How SSL Misconfigurations Impact Your Attack Surface

When assessing an organization’s external attack surface, encryption-related issues (especially SSL misconfigurations) receive special attention. Why? Their widespread use, configuration complexity, and visibility to attackers as well as users make them more likely to be exploited.

This highlights how important your SSL configurations are in maintaining your web application security and minimizing your attack surface. However, research shows that most (53.5%) websites have inadequate security and that weak SSL/TLS configuration is amongst the most common application vulnerabilities.

Get your SSL configuration right, and you’ll enhance your cyber resilience and keep your apps and data safe. Get it wrong, however, and you can increase your organization’s attack surface, exposing your business to more cyberattacks. We’ll explore the impacts of SSL misconfigurations and explain why they present such a significant attack surface risk. Then, we’ll show you how a solid EASM platform can help overcome the challenges associated with detecting misconfiguration issues.

Understanding SSL misconfigurations and attack surface#

An SSL misconfiguration occurs when SSL certificates are improperly set up or managed, top to vulnerabilities within an organization’s network. These misconfigurations can include outdated encryption algorithms, incorrect certificate setup, expired SSL certificates, and more. Such vulnerabilities directly affect an organization’s attack surface by creating possible entry routes for hackers.

SSL misconfiguration: A significant attack surface risk#

SSL certificates provide a secure channel for data transmission between clients and servers. They authenticate websites’ identities, ensuring users communicate with the intended entity. Misconfigured SSL certificates, however, can lead to risks, such as:

• Man-in-the-middle (MITM) attacks: MITM attacks occur when an attacker intercepts communication between two parties , typically a user and a web service , without their knowledge, allowing the attacker to eavesdrop on, modify, or redirect the communication. SSL stripping and certificate impersonation can both lead to MITM attacks.
• Eavesdropping: Eavesdropping is when an attacker passively intercepts communication between two parties. The attacker doesn’t alter data but simply listens in, gathering sensitive information. Weak encryption ciphers and expired certificates can make it easier for bad actors to eavesdrop.
• Data breaches: Breaches occur when a cybercriminal gains unauthorized access to (and steals sensitive data from) your system. SSL misconfigurations, like insecure redirects or the presence of mixed content, can both lead to data breaches.
• Desensitization: repeating issues with expired or invalid SSL-certificates on your companies websites can desensitize your users against common cybersecurity practices. Months of cybersecurity awareness trainings drilled into them that websites without working SSL certificates pose a danger and should not be visited. Asking them to overlook the issue on your own websites can make them more receptive to phishing or fraud attempts later down the line since they are “used to” HTTPS-errors on your sites.

Challenges in identifying SSL misconfigurations#

Identifying SSL misconfigurations without a complete External Attack Surface Management (EASM) solution is challenging. The fact is most traditional security tools simply don’t have the capacity to continuously monitor and analyze all of your organization’s internet-facing assets. Combine this with the dynamic, ever-changing nature of digital environments , where assets are frequently added and updated , and it becomes even more difficult to effectively maintain secure SSL configurations. Specifically, for two reasons:

1. Traditional security tools have limited capacity: Most conventional security tools are designed to monitor and protect internal networks and assets. However, they often lack the specialized capabilities to scan and analyze the wide array of internet-facing assets, including websites, web applications, APIs, and more, for SSL misconfigurations. Traditional tools can easily miss things like SSL certificate expirations and weak cipher suites, leaving your organization vulnerable.
2. The digital environment is always changing: Your organization’s digital environment is dynamic as your team continually adds, removes, or updates content, applications, and services. And this constant change means you can inadvertently and easily introduce SSL misconfigurations.

Mitigating SSL misconfigurations with EASM#

To take a proactive approach to managing and securing your organization’s external attack surface (including SSL configurations), consider investing in an automated, cloud-based EASM solution that monitors all your known and unknown assets. The best solutions can:

• Perform continuous discovery and monitoring: Invest in a solution that scans and monitors all internet-facing assets for SSL misconfigurations, ensuring that any vulnerabilities are quickly identified and addressed.
• Monitor encryption certificates: Your chosen solution should also monitor SSL certificates for expiration dates, the certificate chain, TLS protocols, and issuers, preventing the use of insecure or expired certificates.
• Benefit from automated analysis: Consider a solution that automatically analyzes your SSL configuration and then identifies potential issues, ranking them based on their potential severity. This ongoing analysis and prioritization can help you better target your remediation efforts.
• Receive proactive alerts: You don’t know what you don’t know. Find a solution that provides proactive alerts about SSL misconfigurations, allowing you to take swift action to mitigate potential security risks.
• Take a hands-off approach: For the most convenient approach to securing your organization’s external attack surface, consider a provider that offers managed EASM service. With a managed EASM provider, the vendor should provide continual 24/7 monitoring and connect with you regularly to review threats and remediate identified vulnerabilities.

One solution that checks all of these boxes is Outpost24’s EASM platform. A cloud-based platform, that allows you to enhance your cyber resilience. The solution continually maps your organization’s growing attack surface, automatically gathering and analyzing data for both your known and unknown assets as well as adding cyber threat intelligence feeds for a more complete approach to cyber risk. Then, the platform offers a variety of potential remediation actions you can take to eliminate security gaps and secure your digital presence against SSL vulnerabilities.

Your organization’s internet-facing assets are ever-growing , and your attack surface is, too. Understand your attack surface and boost cyber resilience with Outpost24’s Sweepatic EASM. Contact us to learn more about how EASM can help mitigate Cyber Risk in your attack surface.