Cloud Pentesting 101: What to Expect from a Cloud Penetration Test

Hold on, let’s guess. 

You’ve moved a ton of your business to the cloud – storage, applications, the whole nine yards. Cloud computing offers flexibility, scalability, and a bunch of other benefits. 

But here’s the not-so-rosy side: 

80% of companies have reported a spike in cloud attacks.That’s right, cybercriminals are flocking to the cloud just as fast as businesses are. 

The cloud presents a vast attack surface, and for many companies, securing it can feel like a complex challenge.But there’s a way to be proactive, not reactive.  

This is where cloud penetration testing (pentesting) comes in.

What is Cloud Penetration Testing?

Cloud penetration testing, also known as cloud pentesting, is a simulated attack specifically designed to assess the security of an organization’s cloud-based systems and infrastructure. It acts like a controlled experiment where ethical hackers (penetration testers) attempt to exploit weaknesses in your cloud environment, just like a malicious actor might.

The primary focus of cloud pentesting is on uncovering misconfigurations and exploitable weaknesses within your cloud setup. These misconfigurations can be 

• Incorrect security settings on cloud resources
• Unintended access permissions granted to users or applications
• Weak passwords or encryption keys
• Outdated software versions with known vulnerabilities

By simulating real-world attacks, pentesters can identify these vulnerabilities before they can be exploited by cybercriminals.

But before going deep in cloud penetration testing, it’s important to know why cloud security is such a hot topic.

Why Are Businesses Shifting to the Cloud?

Here’s the big shift: companies are moving away from traditional on-premise infrastructure in favor of the flexibility and efficiency of cloud-based solutions. This transition brings numerous benefits, making cloud computing highly appealing.

1. Cost Efficiency and Resource Optimization

Moving to the cloud helps businesses reduce IT expenses by eliminating the need for costly on-premises infrastructure. Instead of investing in physical servers and data centers, companies can leverage cloud providers to handle storage, computing, and security needs. This shift also allows businesses to scale up or down based on demand, optimizing resources and reducing operational costs.

• Pay-as-You-Go Model: Cloud services operate on a subscription or pay-as-you-go basis, allowing businesses to pay only for their resources, which can greatly reduce capital expenses.
• Reduced Maintenance Costs: Cloud providers manage infrastructure maintenance, so businesses save on hardware upkeep and IT staffing.

2. Scalability and Flexibility

Cloud solutions provide unparalleled scalability, allowing businesses to expand or reduce resources quickly. Whether it’s handling seasonal traffic spikes or accommodating business growth, the cloud makes it easy to adjust capacity without significant time or cost investments.

• On-Demand Resource Allocation: Cloud platforms allow businesses to allocate resources in real-time, meeting demands as they arise without overprovisioning.
• Global Reach: With cloud infrastructure, companies can deploy applications or services across multiple geographic regions, ensuring global reach and low-latency access for users.

3. Enhanced Collaboration and Remote Work Enablement

The cloud fosters real-time collaboration by allowing team members to access, share, and work on files and applications from any location. As remote work becomes a staple for many organizations, cloud technology provides employees with a flexible, accessible, and seamless way to connect and collaborate.

• Centralized Data Access: Cloud-based platforms ensure that employees can access essential documents and tools from any device, regardless of location.
• Collaborative Tools: Cloud solutions often integrate with tools like Google Workspace, Microsoft 365, and Slack, enhancing productivity and teamwork.

4. Data Security and Compliance

While security concerns were initially a barrier to cloud adoption, today’s cloud providers have advanced security measures in place, including data encryption, threat monitoring, and compliance support. Cloud providers regularly update their security protocols to help companies meet industry standards and comply with regulations.

• Built-In Security Controls: Cloud providers offer tools like identity and access management (IAM), firewalls, and data encryption by default, enhancing security.
• Compliance Support: Many cloud services are compliant with major regulatory frameworks, such as GDPR, HIPAA, and SOC 2, helping businesses meet their compliance obligations more easily.

5. Innovation and Agility

The cloud enables businesses to innovate faster by providing access to the latest technologies without the need for upfront investments in hardware. Cloud platforms offer services like artificial intelligence (AI), machine learning (ML), data analytics, and the Internet of Things (IoT) that can be integrated into business operations to drive competitive advantage.

