Cloud security vulnerabilities evolve at breakneck speed. New vulnerabilities emerge, configurations drift, and what was secure yesterday might be exposed today. If you’re responsible for cloud security, you’ve probably asked yourself: “When should I cloud penetration test?”
The short answer? Most organisations should conduct cloud penetration testing quarterly, with additional tests triggered by significant changes. But the real answer for how frequently you should be penetration testing depends on your industry, compliance requirements, cloud maturity, and risk tolerance.
Let’s break down exactly how to determine the right testing frequency for your organisation and what to test.
Industry Standards for Cloud Penetration Testing Frequency
Annual Testing: The Bare Minimum
Annual penetration testing is the baseline requirement for most regulatory compliance frameworks, including PCI DSS, SOC 2, and HIPAA. If you process payment card data, store protected health information, or need to maintain security certifications, annual testing isn’t optional: it’s essential!
However, annual testing alone is increasingly inadequate for cloud environments. Unlike traditional on-premises infrastructure which changes slowly, cloud environments are agile, enabling teams to deploy new services, modify IAM policies, and update configurations daily.
Consider it this way: a vulnerability that doesn’t exist in January could be exploited by March. That’s why regular security testing is essential in fortifying your cloud environment.
Quarterly Testing: The Recommended Standard
For most organisations with active cloud operations, quarterly penetration testing offers a healthy balance between security assurance and resource investment. A quarterly frequency allows you to:
- Catch configuration drift before it becomes critical
- Validate security controls after routine updates or system upgrades
- Stay ahead of emerging cloud-specific security vulnerabilities, especially those related to your cloud service provider.
- Maintain a proactive rather than reactive security posture, ensuring enhanced data security
It’s not uncommon for industries handling sensitive data- fintech, healthcare, and SaaS providers, for example- to test quarterly as a standard cybersecurity practice. Regular cloud penetration testing is essential in identifying security flaws before they can be exploited, and providing your organisation with a good understanding of the present cyber threat landscape you may be facing.
Continuous Testing: For High-Risk Environments and Proactive Security Leaders
Organisations in critical infrastructure, those with frequent deployments, or companies operating bug bounty programs often implement continuous security testing. This approach combines automated scanning with periodic manual penetration tests and ongoing security assessments, minimising business risks and providing clear insights into emerging threats.
Continuous testing remains the optimal testing option because it guarantees a complex overview of your security posture at any point in time. Security leaders seeking to be particularly proactive and robust in their security strategy- particularly those in enterprises- should strongly consider continuous testing as their choice for cloud pentesting frequency.
7 Critical Triggers That Mean You Need to Test Now
Beyond your regular testing schedule, certain events should trigger immediate security assessments:
1. Major Infrastructure Changes Deploying new cloud services, expanding to additional regions, or migrating workloads creates new attack surfaces that need immediate validation.
2. Significant Code Deployments: New applications, API modifications, or third-party integrations can introduce vulnerabilities that weren’t present in your last test.
3. IAM Policy Modifications: Changes to permissions, roles, or access controls are among the most common cloud security misconfigurations and deserve dedicated testing.
4. Security Incidents: After any security event, penetration testing verifies that remediation efforts were effective and no additional vulnerabilities were introduced during the response.
5. Compliance Deadlines: Schedule tests well before audits to ensure you have time to remediate any findings.
6. Major Product Launches: Customer-facing features or high-visibility releases warrant pre-launch security validation.
7. Mergers and Acquisitions Integrating new cloud environments or inheriting infrastructure requires a thorough security assessment to understand your expanded attack surface.
Common Vulnerabilities in your Cloud Networks
For your cloud infrastructure penetration testing to be truly effective, you should consider going beyond traditional, periodic network security assessments.
| Attack Vector | What is it? |
|---|---|
| API abuse and rate limiting | Attackers send too many requests to cloud APIs or find ways around usage limits to gain unauthorised access or crash services. |
| Advanced persistent threats | Skilled attackers who quietly break in and remain hidden in your cloud systems for long periods, using multiple tricks to avoid detection. |
| Cross-tenant data leakage risks | When cloud providers don’t properly separate customers, one customer might accidentally see another customer’s data. |
| Cloud service misconfigurations | Simple mistakes in cloud settings, like leaving things open to the public or turning off security features, can be exploited by hackers. |
| Supply chain vulnerabilities in cloud services | Security problems that come from third-party tools, code libraries, or container images you use in your cloud environment can be exploited by hackers. |
What Testing Frequency is Right for Me?
The right frequency depends on several factors:
Cloud Maturity Level
Early Stage (First year using cloud networks): Quarterly testing helps you learn cloud-specific risks unique to your business and establish baseline security.
Growing (Expanding footprint): As best practise, strive to maintain quarterly testing while adding trigger-based assessments for significant changes.
Mature (Established operations): Implement risk-based scheduling with continuous automated testing and periodic manual assessments.
Your Cybersecurity Budget
As with any pentest cost, cloud penetration testing costs will vary based on scope, ranging from a few thousand pounds for focused assessments to £30,000+ for comprehensive tests of complex environments within larger organisations. Think about your current budget and how this can account for cloud penetration testing without breaking the bank.
The average cost of a data breach now exceeds $4 million, making regular testing a clear ROI investment (and a great metric to share with your board for buy-in). For more information on how to optimise your pentesting ROI, check out our expert-led webinar, “The True ROI of Pentesting: How to Cut Costs Without Cutting Corners”.
How to build your testing schedule
Businesses that thrive most from their security best practices are stringent about creating a testing schedule. Create a testing calendar that:
- Aligns with compliance and audit cycles
- Avoids major deployment or business-critical periods
- Includes buffer time for remediation
- Accounts for multiple cloud providers if applicable
Maintaining Security Between Tests
Penetration tests are point-in-time assessments. To sustain security between tests, implement:
Cloud Security Posture Management (CSPM): Automated tools that continuously monitor for misconfigurations and compliance drift.
Infrastructure as Code (IaC) Scanning: Catch security issues before deployment by scanning Terraform, CloudFormation, or ARM templates.
Automated Vulnerability Scanning: Regular scans identify known vulnerabilities in your cloud resources.
Security Monitoring and Vulnerability Scanning: Real-time alerting for suspicious activities and policy violations, giving you an overview of your attack surface to proactively defend against potential threats.
Actionable Next Steps
Start by assessing your current testing frequency against your risk profile and compliance requirements. For most organisations, this means:
- Establish quarterly penetration testing as your baseline
- Define clear triggers for additional internal testing – thorough analysis
- Implement continuous monitoring between tests
- Document findings and track remediation
- Review and adjust your schedule annually – cloud configuration review
Cloud security isn’t a one-time checkbox; it’s an ongoing commitment. The question isn’t whether you can afford regular penetration testing, but whether you can afford not to. The more frequently you strive to conduct penetration testing, the more secure and threat-resilient your cloud platforms will be.
Ready to build your cloud penetration testing schedule? OnSecurity can support your organisation in identifying security weaknesses within your cloud environments with our cloud security testing services. Get a free, instant quote today.
