Penetration testing (aka pentesting or ethical hacking) might sound intense—and honestly, it is—but think of it as your digital stress test. Ethical hackers mimic real cyberattacks on your systems to find weak spots before the bad guys do. The coolest part? Pen tests come in different flavors, each targeting specific risks. 

So, how do you know when it’s time for a pentest? How often should you schedule them? And which one is right for your business? Don’t worry—we’ve got you covered! Let’s break it down in plain English. 

Signs Your Business Needs a PenTest 


If anything below sounds familiar, it’s time to bring in the friendly hackers: 

  • Big changes: You’ve upgraded your network, apps, or infrastructure. 
  • Compliance time: Certifications like SOC2, PCI DSS, HIPAA, or ISO 27001 are knocking on your door. 
  • Cyber insurance check: Your insurer wants proof your security posture is airtight, or you’re seeking a policy that won’t break the bank. 
  • Suspicious activity: A breach or weird incident has you sweating. 
  • Tech-heavy vibes: IoT, mobile apps, cloud tools, or custom-built systems are part of your daily grind. 
  • Growing pains: Expanding, merging, or adding new systems that make your network a bigger target. 
  • Human factor: You’re not sure if your employees can spot phishing emails or handle sneaky USB attacks. 
  • Risk clarity: You want to understand your actual vulnerabilities, not just run a checklist. 
  • Customer requirement: Clients demand proof you’re staying ahead of cyber threats before signing a contract with you. 
⭐
Pro Tip: Pen tests aren’t just about finding problems—they’re about staying one step ahead. Regular testing validates your fixes and keeps threats at bay.

How Often Should You Test? 


The short answer: It depends. But here’s a cheat sheet: 

  • External Pen Tests: Do these quarterly or bi-annually to test your firewalls, websites, and anything exposed to the outside world.  
  • Internal Pen Tests: Bare minimum is annually or after big changes to your network. Schedule these quarterly if you want to meet best practices to uncover risks from inside threats, like rogue devices or misconfigurations. 
Regular testing keeps your defenses sharp and trust us—you don’t want to play catch-up when threats are evolving daily. 

8 Types of Penetration Testing

1. Network Penetration Testing 

Think of this as a full diagnostic and health check for your network infrastructure. Ethical hackers mimic real-world attacks to uncover vulnerabilities that matter most in your internal and external network environment. 

What they’ll find: 

  • External:  
    • Public-facing services like web servers, VPNs, and email systems. 
    • Firewall misconfigurations or bypass opportunities. 
    • Open ports and exposed services accessible from the internet. 
  • Internal:  
    • Misconfigured devices, such as routers, switches, or servers. 
    • Unpatched software, outdated firmware, and default credentials. 
    • Network segmentation issues that allow lateral movement by attackers. 
    • Weak password policies and ineffective authentication measures. 
    • Vulnerable desktops, laptops, or mobile devices connected to the network. 
    • Open management ports or insecure remote access protocols. 
    • Privilege escalation on user machines. 
    • Susceptibility to man-in-the-middle (MITM) attacks. 
    • Gaps in user and admin access controls. 
    • Testing for vulnerabilities against known exploits like EternalBlue or ProxyShell. 
    • Identifying susceptibility to ransomware or other malware. 
    • Gaps in intrusion detection and prevention systems (IDS/IPS). 

When you need it:  
If you’ve added new systems, expanded your network, or it’s been over a year since your last check. It's also critical before major compliance audits or after an incident to validate your defenses.   

Your network is the backbone of your organization—make sure it’s fortified against every angle of attack. 

 

2. Web Application Penetration Testing  

Your web apps—like customer portals, custom-built applications, APIs, or e-commerce sites—are prime targets. This test dives deep into your apps to expose vulnerabilities lurking in the backend to ensure sensitive data and user interactions are safe. 

What they’ll find: 

  • Authentication flaws that allow unauthorized access. 
  • SQL injection vulnerabilities that can expose your database. 
  • Cross-site scripting (XSS) flaws that enable attackers to execute malicious scripts. 
  • Weak or improperly secured session tokens. 
  • Sessions not expiring properly, increasing the risk of hijacking. 
  • Exposed endpoints with insufficient access controls. 
  • Broken object-level authorization vulnerabilities. 
  • Sensitive information stored or transmitted without proper encryption. 
  • Leaky error messages revealing system details to attackers. 
  • Insecure default settings or unpatched software. 
  • Flaws in application workflows that attackers could exploit to bypass protections. 

When you need it:  
If you’ve launched a new web application, made significant updates to an existing one, or integrated new third-party APIs.  

Web apps are the front doors of your business—make sure they’re locked and secure. 

