How to Ensure Your SSL-TLS Connections Are Secure

By: Morpheus Data

Encryption is becoming an essential component of nearly all applications, but managing the Secure Sockets Layer/Transport Layer Security (SSL/TLS) certificates that are at the heart of most protected Internet connections is anything but simple. A new tool from Google can help ensure your apps are protected against man-in-the-middle attacks.

In the not-too-distant past, only certain types of Internet traffic was encrypted, primarily online purchases and any transmission of sensitive business information. Now the push is on to encrypt everything — or nearly everything — that travels over the Internet. While some analysts question whether the current SSL/TLS encryption standards are up to the task, certificate-based encryption isn’t likely to be replaced anytime soon.

The Elecronic Frontier Foundation’s Let’s Encrypt program proposes a new certificate authority (CA) intended to make HTTPS the default on all websites. The EFF claims the current CA system for HTTPS is too complex, too costly, and too easy for the bad guys to beat.

Nearly every web user has encountered a warning or error message generated by a misconfigured certificate. The pop-ups are usually full of techno-jargon that can confuse engineers, let alone your typical site visitors. In fact, a recent study by researchers at Google and the University of Pennsylvania entitled Improving SSL Warnings: Comprehension and Adherence (pdf) found that 66 percent of people using the Chrome browser clicked right through the CA warnings.

As Threatpost’s Brian Donahue reports in a February 3, 2015, article, redesigning the messages to provide better visual cues and more dire warnings convinced 62 percent of users to choose the preferred, safe response, compared to only 37 percent who did so when confronted with the old warnings. The “opinionated design” concept combines a plain-English explanation (“Your connection is not private” in red letters) with added steps required to continue despite the warning.

Researchers were able to increase the likelihood that users would make the safe choice by redesigning SSL certificate warnings from cryptic (top) to straightforward (bottom). Source: Sophos Naked Security

Best practices for developing SSL-enabled apps

SSL has become a key tool in securing IT infrastructures. Because SSL certificates are valid only for the time they specify, monitoring the certificates becomes an important part of app management. A Symantec white paper entitled SSL for Apps: Best Practices for Developers (pdf) outlines the steps required to secure your apps using SSL/TLS.

When establishing an SSL connection, the server returns one or more certificates to create a “chain of trust.” The certificates may not be received in a predictable order. Also, the server may return more than necessary or require that the client look for necessary certificates elsewhere. In the latter case, a certificate with a caIssuers entry in its authorityInfoAccess extension will list a protocol and extension for the issuing certificate.

Once you’ve determined the end-entity SSL certificate, you verify that the chain from the end-entity certificate to the trusted root certificate or intermediate certificate is valid.

To help developers ensure their apps are protected against man-in-the-middle attacks resulting from corrupted SSL certificates, Google recently released a tool called nogotofail. As PC World’s Lucian Constantin explains in a November 4, 2014, article, apps become vulnerable to such attacks because of bad client configurations or unpatched libraries that may override secure default settings.

Nogotofail simulates man-in-the-middle attacks using deep packet inspection to track all SSL/TLS traffic rather than monitoring only the two ports usually associated with secure connections, such as port 443. The tool can be deployed as a router, VPN server, or network proxy.

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