• Access to Cutting-Edge Tools: Cloud providers offer a range of advanced services like machine learning, big data analytics, and IoT platforms, which empower businesses to harness the latest technologies.
• Faster Time-to-Market: With cloud solutions, businesses can develop, test, and deploy applications more quickly, allowing them to respond rapidly to market changes or customer needs.

6. Disaster Recovery and Business Continuity

The cloud offers built-in disaster recovery (DR) solutions that protect against data loss and ensure business continuity during unexpected events. With automated backups, data replication, and easy failover options, the cloud helps businesses recover quickly from incidents without major disruptions.

• Automated Backups: Cloud providers offer automated backup and recovery options, reducing downtime and protecting critical data.
• Redundancy Across Regions: With multi-region redundancy, cloud services can replicate data and services across different locations, minimizing the risk of total data loss.

Major Cloud Service Providers

Amazon Web Services (AWS), Microsoft Azure, and Google Cloud Platform (GCP) are the top 3 cloud service providers, controlling 62% of the market as of 2024. 

The cloud offers a compelling value proposition for businesses. It’s no wonder companies are flocking to it. But with great opportunities come potential risks. 

You can also checkout detailed guides on penetration testing for each major providers –

AWS penetration testing

Azure penetration testing

GCP penetration testing

Why the Shift to Cloud Can Be Dangerous?

So, we’ve established that the cloud is fantastic for businesses—flexibility, efficiency, cost savings, the whole package. 

But hold on; let’s not get too comfortable. 

The very things that make the cloud so attractive can also introduce security risks.

Here are the snapshots of some recent cloud security breaches. 

Let’s take a look at 10 cloud security threats that you should be aware of:

1. Misconfiguration: With the wide range of options in cloud platforms, missing a single setting can expose data to attackers. A minor misconfiguration can result in significant security vulnerabilities.
2. Unauthorized Access: Cloud security operates on a shared responsibility model. Providers secure their infrastructure, but you’re responsible for access controls within your environment. Weak passwords, insecure access policies, or compromised credentials can lead to unauthorized access to your data.
3. Insecure Interfaces and APIs: APIs provide access to your cloud resources. If not secured properly, these interfaces can be exploited, allowing attackers to breach data or launch further attacks on your systems.
4. Data Loss: Data breaches, accidental deletion, insider threats, or poorly configured storage can all lead to data loss. The cloud is no exception to these risks.
5. Denial-of-Service (DoS) Attacks: DoS attacks aim to disrupt cloud resources, affecting availability for legitimate users. While cloud providers offer protections, having your own mitigation strategies is essential.
6. Malware: Malware can infiltrate the cloud environment through infected uploads or vulnerable cloud applications. Using both cloud-based and endpoint security solutions helps mitigate these risks.
7. Shared Technology Vulnerabilities: The shared infrastructure in cloud environments means that vulnerabilities in the underlying system can impact all users. Regularly applying cloud provider security updates and promptly patching your systems is essential.
8. Insider Threats: Insider threats can arise from within the organization, as malicious users leverage authorized access to steal data or disrupt operations. Implementing strict access controls and monitoring user activities is critical.
9. Lack of Visibility: Maintaining visibility in the cloud can be challenging. Although providers offer monitoring tools, additional solutions may be needed to get a comprehensive view of your cloud security.
10. Data Residency and Compliance: Regulations around data storage vary by industry and region. Knowing and adhering to these data residency requirements is necessary to stay compliant.

This is where cloud penetration testing plays a vital role—ensuring your cloud environment is secure and resilient against potential attacks.

Benefits Of Cloud Penetration Testing

Types of Cloud Penetration Testing

Cloud penetration testing can be tailored to your needs using different approaches, each offering unique insights into your security posture. Here’s a breakdown of each approach, detailing the Process, Benefits, and Ideal For scenarios.

White-Box Cloud Penetration Testing

Process:
In white-box cloud penetration testing, testers have full access to system configurations, source code, and user accounts. This approach allows penetration testers to conduct an in-depth assessment of the cloud environment, including both infrastructure and applications. Since testers have complete visibility, they can thoroughly examine potential vulnerabilities and security controls.