3. Wireless Penetration Testing  

Think of this as a deep dive into the airwaves that connect your organization. This test checks the security of your wireless networks, looking for vulnerabilities in configurations, encryption, and access controls that would allow attacks to break into your systems. Spoiler alert: weak Wi-Fi is an open door for hackers. 

What they’ll find: 

  • Weak or outdated encryption protocols (e.g., WEP, WPA, WPA2 with poor setup). 
  • Rogue access points posing as legitimate network entryways. 
  • Misconfigured or overly permissive SSID settings. 
  • Poorly implemented multi-factor authentication (MFA). 
  • Weak or reused passwords for Wi-Fi access. 
  • Mismanagement of guest or employee network segregation. 
  • Vulnerable IoT devices, printers, and mobile devices connected to the wireless network. 
  • Default credentials left on wireless-enabled devices. 
  • Susceptibility to replay attacks or wireless packet capture. 
  • Open or improperly secured hotspots vulnerable to eavesdropping. 
  • Attackers’ ability to intercept or manipulate wireless traffic. 

When you need it:  
If you’ve deployed new wireless networks, expanded office locations, or noticed an uptick in wireless devices. It's especially important for businesses with IoT systems, BYOD policies, or public-facing guest networks. 

Your wireless network is an invisible extension of your infrastructure—don’t let unseen vulnerabilities create a backdoor into your organization. 

4. Physical Penetration Testing  

Cybersecurity isn’t just digital. Physical pen tests assess how easily someone could waltz into your building and access critical areas. Ethical testers attempt to exploit weaknesses in physical security measures, from locks and cameras to human vulnerabilities like social engineering. 

What they’ll find: 

  • Unsecured entry points like unlocked doors, windows, or gates. 
  • Weaknesses in badge systems or keycard access controls. 
  • Tailgating or piggybacking risks at secure areas. 
  • Blind spots in camera coverage or ineffective monitoring practices. 
  • Non-functional or poorly positioned security cameras. 
  • Insufficient alarm or intrusion detection systems. 
  • Social engineering vulnerabilities, such as employees holding doors open for strangers. 
  • Lack of training on how to challenge unauthorized individuals. 
  • Unsecured sensitive documents, badges, or devices left unattended. 
  • Weak locks, broken barriers, or easily bypassed fences. 
  • Poor security for server rooms or other critical infrastructure. 
  • Inadequate storage or disposal of confidential materials. 

When you need it:  
If you have physical offices with sensitive data stored onsite. If you’ve moved into a new office, expanded your facilities, or recently upgraded your security system. It’s essential for industries with compliance requirements or a high risk of physical theft, like financial institutions or data centers. 

Your physical defenses are your first line of protection—ensure they’re as secure as your digital ones. 

5. IoT Penetration Testing  

With smart devices everywhere, IoT security can’t be ignored. Think of this as a security checkup for the interconnected devices that power your organization. This test identifies vulnerabilities that could be exploited in your smart systems, like device configurations, communication protocols, and access controls that could allow attackers to infiltrate your systems. Spoiler alert: unsecured IoT devices are a hacker's playground. 

What they’ll find: 

  • Default or weak passwords on IoT devices.  
  • Outdated firmware or unpatched vulnerabilities. 
  • Insecure communication protocols (e.g., MQTT, CoAP, HTTP). 
  • Vulnerabilities in Wi-Fi, Zigbee, or Bluetooth connections. 
  • Exposed or misconfigured ports allowing unauthorized access. 
  • Lack of proper authentication and authorization mechanisms. 
  • Vulnerable APIs and web interfaces. 
  • Misconfigured network settings exposing IoT devices to the internet. 
  • Insufficient encryption of data in transit and at rest. 
  • Poorly implemented device management and update processes. 
  • Susceptibility to denial-of-service (DoS) attacks. 
  • Inadequate logging and monitoring of IoT device activity. 
  • Attackers’ ability to exploit device vulnerabilities to gain network access. 
  • Integration vulnerabilities when IoT devices connect to legacy systems. 

When you need it:  
If IoT is a big part of your operations—think smart devices, industrial tools, or sensors. If you’ve deployed new IoT devices, expanded your IoT infrastructure, or noticed an increase in connected devices. It's especially crucial for businesses with critical IoT systems, smart office setups, or industrial IoT deployments. 

IoT devices are the gateway to your smart systems—ensure they’re not leaving the door open for attackers. 

 

6. Mobile Application Penetration Testing  

This test focuses on vulnerabilities in mobile apps for iOS and Android. Think of this as a deep dive into the apps that keep your organization connected on the go. This test scrutinizes the security of your mobile applications, their backend APIs, and how they handle sensitive data, ensuring your apps are as secure as they are functional. Spoiler alert: insecure mobile apps can be a goldmine for hackers. 

