is supported by the following testing phases:

MCSL Passive reconnaissance – Pentesters collect publicly available information about the target, including historical DNS records, internet archives, and leaked data repositories. This information is examined for any details that could be useful in launching an attack against the target organization.

MCSL Active scanning – Pentesters identify potentially vulnerable attack surfaces by scanning to map network topology, including data on operating systems, applications, services and their versions, user accounts, exposed files, directories, and APIs. They also gather other available network data, such as protocols and encryption standards in use.

MCSL Vulnerability assessment – The collected information is cross-referenced with known exploit data, and attack strategies are developed to exploit any identified security weaknesses. This involves leveraging cybersecurity threat intelligence (CTI) to orchestrate activities that mimic known adversarial behaviors.

MCSL Exploitation – Pentesters conduct real cyber attacks against the target’s infrastructure to exploit the vulnerabilities identified in earlier stages. Common tactics include gaining initial access to unauthorized systems, escalating privileges to obtain administrative access, stealing data, intercepting traffic, and mapping any newly accessible systems or data.

MCSL Reporting – Pentesters prepare a detailed report that outlines any vulnerabilities discovered, their severity scores, and includes evidence gathered during the testing process. The report also provides thorough descriptions of recommended remediation steps.

PlutoSec’s Cloud Penetration Testing methodology targets security weaknesses in cloud-native infrastructure and incorporates a range of cloud-specific activities, in addition to evaluating traditional infrastructure security.

Some of the cloud-specific activities included in PlutoSec’s Cloud Penetration Testing service offering are:

MCSL Evaluating cloud architecture against the OWASP Top 10 Cloud Security Risks

MCSL Testing serverless cloud services like AWS Lambda, Azure Functions, and Google Cloud Functions

MCSL Targeted activities for addressing the most common cloud vulnerabilities

    • Cloud Misconfigurations

    • External services and applications including APIs

    • Exposed sensitive information, data, and documents

    • Internal testing of cloud servers and services

    • Internal testing of cloud servers and services

    • Container and Pod security testing

    • Identity and access management (IAM)

Who Will Conduct This Test?

The pentester role, also known as an ethical hacker, is a specialized IT security position that requires specific training and certification. Ethical hackers can be generalists with broad penetration testing skills or specialists with in-depth expertise in certain aspects of the pentesting process. Specialists may focus on particular exploitation frameworks, protocols, operating systems, or procedures. For Cloud Penetration Tests, PlutoSec provides specialized experts, including GIAC Cloud Penetration Testers (GCPN).

The OSCP is a widely recognized and leading ethical hacking certification provided by Offensive Security. Although Offensive Security offers several certifications, the OSCP is the most comprehensive and renowned. PlutoSec is a dedicated team of highly skilled ethical hackers with the industry’s most advanced certifications. All PlutoSec pentesters are required to hold at least an OSCP certification. While OSCP is the minimum requirement at PlutoSec, many team members pursue additional certifications to further enhance their expertise, including:

MCSL Offensive Security Experienced Penetration Tester (OSEP) (OSEP)

MCSL Offensive Security Wireless Attacks (OSWP)

MCSL Offensive Security Exploit Developer (OSED)

MCSL Offensive Security Web Expert (OSWE)

MCSL Certified Information Systems Security Professional (CISSP)

MCSL Certified Information Systems Auditor (CISA)

MCSL GIAC Web Application Penetration Tester (GWAPT)

MCSL GIAC Mobile Device Security Analyst (GMOB)

MCSL GIAC Systems and Network Auditor (GSNA)

MCSL GIAC Exploit Researcher and Advanced Penetration Tester (GXPN)

MCSL GIAC Certified Incident Handler (GCIH)

MCSL Burp Suite Certified Practitioner

This enables our team of OSCP-certified penetration testing professionals to showcase industry-leading, hands-on expertise in comprehensive penetration testing.

PlutoSec provides thorough cloud penetration testing solutions designed to safeguard your cloud environment from malicious threats. For more details, download our sample cloud report today.

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