Benefits:

• Comprehensive Analysis: By accessing all available information, testers can perform an exhaustive evaluation of cloud resources, revealing issues that may go unnoticed with limited visibility.
• Targeted Remediation Suggestions: Detailed knowledge of the cloud setup enables testers to provide highly specific recommendations tailored to your cloud infrastructure and applications.
• Improved Efficiency: Having prior access to internal documentation speeds up the testing process, as testers can dive directly into evaluating and exploiting potential weaknesses without the need to gather additional information.

Ideal For:

• Custom Cloud Environments: Companies with unique cloud configurations or proprietary applications that require a thorough security check.
• High-Security Industries: Organizations in sectors such as finance or healthcare where comprehensive security evaluations are necessary due to strict regulatory standards.
• Infrastructure Overhaul: Businesses undergoing significant cloud infrastructure changes, such as migrations or reconfigurations, benefit from an in-depth evaluation.

Black-Box Cloud Penetration Testing

Process:
Black-box cloud penetration testing simulates an external attack with testers having no prior information about the system, much like a real attacker would. Testers rely on reconnaissance and other standard penetration testing tools to discover weaknesses in cloud defenses. This approach replicates how external malicious actors attempt to infiltrate your cloud environment without insider knowledge.

Benefits:

• Realistic Attack Simulation: By taking the perspective of an external attacker, this approach provides a clear picture of vulnerabilities that are exposed to the outside world.
• Unbiased Assessment: Without prior knowledge of system details, testers reveal potential entry points that may be visible to unauthorized individuals.
• Enhanced Prioritization: Since testers focus on easy-to-access vulnerabilities, the results help prioritize high-risk areas that might be more vulnerable to external attacks.

Ideal For:

• Standardized Cloud Setups: Businesses using popular cloud applications or common configurations that external attackers are likely to target.
• Testing External Defenses: Companies looking to evaluate the strength of their perimeter defenses against external threats.
• Newly Deployed Environments: Organizations that have recently migrated to the cloud and want to verify the security of their default setup.

Gray-Box Cloud Penetration Testing

Process:
Gray-box cloud penetration testing is a blend of white-box and black-box approaches. Testers have partial knowledge of the cloud environment, such as basic configurations, system types, and functionalities. This semi-informed perspective allows testers to efficiently identify potential risks without the need for complete access to system details.

Benefits:

• Balanced Insight: Testers get a focused view of potential vulnerabilities, optimizing the time spent while still providing a deep examination of critical areas.
• Enhanced Focus on Key Areas: With some knowledge of system configurations, testers can target specific, high-risk components more effectively.
• Cost-Effective Approach: This middle-ground approach often saves on time and resources compared to full white-box testing while still providing a thorough assessment.

Ideal For:

• Hybrid Cloud Environments: Organizations with a mix of custom and standardized cloud solutions that require specific areas to be tested without a full white-box approach.
• Testing Key Controls: Companies that want to examine specific aspects of their cloud security, such as particular applications or services.
• Resource-Conscious Security Assessments: Organizations seeking a focused, cost-effective penetration test that offers a blend of thoroughness and efficiency.

Cloud Penetration Testing Methodology

1. Reconnaissance

• Objective: The reconnaissance phase aims to gather as much information as possible about the target cloud environment. This stage sets the foundation for subsequent testing by identifying entry points, system configurations, and potential weaknesses.
• Key Activities:
  • Identify Cloud Service Providers: Determine which providers (e.g., AWS, Azure, GCP) are in use and understand their specific services relevant to the environment.
  • Asset Discovery: Locate resources within the cloud, such as storage buckets, databases, and servers, which could be potential targets for attackers.
  • Network Topology Mapping: Understand how resources within the cloud environment are connected to outline paths that an attacker might exploit.
  • Access Point Analysis: Identify APIs, user accounts, and endpoints that provide access to the environment.
  • Configuration Review: Evaluate documentation and any provided configuration details to identify areas that may warrant closer examination.
• Outcome: A detailed mapping of the cloud environment’s layout, access points, and initial observations on potential security gaps.

