Single annual penetration tests don’t cut it anymore. There, I said it.
Not because they’re useless. They’re not. But if you think one test a year is protecting you in today’s environment, you’re kidding yourself.
Attackers Don’t Think in Silos
Here’s the problem with how most companies approach security testing. They test their network. Then maybe their web applications. Perhaps their cloud infrastructure if someone remembers. Each test happens separately, often months apart, by different teams who don’t talk to each other.
But attackers? They don’t care about your organisational boundaries. They’ll exploit a vulnerability in your web application to get credentials. Use those credentials to access your cloud environment. Pivot from there to your internal network. Escalate privileges. Access sensitive data. All in one connected attack chain.
Your testing needs to reflect that reality. Not separate, isolated assessments that ignore how everything connects. Integrated testing that understands how a weakness in one layer becomes an entry point to everything else.
When One Weakness Opens Everything
Let me give you a scenario I’ve seen variations of dozens of times.
Company does web application penetration testing. Finds some medium-severity issues. Nothing critical. They fix the obvious stuff, leave the rest on the backlog.
Few months later, they do external network testing. Again, nothing critical. Some outdated services, minor misconfigurations. Gets noted, doesn’t get fixed urgently.
Then someone actually tests how these issues connect. Turns out that medium-severity web app vulnerability? It exposes internal hostnames and API endpoints. Those external network misconfigurations? They allow access to those internal endpoints from the internet. Combine them and suddenly an attacker can access internal systems without ever touching the VPN.
Neither test alone showed this. Both together? Critical vulnerability. That’s why isolated testing misses the real threats.
Your Perimeter Doesn’t Mean What It Used To
Companies still obsess about perimeter security. Firewalls. IDS. Network segmentation. All important, sure.
But your perimeter is fiction now. Your staff work from everywhere. Your applications run in the cloud. Your data sits in SaaS platforms. Contractors and partners have access to internal systems. Your “perimeter” is wherever your users happen to be at any given moment.
So yeah, external testing matters. But internal testing matters just as much. Because assuming attackers are always external is naive. Compromised credentials. Malicious insiders. Supply chain attacks. Breached partners. There are loads of ways attackers end up “inside” without ever touching your perimeter.
Internal network penetration testing shows what someone with internal access can actually do. Can they move laterally? Access systems they shouldn’t? Escalate privileges? Exfiltrate data? These aren’t theoretical questions. These are the actual paths attackers take once they’re in.
And if you’re only testing your external defences, you’ve got no visibility into whether your internal security controls actually work.
Cloud Complexity Is Out of Control
Cloud environments are brilliant. Flexible, scalable, powerful. Also incredibly complex and ridiculously easy to misconfigure.
You’ve got identity and access management with hundreds of possible permission combinations. Storage with multiple security settings. Networking with complex rules and policies. Serverless functions that might or might not be properly secured. Container orchestration with its own security considerations. All of it changing constantly as teams deploy updates.
Traditional testing approaches cannot handle this. The environment changes faster than you can test it. What was secure yesterday might be completely exposed today because someone deployed a new service with default settings.
Cloud penetration testing needs to be continuous. Not necessarily full-scope testing every day, but ongoing monitoring and regular assessments that adapt to your deployment pace.
For Azure environments, that means specific Azure penetration testing that understands Key Vault configurations, managed identities, role-based access control, and all the Azure-specific security considerations. For AWS, it means AWS pen tests that cover IAM policies, S3 bucket permissions, Lambda security, and the dozens of other AWS-specific attack surfaces.
Generic cloud testing doesn’t cut it. You need testers who understand the specific platform you’re using and the specific ways it can be misconfigured or exploited.
Web Applications That Change Every Week
Your web applications probably change more frequently than you realise. New features. Bug fixes. Updated libraries. API changes. Performance improvements. If you’re doing agile development, you’re pushing updates constantly.
Every change is a potential security issue. New code might introduce vulnerabilities. Updated libraries might have known flaws. Changed authentication logic might break access controls.
Annual web application testing cannot possibly keep up. By the time you get the report, the application’s different. The vulnerabilities might be fixed or new ones might exist. The findings are already outdated.
