Your organization might have many cybersecurity defenses in place, but defenses alone are not enough to protect you from today’s multi-faceted cyberattacks.  Proactively adding a layer of offensive security assessment and testing helps you pinpoint your system weaknesses before they are exploited.  Proactive security measures help you stay ahead of attackers by:

• Identifying vulnerabilities and potential attack paths in your environment
• Quantifying the risk they create for important assets
• Testing your detection and response efficacy
• Providing companies with the transparency they need to prioritize and allocate resources

Proactive security also helps fulfill regulatory requirements so that organizations achieve compliance and ensure sensitive systems and data are properly secured. Below are three crucial components to any proactive security strategy.

1) Vulnerability Management (VM)

Vulnerability management solutions identify, evaluate, prioritize, track, and report on the weaknesses that can undermine your organization. Once a vulnerability scan has been completed, teams will not only know which CVSS scores to watch out for, but which ones present the most present and immediate risk – and which ones can wait.  

This must be done early and often. Scanning for vulnerabilities is not a static task, as each new service, device, application, and API introduces new opportunities for trouble. Vulnerability management is an ongoing process and an important level-set for proceeding to further offensive security techniques.  

Application Security: A Crucial Component of VM 

Application security is an integral part of VM, as it targets the software development lifecycle and leans on proactive shift-left principles. Its two main components are: 

• Static Application Security Testing (SAST): SAST hunts for weaknesses early in the software development process, identifying and eliminating them before the product is built, packaged, deployed, and in a position to endanger other players in its software supply chain.
• Dynamic Application Security Testing (DAST): DAST covers the front-end of application security testing, once the application is running. Testers are given no foreknowledge of the app’s internal designs, programming, or systems, and must probe and attack it blind, like an attacker (or a pen tester). The purpose behind DAST is to test the application in the real world and see how it responds to this “black box” testing. Its behaviors under pressure will indicate whether it might have unresolved vulnerabilities that require further examination.  

What to Look for in a VM Solution 

When looking for the right VM solution for your organization, it’s important to keep in mind that enterprise-grade vulnerability management can: 

• Scan local systems and the entire network.
• Correlate data from and on dynamic assets.  
• Save time by being easy to deploy, learn, and maintain. 
• Segment reports by location, team, department, and more. 
• Integrate seamlessly with other tools in your stack.

2) Penetration Testing  

As captured in our 2024 Penetration Testing Report, a full 72% of respondents said that penetration testing has prevented a breach in their organization. And it’s no surprise; penetration testing lets you exploit latent vulnerabilities before the threat actors do, allowing you to simulate a breach of your own network instead of letting Black Hats do it for you.  

Penetration testing, or pen testing, uses the vulnerabilities discovered in the VM stage as a jumping-off point to see if they can be exploited – and how far. Per our 2023 Penetration Testing Report, 69% perform pen tests to assess risk and prioritize remediation, many using it as a precautionary practice against ransomware (72%), phishing (70%), and misconfigurations (58%).  It can also be used after remediation is completed to gauge the effectiveness of the fixes.  

Where to Find Pen Testing Resources 

Pen testers are worth their weight to an organization, but at a time when most companies are struggling to fill cyber talent gaps, they might not be part of the in-house team at every organization. That’s fine. Penetration testing, as a service or a technology, can be outsourced.  

Fortra’s Core Impact leverages guided automation and certified exploits so teams of any skill level can test their environment using the same techniques as today’s threat actors. You can also use our penetration testing services (Core Security SCS) if resources are running short. 

Another option is to upskill current employees to give them the pen testing skills you need them to have. More and more organizations are turning to upskilling and reskilling to plug cybersecurity skills gaps and offer their employees more job security, flexibility, and growth opportunities.  

Key components for successful pen testing 

In a successful penetration test, the following elements will be present: 

• Network security tests | Uncover network vulnerabilities as well as weaknesses on your routers, switches, and network hosts.
• Web application tests | Test web applications for coding errors, broken authentication, and injection vulnerabilities.
• Social engineering tests | Put your employees and defenses to the test by launching phishing simulations and vetting the effectiveness of your detection tools in action.
• Automation | Automated pen testing tools systematically compromise potential places of exposure.

3) Red Teaming

Red team engagements take things a step further than pen testing, subjecting the whole cyber defense strategy to adversarial-level scrutiny.  Red teaming can include anything from phishing to social engineering executives to leveraging the most advanced techniques used by threat actors today. And the test is for the security team as much as it is for the security defenses; In a crisis, what you can do under pressure is worth ten times more than what you know in theory.  

Fortra offers advanced tools that enable red teamers to perform advanced engagements. 

• Cobalt Strike enables teams to emulate a stealthy, advanced adversary that’s been embedded in the network long-term and supports the use of different malware and social engineering ploys likely to be encountered. Its flexible Command and Control (C2) framework  gives in-house staff the ability to modify, work around, or use built-in behaviors.  View a Cobalt Strike demo here. 

• Outflank Security Tooling (OST). Dive more in-depth with evasive attack simulation. This a broad set of tools designed to help red teamers create attacker scenarios that put defensive measures, detection tools, and response skills to the test. These offensive security tools also simplify red teaming engagements, allowing users to easily perform complex tasks safely. 

When layered together, offensive security can help prevent sensitive data breaches, even as your network environment expands. This methodology provides piece of mind for security professionals, knowing they have discovered and addresses high-risk vulnerabilities and other weaknesses that might make their organization an attractive attack target.