What they’ll find: 

  • Weak or outdated encryption methods for data storage and transmission. 
  • Insecure coding practices leading to vulnerabilities like SQL injection and XSS. 
  • Poorly implemented authentication and authorization mechanisms. 
  • Inadequate session management and token handling. 
  • Exposure of sensitive data through insecure APIs. 
  • Lack of proper input validation and sanitization. 
  • Vulnerable third-party libraries and SDKs. 
  • Insufficient protection against reverse engineering and tampering. 
  • Misconfigured app permissions and excessive privilege requests. 
  • Inadequate logging and monitoring of app activities. 
  • Attackers’ ability to exploit app vulnerabilities to gain unauthorized access. 

When you need it:  
If your company relies on mobile apps to connect with customers or employees. If you’ve launched a new mobile application, updated existing ones, or integrating with new APIs or third-party services. It’s a must for apps handling sensitive customer data, like banking or healthcare apps, or those subject to regulations like PCI DSS or HIPAA. 

Your mobile app is your brand in your users’ hands—make sure it’s secure, trustworthy, and protected from attackers. 

 

7. Cloud Penetration Testing  

Think of this as stress-testing your organization’s operations in the cloud. Ethical hackers analyze your cloud infrastructure, configurations, and applications to uncover vulnerabilities attackers might exploit. From misconfigured storage buckets to overlooked permissions, cloud pentesting ensures your data stays secure in the digital skies. 

What they’ll find: 

  • Misconfigured cloud storage exposing sensitive data. 
  • Improper security group rules, like exposed ports or unrestricted access. 
  • Inadequate identity and access management (IAM) policies. 
  • Default or weak passwords for cloud services. 
  • Weak or poorly enforced multi-factor authentication (MFA). 
  • Unencrypted sensitive data stored in the cloud. 
  • Weak or outdated encryption methods for data at rest and in transit. 
  • Improper key management for encryption, including exposed API keys. 
  • Vulnerable APIs and web interfaces. 
  • Susceptibility to denial-of-service (DoS) attacks. 
  • Insecure configurations of virtual machines and containers. 
  • Exploitable vulnerabilities in web applications hosted on the cloud. 
  • Lack of proper logging and monitoring of cloud activities. 

When you need it:  
If you’ve migrated to the cloud, expanded your cloud infrastructure, deploying new cloud services, or noticed an increase in cloud service usage. It's especially crucial for businesses with critical cloud-based applications, hybrid environments, or remote workforces. 

Your cloud infrastructure is as secure as your configurations—make sure there’s no room for error on the horizon. 

8. Red Team Assessment: A comprehensive approach to pentesting 

Think of this as the ultimate test of your organization’s readiness to handle real-world cyberattacks. A Red Team Assessment is designed to challenge your defenses by mimicking the tactics, techniques, and procedures of actual attackers. The goal? To uncover vulnerabilities and test how well your organization’s people, processes, and technologies respond to advanced threats. Spoiler alert: it’s not just about finding weaknesses—it’s about proving how resilient your defenses truly are. 

What they’ll test: 

  • Physical Security: Can attackers bypass physical barriers like doors, locks, or security systems? 
  • Network Defenses: Vulnerabilities in firewalls, routers, and internal network segmentation. 
  • Endpoint Security: Weaknesses in employee devices, workstations, and servers. 
  • Social Engineering: Can attackers trick employees into revealing sensitive information or providing unauthorized access? 
  • Incident Response: How quickly and effectively your team detects and reacts to an intrusion. 
  • Privilege Escalation: Opportunities for attackers to gain admin-level access after breaching the network. 
  • Exfiltration Paths: How easily sensitive data can be removed without detection. 
  • Persistence Mechanisms: Testing how long attackers can maintain access without being noticed. 

When you need it: 
If you’re ready to move beyond traditional pentesting and want to challenge your entire security program. It’s particularly important for organizations handling sensitive data, those with strict compliance requirements, or businesses preparing for advanced, targeted threats. A Red Team Assessment is especially valuable after major security upgrades or to benchmark your incident response capabilities. 

Your defenses are only as good as their ability to stand up to a real-world attack. Are you ready to see how they hold up under fire? 

Automate Network PenTesting with vPenTest  


Let’s face it—traditional network pen testing can be slow, expensive, and only performed once a year. That’s where vPenTest changes the game. 

Why businesses love vPenTest: 

  • Real-world simulations: Mimic actual threats to find your weak spots. 
  • Actionable reports: Clear findings with prioritized fixes. 
  • Frequent testing: Affordable monthly or quarterly options keep you ahead. 
  • Compliance-ready: Perfect for SOC2, PCI DSS, HIPAA, and more. 

With vPenTest, you get consistent, automated network penetration testing that’s easy, effective, and budget-friendly. Don’t wait for a breach to act. Discover how vPenTest can automate network penetration testing and keep your organization protected year-round. 

SCHEDULE A FREE DEMO