2. Build Test Cases

• Objective: After gathering information, penetration testers design targeted test cases. These scenarios simulate potential attack methods an attacker might use to compromise the cloud environment.
• Key Activities:
  • Cloud-Specific Attack Simulations: Design test cases based on common cloud attack vectors, such as exploiting misconfigurations, weak permissions, and unsecured APIs.
  • Access Control Testing: Check for gaps in identity and access management (IAM), ensuring that permissions are not too permissive or easily exploitable.
  • Data Leakage Scenarios: Develop cases to simulate accidental data exposure within the cloud, such as public storage buckets or unsecured databases.
  • Privilege Escalation Paths: Map out potential paths where attackers might move laterally within the environment to gain higher access privileges.
• Outcome: A comprehensive list of test cases tailored to the specific configurations and known vulnerabilities in the cloud environment, forming a blueprint for the next phase.

3. Deploy Scanners

• Objective: In this phase, automated vulnerability scanners are deployed to quickly identify common and high-risk vulnerabilities in the cloud environment.
• Key Activities:
  • Misconfiguration Detection: Use cloud-focused scanning tools to find configuration errors in storage, databases, and network resources.
  • Patch Status Checks: Identify outdated software and known vulnerabilities that have not yet been patched.
  • Weak Credential Scans: Look for weak or default passwords that attackers might exploit for unauthorized access.
• Outcome: A list of vulnerabilities and issues that can be used to prioritize manual testing efforts, ensuring that critical weaknesses are addressed promptly.

4. Manual Penetration Testing

• Objective: Unlike automated scanning, this phase involves testers manually validating and exploiting vulnerabilities to simulate real-world attacks.
• Key Activities:
  • Targeted Exploits: Testers actively exploit vulnerabilities based on the reconnaissance and automated scanning results, confirming their impact.
  • Privilege Escalation Testing: Attempt to escalate permissions within the cloud environment to access sensitive systems or data.
  • Lateral Movement Simulation: Move through the network as an attacker might, trying to reach valuable assets or gain higher-level access.
  • Validation of Security Controls: Check that security controls, such as firewall rules and access policies, effectively block unauthorized access.
• Outcome: A validated list of vulnerabilities, each with evidence of potential impact, demonstrating how real attackers might compromise the environment.

5. Report Generation

• Objective: This phase involves compiling the findings into a clear and actionable report, helping the organization understand its security posture and take necessary steps.
• Key Components:
  • Methodology Summary: Describe the testing methods, tools, and approaches used, giving stakeholders a clear understanding of the testing process.
  • Vulnerability Details: List each identified vulnerability, including risk levels, potential impacts, and exploitability evidence.
  • Remediation Recommendations: Provide actionable steps to address each vulnerability, including specific configurations or patches needed to secure the environment.
  • Compliance Insights: If relevant, outline how findings may impact compliance requirements, such as GDPR, SOC 2, or HIPAA.
• Outcome: A detailed, structured report that serves as both a roadmap for remediation and a record of the organization’s security standing at the time of testing.

Cloud Security: The Shared Responsibility Model

In a cloud environment, security is managed through a shared responsibility model. This approach divides security duties between the Cloud Service Provider (CSP) and the customer, assigning each party specific responsibilities based on their level of control and expertise. This collaborative model promotes a well-rounded security posture for cloud operations.

Understanding the Division of Responsibility

Why is the Shared Responsibility Model Important for Penetration Testing?

Understanding the shared responsibility model is essential for conducting effective cloud penetration testing. Here’s why:

• Focused Testing: By defining specific security responsibilities, organizations can focus penetration testing efforts on areas within their control. This targeted approach allows for efficient testing, pinpointing vulnerabilities that are directly manageable by the customer.
• Enhanced Security Posture: The shared model fosters collaboration with the Cloud Service Provider (CSP). Penetration testing guided by shared responsibilities helps identify weaknesses across both the customer’s configurations and the CSP’s infrastructure, strengthening overall security.
• Regulatory Compliance: Many compliance standards require organizations to understand and act on their security obligations in cloud environments. Penetration testing that aligns with the shared responsibility model demonstrates a proactive approach to meeting regulatory requirements.