Modern development requires modern testing. Testing integrated into your development cycle. Automated scanning for obvious issues. Manual testing for business logic flaws and complex vulnerabilities. Regression testing when significant changes happen.
Applications handling sensitive data, authentication, or financial transactions need even more frequent testing. Because these are the high-value targets attackers focus on.
The Testing Partner Question
Right, so if you’re convinced you need more integrated, continuous testing, how do you actually make that happen?
First, you need to work with the best penetration testing company you can find that understands cross-layer testing. Not companies that just do network scans or web app tests in isolation. Companies that can assess how vulnerabilities in different layers connect and compound.
They should understand multi-cloud environments. They should be able to simulate realistic attack chains. They should provide reporting that explains business impact, not just technical findings. They should support continuous testing models, not just annual assessments.
And critically, when you’re getting quotes, make sure the scope covers all the relevant attack surfaces. Your external network. Your internal systems. Your cloud infrastructure. Your web applications. All tested in a way that understands how they connect.
Cheapest quote isn’t best quote if it’s only testing half your environment.
What Continuous Actually Means
Continuous testing doesn’t mean running full penetration tests every day. That’d be impractical and probably counterproductive.
What it means is adapting your testing frequency to how your environment changes. Critical systems or rapidly changing applications might need monthly testing. Stable infrastructure might be fine with quarterly assessments. Cloud environments probably need continuous monitoring with deeper testing quarterly.
It also means retesting after significant changes. Major application updates. Infrastructure migrations. New cloud services. These aren’t “wait until next year’s test” situations. These need immediate security validation.
Some companies are implementing DevSecOps models where security testing is integrated into deployment pipelines. Automated checks happen with every build. Manual testing happens before major releases. Continuous monitoring catches configuration drift.
That’s where things are heading. Security testing that moves at the speed of development, not testing that’s always six months behind.
The Reality Check
Look, implementing proper multi-layer, continuous testing is more work than annual point-in-time assessments. It costs more. It requires more coordination. It’s more complex to manage.
But you know what’s even more expensive? Getting breached because you missed the connection between vulnerabilities in different layers. Or because your testing was six months out of date. Or because you only tested your external network and ignored your cloud environment.
Attackers are sophisticated. They chain vulnerabilities together. They move laterally through environments. They exploit the gaps between your different security controls.
Your testing needs to match that sophistication. Isolated, annual assessments don’t show you how an attacker would actually breach your systems. Integrated, continuous testing does.
Making It Actually Happen
So what does implementing this actually look like?
Start by mapping your actual attack surface. Not what you think it is, what it actually is. Your public-facing systems. Your cloud environments. Your web applications. Your internal networks. Everything.
Then build a testing programme that covers all of it. Some stuff needs frequent testing. Some can be less frequent. But it all needs regular assessment, not just hoping it’s fine.
Work with testers who understand how to assess cross-layer attack paths. Who can show you how a web app vulnerability leads to cloud access leads to internal network compromise.
Integrate testing into your development and deployment processes. Don’t treat security as something that happens separately from development. Build it in.
Monitor continuously for configuration drift and new exposures. Especially in cloud environments where things change rapidly.
And actually remediate findings. Promptly. Testing that finds problems but doesn’t lead to fixes is pointless.
The Uncomfortable Truth
Security isn’t a state you achieve. It’s a process you maintain. Your environment changes constantly. New vulnerabilities get discovered. Attackers develop new techniques. Your threat landscape evolves.
Static, annual testing made sense when environments were relatively stable. When changes were infrequent. When attacks were simpler.
That’s not the world we live in anymore. Modern environments are dynamic. Changes happen constantly. Attacks are sophisticated and multi-stage.
Your security testing needs to evolve to match. Not because it’s trendy or because vendors are pushing it. But because it’s the only approach that actually reflects how modern attacks work.
The companies getting this right aren’t the ones doing massive annual tests. They’re the ones doing continuous, layered assessments that adapt as their environment changes. That understand how different attack surfaces connect. That test the way attackers actually attack, not the way testing has traditionally been scoped.
That’s where security testing is going. And if you’re still relying on annual point-in-time assessments in isolation, you’re already behind.