Aligning Cloud Penetration Testing with the Shared Responsibility Model

• Map Your Responsibilities: Clearly define your security boundaries within the cloud environment based on the service model (IaaS, PaaS, SaaS) you utilize.
• Collaborate with your CSP: Establish clear communication channels with your CSP to understand their security practices and testing methodologies.
• Focus on Your Security Domain: Design penetration tests to target vulnerabilities within your control, leveraging the expertise of the CSP for any identified infrastructure weaknesses.

Best Practices for Cloud Penetration Testing

1.  Understand Cloud Service Models: 

Understand the division of security responsibilities between you and your cloud provider. This clarity is essential for identifying which vulnerabilities fall within your scope to manage and which are the provider’s responsibility.

2. Obtain Proper Authorization:

Before conducting penetration testing, always obtain written consent from both the cloud service provider and the resource-owning organization. This is essential to prevent legal complications and avoid service interruptions.

3. Define Clear Objetives:

Clearly define the objectives of your penetration test, specifying the services, applications, and data to be tested. This ensures the testing team can concentrate their efforts effectively.

4. Choose the Right Testing Approach: 

• White Box Testing: Provides complete access to the environment, enabling comprehensive assessments.
• Black Box Testing: Mimics an external attack with no prior knowledge of the system, simulating a real-world threat.
• Gray Box Testing: Blends both approaches, giving testers partial knowledge for a balanced assessment.

5. Plan and Scope Effectively:

Create a detailed pentesting plan. Identify the cloud services to be tested, set clear timelines, and inform stakeholders about expectations and any potential effects on service availability.

6. Conduct Comprehensive Reconnaissance: 

Gather information about the target environment. This includes identifying IP ranges, subdomains, and services in use to uncover potential attack vectors

7. Perform Vulnerability Assessment:

Combine automated tools with manual testing. Run vulnerability scans to spot known weaknesses in cloud infrastructure and applications. This combined method improves detection capabilities.

8. Document Findings Thoroughly:

Document every aspect of the penetration testing process, covering the methodologies used, findings, and remediation recommendations. A clear and structured report is crucial for effectively addressing identified vulnerabilities.

9. Establish Incident Response Plans:

Have a rapid incident-response strategy in place to address any security issues that may arise during or after testing

10. Verify Patch Effectiveness:

After identifying and addressing vulnerabilities, confirm that the patches successfully reduce risks. Perform follow-up testing as needed to maintain security.

Major Cloud Penetration Testing Tools

1. Scout Suite

A comprehensive, multi-cloud security auditing tool, Scout Suite empowers organizations to assess the security posture of their entire cloud infrastructure. It supports major cloud providers like AWS, Azure, and GCP, enabling a holistic view of potential vulnerabilities and misconfigurations.

2. Pacu

Specifically designed for AWS security, Pacu is an open-source tool that automates the identification of vulnerabilities and misconfigurations within AWS environments. It offers a streamlined approach to security assessments, helping organizations pinpoint weaknesses and prioritize remediation efforts.

3. Metasploit

As a powerful penetration testing framework, Metasploit provides a wide range of exploits and modules to simulate real-world attacks. By leveraging Metasploit, security professionals can evaluate the effectiveness of their cloud security controls and identify potential attack vectors.

4. Burp Suite

Burp Suite is a versatile web application security testing (WAST) platform that plays a crucial role in securing cloud-hosted web applications. It offers a suite of tools for manual and automated testing, enabling the discovery and exploitation of vulnerabilities such as SQL injection, cross-site scripting (XSS), and more.

5. Netsparker

Netsparker is a robust web application security scanner that can be deployed on-premises or in the cloud. It provides in-depth vulnerability scanning, accurate vulnerability detection, and proof-of-concept exploits for cloud-based web applications.

Cloud-Based Penetration Testing Service with Strobes

Free scanning tools can help identify basic vulnerabilities, but a professional cloud-based penetration testing service like Strobes provides a comprehensive approach. Strobes combine industry-standard tools, such as Nmap and Burp Suite, with expert manual testing to uncover deeper vulnerabilities. This approach yields actionable insights to help you secure your cloud environment effectively.

1. Add best practices
2. Update the tools with indepth content